Learning from Your Journey to Overcome Growth Marketing Challenges

Published on: | Updated on: | Trisha Miles


Sometimes, the journey is just as important as the destination. If you’re involved in a start-up, you might operate in a vacuum, mostly focused on how to make your current endeavor succeed.

By pulling from past experiences, maintaining a growth mindset, and building trusted relationships, you can help yourself and your business continually evolve and succeed in a way that acknowledges your journey in addition to your goals.

You’ll find that with the right attitude and understanding of your background, you’ll be able to overcome start-up scaling challenges, become a well-rounded leader, and reshape the way your start-up is built, scaled, and monetized.

“...This is a relationships game, and you work with people you trust, and people stick with companies they enjoy working with.”
Kyle York, Co-founder, CEO, and Managing Partner at York IE


Why the Journey Matters

In this week’s Growth Marketing Chat episode, Kyle York, Co-founder, CEO, and Managing Partner at York IE, shares his own fascinating path and experiences to drive home how every stage of your journey prepares you for the growth marketing space.

Tune in for insight on:

  • Challenges that start-ups face

  • Marketing channels that perform well for start-ups

  • Why being pragmatic isn’t everything

  • How building strong relationships will help you throughout your career 

  • York IE and its role in developing a holistic go-to-market strategy

With the right perspective, you can use your past to ensure your start-up's future. Watch the full interview to find out why the process is just as important as the progress!

Video Transcript:

NICK: So today we have a very exciting guest. Kyle York, co-founder, CEO and managing partner of York IE. York IE has the ambitious vision to reshape the way startups are built, scaled and monetized. Kyle, welcome to Growth Marketing Chat. 

KYLE: Hey, thanks for having me, Nick. 

NICK: Thank you for being on. So Kyle, maybe we can start the conversation by having you walk us through your entrepreneurial journey and kind of what led you to this point. What led you to start your company, York IE? 

KYLE: Yeah, great. So not like many people, my journey starts at birth.You know, I was born into a multi-generational family business that my maternal grandfather started in 1946 with his Greek siblings-in-law, cousins. And it was a shoe manufacturing company here in Manchester, New Hampshire, actually in mill buildings, just like the one over my shoulder. 

NICK: Beautiful. 

KYLE: And that business ran from 1946 to the 70s when they all became retirement age. It was also the same time when manufacturing of footwear went abroad. And so my father had married in to my mom. My dad, Don married Gail and he actually worked for the shoe company and he helped run their outlet store and did shoe sales. And he turned that into, for 45 years, a sporting goods retailer. So they did all like little league, pop Warner, college, uniforms, apparel. But even more so, like they were like the high end, you know, baseball, football, lacrosse, you know, equipment store. So I ended up born the middle child of five kids into this small business that, you know, was kind of multiple businesses at one. It was the sports retail store. 

There was a screen printing and embroidery store. It was the team and leagues, B2B sales. They owned real estate. They also had a parking business because we were across from a big arena that was in downtown Manchester, New Hampshire, where I was from. So I just grew up in that, right? So from the very earliest days of my life, I remember being at the store, you know, unpacking boxes, stacking shoes on shelves in the back, and then eventually working retail there. I screen-printed shirt and silk screened hats, did a lot of deliveries, ended up working in the parking lot. 

So my whole life, I was kind of just around family business and I think most importantly, you know, learning from my dad who was really hardcore, you know, straight shooter, salt of the earth, as hard working and integrity rich as you can But also with my mom, who came from growing up with the daughter of the president of a shoe company, very successful, very smart, very sharp. Both of them together, I think we became, the kids became like perfect blends of them, to say like, okay, how do we take this foundation and take it forward? 

So that's a big part of the beginning parts of my entrepreneurial journey. And what I really took away from it was like, you know, control your own destiny. Like, don't work for the man. Like, you know, like be in charge and be accountable. And I think that's been a big part of my career. So anyway, I went off to Bentley University, business school outside Boston. Got my degree there. I played college football there. So always been very competitive. I got middle of five boys, right? And then ended up, fortunately, I interned first after my freshman year at a market research firm. That was really a ton of great learning experience. A lot of data analytics. And then ended up as a marketing and sales intern for a software company that was in the education software space. They sold private schools, K-12 private school software. I ended up interning all the way through being their regional director of go-to market, moving to California for them. Helping that company scale. 

They inevitably sold to a public company called Blackboard, Blackbaud and fundraising software. And then when I was in California, I got recruited by a high school classmate. And this is really the catalyst for the Kyle now, right? And the journey now is I got recruited by a high school classmate and co-founded a company called Dine, which was an internet infrastructure, domain name system, DNS company here in New Hampshire, my hometown. I was living in California and I moved home and became the chief revenue officer of that company. We took it from 15 people to 500. I took it to a hundred million of annual recurring revenue. We sold that business to Oracle in 2016. 

I stayed on at Oracle for three years. Talk about the man, right? I'm totally different experience but I felt like I needed to learn that. Spent three years doing that as the general manager of our business unit, running our P and L. I was always running cloud strategy for Oracle cloud. And, you know, that's my story. And in parallel to the Dine and Oracle incredible success and Ryan, I started to do a lot of advising, angel investing. I was creating investment vehicles. I was helping launch new startups. Taking a lot of that entrepreneurial juice and playing the long game of like, hey, I wonder if I could moonlight and build this up. Could that lead me to York IE? 

So we'll get into York IE, my company today, in a few minutes, but that's kind of the manifestation of my operating experience, my advising and investing experience kind of coming together for what I'm doing now. 

NICK: Yeah. No, wow. What a journey it's been. And especially and I love how you started from the beginning with the background and the small business and working there as a teenager and kind of that apprenticeship coming up. That's awesome. You know, you mentioned something. You know, you've been kind of a small business guy, a startup guy, your whole life, but then you worked Oracle for a few years to get that kind of the big corporate perspective. What did you learn from those few years at Oracle that's kind of helping you become a better rounded leader? 

KYLE: Yeah, well, I mean, I think I've always been incredibly self-aware. I think people view me as an extrovert and view me as sort of an alpha and view me as like highly confident, maybe even ego sometimes, right? But at the end of the day, a lot of people's confidence comes, it's like the inverse of their insecurities, right? And so for me, you know, you've got to remember the Dine journey from, you know, up to a hundred million dollars was in my mid, late twenties and early thirties. You know, we sold the company and I was 33 years old and I didn't have an MBA. I hadn't been like traditionally trained in sales and go to market and business growth. I actually didn't feel like I even had like a ton of mentors that were relevant to that journey. 

You know, clearly my parents and my siblings and other mentors who were relevant, like general business and life were very valuable to me, but not a lot of people have been on that like ride, right? Like now you see more and more big tech companies and success stories, but you know, this is back in 2008, 2009, when I joined Dive, this didn't exist. So when I got to Oracle, a big part of it for me was like, wow, I'm going to have like access to, you know, large mentorship, you know, learning from some of the best. I mean, I reported to Thomas Currian for a bunch of my time there. And Thomas is literally the CEO of Google Cloud now. He was the president of Oracle, right? And then I reported to this guy named John Johnson, who came from Amazon, AWS, Amazon Web Services. And John was, I reported to John, John reported to Larry Ellison. 

You know, so I just felt like the level we were at, the time and place we came into Oracle as they were in a transition from licensed software and services to SAS, recurring revenue, from top-down in CIO field selling to bottoms up digitally native, inside selling, go to market. I just felt like my experience on the scale, the timing was going to be a great training and fertile ground for me to just round out, polish up, learn a lot. Even like decompress, not rest invest or anything, but like sort of get out of this sort of cycle of building a startup. You know how it is. It's incredibly hard, incredibly challenging when you're in an environment like that, 150,000 people, you're cocooned and you're sheltered from a lot of it. 

And, you know, it's an interesting and different and divergent path. So learned a lot. The other thing, and again, we'll get to this as we get to York IE, but like, we also took a lot of processes and like maturity of that organization and we sort of down scoped them to help support startups and private companies on their growth path. It's like the sooner you get to like some of that maturity, some of that systemizing processes, some of that rigor, the more healthy of a company you're going to build in the end. And I think, you know, clearly at Oracle, it gets pretty political and pretty bureaucratic at the very top. One of my annoyances of a huge company. But if you take the good of what they're trying to do and eliminate a lot of the personalities and archaic-ness that might exist just by inertia of the company that big and successful. 

There's a lot of really good that you can down scope and implement, whether it's go to market, whether it's financial operations and capital strategy, whether it's marcom, messaging, positioning, crisis comms, right, analysts. Whether it's, you know, product strategy, sequential ordering of your roadmap and sprints, like all these different things. Like when you're in a big company like that, there's a lot of expertise and experience to then take and then bring to a startup scale. 

NICK: Yeah. Well, they're definitely doing a few things right. And one of the biggest companies in the world. 

KYLE: One of the biggest companies in the world, and, you know, they're recently starting to turn a corner on cloud adoption and, you know, they bought net suite and they've made a lot of great acquisitions like Dine. And I think that's been a real catalyst and it's showing in their stock and the rest. 

NICK: Yeah, yeah. That's great, great experience. And then right after that, you founded York IE.  And as part of York IE, you work with a lot of startups and early stage companies. And, you know, if you could talk a little bit about the company and then also how some of the challenges that you see in some of these companies scaling growth. And a follow-up would be, how are these companies overcoming these sort of common challenges? 

KYLE: Yeah, so I mean, we decided to build York IE, we call ourselves a vertically integrated strategic growth and investment firm. We did it on the heels of our operational expertise. Like every job I ever had, I was the go to market business counterpart for technical engineering founder. No software and internet companies are founded by someone who can code, right? It doesn't mean they know how to scale it, you know, build it, finance it, build go to markets, build quarter models, build comp plants, take it to the moon, right? 

So when I thought about that, okay, this is what I did operationally. This is what I'm sought after for, you know, while I'm advising and angel investing. I'm only so scalable. So how do I turn this and package this into a company that I can invest in human capital and a team, a diverse and complimentary team, as well as in a data and automation platform that we call fuel, it's our strategic growth platform, to automate a lot of the marketing dependent intelligence or tracking of industries or competitors and comparators or content curation, aggregation, amplification? 

Like, how do we go do a lot of this, right? So what we did right out of the gate was we looked at startups and we said, what are the things that startups, where do they turn to today for strategic growth support? And it was everything from, you know, they create an independent advisory board of a bunch of either retired or busy operators. They might bring on a PR content agency to help support them. They might bring on an iBanker to help them fundraise. They might add a back office or CFO consultancy. They might bring on a VP of sales consultancy. And a lot of these companies can't hire a CFO, a CRO, a CMO, CTO, all right away, right? So we said, well, instead of all these things that are silo, what if we modularize a bunch of services, advisory services and capability, that are foundationally tech enabled services on top of our fuel platform and deliver those to the market in a low cost, accessible monthly retainer structure, right? So we always knew we were going to do that but to do that, we decided to go to market first with our investments practice business, which is a B2B SAS, early stage, we call it an evergreen syndicate. 

We basically have a capital pool of $10 million a year, high net worth individuals, family, and growing, by the way. We're going to three X that. High net worth individuals and family offices, and we're going to create a big inbound funnel, content, you know, we call it drumbeat marketing, bring them in the front door. And we see about 100 inbound B2B SAS companies a month. And we're going to do one investment a month. Right now we're averaging about 750K to a million dollar check. We're going to do 12 to 15 deals a year, and guess what? 

We're not going to invest in everybody. And they're not all going to be B2B SAS. They might be marketplaces or hardware businesses, or consumer businesses. So it ended up turning into this integrated funnel where come in the front door, you're looking for help, investment, whatever, and we're going to convert, right? We're going to keep you in the family. We're going to create this flywheel. So anyway, it's been working. And then I think startups, we found product market fit. They really like having kind of a single partner who can help them with a bunch of different capabilities. So we assign an account manager to every deal. And then we have practice leaders for every advisory services module, they're on our website at york.ie, and we are enabled or enabling companies to sort of get the support in a box that they need to get to the next level. 

With all that said, I think, how is it going? I think the startups are finding that we're able to help challenge a lot of their assumptions, help them avoid some of the traps or pitfalls or expenses that early stage startups get into. But honestly, there's no straight line. I think what startups really want is just someone who is in aligned incentives, who's in the game with them, who's an extension of their operating team, who they feel like gets their pace, gets their urgency, gets the ups and downs. Isn't just chasing, how do I get more money out of you this minute? And how are we playing the long game together? I think that's really what's making us some pretty unique and differentiated the market. There are definitely VCs who offer services, right? There's definitely services firms that invest, but there's not, you know, ones that are doing all that with a SAS platform, with I think as big of an ambition and aspiration that we have. 

NICK: So you guys are like a strategic partner to some of these? 

KYLE: Absolutely. I think in the earliest company engagements we have, like, you know, early stage, genesis stage, early revenue, I think of as kind of like a Swiss army knife. It's almost like executive coaching and advisory in a box. Like you want a little bit of help everywhere. We have companies doing 50, 60 million ARR. Those companies that are our clients, they look at us as a, you know, I'm going to work with York IE instead of an M&A advisory firm. Or I'm going to work with York IE instead of PR. I'm not gonna work at Edelman for PR, I'm gonna work with York IEbecause I like your model and your approach better. I got access to some different capabilities, right? 

So I think it's a little bit different with each. But yeah, I think that's a good way, a good way that we're positioning it is that, we lived a day in your shoes. We're also not from the cheap seats, right? Like we're still building our company and our SAS business and so I think people really relate to that when I can say, hey, the recruiting challenges, you're having the same recruiting I'm having. Or we're thinking about office expansion too. But in the world of COVID, people aren't coming in as much. There's four people in my office today, right? Like how does this work? And so when we're able to not only relate to that one time at band camp, at Oracle and Dine and Whipple hill was my first company in ed tech before that. And we're able to say like, hey, real time right now, here are our challenges and oh, by the way, I've talked to a dozen other startups this week. A couple of them have very similar challenges and be able to sort of do that osmosis training and collaboration. I think this is incredibly reassuring. 

I say a lot of times like a warm blanket, you know. I think they feel like they're just like safe. And again, that's not how you feel if you're a venture backed startup. No matter how friendly or value add your VCs are, it's still governance and their client is the LP, right? They are the money behind their fund. And so it's still governance and they're still a financial institution looking for return. We're looking for a return too, but ours is more of a wins in the win column. How do we help startups be successful relatively? We don't need to be chasing decacorns and unicorns with every investment or every advisory client. And I think that's just a very different, natural relationship that we see our founders having with us. 

You'll have to have a few of our founders on and many of them are in MarTech and sales tech. And, you know, see if they feel the same way. I hope so. 

 NICK: Absolutely, absolutely. We'd love to have that. And of course, we work with a lot of B2B SAS companies as well and marketing and growth marketing in general is a big, usually a big piece of their budget, a big piece of their focus. What are some marketing challenges, and I know you guys offer marcomms as well. What are some of the marketing channels that you've seen perform really well for startups and early stage companies? On the paid side, on the organic side? What works? 

KYLE: Yeah, so I mean, from our perspective, where we focus on, go to market marketing, we definitely are very focused on like go to market strategy, sort of like program mix at the top, you know, demand gen, program mix, team building. And then on the marcomm, we're really focused more on like content, media relations, analyst relations, like side of things. So we don't get into like performance marketing, paid channels, paid execution, the way that you do. We talk a lot about, from a marketing perspective, drumbeat marketing. What drumbeat marketing is, you know, a very tight messaging and positioning. Have two or three key pillars of points of view that your company stands for. And then beat the drum every day through all channels. Owned, earned, paid around those unique points of view. You have to market that bring your value prop to the customers you're trying to sell, right? 

For B2B specifically, that's a very brand building, community building kind of long tail play that we offer. But for B2B specifically, the programs we see where it worked the most are both, you know, it's coming back but in-person and digital events and programming. So, you know, even events like podcast interviews, or webinars are really great programs, but not just as owned, but also as syndicated or partner or paid, you know, with others, with different audiences than your own. I think that third party syndication is a big one. So where are your customers? Meet them where they are. From a content and collateral perspective. LinkedIn clearly is taking a big part of budgets these days, especially if you're B2B, software B2B SAS, because you can get reasonably targeted. I think those are kind of the areas that we're seeing the most. If you're going enterprise, unfortunately, a huge one's also analyst. 

If you're a B2B SAS play going analyst, you need the analysts that know who you are. That's a very pay to play, unfortunately. Is it earned, is it paid, right? A way it works, but that's the other area I'd say, especially if you're going more out market. We do a lot in vertical SAS sticks. So like B2B, which is a much more targeted, where there's like periodicals and industry rags and industry events and lists you can, you know, acquire or partner on. So it becomes much more what we call point and shoot from a go-to market targeting perspective, where if you're a horizontal play, we're all about spending the time on clear buyer personas, clear vertical targeting, clear market segmentation, clear value prop to those markets and repeatable use cases. 

NICK: Great, great. No, that makes a ton of sense. And you know, you guys are kind of focused on the strategy and then really on the tactical level, you led, I guess, you led the teams at each startup and based on the verticals and based on kind of the target metrics to determine which channels are most successful but you guys kind of own and really support them through that strategy. 

KYLE: We'll support them through the strategy. We'll bring in partners like your firm to execute, right? They're either going to do some of this in-house or they're going to do it all in-house or they're going to partner and do it. Again, it depends on the scale and stage of startups. Similar for you, I'm sure, in the earlier stage companies, you're doing more of the work and heavy lifting and as they grow, you're augmenting broader strategies. So it's very similar. I think what we try to do is tie it back to like, the core financial operations, capital strategy, go to market planning, scaling, marketing, competitive strategy, M&A strategy. I mean, even at Dine, we bought 11 companies on our path to a hundred million and we divested four product lines. And, you know, it's like, so we're always thinking about how do we, you know a lot of those were really little roll-ups or acquihires, but always being mindful of the market around you. 

We call it the market and approach to company building. And I think that's the way to build companies, right? And so for us, yeah, marcomm and marketing, go to market's one component, but obviously like, you know, there's a lot of companies these days burning tens of millions a year to get their growth and we try to at least help companies be a little bit more pragmatic. It doesn't mean we're not going to have companies, we invest in our advise that raise a hundred million dollars. It's just, we're going to hopefully coach them to do that in a way that's pragmatic and helps preserve optionality for them along the way, that doesn't, you know, the last thing you want is raise money at this valuation and then sell the company someday for half the valuation. Like no one wants that, right? So we're trying to really be a partner in that journey to help companies be successful relatively. 

NICK: Yeah, yeah. And I think that there's really a niche and a need in the space for that kind of a holistic offering. I think a lot of firms are kind of focused on what they do well, and it's a small piece of this cycle, but you guys are just kind of bravely saying, we'll handle, we'll take a holistic approach to this and support you in a lot of these different areas, which is what ultimately these startups need. 

KYLE: Listen, it makes it hard to bill. It makes it hard to bill, right? If we just picked one sliver or area, it's its own company and its own industry, right? So it makes it hard to build. The only companies that sort of look like this, the biggest management consultancies in the world, right? And they still have their angles but look at the Deloittes, the McKinseys, the Bains, the BCGs, like, those are the ones who kind of like do this, but would you ever as a startup founder think of calling them? No, right? So where do you go, right? You literally go to individual consultants and advisors, mostly, or small boutique shops and firms that are just siloed, busy, you know, can get expensive because their whole model's all about short-term cash returns. 

So it's just a different game we're playing. I feel very fortunate to be in the position to go create this company because I really believe it's like, you know, an evergreen company, it's very germane an authentic to my upbringing, to my background operationally and as an advisor and an angel to be able to bring that together and then figure out how to like systematically operationalize and scale that to deliver value to our portfolio is something that I think is a multi-decade, you know, evergreen business that could, we can grow quite large. 

NICK: Plus you've done it before. You've walked this journey. And you're not just teaching people theory. You're borrowing from your experience and kind of extrapolating. So that's great. 

KYLE: Yeah and back to your point earlier of like it's the experience as a child in small business and sort of this portfolio approach to business mixed with my fast growth, like ripping my hair out at night, mental health challenges. I thought I had brain cancer because I was getting migraines along the way, right? It's very hard to get into Oracle and the other side of an exit saying, wow, we did it, right? Thinking about like how to integrate the company and our technology and our customers, our offering, our people. And then like the learning from an organization like that. So I think like, everything happens for a reason. Like every stage of my journey, I feel like has prepared me to go build this company, prepared my co-founders Joe, Adam, Mike, the team, Janelle, Ashley, Kate. Everybody to go deliver, marshall on this journey, right? 

And I think this is a unique position. A lot of our York IE people have come from New York, from Dine and Oracle, have come from past portfolio companies. You know, so we're building our organization based on, I mean, Kate who runs our advisory services practice was our PR agency account director at Dine, right? So as you know, this is a relationships game and you work with people you trust and people stick with companies they enjoy working with. And I think we can do this and continue to make an impact on the startup space and as you said at the beginning, reshape the way startups are built, scaled and monetized. You know, there's a flood of capital. But what that means is there's going to be a heck of a lot more losers. There'll be more winners and there'll be bigger, but hey, you know, I really truly believe that if you can bunt single into first base, that's life-changing for most founders and most VCs would think that's a terrible exit. Right now in our portfolio, closing early next week, we have a 2X, a company that's 2X in a couple years, gonna be a seven figure payday for their female founder. And you know, it's in 15 months, right? Since we invested, right? Like to me, that's amazing. 

NICK: That's a win. 

KYLE: It's a huge win. It's changing her life, her husband's life, their family, their future, their kids, right? And a lot of other people involved in the company. And it's very meaningful and I feel a lot of pride in that. But if you measured that up and I talked about that with a tier one VC, they'd be like, oh man, what a failure, you know? And it's like, so again, I think this is, this is what's wrong with the space. And I think the places startups go for help are failing them and they're not available and accessible to them. And they're also just playing a different game with a different scorecard. And I think there's a lot more pragmatism. Like most of the world is smaller businesses with very successful people, like my parents, doing incredibly well for themselves and the future generations. And I want to celebrate that. 

NICK: Yeah, yeah. And I think we need more of this kind of thinking. Not everything is unicorn or a bust, right? There's a lot in between there. So I'm glad you had that approach. But I could talk to you all day, but I know you're busy. I really appreciate you stopping by and sharing your insights with us. This was extremely fun and insightful. So I appreciate it. 

KYLE: Thank you, Nick. Appreciate it and feel free for folks to reach out anytime. We're just at york.ie. We're on social channels at York Growth and I'm kyork20, that's my old football number, across all the channels as well. So I look forward to engaging. Thank you so much for having me. 

NICK: Thank you. Appreciate it.