In this week’s episode of Scaleup Marketing, I talk to Kyle York, the co-founder, CEO, and managing partner at York IE, an investment firm. Kyle and I talk about our love of New Hampshire and how his early focus on brand helped build Dyn into a $100m company that was eventually acquired by Oracle. Enjoy.

[00:00:00] Tom Wentworth: [00:00:00] Hey Kyle. What’s up.

Kyle York: [00:00:01] Hey, good to see you Tom. 

Tom Wentworth: [00:00:02] So you and I have known each other for a long time.

You’re one of the few people that has successfully bounced around between sales, marketing strategy, and now venture cap. How did that all happen? 

Kyle York: [00:00:15] Yeah, it’s interesting. Yeah, loaded question. And I’m like just really entrepreneurial, you know, I think self as more of just a business person who happens to be good at the outside game stuff.

Right. Like, you know, I, I grew up in a family business actually majored in marketing at Bentley and wall fam, not too far from you and Winchester. Right. And you know, my first jobs were actually marketing, you know started out as a marketing associate doing a bunch of content writing. And then, you know, pretty quickly realized I could probably do some BDR work.

And then did your kind of classic, you know, sales ladder climbing from like BDR to junior aid, AAE to account director. And then I had an opportunity in my early career. I worked for an ed tech software company. I might have been when we first met, cause they had [00:01:00] a CMS for schools and you’re obviously you’re, you’re deep in the CMS game.

Right? When I was at Whipple Hill and I ended up running West coast sales and marketing for them where, you know, the marketing side of it was really more, it was out outbounding demand gen, and, you know, it was in positioning to the different types of prep schools that were on the West coast. And so, but when I got recruited back to New Hampshire we’ll get into that in detail.

I basically had learned in my first company that if sales and marketing aren’t in lockstep, which my. First company, they were not, it was like head of sales versus head of marketing. They were not friends and it was incredibly siloed and neither side was accountable for the other. I basically the job I knew I’d take as my first head of sales job, it had to be head of sales and marketing, and I was pretty firm on it.

And so I ended up becoming a VP of sales and marketing and then. When I was CRL, I still had marketing success, support BD Corp dev, which is all strategies. So it’s, it was kind of just natural take on more, take [00:02:00] on more. And really, it was just about owning the number and own the enterprise value creation.

It’s funny, 

Tom Wentworth: [00:02:05] there’s the CRO title became really popular, but I think very few CRS actually on marketing, like you own marketing, the team reported up to you. It’s sort of a vanity title. You’re going to call it a CRO and you give them marketing, if you’re going to do that, but it’s not how it works out.

Kyle York: [00:02:21] Well, honestly, when I got it, I, it was probably, I think. I was VP of sales and marketing from like late 2008 to probably 2011 or 12. And then we created like a C-suite because it was basically two founders of dye and that’s the company help build a Dyn, the DNS domain name, system, company. And I, we basically created a C-suite and I became CRO.

And I actually, at the time, I always like CMO CRO, like chief growth officer, chief commercial officer, president. Like we were kind of like just kicking them all around. And then I was like, no, I need to say revenue because. I, I need, we need ultimate accountability to the top line of the company and do our growth.

And. I kind of like, felt like back then, [00:03:00] like in hindsight, I’m like I made it up. Like there weren’t a lot of CRS in 2011, 12, and you’re right. It like became this, like, I want a C suite title. I’m the head of sales. I’m reporting to the CEO, call me something that’s C-level officer. And then it became like, it’s really just the SVP of sales.

Right. And so, yeah, I think it’s interesting, you know, I’m buddies, I just did the Kyle Lacy podcast, you know, Kyle on revenue DIYers. And he was like, he’s making a big fight that like, why are marketing leaders, you know, taking over the, you know, sales teams? And I’m like, Hey, like, I don’t really like discriminate.

Like I’m a marketing major. My first jobs were in marketing. I went into sales only, honestly at the time, because I wanted to make more money and I was in-patient and then, you know, I ended up running both and I don’t, I think I’m kind of a brand guy and a sales guy and a BD guy. Like I don’t overly identify in the, in the straight lane of either function.

Tom Wentworth: [00:03:53] The answer to Kyle’s question is. It’s a whole different game. When you own the number you’ve got to forecast the [00:04:00] number you got to deliver the number quarter after quarter, month after month and marketing, we kind of get there a little bit with leads, but you miss your lead target.

No one’s getting fired. You miss your, you miss your ARR target and you’re getting fired. I don’t think most marketers are ready for that. It’s a big step. 

Kyle York: [00:04:16] I mean, carrying a court, I know you’ve got some se se bone in your body, right. And wounds from the early days. Yeah. But like carrying a quota, I mean, sales job is a horrible job.

Like it’s horrible. I mean, and I had a quota and I, I mean, for Don, I own that number though, top line, but like I co quota directly tied to you in the deals you win, that’s yours and yours only. It’s a really lonely existence. And I think what a lot of people forget is. No there’s base in variable comp you know, variables commission, and then there’s an OTE, which means on target earnings.

So like, if you’re a salesperson and you make a $60,000 base salary with an OTE of one 20, you have to go chase like [00:05:00] hunt for 60 grand. I mean, imagine you were an engineer or a marketer and someone told you half your pay was performance-based on like, Hardcore numbers and analytics like, like people that’s, that’s a tough existence, honestly, for people that live with that, I 

Tom Wentworth: [00:05:15] there’s always the stories of that rep that made a million dollars.

Every company hopefully has that, that story and all the marketers hear that and say, you know, why, why wasn’t that? You know, I contributed that deal. They close, I sourced it. And my answer to that is always then go carry a bag. Like go do it. I encourage you. I encourage everybody to go through sales. It’s an awesome experience, but it’s a lonely experience too.

Kyle York: [00:05:40] Yeah, it’s incredibly difficult. I sometimes still wake up in like deep sweats, you know, like thinking about like my quota as an individual seller from like 15 years ago. Right. Like, I mean, it, it really, and when I worked for Whipple Hill, the ed tech company, I actually moved to California and I was like remote and alone.

You’re trying to build out the region. And I [00:06:00] remember just. You know, not even knowing where to turn like marketing was more and, and like creative back then, you know, it wasn’t very like metrics driven and lead driven. That’s a newer thing in SAS. I think people forget that like the analytics and the metrics and the digital and the inbound is all really over the last decade, you know, it wasn’t really like that.

So sales people also had the light. Find their own dinner. And, you know, that was, that was really difficult back then. I mean, again, you can be an enterprise Oracle, which I got some experience that we’ll talk about later, very different game when you, when you can win a million dollar deals. But you know, most SAS services are not, you know, million dollar deals plus only to the enterprise market.

So it’s, it’s really a lot of deals, high velocity. And, you know, you have the bottoms up your way there, and you know, it in mythical 12 months, you know, calendars, right. Like I always used to get so annoyed this time of year you’re near the holidays and the end of the year is coming and I’m like, ah, but you know, if you really are good at sales, you game your [00:07:00] comp plan and you do make a lot of money.

If you’re good at it, you can handle it. 

Tom Wentworth: [00:07:03] Let’s talk about New Hampshire. So one of the things that you and I always bonded over is our love, the great state. I was born in the six Oh three Concord high grad shout out Crimson tide. You went to school in Manchester somewhere.

Kyle York: [00:07:14] I went to West. Yep.

Football player. I played football. I played football at Manchester West high school in Manchester, New Hampshire. And then also at Bentley and Walton. 

Tom Wentworth: [00:07:23] Nice. I was a, I played tennis. We were a state champions three or four years. I was there. 

But what I’ve always sort of respected about you is your loyalty and commitment to New Hampshire. You built Dyn in New Hampshire, you built a really great, you know, a sort of a West coast presence at Dyn. Nick. I remember first coming to your office. I’m like, wow, this is  awesome.  Talk about like your low to New Hampshire and why you kept dying there.

And did you get pressure to move? 

Kyle York: [00:07:48] Yeah, I mean, so it’s an interesting story. So I joined Dyn seven years in and two years after they had moved up to New Hampshire Dyn was actually found that it was stir Polytechnic Institute in Wester as a [00:08:00] kind of a college dorm room project. Basically the original company enabled companies to, or people to remote access back into their home networks.

You remember, of course,  and so the, it actually hit the two of the co-founders were actually from Manchester and they didn’t know each other in high school either. They just, they just were like, Oh, you’re prevented aren’t permission. We should move to the mill yard, build, you know, the mill yards or like, you know, these huge skyscrapers on their sides.

Right. They’re massive. And it was incredibly cheap, you know, even our huge space. He went to his $5 and 50 cents per square foot per year. Again, I, there there’s much better now. I think we made the prices go up. But, you know, it was an amazing thing, but I grew up there. I mean, I had moved. Went to school in Waltham.

I had moved to California for a few years for my career. And, you know, I didn’t think I’d necessarily end up back. There are, I thought I ended up in Boston and the tech scene or what have you. But, you know, I was raised in a small family business and it was all about like, Community and give back and know your neighbor and, [00:09:00] you know, really the kind of like spirit of New Hampshire is very communal.

Like I, I text with the governor, I don’t say that to brag, but like, that’s just the state, right. It’s very accessible. It’s just very different. And so, you know, I think when I moved back here, the Dyn opportunity was interesting, but I also like. Didn’t know if it was going to work out. I didn’t understand the domain name system that, well, I didn’t know if there was an enterprise market for it.

You know, I was young. I was in my mid twenties. I didn’t know if I was even that good. You know, like, like maybe I’m like, you know, not as good as I think, like, let’s see how this plays out. So, you know, but I’ve always been just very committed. I have a very large family in the middle of five sons. So my parents, Don and Gail.

So I also think like when you’re the middle, you’re sort of like the glue child and I, I’ve kind of always treated. The companies, I run like families and try to like rising tides, lift all ships. And I think it’s just, it fits, it just fit with New Hampshire. It fit with dime the culture recreated. I mean, in a lot of the culture, our clients were the Twitters, the Netflixes, the Airbnbs, like [00:10:00] the Acquia is as you know, and, and there were cool brands that were also stealing cultural tenants from West coast companies and Silicon Valley.

And, and, but doing it, I think in a more pragmatic. No different way, because you know, we, we can we’re Yankees, that’s the way we think. So it’s still all mixed up in that, but like, it’s just like community impact. Like how do you drive up up a market and, you know, I think we’ve attached ourselves pretty nicely to the greater Boston tech scene.

And, but also with a little of our own 

Tom Wentworth: [00:10:29] yeah. And Dyn was bootstrapped forever, but then you eventually fell victim to the venture world. Was there any pressure when you started taking money to, Hey, you can’t build a billion dollar business in Manchester, you guys crazy. Is there any pressure there to, to move 

Kyle York: [00:10:46] well meatless and there was pressure.

We didn’t raise money to where 30 million air. So not a dollar of outside funding. It was bootstrapped. And then, and then, you know, e-commerce sort of funded and, you know, One of the reasons we raised money was we, [00:11:00] we knew we needed the mature to sustain. Right. And we also one of our co-founders wanted to get a bunch of secretary off the table.

I mean, that’s the fact so we actually raised a $38 million series a and you know, somewhere North of 90% of that was secondary. So we put very little primary capital in the business. But even long before that we were getting like, Oh, you got a lot of questions. And a lot of eye rolls, even from the Boston scene, like, ah, you can’t possibly continue to scale it out talent.

And especially when you start to work with the internet elite, right. Those people at the internet elite. The high traffic, web properties, top hundred, top 500 Alexa rankings. And these companies are basically like, wait, you’re in New Hampshire. Where’s that? Can you point it out on the map? Is that, is that part, is that in New York?

And I remember I’ve got it that asked that a lot. It’s like the most ridiculous question. But you know, so yeah, the pressure was big. I think the. The board and the investors really embraced the culture, but they were really one to like push remote [00:12:00] offices and, you know, feel that, you know, get the field built.

I think by the time we were, I think it would have been different if we weren’t already 30 million and already whatever that was like 80 a hundred people. I don’t remember exactly, but we already were foundationally solid. By the time it happened, but yeah, I mean, I’ve got it. I mean, Famously. I remember Jason Calacanis, who was on our board for awhile, who everyone knows that kind of super angel investor.

I mean, he joined our board and he, he not only challenged with the company on that, he would challenge me personally, like on like what career success I could have, like how much enterprise value I can create for Dyn or other companies, or even for myself in personal wealth generation. You know, you’ll never get to these targets.

If you stay in New Hampshire. No, I can’t wait. I cannot wait to write him a letter when I hit the targets. He said, I couldn’t, you 

Tom Wentworth: [00:12:48] gotta be pretty close to that.  I don’t want you to name and shame, but I bet there are VCs too. The big name West coast wouldn’t invest in New Hampshire company who looked back and probably do the math and say we would have done pretty well at, we put a [00:13:00] little bit into that.

Kyle York: [00:13:01] I think, you know, Yes, that’s that’s spot on. But I also, you know, we did an internet protocol, you know, I don’t, and we monetize it better than anyone else in history, maybe with the exception of open DNS, you know, I think, I think it was also that mixed in and, and I, again, maybe I’ve matured, but you know, We were pretty young, you know, the five of us who really built Dyn that the original executive team, you know, no one had really done it before.

I mean, there was a lot of factors of why people maybe passed on us or missed us, or didn’t push hard enough on us. But you know, the exit ended up being a phenomenal exit. It was a ridiculous journey. We, you know, we created lots of jobs. There’s actually a alumni Dyn alumni group on Facebook. And everyone’s been posting like old photos from the years.

And it’s just like, when you look at the culture, I think that was one of the challenges. I think I was just talking about this with somebody. Our culture was so good that like, when someone went to work at Dyn, they very rarely left. Right. And I actually think that [00:14:00] hindered the taquito system up in New Hampshire because people didn’t leave to go start because they loved it so much.

And, you know, near the end, it started to sort of suck as the VCs sauce on an IPO path or an exit path. And we raised more money from PE and we brought in a lot of higher gun executives to compliment us and the culture did change and became more like hardened and matured. And I don’t say that all. Good.

And you know, people started to leave, but I don’t think it created the same entrepreneurial culture. I wish it did that. Like, even like a HubSpot, I think has been able to spawn off a lot of good startups and now, you know, and that segues a lot to what I’m doing now, but I think we can change that over the coming years.

Tom Wentworth: [00:14:39] I think the thing that you did that was really smart as you know, DNS, I was a DNS admin in college, so I was computer science major. I literally got paid like $4 an hour to go manually set up. You know, and I switched.com files across a bunch of Solaris boxes and next boxes, like I got DNS [00:15:00] and I remember explicitly your DNS is sexy campaign.

 The thing that was a little bit unique for you for being a sales. Guy is you really focused on brand and not only do you focus on brand, but for the most boring internet infrastructure thing, there is the phone book for the internet. How do you make DNS?

Kyle York: [00:15:20] Yeah. Well, the DNS sexy campaign, I think made Don and here, here’s why. People who knew DNS, who would be like, just like you would be like, wait, DNS is sexy. Like, Oh, you’re dying, you’re dying DNS. Like it is an icebreaker beyond icebreakers, every internet trade show. You know, we, we gave out over 20,000, t-shirts over the life of the company in that one campaign.

Right. I mean, it was insane. And then anyone who didn’t know what DNS was, would say what’s DNS. Like it was literally like an education. Opener for every single conversation across the entire landscape, whether it was a [00:16:00] employee you were trying to recruit or, you know, someone in the community, or was that a trade show with a customer or a partner, you know, you’d literally be able to open the door and have a conversation.

And I really think it like. Elevated the space in general, you know, the, the open DNS is the new stars that they’re assigns the optimized, you know, and this one exists today. A lot of Infoblox is like, when people start to say, Oh, like maybe this isn’t just the protocol. Maybe we can do some tricks with the protocol to make it a more valuable service delivery mechanism to do more things for security or performance or reliability or availability.

And it was just an absolute shot in the arm for the brand and also gave The company end to end a rallying cry. Don’t underestimate that. I mean, you’re in a security business, right? You have a lot of security depth in your company and data science and all that. If all of a sudden they don’t think of sales and marketing as this, like.

A femoral thing that lives over here that has no relation to them. And all of a sudden they can become [00:17:00] brand advocates and loyalists and evangelists and feel like you get them. That’s kinda what the campaign did like, but it was like, it was bearded engineers in Tivas in shorts in winter time, you know, rock and DNS is sexy shirts.

Like, like it was, it was amazing. And everybody, everybody loved it and everybody wanted a shirt. And so. It was, it was a big, big deal. The other, like, I don’t talk about this that much, but we actually launched DNS is sexy at the same exact time. A lot of the company’s story is built the same trajectory of Twitter.

Twitter was one of our first clients. They’re originally a $30 a year client. And by the time we sold, they’re paying over seven figures a year and I actually launched a tweet nerdy. Tweet to me, kept pain at the same at the same time. It’s dude, it’s a sexy at South by Southwest in Austin. And I thought, for sure, we actually printed like double or triple the tweet, nerdy to me, shirts thinking that, that, you know, the Dyn logo on the side or whatever.

[00:18:00] And I thought that thing was going to be the thing I was like, nothing’s going to take off. That’s going to be the thing, even I was wearing those shirts, not the VNS, the section shirts, and right away, we actually sent a bunch of those back to New Hampshire and all the DNS sexy shirts where like I was having to do like orders from Austin to get new ones.

So, you know, it’s just a funny, like little tangential thing that no one really knows, but it was like, I didn’t think it would be the campaign that would stand out. 

Tom Wentworth: [00:18:26] I think it’s probably two things. One you spot like the audience that owns DNS are. The sort of classic it TiVo wearing no one spoke to them.

It’s sorta like customer success in Gainsight. They validated a whole category of people who now felt they had somebody who got them. But I think the other part is, and this is the, this is the part about marketing that no one gets you can’t put in a marketing plan, give away 20,000. T-shirts like, what’s the value creation for doing that?

But we all know that a lot of it, Mongo DB did that and [00:19:00] InVision did that super successfully. And you did that super successfully. Don’t sleep on schwag as much as it sounds. You get people to do that. All of a sudden you will walk around South by Southwest and see Dyns schwag rolling around. 

Kyle York: [00:19:15] I believe in schwag, I believe brand is culture.

I believe culture is brand. I believe your people and the people affiliated with your company are your best advocates. And they’re the ones that are going to take you to the promised land. And, and part of that affinity is schwag. I mean, I have a York athletics shoe company Cousy in my hand, you know, like I believe in that, I believe that’s how you drive relevancy.

You continue to stay in the hearts and minds. The other thing is. And the dime story, the people we were selling against were like, you don’t get fired for IBM people, right? Like, like, like when you look at like Infoblox or Neustar Verisight or  at the time we were starting, who are the big juggernauts public companies who we competed against for DNS, the people selling [00:20:00] you, if you were assisted in, we’re rolling in.

10 deep in suits with briefcases, completely unrelatable to the system administrator, to the tech ops person and the SRE. And we walked in and, you know, we looked like that. We talked like them, we got them. We, we brought out and made friends with him and her and, and really got to know the people and. I think we’re very clear, like, Hey, you know, you can help us get to the next level.

You know, we are a launching pad for your career. You’re a launching pad for us. We can be sounding boards for each other. We really did consultative selling, but at small tickets, like it was, it was not like consultative selling at a hundred K or our deals. I mean, our company. Ended up having, like, I think our average ARR per customer at, at exit was $18,000, but it was pulled up dramatically.

We had one, $4 million deal. We had a handful, a million dollar deals. We had a couple dozen 500 K deals. And then most of it was 200 to [00:21:00] $500 a month deals at high velocity. And I just don’t think people like treat those customers. They become too. Self-serve too passive to sales assists. To to forgotten.

And we treated them all like, like gold. And the best story of that is actually I told the Twitter one a bit ago, but Oracle, guess what? Oracle paid us on their first contract per month. 

Tom Wentworth: [00:21:23] Thousand hours, 

Kyle York: [00:21:24] 12, 600 bucks, 600 bucks a month. And it was for some like QA testing thing on their storage platform and like $600 a month when Oracle acquired us for a very good multiple on our enterprise revenue.

They were spending 900, like 80,000 ARR we land and expanded that account like six or seven times over the four or five years that we’re a customer because we realized like it’s worth going through procurement hell, it’s worth going through an enterprise sales process because we know our products act good and our customer successes that good and that we can get them to expand to [00:22:00] something better.

And, you know, and again, I just don’t think there’s a lot of patients in the venture capital. Yeah, culture we have right now to like, to, to do that. 

Tom Wentworth: [00:22:10] It was more patients now and there was back then that looks good in a cohort analysis. That’s that’s what you, if you’d gone public, you would have shown that look 600 to a million is a pretty good, pretty good cohort.

That’s also why I sort of think that you, I remember hanging out with a bunch of South by Southwest, and again, why does a DNS company sponsor you through the best party at South? By Southwest? Every year I went there and I still remember. Actually, I don’t remember it that well, to be honest with you for a other reasons, but you’re like, dude, one of her I Werner Vogels from AWS is going to show up in my party and I’m like, no, he’s not.

And lo and behold at about 4:00 AM or 3:00 AM every year at your party, he rolls in like a superhero. Like that’s brand building, right? 

Kyle York: [00:22:54] Gosh, like we were drinking lone stars and smoking Marlboro reds. Like I actually joke, I’ve never smoked [00:23:00] cigarettes in my life except with murder Vogels. It’s unbelievable.

I remember the first year he did our sales guy for the Amazon account Kyle Kermani again says to me Werner Vogels is here to see you. It’s like four in the morning for just shutting down. I’m like, nah, and as a gay seriously, he’s upstairs in the VIP. And so, you know, that’s the way it worked though.

W I think companies need to go with their customers are right. Yeah. Like it’s very easy to go to interrupt shows and, you know, cause that’s where every infrastructure company goes. It’s better to go to the, go to those companies or to the shows where like the executives are of the brands that you want to work with.

Right. And I think a lot of companies screw that up. They, they over pattern match to what you should do and don’t try to differentiate and what hasn’t been done before. And there were no other infrastructure companies that their shares. The other one that actually kind of was, was media temple. I remember media temple had a killer party every year.

It stubs the barbecue joint and you know, it [00:24:00] was unbelievable, but that was the only other company that was kind of like us. Who really embraced it and went for it. And they had, I played Cedar street courtyard, and the music we’d bring in there. 

I 

Tom Wentworth: [00:24:09] mean, unbelievable. Yeah. Tears tear tick. Well, I still listen to them from me, from them being at your your place.

Dave Kellogg, an old sort of old school SAS guys,  if you’re a CMO, it can be good at two of these three things, product marketing. Brandon comms or demand gen. I’m a demand gen and product marketing guy brand is not my thing. And I remember at South by Southwest I’m like, Kyle man, can I give you some money to try to make us cool.

And and we did look cool. And music was a big part of your world, too. You guys used to bring bands in to Dyn. You’d bring big bands into, I had a great time at, at your the one we sponsored at South by Southwest.

Kyle York: [00:24:48] Delta skirt. Yeah. I mean, that was a lot of the brand alignment with like dying, like that sort of independent spirit. We weren’t venture capital back we’re in New Hampshire and the lip for your guys’ stay. Like [00:25:00] it was a lot of like indie bands that the Lumineers played there, you know, with the Lumineers and they played, they were like the.

Like there was seven bands and they played like fourth last, like they were not the Lumineers of today. Right. So like, it was, I was a lot of the correlation between like an independent brand and a startup, and then just like fighting for relevancy, fighting for air time, fighting for revenue, fighting for growth.

You’re fighting for survival. Right? Like that, that paradox in that correlation was like, Absolutely perfect. I mean, we even took a band called quiet life out of new London, Connecticut on tour with us through Europe, we took on day Amsterdam, Berlin. I remember like caring. Yeah. They’re like guitars and drum kits, like through the streets of London and Brighton, England, like, and it was just unbelievable.

And in this people, like, again, it’s like the DNS is sexy campaign. They literally like, Oh, I want to work with that company. I want to be a part of that community. I want to support startups. I want to support that [00:26:00] Dyn. I want to support bands. Like it was this weird connection. And again, we really embraced, we called the music meets tech series at our Dyn TVs, you know?

Yeah. You know, it just really, it really, really worked. And, you know, I still stay in touch with a lot of these bands. Like that’s the other crazy, like, like Dawes who headline? I think the self by party, they use fire the best one, you know, duh, he’s married to Mandy Moore Taylor Goldsmith. Now, like I was walking to back to like the Hampton Inn.

It’s just like a crate actually in, in And the deer tick lead singer McCauley John McCauley is married to Vanessa Carlton, Gino. Remember these names from our high school you know, days, but, you know, so it’s, again, it’s just funny to see the rise and watch who makes it, who doesn’t, it, it parallels startups really closely.

Tom Wentworth: [00:26:48] I, you know, I look back in and, you know, Aquia was a success story. I sort of feel like though the biggest stick I made was  I under-invested, I wasn’t willing to make the kind of big bets that you made. And I think it hurt the company. [00:27:00] Potentially even a company could have been public if we had gone bigger there.

Cause I think you underestimate, it’s easy to look quarter to quarter to quarter and we hit our numbers, but to make the big brand bats is the thing that can actually take you to another step change level. And I never did that and I will never make that mistake. 

Kyle York: [00:27:16] And I think, I think you were playing in a much larger market.

I think Dyn Dyn was outpacing the market and monetizing something that it was hadn’t been monetized before really. Right. So, so like for us, we had to like, Aggressively stand out. I got, again, it didn’t have its challenges. I mean, it was, it was actually very hard to fundraise for dying. It was actually very, very hard to climb up market for dying.

It was, it was really, really difficult to recruit, you know, when we started to need the talent that maybe it wasn’t in you know, kind of New Hampshire North of Boston ecosystem. Right. So it also had challenges to the brand part and the culture part. Like had to be a differentiator. We had to be an employer of choice or else it was, it was kind of like existential almost.

I do [00:28:00] credit Jeremy diamond CEO for like, just flipping me the keys too though in founder, because he was, he is an introvert and he is not a brand guy and he didn’t get it a lot. And a lot of times I’d be like, just trust me. And the only way, the only reason I actually think it worked and I got the, the, the rope I got.

Whereas, because I own revenue. If I didn’t own the sales number, I would never have gotten away with it. 

Tom Wentworth: [00:28:23] That’s why it’s a CRO thing. Right? That’s exactly what I was just going to say. Cause that’s a big bet like you, and the only way you can do that to better hit your numbers. And that’s this sort of advantage of have at recorded future is, you know, we hit our demand gen numbers.

We have lots of rope to make brand, you know, quote unquote brand investments, which I’m doing at a much bigger rate now, but it’s only because you’re hitting the numbers and and you know, 

Kyle York: [00:28:48] the numbers are here to a scale. Or the budgets are just big enough that you can do things with 

Tom Wentworth: [00:28:55] they’re just big enough.

Kyle York: [00:28:57] I’m giving a little pitch to get a little bit [00:29:00] more budget for my man, Tom, 

Tom Wentworth: [00:29:01] The other thing that you did really well, so brand was a big one. I think it all culminated.

I remember this vividly, you guys got hit by a huge DDoSs 

Kyle York: [00:29:09] attack. 

Tom Wentworth: [00:29:10] And of course you’re doing this, I think right around the time you’re getting acquired or right before. And I actually  I see you on the today show.

 Tell me about that? Cause you guys steered into it in a way I rarely see. 

Kyle York: [00:29:22] So here here’s, here’s the deal and this is not an overly spoken about thing. The night. That was no, no, that was sorry. That was what was the date anyways? November 21st I believe, or a cover 21st and I wish I knew the exact date.

It was the day we set. No, it’s October 21st. The night before we closed the deal signed the definitive agreement with Oracle on November 21st on October 21st was the DDoSs. Okay. Or whatever, maybe I’m getting the dates wrong. I’m sorry. I’m screwing it up. But whatever the date was, that’s the day we signed the LOI with Oracle [00:30:00] the night before we had actually signed it and had a board vote and Oracle had not counter signed it the next day.

So I wake up in the morning, I’m driving into work. I’m on the phone with my dad and I actually was just calling my dad to catch up and I keep getting missed calls from an international number. And so on the third one that let me call you back. And it’s Amazon AWS team in Dublin, Ireland, who was, who we worked with on, we ran AWS ECE, DNS naming.

So whenever you provision an instance, we were doing the naming and the global propagation. And so their monitoring systems were better than ours. Right. And they were literally like, Hey, there’s something up on the East coast you asked, blah, blah, blah. So I hustled into the office. I bee-lined to Adam Kauflin, who’s one of my co-founders of York IIE now, but at the time was our head of corporate comms at dime.

I said, this is the most important day of your career. And I said, we need to own this. So [00:31:00] proactively we need to be like way more transparent, way more open, way more aggressive, way more assertive. Because Oracle’s acquiring us, he had no idea. And he’s like, Oh, he’s my best friend from kindergarten. And my high school quarterback and Magister West, but had no idea because we were under lock and seal.

And, you know, I was afraid that, that, that anything can go wrong with the Oracle, you know, the mothership on the deal. Right. And so we just went on this. We, we, we did a quick session. We said, we’re going to be so responsive. We’re going to be so proactive. We did PR media like, like, like literally like, like, like media calls with like a hundred media people at once.

Like, you know, like, like press conferences. And you know, w when I looked around the room, to be honest, I was like last man standing at dying, like all the. Co-founders had left like early executives who would help build the company had left. And it was just very clear. I mean, also my role at the time [00:32:00] to strategy officer, but like, but like, it was very clear that I had to be the guy, you know, we have like an interim CEO, we were selling the company, you know?

So I had to be the guy and we just stepped it up. I mean, there was three letter agencies in our office all day long. Every Infrastructure company on the planet was calling us the collaborative because they were afraid of their own networks and systems. Obviously customers, obviously employees.

And in the back of my mind, I’m more insect that our deal with Oracle is going to implode. Oh my God. So we really crushed it. I mean, it was, it was like, you know, get on the today show you know in the USA today, wall street journal, New York times front. Paige, you know, quotes from me and articles with like Obama.

It was like, it was almost like high comedy know me. I’m sorry. I was like, geez. It’s like unbelievable. And I guess what ended up happening on the Oracle side, which they told me about later was they sat on it. They sat on the L the term sheet to execute it. Yeah, it must’ve been that October date then.

And basically they sat [00:33:00] on it and Safra, Catz said something along the lines of No. Well, at least now we know dad’s important and the world will know Oracle’s very serious about cloud and ink it and they suck it back. And honestly, the moment it came back, it was actually, we got attacked by three waves.

It was the ride bike net. So it was like a globally distributed, like it turned IOT thing, IOT devices into attack vectors on the scale of millions and basically We were the second wave when we got the counter signed agreement from Oracle of three waves that lasted the entire day. And it was just, it was just intense.

It was crazy. I thought it was some twisted, perverse, like due diligence by a workaholic or something 

Tom Wentworth: [00:33:45] engineered the whole thing to see how your, how you’d hold up. Did you guys work with an agency at that time that this is classic crisis communications? One-on-one you guys do this yourselves? We did it 

Kyle York: [00:33:54] all of our, all ourselves.

We had no time to work with anybody. Like it was like, it was just [00:34:00] like, write me what I need to say. Like, no, at a, at a, at a, it was all ourselves at the time. You know, over the years we worked with different PR firms. We worked with launch squad. We work with, we worked with a K antler marketing agency.

We had different. Players in the mix. But that was honestly all us. I mean, there wasn’t enough time. Right. We had that. We had to react and respond pretty quickly. You know, we had to put together Root cause analysis RCAs. Like we had to just do a lot of like customer comms. And again, I think we were, I think, honestly, the thing that we did differently than we normally would have done culturally, we had done a lot of crisis comms planning was because we had our high SLA business tagline was uptime as the bottom line.

You know, it’s like, you kinda kind of are used to this. But I think the thing we did differently was actually the media blitz that, that was completely intentional to show Oracle the asset they were getting, because we sat on so much internet data and internet traffic view that, you know, it just was like record a future and your [00:35:00] security data, like, you know, it was very much for us like, Hey, we need to like, also use this as an opportunity to show them that like we’re, we’re serious and we’re legit.

And obviously it worked. I mean, when I got into Oracle. For three years, I was one of the top spokespeople for Oracle cloud. I was on stages speaking in front of 10,000 people. I was doing major customer calls with the biggest clients in the world. And I really turned more into like an evangelist BD strategy, Corp dev guide, Oracle product marketing guy at Oracle.

And, you know, I don’t know if it would have happened if we didn’t show them ourselves. In our full glory during the DDoSs. So weirdly maybe the best thing that ever happened to us was, you know, cause even now, like when I tell the Dyn story, even this morning, I was talking to former CSO or rapid seven and a few other places and he was like, Oh Dyn, man.

How has that DDoSs day? And it’s like, I don’t know if everyone, like, outside of having to explain you remember dying DNS and your home router, like, like, like we’ve actually been able to like graduate from [00:36:00] the like early few years of the company because of that dude, us and the storyteller. 

Tom Wentworth: [00:36:05] Did you have to get certified at Oracle?

Cause you’re pretty, you’re pretty you know, you’re a great speaker, got a lot of energy, but you don’t really necessarily fit the ICP of an Oracle spokesperson. 

Kyle York: [00:36:16] How did you 

Tom Wentworth: [00:36:17] get 

Kyle York: [00:36:17] through that? Yeah, I mean, I did the, the, the media trainings of them internal media trainings or corporate comms. I developed an unbelievably, mutually respectful relation with Deborah Ellinger who’s, you know, she’s the bottom of every press release that Oracle puts out.

She’s been there, Mitch. Geez, maybe 20 years. She’s out in New York. She’s tremendous woman. We’re friends, you know, we’re Instagram pals. Right. But Deborah, you know, They very rarely would let me be alone. Anybody. There, there was always a PR counterpart in the mix. I would also, we earn a lot of respect with them or Adam who’s my co-founder in New York.

And my long-term friend, I mentioned a minute ago would proxy for PR a lot, which is really good. So I could be a little bit more me. [00:37:00] I also realized really early Oracle is in a existential transformation, as databases are moving to the cloud. And as they need to pivot to more of an infrastructure security business, And, and I was like a cruise missile for them to better relate to developers.

I mean, people forget that they own Java my sequel. Jeez, I mean, they’re doing tons and, and server lists and Coopernetties, and you know, it, there’s a huge developer investment in that place and who better to sort of help evangelize and make that. That don’t call it a pivot, but that evolution reinvention a bit than somebody who just built a startup in the, in that community.

So, you know, they gave me way more rope than you’d think. I mean, I remember once I did a seeking alpha, which is like financial inner interview and I was like, shocked. They let me but again, I think. W what’s your immediate dream? Like I can shoot from the hip a lot, but like, you know, I knew the lines.

Right. And I didn’t, I didn’t tell them, like I didn’t die. Right. I, I stayed reasonably distant from them to make sure, because I didn’t want to [00:38:00] sacrifice myself, my team, the company, the stock lots of different factors, you know, that wasn’t going to be on my hands. 

Tom Wentworth: [00:38:07] You get yelled at at all. 

Kyle York: [00:38:09] Oh yeah, yeah.

Yeah. I get yelled at a lot because you know, I w I I’m. Pretty prolific on social media in like, you know, like. I think occasionally I would put stuff out there that wasn’t completely sanctioned. We got yelled at a lot because if you remember, we were in the internet intelligence technology, by the way, I wish I wish I wish that was living in your company now because I don’t think they’re doing a lot with it anymore, but, you know, we would see things that would happen and the BGP or in the traces of the internet or carriers around the world.

And that’s actually, when we got most in trouble, when we put something out that was maybe like, You’re talking about Comcast or talking about NTT. You’re talking about someone who is probably a customer of Oracle, basically everybody, whether they like it or not, as a customer somehow [00:39:00] are connected by one degree of separation as a customer of Oracle.

And so those are the only times we really heard it. So what I would hate actually is the way they would deliver me a feedback after like Like a panel at a conference or a speaking gig at a conference or at an analyst summit. That was actually the most annoying because they’d be like, Hey, you should really not like, say that next time you, you, you know, no one, no, one’s, you know, I remember once they were like, no, one’s allowed to talk about Larry that way.

And I was like, what do you mean? I said, I said, good things about where, like, you’re not allowed to talk about he’s off limits. I get it. Okay. Yeah. 

Tom Wentworth: [00:39:37] I used to live in Redwood shores. So I live near Oracle and I would see Larry has this famous garage with all this super high end sports cars. And if you if you hung around, you’d see him in a new one.

Every so often look, I’m a big Larry Alison guy because he went to university, Illinois, my Alma mater, so, and Oracle great thing about it was when I lived there. They had a [00:40:00] subsidized cafeteria that for employees and you can get incredible sushi for dirt cheap. So Oracle’s always in my heart 

Kyle York: [00:40:08] for that.

A lot of my time. I mean, I spent a lot of time at Redwood shores building 500. But I also spend a ton of time in Seattle because a lot of the cloud infrastructure group that was like 10,000 people that I ran strategy for. Was in, was in Seattle. They’re all former Azure and AWS people. And that’s the cloud infrastructure cloud platform, capital of the world.

So you know, it was, it was a lot of trips there, which I actually, I prefer. 

Tom Wentworth: [00:40:37] Yeah. And think about that New Hampshire kid, Whipple Hill, tiny little company starts dying, ends up at Oracle of all places. That is a pretty fucked up story. 

Kyle York: [00:40:50] It is. And, you know, I reported for awhile, right? When we got acquired, I reported to Thomas Currian.

Thomas is now the CEO of Google cloud. And then are a part of the Don [00:41:00] Johnson who, who both of them reported to Larry gone still there and Don runs Oracle clot. And so, you know, it was a fascinating, it wasn’t just that we were there in a workable it’s that we were like, I’ve been to Sanford’s house.

I’ve been to Larry’s house in San Francisco. Like, you know, it was the weirdest, most surreal. Experience, because again, I didn’t identify as a senior executive that Oracle at all. Right. And it was almost like I moved to San Diego for awhile, my early career for Whipple Hill. And I always felt like I was on vacation.

Right. I I’m a tourist here. This is not my home. Like, I don’t like, it’s great. It was awesome. Don’t get me wrong. I, I had the best experience of my wife, Katie there, but that’s kind of how Oracle felt. It was like. I have a lot of like out of body experiences where I’d be like, be like, like what, where am I?

Like, I can’t believe I’m on stages here. Like I keynoted the backup you security conference, you know, like, like, like literally in Vegas, like keynote at the conference, like with, with Krebs, Krebs [00:42:00] was like the year before. And I was thinking that you’re after, you know, so, so it was this really interesting thing.

I wouldn’t change it for the world. I mean The experience I gained, I never got like a hardcore MBA. I never worked in a big company before to see how it all works. I never worked in like traditional enterprise and top down selling and CIO selling. So there’s just a huge organization with different bureaucracy politics to navigate.

I learned an absolute law and I, and I think it, it, it. Really helped me sort of evolve and be more than just a startup guy or more than a sales guy or more than a marketer and then more of a general business person. And you’re going to remember that was the first time inside. I ran a $150 million dime P and L and then I was head up strategy for a multi-billion dollar cloud division, like I said, kind of dual role.

That was the first time I ever ran Dyn as at the tippity top as the, like the guy accountable to the P and L. So, you know, I mean, it was always at the top CRO charter revenue or chief strategy [00:43:00] officer in charge of strategy, but I wasn’t like the, the, the be all end all and having to report to Thomas and Safra and Larry, how we’re doing.

And Mark heard at the time, rest in peace, but like, you know, it was a different game and it was a great experience. 

Tom Wentworth: [00:43:13] It tied it all back to brand. The other thing I admired about what you did is. And you held onto this for a long time. Oracle Dyn. I remember driving by the building and  it was important to keep the Dyn brand.

And I’m sure that was not an easy conversation. 

Kyle York: [00:43:27] No. And even when we got, even when they were fed up with it and they wouldn’t do it anymore, I got into replace the Dyn side on the big, the big building with an Oracle sign. By the way, they actually moved the office to Nashua. They moved the employees that Ashleigh, because it wasn’t a Oracle owned, died in own the building, just the tight end, massive, massive mill building.

And the Oracle sign’s still there. And, you know, the thing was like pretty petty. I don’t even know how they’re going to get it down, like, but the thing is still there. So we have like an over under of like how many years now is Oracle [00:44:00] going to be in Manchester, in the old Dyn space with a huge sign, lighten up familiar.

If you’re actually, if you head up today, don’t go 93, go to 93 and you’ll get a great glimpse of it. It’s probably still lit up. 

Tom Wentworth: [00:44:11] I will do that for you. All right. And last thing, this has been fantastic. So you, you went back to your true calling, your your you’ve always been a startup guy. You know, I remember you pitching me angel investments for the past eight years, and now you started your own, your own firm.

So how did that happen and what problem were you trying to solve? 

Kyle York: [00:44:36] Yeah, so here’s what was happening to me for the last couple of years of dying. And then certainly after the exit and then inside Oracle, you get asked all the time as an entrepreneur. What are you going to do next? And, you know, I was getting asked a lot.

Are you going to go be a VC and join a firm? A lot of people, you know, that I respect have gone and done that become a managing partner you know, a battery as a coy Andris and a [00:45:00] general catalyst to a tier one venture firm. Or are you going to go be an entrepreneur? You’re going to join a startup, or you’re going to, you got to start one yourself.

And it was like incredibly binary. Right? I was like, this is like so annoying. Like I love doing both. Imagine, imagine there was a, a business, a company. A scalable enterprise that enabled bolt. And you know, when I, when I surveyed the landscape, I looked at like investment banks. I looked at analysts firms.

I looked at management, consultancies, PR, and marcomm shops. I, I looked at SAS businesses. I looked at BCC funds and I was like, man, they’re all like, like one of thousands, like there, there, there there’s the top ones. And then there’s like a ton of others. And I feel like if I just pick one, I’m going to be like an aunt for a while and I’ll get lost in a sea of noise.

And so at York it is, we call it a vertically integrated investment firm powered by market data and analytics focused on growth, go to market strategy. And how we provide to the market is we’re building a marketing competitive intelligence platform called fuel. Think of it like operator [00:46:00] version of Crunchbase or PitchBook or Traxon or Owler.

But for operators is a lot of operational workflows. We call smart notebooks on top of the private company, private market database. And then we launched managed services, advisory services on top for market product strategy, business growth strategy, and marcomm services. So PRA AR content social, and we we’ve tailor made them and modularized them for startups.

And then in the cream of the crop, B2B SAS businesses, early stage, where we can lean in and be an operational extension of those teams, we will invest half a million to a million dollars out of our. We don’t have a fund. We call it a syndicate model that you’re eventually going to be a member of. That’s basically, you know, it’s high net worth individuals, family offices.

They give us an annual commit, a five-year pledge, and they’re part of an evergreen syndicate. We’re not a fund. So we don’t charge management fees or pass through fees to you. We only make money like a commission, like a sales guy at carried interest on the gains on a deal by deal basis. [00:47:00] And so we, we launched this thing in September of 2019.

We’ve done 18 investments. We’ve deployed about $8 million into those startups. They’re all B2B SAS up and down the stack, obviously have an affinity for cybersecurity, for infrastructure, for cloud platforms, for dev ops, for dev tools. But we’ll do, we’ll go all the way up to horizontal and vertical SAS solutions and tech laggard industries are where we think those right players, right.

For disruption. And, and we’re having a great time. We’ve got, you know, about 30 outside consulting and advisory customers. Our a R a R R is growing. So like, we’re not like retired operators, like we’re building a company, supporting other companies. And I really think we’re going after like McKinsey Bain, BCG meets Gartner Forrester.

Yeah, IVC meets Mark on PR shops speeds. Boutique investment banks meets seed funds meets marketing, competitive intelligence platforms like, like all-in-one in a vertically integrated way. [00:48:00] And. COVID weirdly has like integrated us way faster, you know, like the beginnings of York, you were like an investments business, a consulting advisory business, and a product roadmap, right?

Like who knows like a, like a studio it’s completely become the vision. I just said where we have the platform, we build services over the platform. We use the platform to do discovery, diligence, market tracking, company tracking, reporting and we’re eating our own dog food. And we plan on launching that SAS.

Business and platform in the first half of next year. So it’s really cool. It’s really fun. I, you know, I’m not raising venture for any foreseeable future for the core operating company where the IP and the technology and the customers live, but we are working with high net worth individuals and family offices who invest with us into the startup portfolio that is growing and emerging.

Tom Wentworth: [00:48:51] Nice. All right. So last thing, this is going to go live on Monday four days before Christmas, is that true? Four days. Can we still [00:49:00] order shoes from York athletics and get them on time for Christmas, or we’ve passed the window. 

Kyle York: [00:49:04] It’s going to be really, really tight, but if you put in the notes, when you order, you need it, they will hustle hustle, and there are options to accelerate shipping, but you should definitely get some New York athletics.

That’s my third generation family business startup. Great gym shoes. I know you’re a supporter and aware. I really appreciate it. Thanks for the shout out. 

Tom Wentworth: [00:49:24] Cal made great catching up with you. Congrats on all your success.