#157: Scaling & Selling a $100M Company with Kyle York (Former Dyn CRO)

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This is a podcast episode titled, #157: Scaling & Selling a $100M Company with Kyle York (Former Dyn CRO). The summary for this episode is: On this episode of Seeking Wisdon, DC sits down with Kyle York, former CRO, CMO, and General Manager of Dyn and current founder and CEO of York IE. Together they discuss Dyn's path to becoming a $100 million business and its ultimate sale to Oracle. Plus, the importance of working through "the Dips," mental health and well-being, the future of field sales and marketing in a post-COVID world, and much more. Like this episode? Be sure to leave a ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ review and share the pod with your friends. You can connect with DC and his co-host, Adam Schoenfeld, on Twitter @dcancel @schoeny @HYPERGROWTH_Pod

DC: Boom. And we're back. Seeking Wisdom's here. I rarely play the host, but this is an exception to the rule. I'm here with Kyle York up in the wilderness, it seems, there at Manchester, New Hampshire. How's it going, Kyle?

Kyle York: It's going great. Good to see you.

DC: Good seeing you, man. It's been a long time. Can you tell the people about yourself, your background, and then I'll crosstalk?

Kyle York: Yeah, sure. We've known each other from way back. I think your former Boulder HubSpot days, but I helped build a company up here in Manchester, New Hampsire called Dyn, internet infrastructure company. I was really early there, 15 people when I joined. It's an internet infrastructure company, so you can imagine the founders are heavily technical. So I was brought in as a go- to- market leader, the first go- to- market leader and was its chief revenue officer. We successfully scaled that company to 100 million ARR and sold to Oracle in late 2016. I then hung out at Oracle for three years, actually learned a lot, enjoyed my experience. I'm sure we'll talk a little bit about the juxtaposition of startup life and big corporates. And had a lot of success with the GM of the dime business there and helped run strategy for Oracle Cloud. And then in parallel to that, as you know, where we've crossed a lot of paths over the years, just do a lot of angel investing, advising board staff, obviously focused in New England a great deal. And I've recently launched a year ago York IE, which is our new vertically integrated investment firm, which I'm sure we'll talk about that as well today.

DC: Nice. I see you have the shirt there.

Kyle York: Yeah. I'm rocking the shirt. Oh yeah, exactly. It's our t- shirt culture, man, right?

DC: That's awesome. What year did you guys get to 100 million in revenue at Dyn?

Kyle York: Yeah. So it's an interesting story. So Dyn was actually founded in'01, and from'01 to'08 got to about three million, and it was all D2C consumers. So they basically enabled you to name your home network. You could do things like dcshouse. com and you name your home router and do nerdy tech remote access things with that. Yeah, you did it, right? And this is obviously before we had all our mobile devices and all that. It was real hot. So that's when I joined. And what they realized, the founders, Jeremy and Tom, they realized that cloud computing became a thing. Web apps and websites were going to need a name servers and cloud instances. The domain name system, the DNS, which was we'd specialized in, was a great technology capability to do that. So they had actually built the enterprise version, but they didn't know what to do with it. It was sitting on the shelf and-

DC: And that was'08?

Kyle York: That was'08. I joined officially January of'09, but really started in late'08 for free. Everyone has those multiple binds where they're forgetting to pay you and you're like," Hey, remember me?" And so yeah, from January of'09 till we signed our definitive agreement in November of'16, we went from three to 100. It was wild. We never had the 300% growth rates or anything. We were always pretty methodically between 40 and 80% growth, and it was a machine. And we used the consumer D2C engine, which a lot of people don't realize. We turned that into like PLG before PLG. We said," Hey, if you're using this at home, you're probably a nerd. You should use this at work." We actually scaled that to 25 million ARR of the 100 along the way, and we used that as a cash cow ATM machine to fund a lot of the business because, as you know, we didn't raise any outside capital till we were already 30 million ARR. One of the best bootstrap stories I think we've got intact.

DC: Yeah. It's amazing. I asked you what year, because in'16 100 was big money, and you did a lot of stuff pretty early. Like product- led growth wasn't really a term that existed. You guys did that with the freemium model. There were so many early things, which is amazing to me, that story.

Kyle York: Think about that. Even the guys who founded it in their dorm room, the way they embraced e- comm. Their original revenue was actually donation. It wasn't even revenue. It was like, hey, if you guys want us to keep running dyndns. org, give us 10 bucks or whatever. And then that became recurring revenue. So they were SAAS before SAAS, cloud before cloud, subscription business model before subscription business model. Even when I was building the go- to- market, I talk a lot about this with inaudible and you over the years, Tom Wentworth, a lot of these guys. There were no playbooks. There were no podcasts. There was no books. There was no blogs to follow. You just made your own rules, and by doing that, I think you obsessed a little less on the KPIs and the metrics and you focused more on creativity. And I think that was a big part of the Dyn brand story and the Dyn business model and the Dyn community we cultivated, as it was really different and unique and creative. I always remind founders now, focus on brand and be creative. KPIs are great, but don't lose the forest for the trees. Right?

DC: Yeah. Because so much of what made these stories happen is because we got creative and we made things up. I started a company in 2000, and back in 2001 when Dyn started, that was still the era that people were telling me, no one's going to put a credit card online to buy software. It's never going to happen. Definitely not a business. We're going to buy books and stuff like that at Amazon. Buy books and that kind of stuff, but no one's ever going to put a credit card online. Because we had tried to do a recurring revenue model when we didn't even know what it was called. We were calling it, we're going to sell software via e- commerce. There was no such thing as SAAS. It was insane.

Kyle York: Yeah, I always picture the Salesforce, their software logo and I laugh. That's what I remember from that time, the red...

DC: That's crazy.

Kyle York: Right? Yeah, it's wild.

DC: The surprising thing to me was after you sold the business and I got to know you during that business, I can't even remember when. I think I had met Corey who was working there somehow, and I came up to Manchester and I was blown away. It was inaudible days so it was probably'09 or 2010, something like that. And to this amazing setup that you guys had up there blew my mind.

Kyle York: Yeah. A lot of us were from up here and had moved away. So I left work in California for a while, moved back home. Manchester, New Hampshire is like an old mill town and it's on a river and it's got basically these millions and millions of square feet of mill buildings that... it's like skyscrapers laying on their sides. These things are enormous. It was like five bucks a square foot per year or something for the office space. It's gone up a lot now. It's like 20 bucks now or 25, but back then it was like these huge offices were empty, and you could retrofit them super cheap, but they were really just like lofts in New York or lofts in Boston or lofts in San Francisco. But everyone in New Hampshire was like, holy cow, you guys are innovating. It's like, no, we're just copying other ecosystems and other cool companies. And I think we benefited because the more traffic you had to your website, not the size of your company. We did market segmentation based on Alexa Rank. So we ended up working with the Twitter's, the Netflix's, the Pandora's, the Spotify's, the Airbnb's, the Hubspot's. The coolest brands were our customers, and we obviously very clearly tried to draft off that and learn from each other, and the space was one physical example of that.

DC: Totally. I think one of the other things that blew me away, and you guys you were one of the first examples of a multi- layered sales model. A product- led growth consumer model then an SMB model, and then I remember you guys going into the enterprise later on.

Kyle York: Yeah, exactly. Even in enterprise we went and expanded there. We didn't say, hey, all of a sudden, out of nowhere, our initial deal was going to be half a million dollars. That was just not going to happen. So we landed and expanded. The best story we actually have there, I love telling this. I don't tell very often because I'm probably not supposed to, but this is great. Oracle's first enterprise deal with us was 600 bucks a month. It was a QA project for their emerging cloud storage group, 600 bucks a month. When they acquired us, that thing was 950K ARR, and they gave us a pretty nice, hefty multiple on our overall revenue. So I always laugh. It was 600 bucks of MRR, so eight grand a year. And then they grew to 900 and then they gave us 10x our enterprise revenue. It was like, wait a second. You just literally paid us with your own-

DC: Best upsell ever.

Kyle York: Yeah. Best upsell ever. But that was the model. And it was not one upgrade to that, it was probably six, seven, eight upgrades over four or five years. What I always remind startups, it's your pricing and your go- to- market motion that determine where you play. I think the old school market segmentation is a real got you for a lot of startups if they're not careful.

DC: Say more about that. Most of the source's organic, but now how do you think about creating a multi segment model like you had? This kind of-

Kyle York: Yeah. I think everybody nowadays can do this from the... I'm not an obsessor over PLG, but generally digital inbound, self- service, self- inquiry, digital assist sales, it's the devOps movement. Sell the practitioner, get them playing with the technology, get it in their hands, and then someone human should eventually reach out. And I think it's a question mark of who that human is. Traditionally, we learned a lot about enterprise selling an Oracle. Tops down, board, CIO level down. That does not work anymore unless you're selling something that off the shelf is a million dollar product displacing a million dollar product. So I think a lot of this really comes down to knowing yourself, knowing the value price of your capability, knowing the practitioner really well and getting the technology in the hands of the practitioner in any way you can. Then obviously you have your BDR inside sales, SMB mid- market model up to your field sales model, but even field sales these days. We're all remote, so I guess we're all field sales. So I think it's just an interesting dynamic. I always, always remind companies that your average selling price, your average ARR per customer, and the number of deals you can win needs to be able to support your quota model. You can't pay an enterprise field rep 400 grand a year if their quota's 400 grand a year, and their quota can't be a million two a year unless they can either close 12 100K deals, or 24 50K deals, or three 40K deals. At the end of the day, it's a lot of math.

DC: What's amazing to me is the smartest founders, the smartest people that you would work with fail to do just back of the envelope math. It's a pretty simple model. It's like how many units you have to sell at what price to be able to pay whatever. It's simple. You don't have to over- complexify this stuff and get lost in these models.

Kyle York: And what data do you have that gives you the assumptions and the inputs to the model that make it make sense. I was just talking to a founder the other day, Boston startup, great startup MarTech. And he's like, we're going to start winning 500K a year of deals. I'm like, your average is 40K a year right now. Go win more 40K a year deals, and I would love it if you expand them to the 200K, into the 500K, but your go- to- market motion needs to be a go- to- market motion to win the 40K deal. And you need more net new logos, you're a million ARR. Get more net new logos that you can expand later or else you're going to over fish the unstocked pond.

DC: You're going to get caught out there. You need a whole new model, a whole new sales team, whole new product possibly before you've proven it out through a natural expansion motion.

Kyle York: And this happens, and I'm sure you're even dealing with this a lot with your board and your investors. As you have early success in the bottoms- up go- to- market and the downmarket, lower ARR per customer. Dirty secret is when we sold Dyn, our average ARR per customer was 18K. We had a$ 4 million deal, a few million dollar deals, a dozen 500K plus deals. But again, they all landed and expanded there, but the overall customer base, the real secret sauce of Dyn was the repeatable go- to- market motion to the 18K a year. Well, it is a little bit of a fool's errand. It happens a lot as you get more near the 100 million or plus, and you have big money into your company and board members who've been there, done that, they're mostly retired. They basically sit there and they say," Why aren't you enterprise yet? And why aren't you winning$ 250,000 deals?" I remember one board member talking to me about... what did they call it? Bluebird deals and how do you limit paying sales reps for bluebird deals, and I was like, well, explain what you mean. And he's like," When we win million dollar deals, how do you make sure your reps don't retire?" And I'm like," We don't win million dollar deal. So that's not a problem." But again, I think this is a problem-

DC: By the way they should get paid. That's a whole-

Kyle York: They should get paid. That's the whole point. And inaudible should get paid too.

DC: Totally.

Kyle York: So I think they all tell you to go enterprise in the old school licensed software, top- down sales models that existed in the'80s, and'90s, and the beginnings of the 2000s. These models are just very different that unless you're workday selling million dollar deals, then don't try to go build a go- to- market to go do that. That's very expensive and you'll burn a shitload of cash, but it's a completely interesting dynamic and it's broken.

DC: Yeah. But it happens no matter what. In some ways it's good. A board is going to ask you for more. They're going to ask you, hey, how many million dollar customers do you have? How many? Why don't you have 10 more? Why do you have 20 more? When's the next one? That's their job. They're just going to continue to ask that, but you have to run the company, right?

Kyle York: Totally.

DC: You mentioned one thing that I though is super impacting us right now, and I want to hear how it's impacting your businesses. Is the last eight, nine months, there is no more field sales. The biggest thing that's happened to asset drift is that, because we play in all those segments, in our enterprise segment, there is no field sales. There is no field marketing. Everyone's selling digitally. But even companies who would sell those multimillion dollar deals, who would never think that they could sell without a field sales organization, 100% in the world have been forced to do it right now. So that's a massive transformation. They thought they can never do it, everyone in the world is doing it right now. And there's no other choice. It's interesting. Do you think they will come back to a field sales model and how's it impacting your companies?

Kyle York: I wish I was still at Oracle, to be honest. This place, from the inside, what we are trying to do was evolve that business and be rabble- rousers and disruptive through a lot of M& A, through a lot of hires like me and others try to train and coach them on a different go- to- market motion. It would be really fascinating to know how that's going for them inside. So yeah, I can answer that in the York IE context. We call ourselves a vertically integrated investment firm. We are powered by market data and analytics. We built our own proprietary SAAS platform that today is internal. It does market and competitive intelligence. And then we layer on managed service modules for market product strategy, business growth strategy, and marcomm services. So the general idea I had when I created this company was, everyone was asking me, are you going to go be an operator or a startup guy, or are you going to go be a VC? And you've been asked this for your whole last 20 years. What are you going to do? And I would say," Well, I'm an operator, but I love investing and working with entrepreneurs."

DC: With entrepreneurs. You would say a hybrid.

Kyle York: Yeah. I want to do both. And then you're like Battery Ventures managing partner job is not going to let you do that, or X startup that you fundraised for is not going to let you do that. And it becomes this pick one problem that frankly was really pissing me off. So I looked at the landscape and I said, what type of modern integrated company could I go build that could be incredibly disruptive to early stage venture, could be very disruptive to business consultancies and management consultancies, could be very disruptive to analyst firms, could be very disruptive to marketing and PR shops and down- scope and scale using tech and automation for private companies and growth companies and bring our go- to- market expertise to lots of companies. And how can I make that scalable? Everything I moonlit on, how do I make scalable and-

DC: It didn't scare you to do so much at once?

Kyle York: It did. Startup growth is scary, but I was basically like, if I just go pick one of those areas and just raise a fund or just launch a new analyst shop or launch a new PR firm, I'll be an ant in a sea of thousands in each category, but my differentiation can be if I can figure out how to integrate this into one model and one company. And so there's a lot of, of course, nuances to how to go do that, but that was in essence my strategy, and you know this, but I am a go- to- market guy who knows a lot about technology. I know a lot about hardcore technology, but I can't even code an HTML webpage. So what I realize when I look back at my two startups and even my role in Oracle, it's like I'm really good compliment to technical founders. So that is very scalable to me across tens, 100s, maybe 1000s if I create IP and technology to automate and just deliver more value. So that's what we're building in York IE. So when you think about our funnels, we have several sales funnels. So speaking back to your question on the field and COVID, I treat basically our funnel as one big integrated funnel. You know how to build a brand, but build a brand super fast. Drive as much traffic, eyeballs, interests, create as much content as you can, stay in your lanes, but grow the top of funnel big time. And then when companies or individuals get to us, they're either thinking, how do I invest with these guys? Join our investment syndicates. How do I pitch these guys my startup idea and get investment? How do I talk to these guys about advisory or consulting opportunities? And then eventually, how do I talk to these guys about buying their product to be launched in public to the market? So when I look at it, it's really one completely integrated funnel, and I don't know if we'll ever have a field sales organization for that. Sure, we'll get to events when they come back. Sure, we'll meet with partners. We'll do days in Boston, New York, the Valley, whatever. But at the end of the day, I don't think we're going to ever go back to that as our firm.

DC: You think crosstalk in general?

Kyle York: I think it will because we're crosstalk

DC: Will it come back as inaudible or will come back as hardware? What do you think?

Kyle York: I think we're creatures of habit a little bit. It's not like everybody who grew up in the field sales model is all retiring. So I think it's going to be more of a slower decay of the field- selling motion and the top- down selling motion. And even honestly, the large ARR initial deal I think is going to dramatically change in SAAS, and so in software in general. And even in hardware. Yeah. I just think it's going to be more of a slow bleed. I think it'll come back a little bit, but then I think it's going to fade away over the coming decades.

DC: Yeah, totally true. So one thing that I've been talking a lot about, even internally- externally is this idea which you went through, which is like, when you have these companies in growth and hypergrowth and people there from the beginning to it's later stages, people expect this linear line, like it's just going to be straight. And it's a constant game of these inaudible because of the dip. You go through these dip toes and then you've got to rework and rework the team and create things, maybe create new products and resegment, and then you have another growth thing and then you hit another dip, and it's always this game of this, but people have this weird notion that it's always going to be the same and go in one direction, which is insane. How many dips did you go through at Dyn?

Kyle York: Oh man. Yeah. And again, I think now too it's crazy because I see it now across dozens and dozens and dozens of companies. When I launched York IE, I had done 60 angel investments. 15 or so had exited, one at IPO- d, four had died. So when I look at the active portfolio now, we've done 16 to 20 new deals in York IE. So there was like 60 active companies or something, and they're all the way back to when I started angel investing, back when I met you. Back then. So it's like there's Fastly public company worth 10 billion all the way down to the guys still struggling to get product- market fit. So I see this every day. At Dyn, hindsight's a wonderful thing. I was laying on MRI tables back in 2015 thinking I had brain cancer because of the stress and the migraines. Oh yeah, man. I was getting migraines.

DC: Talk about that. Tell the people.

Kyle York: Yeah, let's get back to that inaudible. Let me answer your question. So when I look back in hindsight, it was always the dips, but I can tell you why our growth rate accelerated, or why our growth rates sustained, or what step function growth we got in that year or that quarter or that month. I can plot it now and say, oh, that's when we won the big partnership with Amazon. That's when we acquired Renaissance and got an extra eight million of ARR. Oh, that's when we launched our email delivery product to compete with SendGrid. Literally I can look back at it now and say, that's the thing that worked. You and I both know whether it was strategic hires or a partnership or a new product launch or hey, that's when we changed pricing and added 7% to everyone's renewal. When I look back on that now, there was 50 other things that year that we did that didn't work, that weren't the driver of the re- correction or the acceleration or the sustaining of it. So what I always try to help startups do is think of the vision and where they want to go. Make sure they work backwards from that and their strategic planning, but also really know the knobs and levers of their business to manufacture growth. Like I can remember one year we peaked at 65 AEs. When we sold to Oracle, we had 45. We just overhired, were inefficient as hell, and that was one lever we used one year because we needed to power through as we were launching a new service. So again, when you live that and you can then look back at it, you can basically say, well, geez. How do you open up more knobs and levers? How do you focus 80 to 90% of the core machine of your go- to- market, but leave yourself 10 to 20% room to try new things and innovate, and what we said at the beginning, be creative. And again, I don't think that's how most boards and most investors think, and it cripples entrepreneurs because they're too worried about that. Yeah.

DC: Yeah. That's why I talk about it so much even internally, and just like, we will look back and it will seem less painful than it was for sure. You'll forget a lot of the pain. You'll look back and think, oh, this worked, that worked, this worked. But while you're going through it, you're just plotting along, trying and experimenting, trying to survive and trying to make incremental progress. And then it'll be obvious one day what works. But we just remember when we tell ourselves these stories, but we forget of the pain that we went through and the stress. And you having freaking migraines on an MRI table.

Kyle York: Yeah. It was like 2014 or 15, the board was getting pretty heavy handed. We were chasing down 100 million ARR, and they started to look at our executive team and our average age was 30 or something. And they're like," Where is the experience?" And we're like," Well, we had it." But it was a layer below our C- suite and it was like they were really pressuring us to evolve. So we started recruiting new talent, new CFOs, new heads of sales, new'independent board members'. crosstalk. Yeah. It became a lot of pressure, and I felt a lot of responsibility to the company's inevitable monetization, exit, IPO, whatever, and a lot to the customer base and to the employees. And I was struggling with whether I wanted to keep putting up with the BS. And I also didn't come from money and this is my real chance to make generational wealth defining capital, and I was scared to death. And the reality is by the time we sold to Oracle, I was like Last of the Mohicans. Everybody was gone. Coy left in'13, Tom Daley left in 2012, Great China left in'14, Jeremy left in early'16. He was still on the board and all, but that was our C- Suite.

DC: You were the survivor.

Kyle York: Even the Oracle LOI, I almost puked. Literally the first sentence said, Kyle York and other key holders must sign employment agreements before we exercise any definitive agreement. And they had no one else named. It was just me, and I was like," Oh, damn it." There's no pulling the rip cord and running from this thing. I got to run this all the way through and make sure it's foundationally solid inside. Yeah, so through that time period I was-

DC: crosstalk performable. All my other company that had pulled the rip cord right before.

Kyle York: Yeah. I know. You're a genius at this. I literally, during that time, started getting migraines for the first time in my life. I was also having kids during that time and I was on the road too much and everything about it. My kids are still little. I felt like I was losing control. That's what I learned about myself. It's not about controlling everything else around me. It's about controlling my own role in all of that. And if I don't feel like I've got a handle on that, then it creates immense amount of stress and anxiety. And I don't think a lot of people talk about this these days. I actually just was tweeting about this last night. A founder online asked me about seeing a therapist or getting a psychologist or executive coach, and it was really a fascinating discussion because my immediate reaction was, well, what do you want to talk about? I'm here for you. And then I was like, what am I talking about? There's professionals at this. And by the way dude, you don't need more executive coaching. You need to talk to someone who's a professional in the mind and the brain and your psyche. Go talk to a professional therapist, professional psychologist. This is not a coaching or mentoring issue. You just need to talk. And so I think that's something that we should, all of us in the startup community, should better encourage for people.

DC: I feel so strongly about that, especially the thing about the executive coaching and mentoring this. I believe in mentors and stuff like that, but most of this is a psychological game. This is psychological game.

Kyle York: Totally.

DC: And that's not only yours, but that then becomes your team's psychology. It becomes the psychology of your customers. I wish someone would have told me that earlier. I spent all my time now thinking about my own psychology but the psychology of this game, because that is the thing that separates it from people who have started stuff and couldn't last, or quit. Most people will quit at the end of the day. So that's the similarity. I don't know anything about sports, but in sports and other things, most people will quit. And then there's very few people that will survive through it.

Kyle York: I was just talking about this the other day. So it's also the empathy you gain as a leader by understanding your own self and your own psychology and the psychology of your team. I think it's also like, we always talk about mentors and exec coaches and your board, and you always talk upward almost. I always talk about loyalists. The more loyalists you create to you who are in your camp and they're not... I don't mean followers or kiss asses. I mean loyalists. People who believe in your vision, believe in your leadership style, support you, your mantra, will follow you anywhere. Those people end up becoming other people's mentors and then they develop their own level of loyalists. And so I love to talk about the other direction of that.

DC: I'd always react negatively towards when people try to rationalize starting a company and they try to talk to me, whether those are kids in school or people in professional life, when they try to rationalize and compare it to something, I'm like," You should definitely not start a company." Because you're rationalizing. You're trying to make a logical like it's a formula. What will happen is you will quit. Crosstalk.

Kyle York: No. It's a complete DNA thing. You can sniff it out right away. I was going to give you a sports analogy because I was just visiting Bentley where I went, and they hired a new athletic director, and they have a new chairman of the board that I was meeting with. And it was a great meeting, but I told this story about how when I went to Bentley, I played four years of college football division two, was never going to the NFL or anything, but grew up an athlete. I've got the shoe company York Athletics, I've always been around sports. I've got four brothers, very competitive. When I went to Bentley, the first day I was there, I realized I plateaued in high school. I went to the freshman orientation inaudible meeting, I looked around the room, and I'm like, good Lord, I should have retired. But basically there was 30 freshmen on the team. And by the time we graduated, there was only 12 of us. And I played all four years, I lettered all four years, but I stuck it out. But the reality is everybody you played as little as me, I was a special teamer, garbage timer, but I also was the guy representing the team on the Student Athletic Advisory Council at the NCAA. I was also the guy who was the life of the party for the team and built the comradery and all that. And so I was always a leader, even though I wasn't the best player. And so a lot of people quit though. There's only 12 of us at graduation. There's like 32 that showed up there who are all good athletes who love sports, and I think that in hindsight, again, I look back at that time and I'm like, wow. That perseverance, that resolve, that stick- to- it-iveness when really I shouldn't have-

DC: It was illogical. That's why the crosstalk gets me because most people will quit because at some point they will suck so hard that there'll be like F this, I could go do something else. Why am I doing this?

Kyle York: Well, and in parallel, I was like, you know what fellas? Well, some of you are going to go do fake tryouts with the Patriots and never make the team. I got internships. And I started working. And I started taking the undergrad business case study curriculum and putting it to practice. And so it's like these same guys now in my late 30s are the buddies calling me going," Hey, you know when we made fun of you on spring break for taking the conference call? I need some career advice." And it's like, inaudible fellas. Well, we got acquired by Oracle. My two best friends from college, Tim Bidi and Mike Arsenault were sales guys at Oracle. You imagine the gratification I have when I send them the press release announcement. And then I just totally messed with them all the time when I'd be their boss's boss's boss's boss. And I'd tell them the story of college and they'd be like," You told them what?" This is the fun of it too. You have to have perspective and you have to have fun or else you will not survive startup life.

DC: Totally. So to wrap things up, I always want to end with, are you reading anything? Are you learning? How are you learning right now? It could be reading, it could be watching, it could be whatever form you want.

Kyle York: Yeah. Honestly, DC, I always try to be the most prepared person in the room. So I am consistently reading basically everything I see or listening to everything I see. So I don't have specificity to it. I am subscribed everywhere. I'm, as you know, very active on social across LinkedIn and Twitter. I also am talking all day long to founders and to investment partners in the later- stage venture capital firms and entrepreneurs like yourself. I feel like most of my learning is through my ridiculously jammed schedule of conversations I'm having with people. One thing is everything's now on Zoom, which is annoying because I like to do the walk- in meeting. And so I keep saying, if it wasn't going to be a Zoom beforehand or it wasn't going to be in person beforehand, don't make it that now. Just have it be a good old fashioned phone call.

DC: I don't do Zooms anymore except when I'm doing something like just a podcast. I do everything as a walk- in call.

Kyle York: Well, I love your kitchen and you love my man room. After this thing, we're going to get some drinks together, right?

DC: inaudible. It was awesome talking to you, Kyle. Thanks for joining us, brother.

Kyle York: You too. Thanks, man. Good to see you.

DC: What's your domain? York IE? Is that the best place to find you?

Kyle York: Yeah. york. ie is the website. Please check us out. Follow along, subscribe to the newsletters, you'll dig it. Also, we're @ yorkgrowth across all social channels and I'm @ kyork20.

DC: All right. Hit up Kyle online and remember what to do. Six star ratings only. Go into Apple podcasts, all of your channels, or wherever you're listening to this thing and leave a six star rating. Shout out Kyle, follow him on social and give them some crap online.

Kyle York: I love it.

DC: Love it. All right. Take care, brother.

Kyle York: Thank you.

DC: All right. Cheers.


On this episode of Seeking Wisdon, DC sits down with Kyle York, former CRO, CMO, and General Manager of Dyn and current founder and CEO of York IE. Together they discuss Dyn's path to becoming a $100 million business and its ultimate sale to Oracle. Plus, the importance of working through "the Dips," mental health and well-being, the future of field sales and marketing in a post-COVID world, and much more. Like this episode? Be sure to leave a ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ review and share the pod with your friends. You can connect with DC and his co-host, Adam Schoenfeld, on Twitter @dcancel @schoeny @HYPERGROWTH_Pod