Author: Tom Wentworth

On today’s episode of Scaleup Marketing, I’m joined by Rick Klau, a long-time startup entrepreneur, former operating partner at GV, and a Product Manager at Google where he worked on Blogger, Profiles, and the YouTube homepage. I wanted to talk to Rick about his work on the OKR framework used at Google, but we ended up talking about his journey from being a lawyer to blogger to product manager on some of the most widely used products in the world.

Rick Klau: [00:00:00] Hey, Rick. Welcome. 

So good to be here. 

Tom Wentworth: [00:00:07] as a part of my podcast process, I do deep, deep research on my guests.

And the first thing that blew me away in doing my deep, deep, deep research was that you and I kind of sorta worked for the same company way back in the day, a company called iManage. 

Rick Klau: [00:00:23] You know, it doesn’t come up all that much these days, given where my career went afterwards. But that is an amazing small world 

Tom Wentworth: [00:00:31] connection.

Yeah. Yeah. I mean, iManage was really the dominant platform for law firm, content management. It turns out lawyers produce a lot of documents. 

Rick Klau: [00:00:40] Yeah. And time is money. 

Tom Wentworth: [00:00:41] You and you were a lawyer, right. You graduated with a law degree, right? 

Rick Klau: [00:00:44] I sure did. 

Tom Wentworth: [00:00:46] So I manage was maybe it was not SAS. Obviously it was classic desktop software, but a really great example of a vertical application.

Like that product was so instrumental to lawyers day to day [00:01:00] operations. and it’s such a, it’s a pretty niche product, but was incredibly successful. So I assume that, you know, being a lawyer, you might have played a little bit of role in the marketing of I managed 

Rick Klau: [00:01:10] is that a. 

I did. I mean, I, when I first joined, I actually joined in the marketing org.

and the expectation was that I brought whatever credibility, having the J D letters after my name might bring, but also a fair bit of technical understanding. I mean, what, what was so. Unusual really unheard of at the time for what was desktop software was that it was this three tier solution that meant that if the server went down, which in those days the server always went down.

before I manage it would take the desktop with it. Oh, that’s right. And so you had lawyers who’d be drafting contracts or reviewing edits. And if a PC docs was the sort of the heavyweight at the time, when that [00:02:00] server went down, they, they were dead in the water. They couldn’t work. And if you can’t work, you’re not billing time.

If you’re not billing time, you’re not making any money. And the, the, the opportunity for an elegant bit of technology to come in and say, look, if. If the server does go down because of course it will, you can still work. And then when it comes back up, we can sync the whatever changes have happened on your end and we’ll resolve any discrepancies.

I mean, it was like we were selling magic to some of the large law firms who were certain that this was just, a fact of life at the time. 

Tom Wentworth: [00:02:38] Yeah, and it complete tangent. We will not go down, but sinking was huge. It’s Lotus notes was so good. Like people underappreciate how good Lotus notes was way before in the early, early days of network computing.

 the fact that Lotus notes could figure out how to sync and replicate databases in 1997 or six or whatever was spectacular. And I managed sort of did that for lawyers, 

[00:03:00] Rick Klau: [00:02:59] right? 

Absolutely. I joined in the summer, I think of 99. And it’s hard to understand now, 20 plus years later, but the internet still felt like a bit of a distraction, right?

The majority of the time spent on computers. I had come from an environment where as a law student, I clerked at a law firm in the, would have been the summer of 95. I was the only non secretary at the law firm that had a computer. 

Tom Wentworth: [00:03:30] Wow. 

Rick Klau: [00:03:31] And that was not unusual at the time. Of course today everyone’s got an iPad and a phone and a laptop.

so when you think about in the late nineties, This work that was being done on computers that were relatively new to the lawyer’s desk, because in the past they’d be dictating to their secretary who would then be transcribing and then they’d edit those. it was [00:04:00] such a need to reconcile those differences.

And these were institutions that didn’t always have the best in class. Network infrastructure. it was not unusual for somebody in a coat closet to unplug something. They didn’t know what it was and suddenly the entire network had gone down. So, that ability to be resilient when things were, unexpected was pretty critical.

Tom Wentworth: [00:04:23] Yeah. So I worked at a company called interwoven. We acquired, I managed, I think, after you left. And I ended up working for the co-founder of iManage Rafiq, who I learned a tremendous amount about, and also. For feet bought me my first iPhone. I did something I guess. Good. And he bought me an iPhone, so I will never, ever, ever.

Forget you repeat. Thank you for, for that. The most interesting part of it I’ve managed, I think is so, I mean, so interwoven inquired, I manage autonomy, notorious autonomy, acquired interwoven, HP acquires autonomy, and I managed sort of survived through all of that. OpenText acquired some of the assets from [00:05:00] HP.

So it goes, I managed to interwoven autonomy to HP, to OpenText the founders, bought the product back. So they bought the product from HP and I manage is doing better than ever. So it’s kind of a weird Testament to this, this product now here, whatever it is, 20 years later is still dominating the law firm market.

Rick Klau: [00:05:21] That’s extraordinary. And also it reflects within that industry legal specifically. I mean, it’s, it’s an industry built around mitigating risk. Yeah. So once you have something, you know, that it works and it solves the problem and it solves it. Well, it’s not broken, so don’t fix it. Don’t try and give me the next widget.

That’s a little bit incrementally better. It is exactly what the market needed 20 years ago. And apparently is what it continues to need today is just amazing. 

Tom Wentworth: [00:05:52] And you started off that. They’re probably still using some of your positioning now, 20, 20 plus years later. So, Oh, 

Rick Klau: [00:05:59] aye. I, I, [00:06:00] I hope for their case, that’s not the case.

Okay, fair enough. 

Tom Wentworth: [00:06:04] So after I manage, you went to social. So you and I had like a lot of pet, not, not exact in the same space, but super close to each other, social taxes, one that’s interesting. So social tax, for those who don’t know, and then feed burner to like classic web two a, I hate the word web too. Oh, by the way.

But I’m going to put them under this bucket just because it’s, I think it’s, it is what those tools were called back in the day. Social, Texas, when I find super interesting. I’d love to get your take on it. I’ve always thought wikis as a paradigm, we’re super underrated and like are still relevant today, but they never took off.

Like I feel writing is such an underappreciated form of communication and wikis are a perfect platform for that. Like what was that experience like and what happened? 

Rick Klau: [00:06:48] Well, I, my first interaction, I went to work for Ross Mayfield at social text. and I met each other through blogging. And, and I had started blogging. [00:07:00]

shortly after I left I’m image, I had joined a company called interface software was providing CRM software and the legal market. And I was a kid illness for the American bar associations law practice management magazine. I was past deadline. Needed something to write about. And on an unrelated project, four separate times had run into John Rob and his blog.

Yeah. I kept Googling for something and I kept ending up at John rubs blog. I had no idea who John was. I had no idea what a blog was. This was, you know, middle of 2001. So I got interested and made that the focus of my column and started a blog so that I could say that I had done it for purposes of this article and then figured out I loved it.

I loved writing. I loved joining this, this community that was nascent [00:08:00] at the time. And one of the people who was saying some pretty interesting things about knowledge management about this emerging crop of tools that as you pointed out, became known as web 2.0. Was a guy named Ross in Palo Alto. I, by this point was living outside of Chicago and on occasion when I would travel through San Francisco, speaking at a conference or meeting with a customer, I would meet and have a beer with Ross, or when I was in New York, I would meet and have a beer with some of the people I met who were blogging from New York.

when I left interface, it was one of the first people I called. Cause I, I had finally decided. I think I might be done with legal technology. I, I think I want to move into something a little bit more horizontal and quickly figured out that Ross had a need. And this was an opportunity to be part of the company I’m answering your question.

Why didn’t wikis really take off? I don’t know. I kind of share your [00:09:00] sense that as a, as a medium for. Enabling the co-creation of information, a Wiki there’s no better 

Tom Wentworth: [00:09:10] tool, no better. 

Rick Klau: [00:09:12] but I do think that much, like I would see later when I ended up at Google running blogger, there is an absolute distinction between people who see themselves as content creators, and people who see themselves as content, consumers, and.

That, that distinction. I think there’s probably something to why, at least in a, in a corporate setting, there are people who feel like committing to content on a page as opposed to consuming it is potentially a step too far. 

Tom Wentworth: [00:09:44] It’s, you know, there’s a few companies, HubSpot is maybe the best example of a company that even today, like their entire world is based on wikis.

They’ve been creating. And updating corporate wikis since they were founded in what, 2007 or so. And it becomes [00:10:00] like this. The great thing about it is if you adopt it, it becomes this great living record of things. And, you know, today Slack didn’t, you know, entirely solved the problem email. Clearly hasn’t entirely solved the problem, but do wikis, right, and hyperlink things and make them editable in real time.

It’s a really elegant solution to the problem of keeping people on the same page. I just. I’m like you, I wish more people would blend that would blur that line. I think more people should be content creators, not just consumers and wikis are so perfect for that. Yeah. 

Rick Klau: [00:10:31] It, it, it does require, a level of abstraction for people who grew up with computers, thinking in terms of files and folders, the Wiki requires, a whole different way of thinking about where the information lives, how.

One page relates to another, I, it, it spoke to me once I started using it. I couldn’t imagine not using it. I think for the same reasons that today I live in air table [00:11:00] as a, as a, as a new document type that is independent from documents and spreadsheets. It is its own thing. but I think it requires an investment of.

Time and understanding that there are folks who are like, look, I just, I have work to do. I just want to get the work done. 

Tom Wentworth: [00:11:20] Yeah. Except getting the work done and then communicating the work is where the challenge happens. And that’s where we use our grade. And then, so from social texts, you went to feed burner, right?

Another like, and feed burner. Describe what feed burner did. Cause that feed burger is one that I, I spend a lot of time in actually back in the day. 

Rick Klau: [00:11:36] Well, it it’s, it’s another, employment opportunity that arose out of blogging. so I was a couple of years into maintaining my own blog. I had started a, political blog as well as I got excited about the Dean campaign, you know, two Oh three and realized that there was an increasing amount of consumption readership of my [00:12:00] blog that was happening.

In feed readers, right? RSS as a, as a file format, as a syndication format was one way for the blog to get delivered. If people came to the blogs, webpage URL on the web, I could, I could see that I could see how many people were reading pages on my site, but if they were reading an RSS that was completely opaque, there was no way to know.

How large, if at all the audience was on the other side of that file. And out of curiosity, I started trying to figure out if that was an answerable question. Well, it turns out not only was it answered, but the team building the answer or the tool that would answer that question was in my backyard in Chicago.

Wow. And feed burner as a product existed to tell you how large your audience was. With an RSS feed, how many people were reading it, how many people were subscribed to that [00:13:00] file, and for a podcast, which is just a RSS file that includes pointers to MP3 files. how many people were actually listening to the podcast, which in the very earliest days, hard to believe this was 15 years ago, but in the earliest days of podcasting, we had no way of quantifying that audience and.

Any, any medium that seeks to be commercial, you need to know those numbers. So feed burner became the platform for knowing what that audience, how big it was, and how they were engaging with that content. See, 

Tom Wentworth: [00:13:39] I’m an open source, open standards kind of guy. And I feel like the world needs RSS again. Like I, I’m sort of tired of people telling me how to consume my content.

I think about RSS, I loved was I made that choice. 

Rick Klau: [00:13:53] You know, I 

Tom Wentworth: [00:13:53] could determine how I wanted that content given to me, not somebody, not a publisher quote unquote, 

Rick Klau: [00:13:58] but [00:14:00] you know, I don’t 

Tom Wentworth: [00:14:00] know if ours is ever coming back again, but those were glorious days. 

Rick Klau: [00:14:04] It really was. I think if you look back at, there were standalone applications, like news Gator was one of the ones on windows.

but Google reader of course famously became this adored product for a small, but very passionate user base that even to this day, he started. Mentioning Google reader, the first words that somebody will reply reply to you with, or too soon, like it still hurts that that product, it doesn’t exist. I just got the 

Tom Wentworth: [00:14:33] chills.

When you said, I literally just got the chills. When you said Google reader, of course you went to Google, any truth to the rumor that you killed Google reader. 

Rick Klau: [00:14:43] I had nothing to do, with, with that unfortunate, time, it was kill FTP on bloggers. That one, I will own 

Tom Wentworth: [00:14:53] that about that. We’ll get to that.

We’ll get to that a little bit, but no, Google reader is a perfect example. A product that looked the writing was [00:15:00] on the wall and it was a very niche, but engage audience. But the funny thing is usually when that happens, somebody, it gives somebody else a chance to step in and take that audience. But no one did no one made a better Google reader, whatever it is, 12 years now later.

Rick Klau: [00:15:14] Yeah. And you look at none of the building blocks have gone away. Right. RSS still exists. It’s still possible to pull an RSS feed and check for the diff and bring in whatever the new items are. feed burner hasn’t really changed from the day it got acquired, but the product still exists. Still works.

Yeah. still a bunch of podcasters who use it because it’s one of the few ways. Now I imagine for those who are using, either tools like anchor or other tools to distribute their podcasts, there are other ways of capturing audience data, but, it does feel like there remains an enormous opportunity, to lean into this as we’re.

Starting to recognize that some of the social platforms, may [00:16:00] not have our best interests at heart, and are not necessarily the best consumption experiences for, for really identifying the sources of news you want. Yeah. 

Tom Wentworth: [00:16:10] So a couple of things there, my favorite, by the way, Speaking of sort of technology history, friend feed was my favorite way ever of consuming content.

And obviously Brett Taylor and the whole team went on to build Facebook and then over to Salesforce and amazing stuff. But friend feed would let you like the way that friends who had, let me build my stream and people could then subscribe my sheet. My stream was amazing. Like I love friend feed. That was the only thing that fought Google reader from my heart.

Rick Klau: [00:16:37] boy, I, I can imagine the fan club. I could introduce you into of some of my close friends who were huge friend feed, acolytes, and, and passionate users before the Facebook acquisition. yeah, you look back at that period of time. Really 2004 or five till about 2008 [00:17:00] was just this unbelievably fertile.

Time where if you were invested in curating your audience and curating the audiences, you wanted to be a part of? I, I, Twitter is a little bit of that for me today, but I think only because I’ve been on Twitter from nearly day one, That there are relationships I’ve formed with people who are the people I engage with.

I think for a lot of people, Twitter is much more unidirectional. It’s very much a, I use it as the equivalent of a feed reader. but which it is absolutely not anything like what the friend feed experience was or, or, or what the Google reader experience was go reader itself was pretty social. If you had a community of people whose shared items you were following, I have friends to this day who they, their [00:18:00] only point in common is me.

Through Google reader. They’ve never met. Wow. But still know of each other because the, the activity feed and the shared items on Google reader was where they met. 

Tom Wentworth: [00:18:13] That’s really crazy. I, you know, I think the lesson in this for me is a lot of there’s so much opportunity you got back, like the history. We talked about Lotus notes, you know, earlier today, like there’s so much technology that’s happened over the years that.

That we could learn from, and that we think is innovative. And you really look at like what Lotus notes did back in 87 was crazy when you really take a step back. And I think we’ll look at some of what, what came and went in this sort of Dawn of web two. Oh. And say, these are things we could learn from, and somebody, somebody could take on the current state of social platforms with a little bit of, you know, a little bit, a good product management, I guess.

Rick Klau: [00:18:56] Yeah, so much of this comes down to timing. Yeah. [00:19:00] And, and if there was, naiveté built into some of these products early on, certainly that got exploited in years to come. It was never worrying about the positive possible negative impact. Yeah. Or ways in which these tools could get weaponized, that allowed us to just lean into the serendipity without putting any guardrails in to prevent what could have come.

I think it would have been extraordinarily difficult. Agreed in 2005, 2006, 2007, to argue that the right product decision for YouTube was to limit. User engagement because at some point nation States might try and weaponize that information that would have been laughed out of that 

Tom Wentworth: [00:19:52] room. Laughed out of it.

The same with Twitter, you would have been Twitter is where you shared what you had for breakfast. 

Rick Klau: [00:19:58] No doubt. 

[00:20:00] Tom Wentworth: [00:19:59] Fascinating. So you ended up joining Google through FeedBurner right. So Google buys, buys feed burner. And I want to talk a little bit about that. So you worked on a bunch of products at Google that I think, you know, most people hadn’t experienced with you worked on.

Google plus a bit, this thing called YouTube, you worked on blogger. what did you start off at and which will be coming through? Feed burger. Wait, where did you go first? 

Rick Klau: [00:20:22] Well, it’s it’s it’s funny. I started in business development. Yep. Google, at least at the time was pretty unusual. Among tech acquirers for interviewing every employee.

Yeah. At the acquired company before the acquisition closed. Wow. Because this was still at a time company was about 10, 12,000 people. Larry and Sergei were still reviewing every employee offer that went out the door. Wow. And they saw acquisitions as a potential vector for people who would not otherwise meet the hiring bar.

[00:21:00] Kind of sneaking in through the side door and then being in the company that much with, with the risk of them sort of polluting the talent pool that existed inside the company. So, so Google interviews, everyone in the company. Wow. At which, you know, we were maybe 25, 30 people at the time. And after the first round of interviews, They, and I both agreed well, that did not go well.

Like I, I liked the people I talked to the, what they talked about doing in their day-to-day job didn’t sound like anything that was interesting to me and their feedback to the Corp dev team was boy seems like a good guy, but he’s not right for this team. Hmm. So I ended up having an interview with a whole different set of folks and the, the terms of the deal were quite clear.

[00:22:00] Four founders to Costello, Steve Ella Koski, Eric , we’re all Chicago guys. And they had me very clear to Google that we are, we are okay. I’ve been to the possibility of an acquisition as long as everyone stays in Chicago. Wow. So Google said, all right, we got that works. We’re about to open a large engineering office.

We’ll just put you there. And a week before the deal closed is when I’m having my second round of interviews panicking. Perhaps I’m not going to get a job that this will be a great outcome. I was one of the first non founder employees at feed burner, and I’m still going to find that I somehow didn’t meet the Google, Google hiring bar.

And in the middle of one of those interviews, my future boss tells me, well, you’re, you’re coming to mountain view. And I said, Oh, I imagine I’ll be in mountain view a lot. He says, no, you’re, you’re coming to mountain view. This is where our team [00:23:00] is and we need you here. So I’m like, did, did he just tell me I have a job?

I think, I think he told me I just have a job, which is great. so sure. Okay. And the postscript there is that my grandfather had just passed away the day before this. So I had to change my schedule to fly to Florida, to his Memorial service. And my wife had flown with our three very young children to Florida, the day I was interviewing.

And, and then I’m spending the entire day, Friday flying to Florida from San Francisco. I don’t see my wife. Or have a chance to talk to her until we’re at the Memorial service where I have to eulogize my grandfather and then she has to drive one of the family to the airport. So we don’t actually get to talk until 72 hours after I’ve had my interview where I have to break the news [00:24:00] to her in front of my entire family at this celebratory dinner.

As we remember my grandfather’s life. That we’re about to move the family to California. 

Tom Wentworth: [00:24:08] Wow. 

Rick Klau: [00:24:10] So I end up in business development, ended up on a, a team called strategic partner development management, which is just a lot of words. That mean you, our job in, in that org was to acquire the content that Google couldn’t index on its own.

Interesting. 

Tom Wentworth: [00:24:26] Hmm. Is there a lot of content, I guess there probably was. Well, 

Rick Klau: [00:24:32] yeah. You think about everything right? From map tiles. Yeah. Satellite imagery. Yeah. To books, to feeds of products for sale and on and on and on. If it was proprietary content for which there needed to be at least a. Contract in place, if not some compensation for access to that content, it was, it was our team’s job to negotiate access to that [00:25:00] content, determine what, if any compensation there would be.

And then there was a whole other part of that team whose responsibility was to manage all of those partners around the world who are, who are providing feeding this content into one or more of the Google products. Nice that we’re in ingesting it. Yeah. And 

Tom Wentworth: [00:25:21] that was, and how did you transition to becoming a product manager?

Cause I have this like, first of all, you’re you’re, you’re not a tech, like you were not, although you’re clearly a nerd. Like I am, you know, you have a JD, your undergrad was. Liberal arts something. Right. How do you, I’ve always figured product managers are at Google, are PhD, CS. Like how did that happen? 

Rick Klau: [00:25:44] I’ve I’ve always, he’s referred to this as the immaculate promotion.

we’ll start there. you’re not far off, right? The, the bias, certainly back when I joined Google in 2007, by this point, you know, I’ve been at Google about a [00:26:00] year in 2008, the bias was all but written in stone. If you don’t have a computer science degree, you cannot be a product manager. There was, there was a little known separate category called a business product manager, ah, which allowed for non CS majors.

Who were seen more as almost an outward facing kind of like a GM yep. To the market. but weren’t expected to be a PM in, in the traditional sense, at least how Google thought of it. I knew from within a week of joining Google that. The absolute ideal job at Google was to be a product manager. Nice. And about a week later, I knew, and I would never be a product manager at Google because no matter how you add up international affairs and French plus a law degree, they do not.

You don’t [00:27:00] rearrange those letters to spell computer science. No. 

Tom Wentworth: [00:27:03] And you were going to go back the school and, and spend four years learning how to write, you know, Java, 

Rick Klau: [00:27:09] right. I, so I, I sorta took both of those things. As, as gospel. I just knew I would be on the fringe. I would get to work with some product managers I admired and I would be close to the center of gravity on campus, but that was never going to be a path that would be open to me.

So Google famously has this concept of 20% time, which, you know, now, 20 plus years into its existence, some people raise an eyebrow and suggest it’s, it’s not as real these days, but back then, I took liberal advantage of 20% time. And one of my first projects was. When I discovered that Google was sponsoring both the democratic convention in Denver in 2008 and the [00:28:00] Republican convention in st.

Paul, I raised a hand and was like, well, I, I worked on the Obama Senate campaign back in Oh four. I know a lot of his tech team as he’s now the nominee for the democratic party. I don’t know if y’all need help, but I’m here and. And, and that’s how I backed into being responsible for managing Google’s partnership in Denver for the democratic convention.

Wow. So it was a blast. It was extraordinary. I got to spend a week in Denver, attending a number of convention events, but also being responsible for a lot of Google’s product presence in Denver. And one of the women who was part of the Google. Team in Denver was a woman named Katie Stanton and Katie and I hit it off.

She’s, you know, we’re the same age. We each have three kids, all of whom are roughly the same age. [00:29:00] We shared a lot of political interest. And so as we’re in Denver with a bunch of, you know, early 20 somethings, finding ourselves sort of the, the folks with experience on the ground and just. Swapping notes.

She was a PM at Google. I was super interested in how she did that. She had previously been at Yahoo and so she becomes one of my very close friends at Google. Somebody I looked up to admired and about three months later, I got 9:00 AM on a weekday night. And she says, I think you need to be the PM on blogger.

I said, well, you know, from your lips to God’s ears, but I don’t think that’s how that works. There 

Tom Wentworth: [00:29:44] probably wasn’t a better job for you given, you know, given, you know, you were a 

Rick Klau: [00:29:49] blogger prior to blogger. Exactly. Right. So I said, well, what, why are you. Why are you suggesting that I would love to do that, but I don’t think that’s in the [00:30:00] cards.

He goes, well, I was just talking to Joe Kraus. Joe is the director in the apps, Google apps world. One of his products is blogger and he was just telling me he needs somebody with business sense who understands the blogging world. and I told him, you’re the guy that he should talk to. So. Okay, right.

Like, yeah, sign me up. she introduced me to Joe Joe and I meet, Joe and I hit it off. Joe has to go to Sergei Brin to get an exception made, to allow me to be a product manager. Wow. And I would love to tell you it’s because Sergei was so blown away by my product acumen. But I think the reality is that blogger was not a strategically vital product to Google at the time.

And the expectation was, yeah, what’s the worst that could happen. We find another product manager to work. 

Tom Wentworth: [00:30:57] You actually blogged. Like I would [00:31:00] assume that your resume was look I’m one of the few people that actually has done this for some period of time. 

Rick Klau: [00:31:06] I, I came at it from two sides, right on the one hand it’s like, I know this world I’ve been blogging at this point for eight years, I ran a campaign blog for a presidential campaign.

I, I worked in the industry on feed burner where I, I worked with all of the different players in the blogging ecosystem. So I know that world Colt, on the other hand, I went to every product manager I had crossed paths with at Google. The more non-traditional the background, the better. Yep. Right. But started with Katie.

And then there’s a guy named Adam Smith, who I’ve worked closely with who, who at the time was working on Google books and a couple of others and said, listen, I don’t know if there’s a process here, but if you could put down a few words on what you think I could or couldn’t bring to the job. [00:32:00] And then send that to Sergei, like that’ll help fill in the gaps.

So I think it de-risked, it enough that, and Joe is a pretty compelling individual. I don’t know if you ever crossed paths with Joe, 

Tom Wentworth: [00:32:13] but now I know of him. 

Rick Klau: [00:32:14] Yeah. It kind of a legend in Silicon Valley in his own. Right. He was the founder of excite when he was still an undergrad at Stanford had sold jot spot to Google, the year before feed burner sold to Google.

Jot spot itself, a social text competitor. So we were all of these paths that seemed to lead to this moment and Joe gets Sergei to, to make the exception and, and, and that’s how I, I moved into the product org, out of what had been more of a BD or sales role, and where I would be at Google for the next three, almost four years.

Wow. 

Tom Wentworth: [00:32:56] And. What were you just curious? What were you [00:33:00] blogging on prior to using blogger for, you know, back at the Obama campaign? What were you actually blogging on? 

Rick Klau: [00:33:05] So my very first blog, I started on blogger. Yep. I got excited by, John Rob was one of the people I ended up talking to for that magazine column.

He was at the time running a radio user land. You remember Dave Weiner’s, company products from back in the day. And 

Tom Wentworth: [00:33:25] inventor of RSS Dave Weiner, right? 

Rick Klau: [00:33:27] That’s one in the same. There you go. I, I, I love learning new tools and this was an excuse to poke at, at a, a new product idea, a new product category that the whole notion of outlining as an organizing tool was interesting to me.

So I used radio user land for awhile. Then movable type came along. Of course I played with that ran my personal blog and moveable type for awhile. we had, I had moved one of the blogs I was responsible for. I think it might’ve been a campaign [00:34:00] blog, onto WordPress. And, and then moved my own blog to word press.

and ahead of taking the blogger job. I remember going through the effort of migrating back to where I started taking what had at that point was eight, almost nine years of content and exporting out of WordPress into blogger, which was not a popular direction to go. It was almost always the other way.

and having a bunch of friends reach out and effectively asking some version of everything. All right. Like why, why would you do that? And then a month later got to announce like, well, because I’m, I’m now responsible for some portion of the product, at, at blogger. And now this is as good an excuse as any to, to eat my own dog food.

Tom Wentworth: [00:34:46] Yeah, I was. So in that same time, I was in the enterprise web content management business, you know, managing big corporate websites. 

Rick Klau: [00:34:53] Sure. 

Tom Wentworth: [00:34:54] And I remember the first time I saw WordPress. I’m like, we’re in trouble. [00:35:00] Like WordPress didn’t into any of the things that we did as an enterprise. They didn’t do security and permissions and complex sites and navigation, but I’m like the user experience is so simple.

This is going to be a problem. And actually I went later to work with the founder of Drupal, a dress at Aquia. And it’s that era again, back to, you know, that was. WordPress and Drupal, just all of a sudden dominated how people publish content, especially WordPress. I mean, WordPress, Matt Mullenweg, you know, his vision is to have a hundred percent of the world’s sites run on WordPress.

And he’s not going to get entirely there because of things like Drupal, but, but that’s a pretty ambitious vision. 

Rick Klau: [00:35:38] And it to Matt’s credit. It was the vision 15 years ago. And they’ve just been chipping away ever since it’s it’s an extraordinary run. What you just described. I mean, it’s textbook innovator’s dilemma.

Tom Wentworth: [00:35:53] Innovator’s dilemma clearly. 

Rick Klau: [00:35:54] Exactly. It’s it’s it’s as if it’s a chapter out of Clayton Christiansen’s book, this is exactly [00:36:00] how it happens. You, you solve for the top of the market. And then suddenly watches the bottom of the market just keeps working its way up the stack and, and hollows out the value proposition of what the six and seven and eight figure, alternatives present.

Tom Wentworth: [00:36:15] See? Yes. And I think that’s going to happen right now. If you follow along with Wix and Squarespace and they’re going to do. To the enterprise side of that business, 

Rick Klau: [00:36:24] you know, like there, 

Tom Wentworth: [00:36:25] what you can do is Squarespace and Wix these days is for 1999 a month or whatever it is is absolutely stunning. 

Rick Klau: [00:36:31] So 

Tom Wentworth: [00:36:32] I feel like that’s, that’s happening now in the corporate side of it too.

All right. So being a product manager at Google, so I’m a marketer I run marketing at at recorded future. You were once a marketer back in the day. How did product managers at Google work with marketing? 

Rick Klau: [00:36:49] Sometimes they didn’t. Okay. Right. I think one of the interesting things is product at Google is not monolithic.

There’s, there’s a pretty wide [00:37:00] spectrum and I should also disclaim for the last nine years. I was at Google ventures. I left the product org and man it’s evolved quite a bit since I left. But in my experience, you have some product managers whose real skill is thinking about. Being a partner with the engineering team on everything from architecture and scale and making hard choices about product design, product execution, et cetera.

I came at it from a very different point of view. I particularly, it was helped by the fact that I was working on blogger, which by its nature was a public product. Yeah. I, I looked at my job as being one of, I needed to be the most visible person at Google with respect to blocker. I needed to be find-able.

Huh? Right. So that meant my blog needed to be [00:38:00] easy to find and understand who I was and what my responsibility was. It is why I was so active on Twitter early days, because. People who use any blogging platform, forget about blogger for a minute are used to speaking their opinion out to the world and having it be heard and if necessary responded to.

And if I was going to sit behind this veil of, you know, my job is to, is to work inside the company on the product itself. I was doing the product and the user base a disservice. And look it also bears mentioning bloggers. Founder is F Williams. Yeah. If ever there was the canonical example of an individual who lived the values of the products that he created.

It’s F yeah. And I felt responsibility stepping into that [00:39:00] chair. To, to, to not try and be F, but to honor that notion of users need to know who the people are that are building their products. my first meeting a week after becoming product manager, I went and sat down with EV at the Twitter offices to say like, let me, let me catch you up on what bloggers up to these days.

But tell me if there’s anything I should know, from, from the guy that was there on day one, I, you know, I’m, I’m all ears. So, in, in regards to your question, the way I worked with marketing was to try and think about, there is a story that blogger is a part of, and it’s the story that every one of the users is writing every day.

Are there product decisions we need to be making in service of that story or worse, but equally important. Are there product decisions we’re making that are absolutely an opposition to that story? Yeah. [00:40:00] Right. So I’ll give you a, a great example. this was less a product decision, but it was absolutely a conversation I had with marketing.

We are a platform for communication. I say we I’m immediately going back to the days when I was the product manager on blogger and we had a user who happened to be the president of the Republic of Georgia. And when the Russians cut the trunk line into Georgia and there were actual boots on the ground invading Georgia, the president of George’s only.

Communication line out to the outside world was a satellite phone that allowed him to blog on blogger. Wow.

I remember taking that pretty seriously as an obligation that we had to make sure that [00:41:00] our product owed to its users to be available. But then when I got an opportunity to write an op-ed for CNN, I’ve a friend of mine worked in, in, at CNN actually was a, a feed burner user from back in the day. And he reached out and said, Hey, if there’s ever anything you want to talk about, like, I can connect you to the folks that run that part of cnn.com.

I made it about the importance of the UN declaration on human rights and that freedom of speech was itself. A human right. Of which online communications were an absolutely critical component. So if you had governments that were trying to stifle speech, wherever they might be, that was itself in opposition to the UN declaration of human rights.

And [00:42:00] that was not a me going rogue. That was me working with marketing. To say, what is the, what’s the story we’re trying to tell blog her. And of course, the challenge at a company as large as Google is it’s a lot of work to ensure that those stories are themselves in concert with each other. Yeah. Cause you can imagine I give, if I’m all, but pointing a finger at a nation state, it’s one thing to do that as a guy running a tiny little.

Product. It’s another thing, if it’s Google saying that, but feeling that it was an important part of bloggers identity, that we had a point of view and that we communicated it. I think there’s two, 

Tom Wentworth: [00:42:45] two things. I mean, first of all, you’re doing this as a, again, a product manager, right? So your taking the approach that typically a CEO would take, right.

A CEO is, is thinking about. You’re not thinking about managing [00:43:00] backlog and what’s going to be in what sprint and how many engineers are on your project. You’re thinking about how we position, you know, you’re thinking about the strategic outcomes your product needs to deliver for users. It’s just such a different way of thinking about it.

Do you think that that’s how most product managers should operate? Like should product managers be worried about marketing in that way? 

Rick Klau: [00:43:24] I mean, I have a bias. I’d like to think that, that my approach was certainly not the only way to go, but I think for that product or that time, it was absolutely the right way to go.

Yeah. And you know, you’ll often hear people talk about product managers that as the CEO of their product, and I’ve always found that to be a bit of a misnomer because. A lot of product organizations are not set up that way. Yeah. They are set up to be more internally focused or more, more outcome oriented where, you know, the job is to ship the next product.

The [00:44:00] job is to hit some set of metrics. I just didn’t know how to do the job if I wasn’t operating horizontally across those components. And, you know, I made a joking reference to killing FTP. earlier, that was an example of me thinking about it. Not from the what’s the next sprint going to be. What’s the bug burndown rate.

What’s the, you know, what technical debt have we incurred that we need to be down? It was me hearing the engineers. Tell me this is a drag on everything we do. Yeah. If we don’t stop supporting this feature that almost no one uses. We cannot deliver on the things that the company expects of us that we think we’re capable of doing.

And so I had to make the decision, okay, we’re going to kill this thing. I will be the bad guy. [00:45:00] I will communicate not a decision has been made, not use the passive voice, make it unclear exactly where it’s coming from or who’s responsible for it. I will go on Twitter. I will answer emails. I will be the one in the forums owning the decision, making it clear that I made it, and then working to at least earn back some of the trust or, or try and lean into the opportunity to earn back that trust, to show the users why we were doing it and why it was critical for the future of the product to do it.

Ultimately candidly and somewhat selfishly the, the reason for doing that is so the engineers would trust me. Cause if, if, if I’m supposed to be the product manager and the engineers don’t trust me, he never listens. We tell them about why these things are terrible or why we shouldn’t do them. No, he, he actually heard us [00:46:00] and went to bat and took the arrows in the back.

Never pointed a finger, never complained, Oh, this is something that so-and-so is making me do. that earned a tremendous amount of credibility with an engineering team that needed to believe that I could and would go to bat for them when needed 

Tom Wentworth: [00:46:22] and how much negative feedback, how many, how many tweets and emails where you’re applying to.

Oh, hundreds, thousands, 

Rick Klau: [00:46:31] definitely thousands. By the time it was all said and done. we had a Hitler video made of us, so, you know, popular downfall, parody videos was actually extraordinarily well done. very funny. We played it at a team meeting, and gave us all a good laugh. it. It was an interesting lesson early in my product time that stuck with me, which is you don’t ever choose to do something because [00:47:00] it will piss off your users.

That’s like, you’re, you’re a sadist. If you do that. But if you know enough about your users, you know enough about your product, you can anticipate the things that may in fact provoke. Sure. That strong reaction. Yeah. And those are some of the best opportunities to earn those users for life. This is 

Tom Wentworth: [00:47:25] what Apple, Apple is masters at this, you know, they released a whole bunch of new hardware today and people are angry because the new Mac book pro only has four, you know, two Thunderbolt, ports, not four, like the old one had, but Apple sees that as an opportunity to explain the decision and now, you know, like, but there is a benefit to doing this and.

Apple makes those sort of tough decisions. Mercilessly every time they release something 

Rick Klau: [00:47:53] it, and it’s, it shows both a confidence in the value of what you are presenting, [00:48:00] and, and a, a conviction that what you are doing, you were doing for the right reasons, even if. The broader audience may not either appreciate all of those factors.

Now I have, I have been a sometimes grudging admirer of Apple. I am an Android phone user. I am waiting for my new , laptop to show up. So I’m pretty excited. It seems like it’s going to be a great step up. And I, I think one of the challenges I’ve always had with them is they don’t seem to talk to their users much.

Right. And this is the other side of the equation that I always took very seriously. 

Tom Wentworth: [00:48:40] So that is an excellent point. And so they, they product marketers at Apple will go out with YouTube journalists and they’ll do highly controlled. Like you can go watch it on YouTube and all the famous tech reviewers, Apple sends out product marketers with very, you know, scripted.

And even the execs do this. [00:49:00] But it’s all it’s controlled by the messages, tightly controlled. They control who they deliver the message to in the form of these journalists. There are no Apple execs out there doing what you did on social media. And I think you’re right, like that is a, it’s something I admire about people who’ve done what you did now.

Apple maybe has earned the right to be the one company that can get away with doing it that way. But it is annoying because, you know, they’re, you know, they know the answers to those tough questions and they just. Want to pretend like the problem doesn’t exist. 

Rick Klau: [00:49:31] and, and look, things worked out really well for Apple.

So yeah, as far be it for me to suggest that the, the approach is either wrong or, or, or inappropriate. I just know from my point of view, the way I wanted the, the PMI wanted to be the product I wanted to represent was one where the users felt a sense of ownership. To the end result, [00:50:00] one of them to feel as if they were part of what we were building, not waiting on the sidelines to be handed something.

Yeah. And of course, when we decided to kill bloggers first feature, you had a, a tiny minority of users, but still a very passionate vocal group for whom it felt like we were just taking something away. Whether it was because we were being vindictive or we were lazy, or we just didn’t know how the technology worked, that, you know, they could, they could fill the emptiness if we didn’t engage with all the worst possible explanations.

Instead, our answer was to say, no, no, we’re, I’m going to explain to you why we’re doing this. We actually, FTP is such a terrible, terrible protocol. That if an FTP socket opens and the [00:51:00] connection doesn’t successfully complete, that socket will stay open and it’ll try again. And the number of ESPs that Google data centers brought to their knees, 

Tom Wentworth: [00:51:10] it doesn’t say it’s a, it’s a nice, fancy, it’s a nice way to DDoSs.

Right. 

Rick Klau: [00:51:14] Absolutely. Right. And so we had ISP that would add Google data centers to it’s block list. Because they had one user who didn’t know what was going on and were just FTP in their blog, up to the ISP and, and bringing their servers to its knees. So, long story short, I just, I felt that transparent communication with listening was, was the only way I knew how to manage through what was a really hard message for this user based here.

Now it was 50,000 users. But 50,000 out of millions. Yeah. So I needed the 50,000 to know that we weren’t just trying to kick them to the curb, but that we [00:52:00] were, we were emphatic. This was in fact the commitment we were making. This was not an invitation to tell us whether they wanted us to kill FTP or not.

Tom Wentworth: [00:52:09] Well, I think time is proven you’re right. To kill FTP or lots of reasons. So you should have, you should be very proud of that decision. Look, I’ll let you go. But my takeaway, and this has been fantastic. And I, I do these podcasts. One to get inspired. I figure if I’m inspired, hopefully others will be inspired as well and to learn things.

And what I’ve learned, and I think is, is a takeaway for all of us is marketer or product manager, whatever, being the face of your product and not the CEO per se, because you’re not managing the P and L necessarily, or maybe you are. But treating your product with the same level of ownership and pride in the case of you building a community like these are things we all product, man, product marketers, product managers, shouldn’t be inward facing.

I think we should be more, much more outward facing because that’s where the magic happens in too much. I [00:53:00] think we, we obsess over the pitch deck, the marketing materials, the things that don’t necessarily 

Rick Klau: [00:53:08] Dillard 

Tom Wentworth: [00:53:08] directly get in front of customers. I think that’s a mistake. 

Rick Klau: [00:53:11] Yeah, I, the number of ways in which, it matters the degree to which you project out into the world, what your values are, what’s important to you.

I’ll tell you about one of my favorite, stories back to my time on blogger. One of the very first decisions I made, I met F. And I, I had the, the engineering team pull a list of the most active blogs, most read blogs by geography, by subject, and then every night for a number of weeks, I would send a handful of emails to each of the people who were, who were on that list.

[00:54:00] Just introducing myself on the product manager, responsible for blogger. Here’s how to reach me. Here’s my cell phone. Here’s my email address. I would love to know what your experience on the product has been. If you’ve got a problem you want fixed, tell me what it is. There’s something you love. Tell me that about three years ago, this is now 10 years after I’d been the product manager on blogger.

I got a LinkedIn request from a guy whose name I didn’t recognize. And he was a product manager at Expedia. He had been a high school student in Richmond, Virginia running a tech blog that had ridiculous engagement. And he got an email from me, introducing myself as the product manager and blogger. And as he would later explain, he’s like, I’d never heard the words, product manager.

But after five minutes of Googling realized, that’s the job I [00:55:00] wanted. Yeah. So I went to college to become a product manager because I got an email from you when I was a sophomore in high school. And I, I think back on that, and the number of times, little gestures can have enormous ripple effects, years and years later, we’ll never know what all those ripples are.

This just for me, that was a wonderful, full circle moment. Yeah. Where, yeah, if I’d been like him, I didn’t know what a product manager was pretty much until I got to Google and then it was like, yeah, I definitely want that. And I’ll never get it. I, if I had been entirely internally focused, like he may have found his way to that eventual outcome regardless.

but it just felt like that was the right way to be true to both the product and to who we wanted to be as a product team. 

Tom Wentworth: [00:55:57] Yeah. I [00:56:00] mean, I think opportunities, I’m trying to think in my own life, how could I do that? And I guess, you know, maybe this podcast will help somebody someday want to be a marketer, but.

Man you’ve had quite the career and I sorta just feel I’m ending this feeling a little bit bummed out and also inspired at the same time. I’m like I made some, I could, I might’ve thought a couple of different choices. Maybe I could’ve been a little bit more where you are, but, thank you so much for doing this with me today.

It’s been great. You know, I think our, 

Rick Klau: [00:56:26] you know, 

Tom Wentworth: [00:56:26] it’s the commonalities that we’ve had a little bit, it’s our obvious love for technology, but you know, you’ve, Obviously accomplished friends, man, I didn’t even ask you, but OKR is which I’m not going to. I’ll, I’ll put a link in my, in my you’re, obviously you’ve done a lot of work there too, but this has been tremendous.

I could spend literally hours slash days doing this with you, but Rick, thank you so much for your time. 

Rick Klau: [00:56:47] Tom, what a pleasure. It’s a amazing how, how parallel our paths have been for as long as they’ve been. I’m thrilled. They finally intersect 

Tom Wentworth: [00:56:55] except for the part where I was able to reach millions of users and work [00:57:00] at Google are in that.

They’ve been exactly the same. 

Rick Klau: [00:57:03] Thanks Rick. Thank you, Tom.

On today’s episode of Scaleup Marketing I’m joined by Anthony Deighton, the Chief Product Officer at Tamr. Anthony has 20 years experience in enterprise software, including 10+ years at Qlik growing it from an unknown Swedish software company, to a public company and market leader.

Anthony and I talk about his experience building Qlik from the ground up, how product and product marketing teams need to work together, and what messaging development has in common with standup comedy.

[00:00:00] Tom Wentworth: [00:00:00] On today’s episode of ScaleUp Marketing, I’m joined by Anthony Deighton. The chief product officer at Tamr. Anthony has 20 years experience at enterprise software, including more than 10 years at click growing it from an unknown Swedish software company to a public company and market leader. Andy and I talked about his experience in building click from the ground up how product and product marketing teams need to work together.

And what messaging development has in common with standup comedy. Enjoy. Anthony. Thanks for joining me. How are you? 

Anthony Deighton: [00:00:32] I am well, and you 

Tom Wentworth: [00:00:34] I’m great. This is podcast number three. So you, you do not have to go through the learning experience. My other two guests have had to go through 

Anthony Deighton: [00:00:43] it’s much more efficient, that way, 

Tom Wentworth: [00:00:45] much more efficient.

So your background is, is really interesting. So just for the audience, just give us a quick, a quick what’s the. Your life story, 

Anthony Deighton: [00:00:57] my life story in 30 seconds or less. So, [00:01:00] began my career in tech at a company called Siebel systems in California. Worked there for six or seven years in the Valley during the.com boom, worked in enterprise software.

So it missed the boom, I guess, joined a small unknown Swedish software company called. Click as you call it, click tech at the time, moved to the East coast. Cause I figured out that working for a Swedish company from California was, a non-starter worked for click for a bit over 12 years. It took click from unknown Swedish software company to a high growth startup to public.

We took it public. We ran as a public company and then we took it private with private equity. so as I like to joke the full life cycle of an enterprise software company, Recently joined a company called Solonus, where I ran marketing. that’s a German software company that was moving to the U S so theme.

There is European companies coming to the U S and then a couple months ago, joined, as chief product officer at Tamer, which is a [00:02:00] Boston-based, software company focused on, data mastering. I should also say, You know, obviously do that. I also, been doing a couple of different boards. So out on the board of a geo analytics company called Carto, on the board of, Icelandic company, called grid, which is working to reinvent spreadsheets, and advising a couple of startups as well.

an interesting one out of MIT called unblock, which is looking at advanced analytics, as a space. So, you know, I try to keep my. Well, all involved, a lot of different things. 

Tom Wentworth: [00:02:32] Do you have time to do anything else or 

Anthony Deighton: [00:02:34] three kids and, you know, that, that also running, you know, homeschooling and, yeah, exactly.

Tom Wentworth: [00:02:41] So I work for recorded future and other Swedish company, our founder, Christopher Ahlberg founded. Spotfire one of your competitors, any comments on. Definitively what was better clicker Spotfire 

Anthony Deighton: [00:02:53] I won’t, I won’t take the bait, but what I will say is, There are some very important differences between [00:03:00] the two approach the Spotfire took and click took that that might be relevant.

you know, Spotfire took a highly verticalized approach. It was really deep in, in pharma and in, financial services and click took a highly horizontal approach. And, you know, you know, I think that may help explain the broader adoption of click. I also think click took a very global approach then, and Spotfire, it was pretty centered on trying to figure out how to be successful in the us.

You know, I think there’s a good argument to be made that the clinic has almost never figured out how to be successful. In the U S even to this day, especially relative to Tableau, but it was very successful. There was a market share leader in South Africa just to pick a random example. so yeah, it was some pretty big differences, but, yeah, 

Tom Wentworth: [00:03:45] congrats on not taking the bait.

That was a smart decision, but it is interesting, you know, Spotfire was very much the whole product, Jeffrey Moore let’s let’s really go deep in a vertical in their case, life sciences [00:04:00] and, and, No, they had a whole product solution for that. If you were in life sciences, building drugs, you use Spotfire.

Anthony Deighton: [00:04:05] Yeah. And, you know, click could almost never sell into those, pharma companies because, they were deeply embedded in using that product. And the product was very specific to, to the use case there. in fact, we, again, like we took a very opposite approach, click. From a product perspective was highly horizontal, not go to market.

The sales teams were organized vertically. We had vertical, specific messaging. we would go to market with different partners vertically, but the thing we shipped you, the product you actually were delivered was the same, regardless of the vertical. 

Tom Wentworth: [00:04:38] Might take, well, we can skip past this, but my take is that having a horizontal go-to-market earliest age works when you get to be a billion plus I, you know, the whole product makes a lot more sense, but, but you know, at that scale, I think a horizontal approach gives you a bigger market to go after which obviously for starters makes no sense.

[00:05:00] Anthony Deighton: [00:04:59] Sure. But I think from a, from a selling perspective, you need to speak the language of the customer. you need to think about who the right references are. you know, Tom Siebel used to say enterprise software as a reference selling business, by which means he means, you know, customers buy because their peers bought.

and so when you’re going to market, you need to be able to step into that account. And th you know, the, in a sense, the first and only question that they have in their mind is who else in my industry is using this thing. and so, you know, so there’s a strong incentive structure once you’ve closed.

The, the lead organization inside that protocol is to go to the find the other ones. I think, the distinction I would draw is in translating that into, okay, well, let’s actually go build a specific product for that, for that industry. I think then I would agree with you. Some amount of scale is necessary before you do that.

Tom Wentworth: [00:05:49] So let’s go talk about Siebel. So Siebel was where I think it was your first sort of job in tech way back in the day. I don’t think enough marketers study the all time [00:06:00] greats and I put Tom Siebel in the all-time greats category. Tom Siebel grew up under, you know, under, before Benioff grew up under Larry Ellison, right.

Who was one of the greatest ever do it? I think a lot of marketers could learn lessons. You know, we study. The current, you know, there’s a lot of current thought leaders, we all admire, but like we got to go back. What was it like to work for Tom Siebel and Siebel back in the day? 

Anthony Deighton: [00:06:26] Sure. So first thing I’d say is, you know, Tom is one of the greats, but there was also a great, team there.

Pat house, was his co-founder, was a phenomenal marketer. And I think, especially from a marketing perspective, Was probably the primary driver of creating awareness and demand behind, behind click, or either behind, behind seatbelt. There are also people like Dave Schmaier who went on to found velocity, which was recently acquired by Salesforce, who ran product there.

you know, a great, kind of at Ebos at C3 now, which is Tom’s [00:07:00] latest company. So there was a pretty, you know, remarkable, senior executive team, there, and, So, I mean, there’s a whole bunch of lessons that I’ve taken and I use frankly to this day, from Siebel and sometimes they’re kind of anti-lessons, they’re things that worked well in the early days of enterprise software that I think we are lessons we should unlearn, today, but I think it would be fair to say that, Siebel systems and Tom Siebel sort of invented the big deal.

strategic enterprise software sales strategy and a sales driven culture and company. and, you know, that reason it took, you know, became, came into its own under, under Tom’s leadership. one of the sort of early lessons that I learned there, it’s something that I, I use to this day. is, is both thinking big and asking for what you actually want, you know, very, you know, Siebel in the early days, you know, wasn’t an enormous company.

It was, it was still very much a startup. [00:08:00] Even when I joined and I joined, it was probably about 700 employees, but it still had very much, the feeling of a startup grew to be about 8,000, so 700 to 8,000 while I was there. you know, but it never acted like a startup. Even as a true raw startup, you know, Tom would walk into deals into negotiations with partners, into, you know, closing a deal and act like, the market leader, and act like, you know, someone who, and, and not him personally, but he would have the whole company act that way.

And a good example of this is, you know, you want to go do some, we, we did a, a big deal, at Segal kind of co-marketing relationship. And, without divulging any secrets, the team met with Pat house and Tom’s okay. We’re going to go into this negotiation with IBM around this co-marketing event or co-marketing program.

You know, what should we ask for? And the team’s like, well, you should ask for X. And Tom said, no, no, no, no, no. We’re going to ask for 10 X and I’m talking here about, you know, tens of millions of dollars. And it seems like there’s no way that we [00:09:00] can’t ask IBM we’re Siebel. Like, and he’s like, Nope. And you know what?

They closed at the co-marketing for five bucks. So, you know, so they had a five X, you can call it a five X return on bravado, meaning like by asking for what they wanted or more than they wanted, they anchored in this case, the co-marketing partner. and, and ultimately did, you know, an enormous co-marketing program with IBM, you know, so it’s a good.

Thing to remember, especially as a startup, you know, you know, you asked for what you want and think about, you know, what your real desires are. And then, you know, it’s almost like multiplied by 10 and then if you ended up back from that still a great outcome. 

Tom Wentworth: [00:09:43] It’s interesting. I think that there’s a lot, there’s a lot of the enterprise selling DNA that came through Siebel that came through Oracle that came through PTC.

You know, we train a generation of account execs to go do what you [00:10:00] just said. Right? They didn’t have access to fancy tools. They just had swagger and confidence in a nice suit. And I think a little bit it’s good that, that, that DNA’s getting lost right now. The new enterprise account reps all come out through inside selling it’s a different skill set and mindset in a lot of cases.

And I worry that we’re going to lose a lot of that DNA in this new world. Right. I don’t know that, that in the new selling models that we see that you see the same sort of skill sets anymore. 

Anthony Deighton: [00:10:34] Yeah, I agree. And I, even if you’re selling, high velocity sales cycles, you know, I mean, obviously everyone’s almost selling over the phone these days, you know, it’s a question of, again, like.

Holding to your guns, asking for what you want, having confidence in your offering and the you as a company. you know, those, those things are don’t change based on the price point. and, you know, it’s also about setting ambitious goals. So as a [00:11:00] marketing team, you know, you’re, you’re going to put on a virtual event, you know, set, an aggressive target for what you want to do.

For attendance or for concurrent viewing or whatever the metric that you care about is, or how much pipeline you want to generate. you know, when you set ambitious targets, people have a tendency to, back solve into how they achieve those. when you, engage a customer. And, and ask for a high price point or reject the, the request for a bigger discount.

You know, you know, you want what, every one of those, but if you win half of them, it’s it’s energy well-spent 

Tom Wentworth: [00:11:34] yeah, we had, you know, we’re, we’re transitioning to the OKR process here at recorded future. And we’re just getting our arms around how to set goals. And, and we recently brought in Rick cloud from formerly of Google and Google ventures, who really was, was one of the big OKR advocates at Google.

And he spoke to us yesterday and talked about goal setting and they found very, it [00:12:00] was interesting, you know, they would set massively ambitious goals, not like. We’re going to make something increment 20% better, but we’re going to get a billion, Chrome downloads. And they, as they did analysis of that, they uncovered that the achievement rate for, you know, for incremental goals versus stretch goals was basically the same.

But people just, it takes a mindset change to set ambitious goals because people don’t, people are afraid of failing. And that’s why they’re like, I’d rather beat an incremental goal. Then miss an enormous goal. And I’m like, actually, no, you don’t want to do that so 

Anthony Deighton: [00:12:35] well, they perceive that the incremental goal is easier, but actually the incremental goal is as you point out the achievement rates the same.

So the incremental goal is. Equally, achievable. And I, frankly, if I look back over my career at all of the fun and the things I’m sort of most proud of and excited about and look at, you know, these were things which when we said them out loud, we said, that’s bananas. Like there’s no way, well, what if, you know, [00:13:00] what if we did that, what would we need to do?

And what could you straight would we need to lift? And, you know, what person would we need to convince or whatever, you know? And. Once you start thinking that way, you know, if, you know, if I’ve been a part of a hundred of those, maybe we’ve only achieved 50 of them or, you know, like, you know, but I can tell you those things 50.

I remember, you know, like, yeah. I don’t remember the fails as it were. 

Tom Wentworth: [00:13:22] But that’s the, maybe that’s the lesson is if, if you set an, whether you’re using whatever goal framework, doesn’t matter if your initial reaction is this goal is not bananas, you’re probably not thinking aggressively enough about it, right?

Anthony Deighton: [00:13:36] Yup. A hundred percent agreement. So, yes. I think almost every goal setting exercise should have a sense of discomfort, about it. 

Tom Wentworth: [00:13:46] yeah. So then you leave Siebel. was this point Siebel’s still independent or they’d been acquired by Oracle yet? 

Anthony Deighton: [00:13:54] Yeah, so I left probably a year, a little less than a year before they were acquired by Oracle and I, I left [00:14:00] quite honestly because of that.

So it had to become clear to me in working their day to day that they were looking for a way to exit the company. And so it was no longer. You know, in a place that sort of was leaning forward and, and, and try and do new things. It was trying to, you know, keep treading water until it could figure out a way and an exit strata.

Tom Wentworth: [00:14:21] Yeah. A little old company called Salesforce. also might’ve had something to do with that too 

Anthony Deighton: [00:14:25] big time. And there were a ton of, ex CBO people that went to Salesforce and were incredibly successful, there. So, yeah, and I, and I think there’s a good, there’s a good lesson in. disruption. I mean, it’s something that I, studied, you know, in, in the MBA program, you know, like disruptive technology and how, industries are remade and Siebel.

Salesforce is a perfect example of that disruptive disruption, upending, a market leader. 

Tom Wentworth: [00:14:56] So you went from you go to see a Siebel to this little tiny company called [00:15:00] click the Swedish company. We talked about it. What’s most interesting for me about your journey at click and maybe your career arc all together is that you’ve bounced back between product, product marketing and CMO roles in various, various times in your career journey.

And I want to probe a little bit on, on what you’ve learned in doing that, but it click, I think your journey was, I don’t know the exact order, but you know, product manager, product marketer, ultimately to CTO, like what was the order of that and how did that journey happen? 

Anthony Deighton: [00:15:33] Yeah. So when I joined click, I was actually VP of marketing, and you know, the, the logic was that I wasn’t a developer, and I wasn’t a salesperson.

So that meant I have to be a marketing, like by process of elimination. you were in marketing if you weren’t a sales person or development. and, and then over time, I naturally gravitate gravitated more towards what I would call product marketing. and then, [00:16:00] the, the CTO of click, who, and in Europe CTO as a bit of a different meaning than it does in the U S but in Europe, a CTO is somebody who runs the development team effectively.

so he was, he was injured in a horse riding accident. So he had to leave the business. He’s he’s okay now, but, so he hit the sort of a sudden departure. So I took over the development team and therefore also took over the CTO title. and it was also right at a very critical time around building sort of re-inventing click and building click sense.

and, and then, you know, I kept that title. I think it would have been fair to say that in the last couple of years that I was act like I was probably closer to a chief product officer than I was to the chief technology officer. Quite honestly, I just never bothered sort of updating the title. So it was good.

but yeah, so, but the arc is right and, and that also relation between marketing product marketing and, product management. And even to some extent engineering management, which again I did for a [00:17:00] little while as well. I think of that as a, as a continuum. I should also say that at Siebel, we did not make a differentiation between product managers and product marketers.

There was no, everyone was a product manager to be. The title, and, you know, that there was no, separate role. and, and the people who were most successful at C able we’re the ones who could figure out a way to both have a conversation with the customer, and support a sales cycle, and then turn around and have a conversation with an engineer and drive a release.

You know, like the same human being could do 

Tom Wentworth: [00:17:35] both. So that’s. Unusual, you know, I think obviously now the model is, you know, product marketing sort of owns more of the go-to-market side of it. And product management often owns more of the. The backlog and the prioritization for better or worse, but, but what’s the, what should it show, does that make [00:18:00] sense, right?

Should we be thinking about, I guess maybe I’d love to understand your now that you’ve been in so many sides of this, how do you delineate between what a product marketer does and what a product marketer should do? 

Anthony Deighton: [00:18:11] Yeah, so, so first of all, I will say that I, I do have a, a bias, which is, I don’t think we should make a strong, a differentiation.

As we do. So, meaning I think this, Organizations which create very strong boundaries between product managers and product marketers. they lose something in that. and while I agree with you that it’s hard to find people who can bridge both. I think just because it’s hard doesn’t mean we shouldn’t do it.

I think you should look for people who can do both. that said, I think that there are different tasks at play here. you know, primarily I see, the product marketer as the person who’s. translating, what we’ve built from a product perspective into language that the customer cares about that they’re, that they’re, they can understand, or they want to engage in and that they effectively want to buy.

[00:19:00] And that the product manager is responsible for translating the needs and requirements, of the customer into something that an engineer can understand that they can then build. and, you know, those are, I think of those two things as two halves of a coin. you know, so, the perfect sort of, is the, a microcosm of it is you show up at a customer site, you pitch your product.

So you’re sharing the product marketing messaging, and positioning for your product. And you know what you’d like the customer to eventually buy. And, and the customer buys it and then they give you feedback as they’re deploying it, which you then bring into your engineering team. Like, like that, to me, that cycle is sort of what I would love to see more of versus this kind of like a process where we sort of throw two different people at that task.

Tom Wentworth: [00:19:50] Yeah, it’s interesting. You know, I’ve, I’ve never been, not true. I was a product manager for a couple of weeks, a couple of weeks, once it’s a [00:20:00] long story. I ejected from a company after getting an, it was not good. I don’t want to get into it here. And on the record, like back in 2000, when I lived in foster city, it’s a matter of fact, But I have been a product manager for brief time, but I have been a product manager for a long, our product marketer for a long time.

And one of the things that, that I, I think is been a blessing and a curse to product marketers is the advent of tools like gong. Right? So gong is this unbelievable. Platform that records every customer call and, and analyzes, you know, creates text transcription and puts in. It looks for specific words and phrases.

But what I always liked as a product marketer was getting out in front of customers, myself, and doing a pitch and gong doesn’t solve that problem. How, how do you think, like what’s the best way if you’re a product marketer and you’re, you’ve, you’ve broken it up the way you’ve described, right. What’s the best way.

Do you think gong is enough to be able to be a good product marketer? 

Anthony Deighton: [00:20:58] Absolutely not. I think gong [00:21:00] is one half of the equation. it’s a wonderful tool, for example, to understand. Can your Salesforce articulate your message? Right. And also to some extent, Can the recipient of that message. You know, what questions are they asking?

Can they, can they understand it? it’s a great tool for that, but it is absolutely no substitute for standing up in front of the customer, you know, virtually or in real life and doing your pitch. one of the things we were talking about Siebold, Dave Schmaier, who, who, who ran product there, you know, I for a bunch of random reasons, I was kind of worked closely with him, over the course of a bunch of times.

So I would watch him do the Siebel pitch. And the thing I noticed about it is he always said the same thing every single time, same jokes, same pauses. Like it was like, you literally wind him up and hit play, and then out it would come in. Now it was 95% the same every time. And it was 5% that was different.

And what you could see, what he was doing [00:22:00] was he had his pitch. And he would see what worked and then he would tweak and he would change 5%. And so each time. Tweaked by 5%. and then, you know, over the course of, you know, a month or two, that the pitch would shift so to speak, you know, you’d see different things being emphasized, et cetera, that sort of rigor, is something that I think is really important.

And there’s a tendency I see for, for product marketers today, they almost take a kind of like textbook a theoretical perspective to building, building a pitch. and you know, they’ll, you know, they’ll write some great PowerPoint. And then you’re like, well, how many times have you delivered this? Like how many times you’ve done it in front of an audience to see what they go for?

and the answer is like zero or one, or I did it for my cat or, you know, no, like. Take it on the road. Go see, go see it. But by the way, I’ve always thought that for me, that work is very close to what it means to be a standup comics. So stand up comics, the way they, you see these one-hour Netflix specials, the [00:23:00] Netflix special, like literally the person could be asleep and do that special.

Like this zero new material there. What they’ve done is they’ve spent the last year and a half traveling clubs, these tiny little clubs and trying material and having a bomb and having it not work and then doing it again and then tweaking it and putting the emphasis here and trying a different punchline.

That’s the same thing. We do a great pitch comes from that. Like it, when you do it well, you’re completely bored by it. Like, it’s like, I’ve done this 32 times this week and I’m just sick and tired of it. that’s when you know, you’re starting to get good. 

Tom Wentworth: [00:23:36] it’s I got three pieces of feedback there. One, I now have the title of this podcast, something about, you know, stand up comedy and product market day.

Number two. I want to be, my dream job would be to be a standup comedian someday. So maybe after, you know, when I’m in my sixties, I don’t know if it’s too late or not. I’ll be at the comedy store in 

Anthony Deighton: [00:23:56] LA 

Tom Wentworth: [00:23:58] working on pitches, but [00:24:00] I came to part of, so my path was I came to. You know, graduated you and I are. And also this is a weird coincidence.

First three guests I’ve had on my podcast were all math majors. I was a math major as well. We’re all former CMOs or CMOs students seems weird to me. None of us went to school for marketing yet. Here we are. 

Anthony Deighton: [00:24:18] well, but the funniest people in the room are always the mathematicians. 

Tom Wentworth: [00:24:21] Yeah, exactly. That’s a lie.

Differential equations are hilarious. and then I came in through an se, so I graduated the CS degree, and, and got to be an se. And I would always have product marketers asking, you know, asking me to go out and pitch pitch customers. And, you know, they they’d come along and hear me do the pitch and like, Oh, you’re pretty good at this.

Maybe we should bring you over to product marketing, but I had some product marketers were fantastic. I would work with and I would use their stuff verbatim. And I always had respect for those product marketers, but then I’d have product marketers would give me stuff that I would tear out 80% of it because it just didn’t work.

And these were product marketers that the field, I [00:25:00] always felt like the simple way to look at how successful something is, is if the field is pulling you in, like your S your pitch is so good, they want to hear you deliver it. And if that isn’t happening, That’s that that’s a sign of something. 

Anthony Deighton: [00:25:13] Exactly. So if, if you’re a, it, if you embark on this standup comedy career, which I have, and when you embark on your Stanford, you know, if the clubs won’t book you, that’s good feedback.

Like that’s just the Navy, your, your, stuff’s not that funny. and, and, and you’re a hundred percent, right? Like if, if you’re a product marketer and you’ve built a pitch and no one’s interested, if it’s not compelling, It’s not the right pitch. It may, if it may check all the boxes, it may be the perfect, you know, sort of.

Structure, but it’s not resonating. and, and there’s no substitute for the answer to that problem is not, you know, to go back into a dark room and rebuild your pitch. The answer to that is, you know, go book another club, meaning like go find someone to do that pitch for that, that you might reasonably be interested [00:26:00] in your product and then do it again and then do it again and then tweak it 5% and then tweak it 5%.

And it’s that, that repetition that gets you to a place where bye-bye. A subtle sort of, allegory or, or, parallel to here. We do these big events. you guys just put on your big user conference, super successful, you know, Tamar did the same thing. We do these big events and the feeling is that what we need to do for those events is build a whole new pitch, right?

We want all new decks, all new PowerPoint. It’s going to be great. It’s always a disaster. 

Tom Wentworth: [00:26:30] Yes. 

Anthony Deighton: [00:26:31] The better thing to do is to take the thing that really works. Sure. You know, clean it up, tune it up, you know, and then in the month before, you know, let’s say it’s either it’s you or you’re a CEO. That’s doing the pitch in the month before do that pitch every single day.

And not to yourself, I go find a customer like by the time you do it, On stage for the, for the audience, you should be so thoroughly bored by it. Then, then you can do it in your sleep. and it be [00:27:00] great. Like the audience will love it because while you’re bored with it, you know, you will have, you’ll hit your marks.

Your timing will be good. Your, you know, the, the, the points that resonate will get emphasized, the things that doesn’t are cut, like it’s, it’s tight. It’s. Crisp. Yeah, it’s it’s a really, you know, if, if your, if your, if, if when you get on stage, at a big event, virtual or not, if that’s the first time you’re doing that PowerPoint, it’s going to fail.

If it’s the first time your CEO seen it, it’s going to fail. But if it’s the 80th time, it’s going to be really great. 

Tom Wentworth: [00:27:31] Yeah, we got lucky. So we just did our presentation, our predict event about a month ago, but we we’ve focused mostly on messaging that we had developed for a launch over the whole summer.

So by the time it predict came around, this was stuff that had been practiced over and over and over again. But it’s good feedback going forward. I think as marketers and I talked about this in my last episode there. Sure. We, we, we like to move on too quickly from things. And my saying is by the time marketing is bored of something, [00:28:00] sales is just starting to get it by the time sales is bored of something.

Customers are just starting to get it by the time customers get bored of something is when it’s starting to work. And you should maybe in a few years think about something new. 

Anthony Deighton: [00:28:10] I think that’s very Sage advice and, and, very consistent, you know, with what I’ve seen. Yes, I think that’s, there’s You know, in some cases the mood, the best thing to do.

And frankly, the hardest thing to do as a marketer is to be consistent. There’s a tendency to want to do new things and try new things, you know, repetition, and, consistency. This is true by the way, in, you know, your product messaging. It’s probably double triply true. When it comes to things like branding.

and that like, I always laugh at these companies that sort of, you know, flip around and change their brand and stuff every, every year. you know, the, the, the consistency and, and in fact, one of the things I think helped make a click successful in the early days, is [00:29:00] the product has this metaphor in the actual product of green, white, gray.

Green is selected. White is included. Gray is excluded anyway. All of the branding we did was green, white, and gray. we also have this early problem and decision we needed to take, which is, you may have noticed with click, we spelled the company. Q L I K there’s. No, you, it’s. Nobody could spell it.

It was a complete disaster as like a brand name. So we needed to sort of solve the problem. And we took a decision, which was a, we called it leaning into the queue. So everything became about the queue. Like we lean into this thing, which was a, it was a challenge. And then we just kept at it. And so even to this day, you know, click is green, white, and gray, and it’s got the cue and it’s, it’s all about that.

It’s, it is a very powerful, a very powerful 

Tom Wentworth: [00:29:47] technique. Done over years, decades and centuries, not done over quarters, which is course like we do is we do it as marketers. 

Anthony Deighton: [00:29:55] Yeah. And again, like, I should be really careful here. That doesn’t mean you never [00:30:00] change anything. What am I, you know, like I think go back to the, the Dave Schmaier example, you know, it’s.

You want to change 5% on every iteration you’re, you’re tweaking you’re you’re you’re tuning. you’re you’re buffing the edges. You’re finding the, the sharp points and taking them off. you know, that is the, that’s the trick. And what you’ll find is that over a period of time, a year or two, a lot will change, but it will not change 180 degrees.

It will, it will become. Sharper tuned, edited, focused, powerful, effective as opposed to different. 

Tom Wentworth: [00:30:39] Yeah. And I think that the only way that lasts to close us off dealing with that last mile tuning works is doing it in front of customers, not doing it, you know, in front of your cat or in a zoom.

But that last 5% can only be done out in the front lines. 

Anthony Deighton: [00:30:54] Yeah. No, a hundred percent. You need to, you need to literally read the room. Like, what are people reacting [00:31:00] to, you know, again, like, you know, like running your material in the comedy cellar in New York, like that’s the way you find out. And, you know, standup is, is much more, visceral and direct in the sense that you will literally get heckled and yelled at and stuff thrown at you and you won’t get booked together.

Like it’s, it’s a very direct point of feedback. but you know what? Enterprise software customers do. Very similar things. 

Tom Wentworth: [00:31:23] I was an se for a long time, man. I used to get some, maybe not things thrown at me, but I’ve had people get up and walk out before a, of a demo that didn’t feel good. 

Anthony Deighton: [00:31:33] Yeah. Again, like, and you know, it feels bad in the moment, but it’s actually, It’s great feedback.

Like if your, if your stuff’s not resonating, you know, better for them better to know that then to do it for six months, you know, on zoom meetings or whatever. And the idea that 

Tom Wentworth: [00:31:50] my quick story was, it was, we were told that we should, this is back when Sarbanes Oxley was a thing and I was selling content management and we were told as se is [00:32:00] going to get out there and pitch our new Sarbanes Oxley solution.

Here’s your pitch deck? And we clearly knew nothing about Sarbanes-Oxley and you know, we’d been given some talking points that were just clearly nonsense. So we’re out there and pitching our Sarbanes Oxley solution to. You know, some sorta risk person at an insurance company like Aetna or Cigna. And they just said, this is a waste of our time.

This meeting is going to stop now. And, we had to do a long drive all the way back from Hartford to Boston and it was not comfortable, but it happens. 

Anthony Deighton: [00:32:31] Yeah, I’ll look it up. Moments like that are an opportunity to go back and do it right into 

Tom Wentworth: [00:32:37] until your product marketers. Yeah. That messaging didn’t quite work.

In fact, we were kicked out 10 minutes into our pitch deck. 

Anthony Deighton: [00:32:43] That is a, that’s a, that’s a, that’s a low bar. One that one should hopefully be able to hop over. But yes, fair enough. 

Tom Wentworth: [00:32:49] But it’s got to happen to you once. All right. So. After Clegg had a bunch stuff at click. And I think we talked about product managers, product marketers.

Then you went to Solonus as the CMO, and I know you’d run [00:33:00] marketing before, but what, what was your, what was the experience like going from product to, you know, all of a sudden now having to carry to manage a number and think about brand and comms and all these things that you probably don’t worry about as much as a head of product?

Anthony Deighton: [00:33:17] Yeah, no, I think it’s a great question. look, I think it was, it was, A fun challenge, that there are the central challenge for Solonus was how to invent a category, that helped them break out of the noise of what they call the category they were positioned in, which was called process mining. and, you know, that was, at its core that as a product positioning and product marketing challenge.

So. At some level, yes, it’s CMOs, but there was this core product marketing challenge at the heart of it, which was partly what was sort of intellectual. Interesting to me. The other side of it, from a pure career perspective is while I had done marketing at Klick, I had never, [00:34:00] owned. Demand gen. And, one of the great opportunities at Sloan is, and partly because it was a very new company, it was moving to the U S the U S operations were very small, was to take on the challenge, of building a demand gen function, and, and having the opportunity to do that.

From first principles, as opposed to working with a broken demand gen that needed to be fixed, which I think is maybe a harder challenge. and so I just. On a purely like fun perspective. That was a great challenge. And, and I was excited for the opportunity to dig into that. you know, the branding, marketing communications work, there were frankly, there was a big opportunity and requirements there as well.

That’s not my strong suit. And so I, you know, I had. you know, I augmented the team with people who are much better at that than I, and I think that, you know, so you, one does need to think about what one’s personal strengths are, versus, where you need to augment, yeah. [00:35:00] With, with, you know, outsiders.

Tom Wentworth: [00:35:01] Yeah. Dave Kellogg talked about that. He said there are three pillars of a great CMO. You can be great at demand gen and growth. You can be great at comms and brand, or you can be great at product marketing, but. You know, only, you can only realistically pick two there isn’t, you know, there there’s five people on the planet who might be great at all three.

And I know I’m a demand gen product marketing guy. Sounds like you might be as well. But, I thought that was an interesting observation. 

Anthony Deighton: [00:35:27] No, I think it’s a, it’s a various doot one and I would actually go further and say, you’re generally good at one. and, and you, you typically, so. and by the way, I think Dave is exactly right on the pillars, right?

it’s really, maybe I’ll call it a product pillar, a sales pillar, demand gen, and then a branding and communications pillar. and you know, it’s clear my strength is on the product side, so there’s no, I don’t have any doubt on that. and, and, you know, for me, you know, doing the demand gen thing, [00:36:00] like I said, it was a fun time intellectual exercise, but I absolutely brought in, I hired people and brought in and, you know, experts, people who are really good at that.

and certainly on the comm side as well, So it’s, it’s partly a question of self-awareness. I think the tendency for people, this is a more general truth, but the tendency for new managers is to believe that you only get credit for things when you do them yourself. So if your hands aren’t in the pie, that you didn’t make it and good and experienced managers realize that, that’s almost exactly a hundred percent upside down that in fact, Credit flows and credit to the extent that that matters, but, you know, credit flows to the team that achieves the outcome, the outcome, and to the leader of that team and great leaders.

You know, really use opportunities to, to point at the, the folks on their team that are, that have achieved those things, recognizing that building them up does not diminish them. In fact, it’s the opposite, [00:37:00] building them up, builds them. Yeah. 

Tom Wentworth: [00:37:01] It’s what creates the, I mean, it’s what creates the opportunity to go in and tackle the next set of challenges.

Right. So, yeah, we’re, we’re going through that now. We’re trying to record a future, you know, w we want to make sure we hire. We continue to hire. We’ve hired. We have really great people with a few years experience, but we need sort of in some areas like product marketing, you know, we want to bring in more experienced people so we can then elevate and tackle the next set of problems.

So it’s, some I’ve learned I’m super good at being able to hire people smarter than me. It’s not that hard to do in retrospect, but it makes me look good for sure. It makes us look good as managers. 

Anthony Deighton: [00:37:41] Yeah. And thinking about. Balancing one’s self. Like there’s a tendency for people to try to hire people that are carbon copies of them.

And in fact, what you should look for are people who, who balance you. And that I think is a, again, a sort of a new [00:38:00] manager fault or, you manage a mistake is, is to sort of look, look to copy themselves as opposed to balance themselves. 

Tom Wentworth: [00:38:07] And it’s a bigger point, but it’s also the fallacy of cultural fit.

Like we used to talk about cultural fit, eight years guy. I remember this explicitly at a company it’s like, we want to hire somebody. You want to get a beer with after work. And I’m like, and that’s fine. That doesn’t mean cultural fit necessarily. Or that might mean cultural fit. It doesn’t mean cultural add, which is, I think the real purpose of this find people that give us a broader perspective who can fill in our blind spots and.

I think that’s not a part of it too. Hiring people who are just like me is not what it’s going to take to build a billion dollar company, you know, 

Anthony Deighton: [00:38:42] completely agree. And I think, you know, it’s, I see that happening a lot. If I, I think you could almost, as an antidote to that behavior is to, when you’re looking for, for hiring, you look for people.

That are very different, that brings something unique and [00:39:00] special. yeah, obviously they need to be skilled and, and you want them to, to bring an expertise into whatever job you’re looking for them. But, but I always liked people that, Have something different that they’ve maybe they’ve done a different job or they have a particularly a unique hobby or their, or no, or they’re willing to sort of disagree in the interview.

That’s always something interesting who were willing to take a contrarian view. you know, it doesn’t mean, they’re always right. but it, if you can’t defend your thinking. To a teammate, especially one that works for you. You know, you probably, it’s probably not a very good, well held, held belief, you know, like that.

That’s not giving you some concern. 

Tom Wentworth: [00:39:41] And one in one, take a nap like in an interview and somebody comes and tells me all the things I’m doing well. Well, like I get, I get the spirit. You’re trying to be nice, but it’s also risky because I had this happen and it was things I hated. It was things that I’m like, I can’t wait to destroy this and break it.

Like somebody tells me your website [00:40:00] is so great. And I’m like, I hated every second. I look at it. so it’s a risky thing. I would much rather have somebody tell me what they don’t like and fight that then there’s no risk or there’s less risk for me. Yeah. 

Anthony Deighton: [00:40:11] And that’s not an excuse, for, for being rude.

I think that people, confuse disagreeing with being disagreeable. and you know, th there’s a really professional way to do that. and by the way, this also speaks to a related issue. There are two types of people in the world. There are a problem identifiers and problem fixers. and you know, I don’t know what the ratio is, but you meet people who are wonderful at sort of like making lists of problems.

and then you meet people who are. Dog it about fixing problems and I’m always attracted to that, to the latter. you know, the, the former make very good consultants. And I mean, I think there can be, especially in big companies, it can be really valuable to have people who are sort of good at sort of finding the issues [00:41:00] so to speak.

But especially in smaller companies and startups and things like that, you know, people who are like lack, latch onto something and then wrestle to the ground and fix it, that skillset, it, it requires obviously being able to identify the problem, but also this kind of dogged determination to try whatever it takes to get it fixed.

again, in interviews, I see that as well, like, you know, somebody can give you a long list of things that are wrong with your website. I’d be more interested in the person who sits and says, here’s the top five things I would do. Do differently on your website to make it better, like great. Those are the five things we can implement tomorrow.

You’re hired, right. Versus there’s a list of 40 things, which I don’t even know where to start to 

Tom Wentworth: [00:41:36] fix. So my last question for you, which, which touches a lot of these things, you sound a lot to me a little bit. I can consultant. And I’m going to guess. That’s because you’re a Harvard MBA guy and I’ve always been fascinated by people with MBAs.

I didn’t, I don’t know what the four P’s are still these days. I’ve never taken a marketing class in my life. but I, I would [00:42:00] love I, but I get asked a lot by people who are earlier in their careers about the value of an MBA. And I tell people to go for it. I think there’s value, especially obviously a Harvard MBA, but if somebody who’s gone through that now, and it can reflect, you know, what, what did, what did the MBA do for you and you think, you know, how would you, how do you talk about that to people that you advise?

Sure. 

Anthony Deighton: [00:42:21] I’d say a bunch of different things. so the Harvard MBA for me was incredibly valuable. and remain valuable to this day. but also understand and appreciate that I did it over 20 years ago. So my experience of it 20 years ago, versus what you would do and get today, I have a harder time commenting on that in the moment.

just cause I’m not, I’m not doing it. It, my, my apotheosis is that it’s, it’s still a very valuable, investment of time. My recommendation to people is to do the MBA sooner, rather than later, there’s a huge opportunity cost associated with taking yourself out of the workforce for a year and a half, two years.

you know, [00:43:00] I did it very young, relative to the, to the average. and I would suggest, you know, if it were, if I were advising someone, I’d say, if your decision between doing it this year and next year, do it this year. If it’s a decision between, you know, like the sooner you can do that, the better.

for the obvious opportunity cost. I also think that it generally is, in generally a master’s degree, in any sort of, higher education, which is high, typically highly specialized, in a focused educational experience is, is very valuable. and then the other thing that the MBA it gives you.

is, network and friends. and I don’t mean like, maybe friends is the wrong word. It gives you a network. and like-minded people who are interested in, in that case business. You know, if you do a master’s in, you know, in, in some other field that you’re, that you’re in, you know, you meet a bunch of people who are interested in that field.

and, and that, that group of people have been. You know, people I’ve kept in. I literally had a phone call with a business school. [00:44:00] Classmate middle of last week is doing a startup. you know, we were talking about all kinds of stuff that, you know, so like it’s a network you can tap into, on demand.

It’s been, I still do it to this day. and I find it very valuable. So I agree with your, advice to people which would mirror very closely mine, which is generally speaking. Yes, you should do it. But I would only add do it sooner rather than later don’t delay it. If you think it’s something you want to do, you know, get on it.

and, you know, and, you know, it’s generally, you know, the only caveat I would give is, you know, I did a long time ago, so, 

Tom Wentworth: [00:44:36] but it’s, it’s the skills you learn are the kinds of skills that give you a headstart, like understanding. The economics of business, like really, really what a P and L is, and like your, how your, how hard it is for your great idea to actually make money on a P and L and how to negotiate and all the things that like you can [00:45:00] learn through your career.

But, you know, it’s, it’s just, bootcamp, right? 

Anthony Deighton: [00:45:04] It’s you in a fairly focused period of time, you’ll get exposure to. A wide range. And in MBA, at least you get an exposure to a wide range of business topics. you, but naturally in your career will take one or two of those and get really focused on them.

so, you know, obviously for me it’s been marketing, but, You know, like I still think back to accounting classes I took or to finish dance classes. I took just a very random thing. when we took click private, we built a discounted cashflow analysis to think about the economics of that go private deal.

As we thought about, the, management incentive portion of the equity compensation. And, but you know, who built the, the DCF. Me, you know, like I sat down with this. I mean, it was literally like what I would have done, you know, in the first year of finance clause, the building a discounted cash flow for a deal.

Like it was, I [00:46:00] almost literally went back to, you know, templates, spreadsheets that we had, at the time. So like, those are skills that, that, you know, that you’ll have and, you know, you know, I don’t build many discounted cashflow analysis today. I hope 

Tom Wentworth: [00:46:12] not. 

Anthony Deighton: [00:46:13] In the rare event you need to, I, I have a pretty good understanding of, of what needs to go into it and I’ll pull that up.

So yeah, no, I think it’s, again, I, you know, I worry sometimes I’m a bit biased, cause I, I I’m thinking about MBA from 20 years ago, but I think it generally is a, is a very strong degree. That forms a really good foundation for anyone who’s interested in, you know, leading a company in the technology space.

Tom Wentworth: [00:46:38] Yeah. Well, I think in a lot of ways, you know, your career arc speaks for itself and sort of validates the approach you chose, obviously not the only way to do it these days, but, I think it’s, it’s still is a very valid way for people to think about their career. And, it’s a hard decision to make when you’re 22 and you want to.

Yeah, get onto the real world again, but it’s, for a lot of people I know it’s [00:47:00] worked out really well, so well, Anthony, thanks a lot for your time today. This has been fantastic. You’re a extremely well-respected, marketer product guy leader in the Boston area and around here at recorded future. So I really do thank you for taking time and this has been great.

Anthony Deighton: [00:47:15] Yeah. Oh my pleasure. And yeah, I look forward to hearing it on the interwebs. 

Tom Wentworth: [00:47:22] Thanks again, Andy. 

Anthony Deighton: [00:47:23] All right. Talk soon. [00:49:00] [00:48:00]

TL;DR I started a new job as the Chief Marketing Officer of Recorded Future. We empower organizations to reveal unknown security threats before they impact business, and enable teams to respond to alerts 10 times faster. If you want to hear the why, read on…

Let’s face it, the 80s was the best decade for movies. This is inarguable. Before you ok boomer me, know that I’m a proud Gen X 🙂 So what’s the best movie from 80s? Acceptable answers include: almost anything from John Hughes, Spielberg, or Kubrick; the Empire Strikes Back; Say Anything. Or the best of them all, Wargames.

Wargames tells the story of bored high school student and aspiring hacker David Lightman. In the first 15 minutes of the movie, they show Lightman playing Galaga, the GOAT of all 80s arcade games. And even better, they show how Lightman was able to break into his school database and change his grades.

But really his dream is to break into the server of his favorite game company Protovision. So he wardials every phone number in Sunnyvale CA until one day he connects to a system that doesn’t identify itself. He pokes around to see if the server hosts any games and he finds a list that starts with chess, checkers, backgammon, and poker, as well as titles such as “Theaterwide Biotoxic and Chemical Warfare” and “Global Thermonuclear War”, but to his dismay, he can’t play any of them. Later, two hacker friends explain the concept of a backdoor password and suggest tracking down the Falken referenced in “Falken’s Maze”, the first game listed. Lightman discovers that Stephen Falken was an early artificial-intelligence researcher, and guesses correctly that his dead son’s name, Joshua, is the password.

Chaos ensues as the server he’s broken into is the WOPR at the Cheyenne Mountain Complex. It uses artificial intelligence to simulate millions of possible outcomes from various military strategies (e.g. wargames). But, the Joshua AI has a hard time knowing the difference between gaming and reality (hey, it happens) and because the WOPR has access to the missile launch codes, Lightman almost causes WW3.

By the time Wargames came out, I was already well into my obsession with computers and programming BASIC on my trusty TI-99 4/A. But Wargames threw my obsession into overdrive. I figured out how to lock down my computer with a password (Joshua obv) to prevent unauthorized access my from snooping parents. I got a 300 baud modem for my birthday, fast enough to read scroll text in real time from remote systems. I discovered the magic of the BBS where I could play games, chat with other nerds, and yes, download WaReZ (look, I was 11). It was absolutely magical. I kept programming all the way through high school and went to the University of Illinois to study math and computer science. At Illinois, I worked as a UNIX admin responsible for maintaining DNS. I read the 1992 first edition of O’Reilly DNS and BIND cover to cover. Eventually I realized at age 22 that I wasn’t very good at programming and that it was time to find something else to do.

Would I have gone down that path without Wargames? Maybe. But decades later I still think back to how inspired I was. And reflecting on it now, I think Wargames is as relevant today as it was to me in the 80s. Sure, we’ve moved beyond wardialing, but anything connected to a network is a potential risk. And while an AI that can pass a Turing-test like Joshua is still a ways away, it’s certainly on the horizon. Could a modern day David Lightman start a real war through an SSH terminal? Quite possibly. Look at the success of the Stuxnet program. Stuxnet is believed to be responsible for causing substantial damage to Iran’s nuclear program by exploiting a collection of zero-day exploits to gain control of programmable logic controllers, ultimately shutting down nuclear centrifuges.

From the national security to risk management at organizations large and small, security has never been more important to our future. Because there are tens of thousands of bad David Lightmans across the globe looking for ways to hack into your organization. The results of their efforts ranges from the mildly annoying DDOS attacks to catastrophic events. And maybe worse.

That’s why I’m excited about the opportunity at Recorded Future.

For the past 10 years, Recorded Future has focused on empowering organizations to take a proactive approach to cybersecurity. We’ve done this by collecting and analyzing threat data from the broadest range of sources and producing threat intelligence to help organizations gain insight into the intentions and techniques of cyber adversaries. This enables them to work smarter and stop threats faster.

I graduated college back in the mid-90s when a 56k modem was considered high-speed internet. I started my tech career in QA at a software startup called AimTech that created authoring software for multimedia apps. We competed with Macromedia Director, and eventually Macromedia Flash.

Through my QA job, I became an expert on our product called Jamba. Anytime someone wanted to learn how our a specific feature of our product worked, they came to me. Apparently, I was pretty good at explaining how our product worked, because one day the head of sales asked if I was interested in becoming a Sales Engineer. I had no idea what a Sales Engineer(SE) did, but I noticed they wore nicer clothes than me and none still lived at home with their parents, so I agreed!

And loved it. It was easily the best career decision I made in my life. 

As an SE, I traveled the world meeting with customers and prospects to talk about how we could help them build interactive applications on the web without having to learn how to write code in this new language called Java (I told you, this was a long time ago).

Eventually, my little New Hampshire startup was acquired by Asymetrix, a company founded by the late Paul Allen. Shortly after I moved to San Francisco to join the SE team at Macromedia. After a few crazy years at Macromedia, I joined a dot com era high flyer called Interwoven, which kicked off my journey into web content management. I started as an individual contributor at Interwoven and later moved into an SE leadership role before being asked to move into a Product Marketing role.

Looking back at that journey reminds me of how much I absolutely loved being a part of an SE team and how much of a lasting impact it had on my career. Nearly every skill I use today as a marketer came from my experience as an SE for well over a decade. 

Here’s are the 5 most valuable lessons I learned in my time as an SE:

Everyone in tech needs to learn how to sell. SEs sell. Most get paid commission and carry a quota just like an Account Executive. Sure, I didn’t have to own the forecast or be responsible for doing whatever it took to get a deal at the end of a quarter. But I always felt like I owned the number and that my success was binary: I either hit the number or I didn’t.

SEs are in the position to sell as a trusted advisor in a way that an Account Executive just can’t. And that doesn’t just apply to getting the technical buyer to recommend your product. The best SEs can shape business conversations in a way that leads to your product becoming the only option. Which leads me to:

The best SEs aren’t always the most technical. The endless debate in SE circles revolves around technical vs. business acumen. Sure there’s a foundational technical knowledge you need to have to get the technical win in a sales cycle. But a great SE can achieve a technical win without always needing to be technical, because they can change the conversation. 

For example, my ex-Interwoven colleagues John Narbaitz, James Santoro, and Ryan Sciandri were highly technical SEs. They were both able to blow customers away with brute technical force using highly customized demos and proof-of-concepts. Yes, of course both John and James were fantastic at driving the entire sales cycle (both are sales execs now) but being technical was a competitive weapon for them. 

Some of my less technical Interwoven colleagues like Rajib SenGupta and Andrew Wamberg worked earlier in the sales cycle to change the conversation from technical to business outcomes. They could do more in a few slides than I could do in a week of writing code. They were much better at listening than I was.

All were fantastic SEs who used different approaches to win. But over time my view has changed, and I now think that the very best SEs are the ones who can win with technical skills but almost never have to because they are so good at listening to the customer and driving the conversation away from the technical to the business value they can deliver.

Presentation skills matter. Life is about selling ideas. Whether you are selling your boss on your next promotion or at home selling your daughter on going to bed on time (my nightly challenge), we are always working to influence people and change behavior. And there’s nothing that will refine your persuasion skills quite like spending a decade on the road presenting to customers and prospects.

In my early SE days, I was a terrible presenter. I talked way too fast (still do). I used big words I thought would make me sound smart. I had awful body language and was too afraid to look at my audience. I talked about product features like anyone cared about them. I eventually became a good presenter by putting in my Freakonomics 10,000 hours. To this day, I’ve never taken any formal presentation training but I continue to work hard to get better because it’s been such an important part of my career (and life).

One easy way to stand out as a presenter is to always bring the energy, whether you are presenting to a small team of colleagues or standing in front of a room of 1000. Sure you’ve shown the same demo and slides hundreds of times, but why should an audience be enthusiastic about something that you obviously aren’t? Make this one simple change and you’ll 10x the results from your presentations.

SEs are the authentic voice of the field. Want to really know what’s happening in the field? Ask an SE. What are customers really looking for? Is your messaging working? What’s happening with competitors? SEs are always on the front-lines and are great at providing a spin-free perspective on what’s working and what isn’t. 

Because of this, SEs have an obligation to have a strong internal voice. If something isn’t working, speak up.

The SE role uniquely prepares you for any career path. There’s no other role that better prepares you for whatever direction you want to take your career. There are so many options:

• You can advance through multiple individual contributor roles into team leadership. My SE journey went from being a Sales Engineer to Senior Sales Engineer to Principal Sales Engineer to SE Manager and eventually SE Director.
• Many SEs eventually move into Sales. As an SE you get to learn a lot about the sales process and the expectations that come from being in Sales. The challenge that new SEs in Sales have are usually related to the start (prospecting &qualifying) and end (forecasting & closing) of the sales process.
• More technical SEs sometimes move into Product Management, where they can use their hands-on knowledge of products and customers to build better products.
• The smartest SEs move into Marketing, often starting in Product Marketing. Okay, maybe I’m biased 🙂 Product Marketing is a great landing spot for SEs as it lets you take everything you’ve learned in the field and apply it at a broader scale. 

I have so many fond memories of my time as an SE. I learned so many foundational skills that have allowed me to grow my career. I love being in marketing too, but I absolutely miss being on the front lines all the time. Which leads me to my next point: 

The SA team at Acquia is among the best I’ve seen

The SE team we had at Interwoven was absolutely amazing. Until I joined Acquia, I was sure it was the best team of SEs ever assembled. Now I’m not so sure.

I’ve been working closely with the SE team at Acquia (we call them Solution Architects, or SAs) for over 4 years and what I’ve seen them achieve is nothing short of spectacular. If you want to be a part of the best and learn from the best, you owe it to yourself to talk to Acquia. 

Here’s what the team at Acquia does that makes them special:

They start with the customer and work backward. The Acquia SA team is obsessed with customer value. They are experts in driving sales conversations by linking a customers high-priority needs to Acquia products. In most companies, this is usually the domain of the Account Executive. But in my experience at Acquia, the SA team is deeply involved in this process, which helps them avoid having to win on brute technical force alone.

They don’t rely on being technical. On the whole, the SA team at Acquia is more technical than the other SA teams I’ve been a part of. To be a great SA at a Acquia, you need to know Drupal and its role in the modern web technology stack.

When we’re in technical evaluations against competitors like Adobe and Sitecore, we almost always always win. That’s because our SAs are able to clearly demonstrate how Acquia delivers business value. They do that through expert discovery that connects customer requirements with unique value that Acquia can deliver.

Acquia nails the SA career path. I’ve never seen a more well defined and supported career path for SA. From formal titles definitions with clear goals and milestones necessary for advancement to support for SAs joining other parts of the organization, Acquia’s got it down.

There are multiple SA levels at Acquia including Associate SA, SA, Senior SA, Master SA, and Principal SA. And Acquia SAs have moved into many other positions in the organization, including Sales, Customer Success, and Product Management.

SA are strategic. There’s nothing an SA hates more than being asked to just “give the demo”. Give a demo of what? To whom? Why? 

The SA team at Acquia is used to drive strategic sales conversations. Of course, giving demos is an important part of this process, but only when it makes sense. And only after the work has been done to setup the demo for success. 

They care deeply about winning. This is near and dear to my heart. The thing I most miss about being an SA is that feeling you get when you win against a competitor. Our SAs know that they are in sales and embrace the challenges and opportunities that come from being responsible for hitting a number.

I believe that the Acquia SA team is the best in the WCM / DXP industry. So if you’re are an SA at Sitecore tired of dealing with all the technical debt and leadership changes, we’ve got a home for you. Or if you’re at Adobe and are tired of crazy quotas and constant reorgs, we should talk! Just drop a note to jakub dot suchy at acquia. Tell him this blog post sent you 🙂

Final thoughts on being a Sales Engineer

• Learn how to command a whiteboard. It’s a lost art and a great way to have an interactive conversation with a prospect.
• Saying “I don’t know” is better than giving a BS answer.
• Never show anything in a demo that you haven’t practiced 100 times before. I don’t care what your rep asked you to show.
• Don’t talk past the sale. When your prospect understands something, move on.
• 9/10 times when something goes wrong in a demo the audience didn’t notice it. Just keep going.
• Be careful when bashing the competition. There’s a right and wrong way to do it. I’ve learned this the hard way.
• I hate blind RFPs too, but unless you are consistently crushing your number you’ll have to do some.
• Be nicer to marketing 🙂 They work really hard too. If you don’t like something, just tell us why.

Okay let me start by paying off this clickbait headline right away: A couple of months ago I was diagnosed with Type 2 Diabetes. TL;DR I made life changes, and so far they are working.

Let’s take a step back.

I’ve never exactly been a skinny guy. Even back in high school when I was in the best shape of my life, I weighed around 180 pounds. Four years of pizza and beer at the University of Illinois took that up to around 200 or so, where I stayed throughout my 20s. In my 30s, relentless travel and all the associated bad habits–usually pizza and beer–drove my weight up even further. I became the Big Tuna (thanks Sal and Capitan Ron for that).

Then in August of 2012, I hit an all time high at 246 pounds. Of course I had just bought a wifi-enabled scale–just because–so all of my glorious highs and lows over the years are tracked forever.

But even worse than clocking in at nearly 246, in my annual physical I learned that my blood sugar was elevated all the way into the pre-diabetes range. Not terrible yet, but it scared me. I changed my diet and started tracking everything I ate using an app called LoseIt! I tried to eat ~1200 calories, a day backing out any exercise. For example, if I burned 400 calories running a 5k I could have three glasses of wine. So I started running, a lot.

And It worked! By the time I started a new job at Acquia in late 2012 I was down 30 pounds, and by February I was all the way down to 202!

Even better, I got my blood work done again and I had fallen out of the pre-diabetes range. For most of 2013, I continued to do really well. I tracked my calories every day. I worked out with a trainer a few times a week. I ran at least a few times a week. I even did three Tough Mudders in one summer.

But then life happened. I had my daughter in late 2013, which made it harder to keep up the insane exercise program I was on. I stopped tracking calories. And by the time I left Acquia for RapidMiner in 2015, I was all the way back up to 231 pounds, and guess what? My blood sugar was again back in the pre-diabetes range.

But this time, I didn’t make any dramatic changes. I did lose ~15 or so pounds over the next few months, and every 6 months or so I got my blood checked and each time I was “safely” in the pre-diabetes range.

Until February 2019.

I had pushed off my bi-annual bloodwork because I knew something was wrong. I just didn’t feel right. I had even started to eat less and workout more in a crash diet attempt to fix my blood sugar. But it doesn’t work that way.

The main measurement used to diagnose Diabetes is the A1C test, a blood test that provides information about your average levels of blood sugar over the past 3 months. Eating well for a few weeks can impact your fasting blood sugar, but moving an A1C over a short period of time is impossible.

So when I finally went in to get my blood tested, I knew it was going to be bad. But I couldn’t have imagined how bad it would be. For context, an A1c of between 4% and 5.6% is considered good, that’s what everyone should shoot for. Anything between 5.7% and 6.4% is considered pre-diabetes. In previous tests, I was somewhere between 6.1-6.3%.

I checked in at a cool 11%, an average blood sugar of 269 over a 90 day period.

What. The. Actual. Fuck.

Looking back, I have no idea how it got that bad. I really hadn’t gained any significant weight, and my diet really didn’t change, I’ve always been a pizza and beer guy. My doctor didn’t get it either, and we even considered running the test again because it was so crazy high. But I knew deep down it was bad and the test had to be right. Normally at such a high A1C you’d be put in insulin, but my doctor trusted that I could get it back under control. To do that, I had to make a change, for real and forever.

After doing some research in lots of places (shout out /r/diabetes) I settled on doing two things to get back on track: Intermittent fasting and Keto.

Intermittent fasting is one of the most popular health and fitness trends. It doesn’t specify which foods you should eat but rather when you should eat them. There are lots of techniques, but I settled in on the 16/8 method: Skipping breakfast and restricting your daily eating period to 8 hours, such as 12–9 p.m. Then you fast for 16 hours in between.

I also starting cutting carbs and eventually went all the way to Keto. The Keto diet aims to force your body into using a different type of fuel. Instead of relying on sugar from carbohydrates, the keto diet relies on ketone bodies, a type of fuel that the liver produces from stored fat. With Keto, you’ve got to limit yourself to like 30-40 net carbs a day. It’s difficult but possible. Especially when you are only eating two meals a day.

I cut out Diet Soda. I cut out my morning Sugar Free Red Bull. I’ve cut out snacks including my all-time favorite Utz Pretzel Rods. I haven’t had more than a slice of pizza in months. I limit myself to a beer or two a week. But let’s not go crazy, wine is low-ish enough carb to keep in the diet.

And the changes worked. I’m a sample size of one, but as of this morning I’m at my lowest weight since New Kids on the Block had the Right Stuff. I donated every XL shirt I own because they don’t fit. I’m never going back.

Through better eating and testing my blood sugar a few times a day, I’m in a much better place with my blood sugar too. My A1C is already down to 7.5% after 6 weeks, and I’m confident that I’ll be down to pre-diabetes levels in a few months. And this time, I’ll stay there. There’s science behind why Keto and intermittent fasting work for Type 2 Diabetes.

I wrote this post to keep myself accountable. If I keep this plan up, I’ll take my A1c back down to pre-diabetic and maybe even non-diabetic levels. I’ll always have Type 2 Diabetes, but it’s totally manageable.

I’ll save my preachy stuff for last: the American diet sucks. I made all the bad choices myself. No one forced me chase a Dominos pizza with a four pack of IPAs. But we make it really hard for people to eat well. Nutrition guidelines are a joke, gamed by minuscule serving sizes that hide the truth behind calories and carbs.

Today I started a new job at Acquia, the open source digital experience company. Yeah, that Acquia.

Since I left in 2015, Acquia has exploded to over $200m in revenue. Dries, Lynne, Tim & team have done a fantastic job turning Acquia into a digital experience powerhouse. Bigger, bolder, better. My journey back is a homecoming to both to a company I loved working for, and a deep passion for the web developed over more than two decades.

See, back in the early 90s, I studied computer science at the University of Illinois. I was a classmate of Marc Andreessen while he was creating Mosaic, the first widely used web browser. I was also a huge fan of the band Phish, and an active poster on the rec.music.phish USENet newsgroup.

I decided to build a web page to list Phish tour dates. For a brief period of time, https://uxa.cso.uiuc.edu/~tww40334/phish.htm was the definitive resource for upcoming Phish shows. It probably looked something like this handcrafted in VI:

<html>
<title>
Upcoming Phish Concerts
</title>
<img src="phish.gif"></img>
<p>1993-08-14 World Music Theatre Tinley Park, IL</p>
</html>

A few years after graduating from Illinois, I moved to the Bay Area for my dream job as a sales engineer at Macromedia. I joined shortly after the acquisition of the company that became Flash (sorry about that) and a little bit before the first release of Dreamweaver 1.0.

Products like Dreamweaver, Homesite, and Frontpage empowered a new “webmaster” role at companies who were in a mad scramble to get the corporate print brochure recreated as a website. Being a sales engineer at Macromedia during the dot com boom was the closest thing in my life to being a rock star. Well before embarrassing moments were shared forever on social media, I remember stage diving during a private Beck during Internet World Los Angeles in 1997.

While Dreamweaver was fantastic (drag+drop HTML tables!), webmasters were overwhelmed. Web pages became web sites. Everyone wanted to publish content but the tools remained out of reach for most. Pure play web companies like Amazon.com were showing that the web could be so much more than just a slightly uglier version of the corporate print brochure. The companies I met with wanted something with the simplicity of Dreamweaver and the ability to handle growing complex sites and applications.

So in early 2000, I joined Interwoven, a pioneer in a new type of application called Content Management Systems. Interwoven had recently held one of the most successful IPOs of the dot com era and was so desperate to hire it offered a free two year BMW Z3 lease to new engineering hires.

This was the pinnacle of the “dot com boom”. Startups would IPO pre-revenue using the proceeds to lease office space along Route 101, buy a Sun E10000. And a Content Management System. Back then you didn’t hire more SDRs to scale, you bought more fax machines.

After years of battling Vignette for Content Management supremacy, Interwoven emerged as the dominant first generation leader. We acquired MediaBin, a digital asset management company and then Optimost, a website testing pioneer. We built a rules-based personalization engine. And in 2007-2008, we helped create the category that became known as Web Experience Management. Websites had become web experiences. In all, I spent 8 years at Interwoven on all the way through our early 2009 acquisition by Autonomy.

I left Autonomy to join scrappy CMS upstart Ektron (now EPIServer) that happened to be located just a few miles from my house. Ektron was battling Sitecore to become the leader in Microsoft .NET content management. We successfully drafted off the growth of the Microsoft/Sharepoint ecosystem, and in early 2012 became a Leader in the Gartner Magic Quadrant for Web Content Management. All was going well until the day I got a LinkedIn InMail from a recruiter:

I had been following both Drupal and WordPress for many years. Back at Interwoven, I once convinced the Interwoven marketing team into setting up a WordPress blog instead of using TeamSite. Sure WordPress didn’t do everything TeamSite did (and still doesn’t) but it was easy. It was fun. It was, in many ways, better. I was less familiar with Drupal, but knew of Dries and had watched Acquia rise to become one of Boston’s best startups under the leadership of Dries and CEO Tom Erickson.

From VI to Dreamweaver. From Dreamweaver to Interwoven and Ektron. In my mind, no company was better prepared than Acquia for the evolution of Content Management to Web Content Management to Web Experience Management to Digital Experience Platforms.

Ambitious Digital Experiences

I forget exactly when I heard Dries talk about Drupal for ambitious digital experiences. But it was brilliant. One of those why didn’t I think of that moments.

See that’s the thing: Most digital experiences aren’t ambitious. They aren’t much better than my Phish page or the sites I saw created through Dreamweaver and Flash at Macromedia in the 90s. Yeah, the technology behind digital experiences is better, but for the most part, the experiences they power remain decidedly un-ambitious.

Sounds like an opportunity to me.

Tesla has made ordering a supercar as easy as buying a roll of paper towels on Amazon. I can order a Dominos pizza through my voice, watch, or just tweeting 🍕to @dominos. Enduring companies and brands win through creating moments that matter.

That’s why I’m coming back to Acquia.

Developers rule the world

You can’t buy an ambitious digital experience. You just can’t. But you can create one.

CMOs buy digital experience platforms with the right intentions but underestimate the importance of developers and the role of the tech stack. It’s the difference between begrudgingly enjoying meal purchased from the frozen section of your grocery store vs. dining at a Michelin-starred restaurant.

Most digital experience platform vendors avoid developers at all costs because they ask too many tough questions: Tell me exactly how your platform supports modern front-end architectures like React? What standards do you support? How exactly does your cloud platform scale? How do you manage and govern hundreds or thousands of sites?

Twilio and Atlassian have built multi-billion dollar companies by giving developers exactly what they need. Acquia gets this.

Open source delivers better innovation

Believe it or not, there was a time when open source was considered “risky”. FUD was rampant: open source isn’t secure! It’s not reliable. It can’t scale!

Once upon a time RedHat the only example of a successful open source company at scale. But then came Acquia, MongoDB, Mulesoft, Elastic, and many more. From the FAANG stocks to century-old Fortune 500 companies, now open source dominates every layer of the modern tech stack.

As more open source companies have gone public, there’s a growing trend to move away from licenses like the aGPL. Yet Acquia remains as pure of an open source company as there is.

Closed marketing clouds are still a bad idea

They were a bad idea (pre-cloud) in 2003 when Oracle released its Frankensuite that brought together Peoplesoft, Siebel, JD Edwards, and other legacy products everyone hated. The only thing unified was the license bill you received from your Oracle rep.

They were a bad idea in 2013 when I wrote this post on the Acquia blog about the rise of the Adobe Experience Cloud. Many years later, the foundational products behind Adobe’s Experience Cloud are still not well integrated and the problem is only growing worse as Adobe acquires everything it can to keep shareholders happy. Do I use Adobe Campaign or Marketo, not quite sure?

And yes they are still a bad idea now. I won’t show the obligatory Scott Brinker infographic to make this point, but history has proven over decades that innovation doesn’t come through product integration alone. While Oracle was busy assembling its Frankensuite, along came pioneers like Salesforce, Workday, and Netsuite.

Creating moments that matter

Machine learning is the next frontier of digital experience Let’s face it: website personalization hasn’t evolved much beyond simple A|B testing and the rules-based approaches I first saw at Interwoven. Mick MacComascaigh of Gartner has been talking about the idea of a “next best experience” for nearly a decade yet most personalization is nothing more than a last-in-first-out queue. Looking at you, retargeting.

One reason personalization remains a challenge is that customer data is stored all over the place. I’ll accept that, but I’m not okay with how companies like Facebook continue to abuse our my personal data in spite of new regulations like GDPR. Consumers want personalization, but on their terms.

I do think machine learning is the future of both creating and delivering digital experiences. There’s just so much that we can do to help guide users to create better content and deliver more moments that matter. While vendors brand their AI machine learning linear regression with cute names like Einstein and Sensei, the reality is that we’re very much still in the early days.

Creating moments that matter means embracing the entire customer journey. Today marketing teams have been restricted by tools that assume linear customer journeys that look like a funnel. But that’s simply not that case. A modern customer experience looks somewhat like a plate of spaghetti with nearly infinite twists and turns. We’ve evolved from delivering HTML files through a browser to delivering content everywhere through mobile apps, voice-enabled devices, screens, chatbots, augmented reality, and places we haven’t dreamed of yet.

Acquia has an exciting roadmap for both the future of customer journeys and machine learning. Stay tuned for more.

The rise of false clouds

Last week Lyft filed its S1 as its about to go public. I love reading S1s for the risk factors. The risk factor at Lyft that stood out was its relationship with AWS and a pre-committed spend of over $300m over three years. There’s was lots of armchair debate on Twitter over cloud economics and why Lyft shouldn’t just build its own bare metal infrastructure. The TL;DR is that it’s just too expensive and hard for almost any company to take on.

The cloud won.

Acquia pioneered delivering digital experiences in the cloud. Of course, these days every digital experience platform vendor offers something -as-a-service but when you really dig in, they are managed-services-as-a-service. They might not scale when you need it. They don’t offer than types of modern APIs that developers expect. They make it difficult to implement modern CI/CD best practices. They are optimized for a few sites, not thousands.

There’s just no better platform to build a digital experience than in than Acquia Cloud. As Steve Jobs used to say about Apple products, it just works.

Pick your boss, not your company

Over my prior three years at Acquia, I grew more than at any point in my surprising long wow I’m old career. My boss Tom Erickson challenged me in a way that made me a better person. I’ve never forgotten those three years: they were fun, challenging, and rewarding.

This time around I get a chance to work for Dries.

10 years from now, many of the products we use daily will go the way of Blockbuster. In 50 years, almost all of them will be a distant memory. Yet in 100 years I bet we’ll still be using Drupal. That’s a testament to Dries commitment to building a community that is bigger than any one person or company. It’s a privilege to be a part of something truly enduring.

Dries told me when I left in 2015 that we’d work together again. He knew then what I only recently re-discovered: that the excitement I felt creating my first web page in 1993 would turn into my life’s work.