From Family Business to Scaling Startups: Tech Investment & Innovation | Kyle York

Ever wondered how a small-town upbringing can shape a big-time career in tech? In this episode of Small Business Pivots, we sit down with Kyle York, co-founder & CEO of York IE, to uncover his journey from growing up in a family-run athletic footwear business in New Hampshire to leading a strategic growth and investment firm for tech startups.

Kyle shares invaluable insights on entrepreneurship, scaling businesses, and the balance between stability and growth. Drawing from his deep-rooted experience in retail, investment, and tech advisory, he reveals how vertically integrated operations can create long-term success.

We also explore the evolving tech career landscape, where remote work and geographic flexibility are transforming traditional industry norms. Kyle’s own transition—from college football to tech entrepreneurship—highlights the iterative career steps that many professionals face. Learn how opportunities beyond Silicon Valley are fostering innovation in diverse locations and opening doors for aspiring entrepreneurs.

As we navigate the challenges of scaling a startup, Kyle contrasts startups' agility with the slow-moving nature of large corporations. He offers insights into the entrepreneurial mindset, problem-solving, and execution. Through the lens of York IE, he shares how startups can turn ideas into successful ventures, build high-performing teams, and redefine success in today’s digital-first economy.

Join us for this insight-packed conversation with Kyle York, and gain expert advice on growing, innovating, and thriving in the fast-paced world of tech entrepreneurship.

Kyle York: co-founder & CEO of York IE

Website: https://york.ie/

LinkedIn: https://www.linkedin.com/in/kyork20/

Podcast: https://york.ie/podcasts/

Blog: https://york.ie/blog/

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Chapters

• 0:00 Entrepreneurial Journey in Small Business
• 9:01 Tech Careers and Geographic Advantages
• 17:52 Tech Advisory and Investment Firm Building
• 27:15 Navigating Entrepreneurship Challenges and Opportunities
• 35:00 Success and Business Growth Insights

Transcript

Speaker 1: 0:00

All right, welcome to another Small Business Pivots. Today we have a special guest from around the world and, as I say week to week, only the business owner can say their name and their business, like the business owner. So introduce yourself where you're from and your business.

Speaker 2: 0:15

We're an advisory and venture capital firm for tech companies and we are headquartered in the Granite State, which is New Hampshire.

Speaker 1: 0:30

We're about an hour north of the city of Austin Fantastic, so you're just a little ways from our headquarters in Oklahoma City, but you said you'd been here and you've got some stories on the IE and all kinds of things. So, listeners, you might want to buckle up as we introduce the show and we will be right back. Listeners, you might want to buckle up as we introduce the show and we will be right back. Welcome to Small Business Pivots, a podcast produced for small business owners. I'm your host, michael Morrison, founder and CEO of BOSS, where we make business ownership simplified for success. Our business is helping yours grow. Boss offers business loans with business coaching support. Apply in minutes and get approved and funded in as little as 24 to 48 hours at businessownershipsimplifiedcom. All right, welcome back to Small Business Pivots. How do you think we're going to help our listeners today?

Speaker 2: 1:25

Yeah, I think it's an exciting time for small business. You know, I think there's incredible momentum in the kind of business climate, especially in America here with the latest election results and inauguration, there seems to be a lot of excitement for both the main street entrepreneur and the world I work in is more technology startups, uh, and you know where I think we're all hoping for more funding and you know, lower interest rates and uh, just continue to continue consumer spending, uh, and that benefits all of us. So, you know, excited to talk today about, uh, yeah, the life of an entrepreneur and how there's no straight line, right, michael?

Speaker 2: 2:06

to success in these businesses.

Speaker 1: 2:09

Yeah, and just to kind of give a timeline, I think it's important because we did just have the inauguration at the time of this recording, two days ago, and just yesterday our new president announced a very robust AI tech. So I think this is going to be interesting to see what we talk about today and, just in a matter of a year, how things are different. So let's go ahead and get started first with. I know for a lot of business owners, they relate to people that they can kind of connect with. So what was your upbringing? I know a lot of people have a different upbringing, but that way we kind of get a place and sense of where you are today.

Speaker 2: 2:52

Yeah, I think it's going to be quite relevant for the audience. I grew up here in New Hampshire, small town, new Hampshire. I think the population of the state is just north of a million, the whole state. I think the population of the state is just north of a million, the whole state and the city and town I grew up in. You know 150 or so thousand people combined, so you could kind of get a little perspective Hour north of Boston. I grew up in a small business. My parents were entrepreneurs, my grandparents were entrepreneurs, generation one of that small business was it actually an athletic footwear manufacturing business? Um, that made athletic footwear uh, long before the days at nike and, you know, reebok and under armor?

Speaker 1: 3:34

um, business started in 1940s I didn't think there was anything other than nike and reebok and I know isn't it weird to think I actually asked that all the time?

Speaker 2: 3:43

I'm like was it like a big brand and it's like you know it. Isn't it weird to think I actually ask that all the time? I'm like was it like a big brand? And it's like you know, it wasn't like your shoes were branded, you know. Back then it was like that's what Nike innovated and it's like oh, um, and the name of that um was actually called Indian head shoe manufacturing company and um, many, many listeners might've even had because they have like ice skates and um. Still on ebay today I can find old shoes and football cleats and soccer cleats it's amazing shoes it's really cool.

Speaker 2: 4:08

Um, yeah, and that business ran for about uh through into the 70s and my father actually married in and he was a shoe salesman and ended up building the outlet store for the manufacturer. And then when the, the manufacturing business shut down at retirement age, at Gen one, my dad turned that for the next 45 years into a main street sporting good retail and team outfitter. So they did like uniforms, equipment for the high schools, little leagues, pop Warner teams, colleges locally, and that's where myself and my four brothers I'm one of five uh sons to my parents, don and gail I'm the middle, which is so obvious at the end of this podcast, but I'm the middle um, I'm in your camp.

Speaker 2: 4:57

I'm the middle child middle child or podcast hosted guests. It sounds like, uh, but you know, I grew up, you know, in the, in the, you know main street. You know small business. You know and this is days again, before big box stores there was no dicks or models, or you know or internet. You know where you buy a glove on Amazon. You went into the local mom and pop shop and got fitted for your shoes and your glove and your and your equipment for sport, and so that's where we all learn business and I always say, growing up in a small business, you learn business fundamentals really, really well.

Speaker 2: 5:35

And it's funny to be in tech where so much funding goes into it and companies lose money to build big businesses. It's so backwards from if you're a Main Street entrepreneur, you need to make more money than you spend and you need to make a profit to go on vacation. It's just a different vibe. But what my parents did really well and I carry this forward to my career is they really vertically integrated their businesses. They bought the real estate, they had the retail store, but then they had the team sales and then they ended up launching a screen printing and embroidery business that would do the uniforms and the hats and then they ended up building an arena not as big as your Oklahoma City Thunder project, but there's an arena here for 10,000 people that they built across the streets and then they did parking. And that's the life of an entrepreneur, right? It's like to capitalize on your brand, your community, your footprint, and my parents taught us that really well along the way in our lives, really well along the way in our lives.

Speaker 1: 6:42

What would you say for those parents that are entrepreneurs? What would you say was probably the biggest thing you learned from your parents being an entrepreneur? Just so they have?

Speaker 2: 6:55

something to hand down to their kids. Yeah, I mean, one of the things about entrepreneurship that I fell in love with is, like it's the kind of like stick it to the man, like the not working for anyone else. You know mindset, you know like I ended up. I'll tell this more in a few minutes but I ended up building a tech business that we sold to Oracle, and independently building the tech business was very different than working after the acquisition for Oracle, which was at the time a couple hundred thousand employees, um, and so it was kind of that independent spirit and sort of like control of your own destiny. Um, and like that to me was like, even if it was hard, right, and even my dad always had to answer calls on weekends and nights and go in if the burglar alarm went off or there was a leak in the roof or whatever, like it was that kind of ultimate accountability.

Speaker 1: 7:45

Um, in that independence, that like really stuck with me and led to my entrepreneurial career in technology that's interesting because my kids one is in his mid-20s fixing to be, and that's what he strives to do is the freedom of not having to answer yeah.

Speaker 2: 8:06

I think it's and the thing I would say to any young you know, getting into their career is also like you got to find the hooks in your work with the passion, because like it's one thing to have the freedom, but imagine you have the freedom. It's something you don't even like to do, like you really need to, like want to get up every day. Like I can remember my dad. He'd make it home for dinner every single night and all of our sports. He never missed them, but he did go into the office every day at like 6am, you know, and you know he was gone right, he was out really early in the morning because he he had to make those trade-offs and sacrifice.

Speaker 2: 8:40

Well, if he didn't like love the business and love working in sports and selling coaches and athletic directors and he grew up as an athlete and he's in the Hall of Fame of the city of Manchester and he loves that environment, then yeah, it would have stunk if he was doing something he didn't love, even if he had the freedom. So it's probably balancing those two things. And too often people wake up 20 years into their career and they're like even you know, and they're saying I don't like what I do Like it sucks, like I you know, and then you're making like a career pivot but it's like, oh man, you're going to throw out two decades of experience Like that's kind of that's there's no, no, no line, perfect.

Speaker 1: 9:16

But you know you want to, at least try to to make, so it's not like you really learned anything along the way.

Speaker 2: 9:24

So that's, that's a good point of the pivots. Like you know, there's pivots that are like just iterative evolutions versus there's like a complete 180 shift. And I, you know, I always try to tell people, like, as you're evolving, like, think of it as iterative steps, don't think of it as like something brand new. Um, you know, so all those things Michael led me to, led me to, um, you know, uh, my my college. I went to undergrad business school, I, I played actually college football division two and I, um, really early on, when I got there, I realized I wasn't going to the NFL. You know, it just took took a bit for that to register. Um, and so, right in school, I started to get internships.

Speaker 2: 10:06

I got very lucky to get internships for very small technology companies. This was early 2000s. Some really great founders saw my energy and interest and ambition and work ethic. One of those first internships led to a seven-year run where I stayed through college all the way to a few years out of school, actually moved me to California and it was a software business in the education space. They sold software to prep schools, the K-12, private schools, boarding schools and even moved me to California. That's actually what brought me to Oklahoma City several times and I just fell in love as I climbed the ladder and kind of sales and marketing functions, which is my background. I just fell in love with, you know, evangelizing, doing deals with solving customer problems and, you know, making a debt right and whatever industry or sector I was going to go into, and so you know it's been an interesting. That was all very foundational stuff for me.

Speaker 1: 11:07

Quick question and that is you know, we all think of Silicon Valley kind of as the hub of tech and of course, where I'm at we have hub is really up and coming. It's probably one of the top three industries now in our city, austin is. Texas is getting real big Florida. There's some other states. Do you still think I mean, this is your opinion only Do you think, having been there, do you think that's an advantage? Do you think you really learned a lot more? Or do you think it's really expanding across the country? Because I know that we have a lot of listeners in the tech space and they're probably wondering the same thing of are we really as good as those companies or that talent out there?

Speaker 2: 11:47

Well, I mean, I'm wildly biased here, and I believe you can build a great company anywhere, even in technology, and I believe, especially in this day and age, with remote work and offshore development and Zoom that we're on now, I think it's all just a heck of a lot easier than it was 20 years ago to build a good company anywhere. But I'll tell you what. I lived out in California, and I moved home to become a chief revenue officer of a very early stage technology and infrastructure company, and it was back in my hometown, and many people said I was an idiot to move back from California to New Hampshire to expand upon my technology career, and we took that company from 15 people to 500 and up to 100 million in revenue, and we sold that company to Oracle, and then Larry Ellison, who just announced the AI initiative yesterday, with OpenAI and SoftBank that you were referring to in the beginning of the program. So I think now, in the year 2025, you could build a tech company anywhere.

Speaker 2: 12:49

There is a concentration of companies and there is a concentration of talent in Silicon Valley, though, and in New York City and in other major tech markets, and there's good and bad to that. Right, there's good in that big, big companies can find the talent they need. There's bad in that small companies have to overpay for talent if they are in those areas right. So it's why you're actually even seeing a lot of companies create different hubs and offices and remote setups and all that around the country.

Speaker 2: 13:19

But you know, I obviously am wildly biased, having built a successful tech career and now my advisory at Venture Capital Firm in Manchester, new Hampshire. It's not like the hotbed of VC or the hotbed of tech, but we advise and invest in startups all over the world, including in Silicon Valley. So I think people should live and work where they want to live and work. I think they should if that's because they yearn for their own community or to be close to family, or they like the culture in one area or the other, the weather, you name it. People should have that choice and they should be able to build good and successful careers in doing that.

Speaker 1: 13:56

Appreciate you sharing, because I just know of someone last year that moved to California because they thought there was probably more opportunities, more skill sets that they could learn and everything. So that's and plus the entrepreneurs.

Speaker 2: 14:08

Yeah, and, by the way, maybe there are, but there are also way more competition. So good luck with that right, exactly.

Speaker 2: 14:15

And the company I moved back to New Hampshire for is a company called Dine. We specialize. It was called the domain name system, but it was like technical infrastructure behind your websites. It was called the domain name system, but it was like technical infrastructure behind your websites. And our biggest clients in the world were all based in Silicon Valley the Twitters, the Netflixes, the Salesforce, the Workdays right.

Speaker 2: 14:38

So I spent the majority of my career also in Silicon Valley and you know, you come to find out that. You know you both put your pants on the same way, you put your shoes on the same way and you know even a lot of people in Silicon Valley, by the way, went to schools in the East coast. You know, with the public school, private school, right. So it's just, it's just, it's just, they just. Silicon Valley has a headstart from the beginnings of like Hewlett Packard and companies in 1960s who just sort of like, created these big trees that drop seedlings down over decades. I think a lot of other ecosystems are going to emerge around that. I think that's a good thing. I also am of the belief that every company should be a tech company or technology enabled in some way. That's the world we live in. Certainly that's how it's moving with AI. How does AI help augment your organization and your role and make you more efficient and more exceptional? I think all these things make the proximity just a bit different.

Speaker 1: 15:40

Great advice and insights for all those questioning their talent level. Yourbusinessyorkie, you have a very interesting story on that, so let's start there.

Speaker 2: 15:54

Yeah, well, I gave you a little bit, so you had asked when we had met prior to the recording. The ie and IE stands for investment enterprise, but the ie is intentional. As I mentioned, my last company we sold at, oracle, was a domain name system provider, so we helped do internet routing for companies in four countries, and so one of our main clients was actually the country of Ireland and the domain name registry of IEDR, which is ie, and we spent a lot of time over there. Actually, back to the point we're making around Silicon Valley, many Silicon Valley companies were actually hiring their technical infrastructure talent in Dublin, ireland, and building pods in there as their entry to Europe and EMEA. I spent an incredible amount of time because those were the buyers of our services at Dime for domain name management in Dublin, and so I just grew an affinity to it and originally I actually launched Yorkie as my personal angel investing advising website, my blog. It was a personal thing while I was working my day job, and when we went to launch the firm, we had this vision that startups need a one-stop resource hub for services and support and infrastructure and capital, and that we thought we could build that firm. Think of us like a modern McKinsey, a modern Bain. That was our vision and as we sat around and talked about it, we realized that there was great traffic and great portfolio and great content already at Yorkie. And we decided and my co-founders, it wasn't my idea, I swear to God they decided, hey, you know what, let's just run with what you've already got and build a brand around it. And we've been off and running and this is about. We've been at this for about five years.

Speaker 2: 17:52

York IE's core operating business provides what we call advisory as a service to technology companies. We have resources to support you across research and development think software development, mobile app development, more technical services. We have go-to-market services to help you with messaging, positioning, content, pr, those types of things. And then we also have GNA services to help with financial planning, financial modeling, bookkeeping, tax, those types of things. And we've technology-enabled, we're experts in all the technology stacks across R&D, go-to-market and G&A.

Speaker 2: 18:27

And we have a massive team in India. So York IE is globally about 200 people. We have about 35 or so here in New Hampshire in our headquarters, but then we have about 170 in India where I'm actually heading in the next week to visit. So it's all full-time employees globally. So it's all full-time employees globally. It's all our own captive IP, proprietary data and tools and our own teams that really become an extension of the startups and technology companies we work with. And then we also have an investment fund. We're a venture capital firm. We invest in early-stage B2B software businesses. That's our thesis. Saas is what it's called the software-as-a-service subscription business model. That's where we focus, and we have 60 portfolio companies and we've deployed around $60 million in these companies. So we have a really big investment base and a really awesome and exciting group of companies that we support.

Speaker 1: 19:23

What triggered you to take? You're listening to Small Business Pivots. This podcast is produced by my company, boss. Our business is helping yours grow. Boss offers business loans with business coaching support. Apply in minutes and get approved and funded in as little as 24 to 48 hours at businessownershipsimplifiedcom. If you're enjoying this podcast, don't forget to hit the subscribe button and share it as well. Now let's get back to our special guest what triggered you to take the leap of faith into entrepreneurship? I know you were raised in the entrepreneurial world, but for a lot of listeners they're like I got this great idea of listeners.

Speaker 2: 20:08

They're like I got this great idea but I like my paycheck. Yeah, you know, with me it was kind of DNA and you know it was pretty organic. You know I was really young when I joined startups Right, and you know as much as I took some risks to join them. I was at an age where, you know, I didn't have a family yet, I didn't have a mortgage. I had fluidity and flexibility in my life. I could take some risks. I could not just chase the paycheck but also chase the experience and the opportunity and see where it went.

Speaker 2: 20:37

I was fortunate to join great companies with great entrepreneurs and founders. In my company, dine that we scaled and sold to Oracle, I was just really fortunate that it was a complementary parts fit. The founders were engineers, they were very technical. They didn't have a sales and marketing business growth guy. I was able to come in and build all those teams and systems and processes and organizations and be entrepreneurial in a very entrepreneurial environment. That led me to launch a bunch of other companies investments companies and real estate companies and other things. We even launched a shoe brand called York athletics to to honor the family.

Speaker 2: 21:18

And so we have all these different businesses and then really it was kind of after my exit, which was a life-changing financial event for myself and future generations, that I sit there and really reflect on like, yeah, I'm in my mid thirties at the time, what am I going to do the next? You know, I don't know next half of my life, right? And and I and I kind of looked in the mirror and I was like you know, if there is a way for me to build a startup of my own that could help other startups, um, and invest in other startups and be this community that can kind of, like you know, help others achieve the mountaintop, whatever that might be right, whether that's financial independence, whether that's some big exit someday to a big tech business, it doesn't matter, everything in between. I just wanted to kind of go see what I could do and build that.

Speaker 2: 22:06

I also didn't like in my world you know a lot of people who are successful exits just become venture capitalists and that just seemed kind of boring to me. You know I didn't want to just show up at the board meetings and, you know, govern businesses I do that too, don't get me wrong. But I wanted to still have a business of my own that I was trying to grow and scale and hire teams and, you know, really try to inspire. So for me it was organic phases and steps and you know, obviously an exit or a financial event makes it easier to take risk, you know relatively. But you know I'm going for it right. I mean I kind of like there's a great line in the movie Rounders about like you can't lose what you don't put in the middle but can't win much either. You know it's like a great matt damon, uh, john malkovich movie and yeah, that's some like lines like that.

Speaker 2: 22:55

I always kind of whispered my in my ears, you know, and I'm like, all right, let's keep, let's keep at it right what advice would you offer tech people trying to build something?

Speaker 1: 23:08

Because I'm sure there's more than a dozen or so people trying to come up with the next big software, probably like a million billion people like everybody's got a great idea. So what would you say? Is that you've learned being in that space? What, what, some insights you could offer.

Speaker 2: 23:26

Yeah, I mean, it really just comes down to the exit, the business building, execution. You know, I think everybody's got an idea. Like you said, I got 50 ideas in my brain but if you can't go all in and you know, build organizations and teams around you to go execute on those ideas, it's just an idea Right. And you know, when we meet a startup who has a good idea, we call it the market-in approach to company building, and what I find a lot of times is ideas that come from especially engineering technology. Founders tend to be like I know I can build it. Ideas, not the market needs this. And here's how I competitively differentiate this idea from anyone else who might try to build it. So that's like the market-in approach. It's like studying your market, looking at competitors, looking at comparators, looking at the legacy players, looking at the innovators, understanding how you can carve your unique path, your wedge, into the market that you can then scale upon. So that's the challenge In tech. It's like no one builds it. No one attempts to build a small tech company. You're not trying to build a tech company. That's like a small business. The reason people build tech companies is to build something big, and I think that's like a. Really you don't really know what you're signing up for when you get into that. Same thing with raising venture capital. If you're going to raise outside money, even if it's angel money or bank debt money, you just need to know what you're signing up for. And when you raise venture capital, you're actually selling a little bit of your company to a partner. They own a piece of it, so you really need to know what you're getting into when you're building it.

Speaker 2: 25:00

I wish I had a magic formula. We make a lot of investments, we advise a lot of startups. Sometimes the ones I think are going to be the biggest end up flopping, Sometimes the ones I question become the biggest right. All you can kind of do in the world I play in is try to help steward as many along as possible. Clearly, when you're an entrepreneur doing your own thing, though, you're making a bet on one, and what I remind people many times is when you start a startup or you join a startup, you're betting on yourself just as much as you are the startup, and you know that's a test of resolve, of persistence, of salesmanship, of follow through. There's a lot that kind of goes into it that you know it's not easy, it's not for the faint of heart.

Speaker 1: 25:43

Yeah, no, it's not. Well, I have some question. For probably more of your service-based businesses, this is applicable because in your world, technology changes on a dime, and so, for instance, the recent guest we just had now, this was a long time ago, but they had this bright idea in the 90s. They built the software. They got a humongous client thinking they were set for life, and then the internet came around, you know. So their software was irrelevant now, and so in the tech world that you're in, that probably happens every day. So how? But in the kind of the service-based world we have a little bit more notice, if you will.

Speaker 2: 26:25

So how do?

Speaker 1: 26:26

you? How do you move quickly to know where those pivots are?

Speaker 2: 26:32

It's a great point. I think what's interesting for us is on the investments business, we only do tech and software and SaaS. On our advisory business, we sort of work with any company who wants to grow or who wants to be more technology-led or implement technology. It doesn't mean they need to become a technology company, but even services businesses are trying to figure out how to better leverage tech to do better service delivery or make themselves more scalable or reach a larger audience. So I think you're right about a little bit more lead time, but at the end of the day, if you're upscale, it's harder to pivot or iterate. If you're smaller, it should be easier to pivot or iterate, and that's kind of the dichotomy. I see is like you know, when I worked at an Oracle, it was very slow moving right, even though it had all the resources in the world. Getting anything done or reinventing yourself was near, damn near, impossible, right? When you're a small company and you're a small team, um, your ability to sort of adapt or die is is right, staring you in the face every day, right? So I think it's just like realizing that the nature of the smaller business that we may all operate in is is not precise and and you can't be so um, so pig-headed to believe that the idea you had at Formation is the same thing you're executing on in five years or ten years or three years. I just think in tech that iterateness is almost a little bit more like week-to-week or day-to-day or month-to-month or whatever. We're in more service-oriented or other more established industries it might be like, yeah, six months or a year to adapt, or three years to adapt, or you know um, but, but, but again, there's also like like big adaption, you know of like, of like existential issue, and then there's a lot of micro. I always say it's like it starts like a lot of death by a thousand paper cuts, right, it's like it's like even if, even if something great happens, you know there's always a lot of bad stuff going on beneath the surface. You know so um it it again, it's just more of the the.

Speaker 2: 28:39

Where I see people fail in entrepreneurship is when they don't go in with that as baseline, right, when they when naively or ignorantly, or maybe they had a great career in corporate world and they want to go off on their own and be a consultant or start a local business. And it's not all sunshine and rainbows everywhere. A lot of times, when someone works in a big corporate, they have no clue what's going on in HR and accounting or in legal these are things that are disjointed and not connected to them. Or in a small business, everything's your problem, especially as a CEO, as you know. That's the type of stuff I like to think about. I do think entrepreneurship is a DNA thing too. I'm not saying you can't teach it or you can't learn and become better at it, but you, you really got a deep down in your core. You know the amount of people I've seen go really early into startups or start their own startups or join a small business or quit their job to watch a brewery and then hate it. Um, you know, in the end it's kind of like if you look at their like personality, dynamic and their you know resolve and, like some of these like you hear grit, grit. Some of these things you think about when you think about an entrepreneur, regardless of type, some people just don't have it. Sometimes you need to go do it to figure out if you have it or not. Other times, you and I, michael, can look at them and go, eh, it's going to be tough.

Speaker 2: 30:06

I worked with a lot of people at Oracle, for example, when I got acquired there, who were like enamored by you know young entrepreneurial guy. I ended up being the GM of our business unit at Oracle. Our group grew to 8,000 people, you know, and a lot of these people who worked there 35 years would come talk to me and we'd trade notes on career and I would like walk out of those meetings. I'm like like how could you stay here this long? We used to call them corporate survivors. It was almost like a reality TV show or something. It's like wait a second, you've had 17 jobs in 30 years, all in different divisions and departments and levels and comp and all this stuff. It's just all about protecting your compensation, protecting your stock you were given or earning. This is a different ballgame in startups, right?

Speaker 1: 30:53

Yeah Well, you make a great point, because I know a lot of small business owners or startups. They think if I just get this business to this level, my life will be set. And one of our past guests on the podcast he said let me tell you the difference, cause he's got a, you know, $500 million company. He said let me tell you the difference between when I started and now. He said when I started it was like writing a sea dew and you can zip and zag and you're not going to do much harm. You might tip over, crash in the water. You try to make those turns on a yacht.

Speaker 1: 31:30

you've got casualties, you've got major damage and A you can't even do that. Like you were saying, an oracle is like moving like a.

Speaker 2: 31:39

An oracle, I would equate to like a, like an ocean liner with that, you know, right, like yeah, that doesn't turn at all.

Speaker 2: 31:50

It doesn't turn at all, like you know, and and sure, like on the ocean liner and the crate in the back, like maybe there's some movement. But, like you know, it's tough to turn the whole thing Right and that's going to take a decade or two, two decades, right, the Oracle cloud has been a two decade thing and it's starting to pay off right Big time. But you know it's a very different environment and I think that's really important for people to just recognize as they're thinking about career paths.

Speaker 1: 32:15

Absolutely, because I always say we don't know what we don't know as entrepreneurs, and until you've been there, you don't know. So I'm just sharing that.

Speaker 2: 32:32

For those that think there is no magical level that you're going to get to, that all your problems go away and your life is set, unless you sell it for a billion dollars. And then yeah, but I would tell you, even like having lived in a small family business, having worked in small startups, having worked in mid-sized startups, having worked in large startups, having sold my company to one of the top 50 corporations on the planet with the top five richest guy at the helm, there's problems at all of them. They're all actually hard. Every one of them is very hard. It's just a different level of hard and there's a different level of context and there's a different level of perspective you need to have at each of them. Then sitting on this side of the table is both now an outside advisor, consultant and board member of many startups. There's different contexts, there's different stages, there's different perspectives and they're all hard.

Speaker 2: 33:13

I think what happens too often is people just pattern, map the different stages or they try to run the same playbooks or templates or give the same advice. One thing that's hard about a podcast interview when you get asked about advice, you have to be pretty generic. They don't know the situation or context of the listener. If I was sitting one-on-one, I'd be like tell me more, learn, learn, learn. If I were you, I would think about the next phase of your evolution and growth. I'm sure you deal with this all the time. It's not like you can just give the same advice to the same five companies, and also you also don't even know the philosophies or ambitions or aspirations of the people running them right. So it's a unique challenge, I think, in our world to coach and guide when everybody's very different.

Speaker 1: 34:05

What is a pivot that you would not do, or do again, or wish you would have done along the way?

Speaker 2: 34:13

Jeez, I don't know. I mean, I think, in scaling dine, you know that was a really interesting time. Um, we, you know, we, we ended up raising a bunch of money by the end of that company for private equity and growth equity. And you know, I think there was like a window of time where, like you know, we, we, if we played our cards right, it made some interesting product development decisions, some different M and a decisions could have been an independent company that went public on its own. And then, you know, again, it's isn't this funny perspective. I'm giving like we sold for $600 million and I'm acting like could have, could have been better. But literally there was a few years in there where I was like man, if we made this product decision or we bought this company, or we have evolved from deep domain infrastructure to cybersecurity, our path ahead could have been very different.

Speaker 2: 35:00

But then again, I look back at the context. These are easy things with hindsight. We were all really young. It was like a wild ride. It was high stress, high, high anxiety. Like you know, I could barely breathe on the end of that journey, you know, just wanting so bad to see it culminate in a life-changing event, which it did, um. But you look back sometimes and you're like I played this a little different, play this a little different. It could have been different, um, but that's a. That's a good problem to have. That's a big pivot, pivot, that's a first world problem, all those terminologies. But again, I've seen it all along the day.

Speaker 2: 35:32

I could have given my dad advice that he should have gone more digital, he should have franchised, he should have built the website. He could have been the next Dix. But then he talked to my dad and he's like I wasn't going to mess with a good thing. He's like I was incredibly successful. I was able to be a small business owner. I supported five sons. I sent you all through college.

Speaker 2: 35:51

I used to always ask him why didn't you want any of us to go to school and come back and work here and help you build this and scale this thing and bring in technology and all that he's like? Well, first of all number one, I didn't work my ass off to send you everywhere to come back and do this here. Number two, I didn't work my ass off to send you everywhere to come back and do this here. Number two I'm not taking a pay cut to hire you.

Speaker 2: 36:13

So you know that's the way it is, and I used to, over the years, always try to bring software into the for inventory management or for, you know, credit card processing or right, and he'd be like, get out of here, I have my way of doing it, I have my systems, like. So again, that's what I mean about the context, right, like he could have tried to go big with it and it could have imploded and ruined a good thing, right? So I think all these things are very relative. Someone said to me when I was very young that success is relative, and I think that's a really, really important lens for everyone listening to think about, like, what's relative success to you and what are you playing for? And that's going to be different for everybody.

Speaker 1: 36:48

So your company York, who is this for? In other words, like size industry. I know you said tech, but yeah on the advisory services business.

Speaker 2: 36:58

It's really any company who's looking to take the next level, to grow, who's looking to technology enable their business. So they want to build an app, internally or externally, whether they need help with marketing or finance or R and D. We have service capability for all that. You know, our biggest company clients probably doing a couple hundred million in revenue Smallest is a brand new idea. Who wants to build the next great app? Right? So it really does fit everywhere in between.

Speaker 2: 37:22

But it's definitely like a more of a tech centric, growth centric, centric, ideal customer. We actually partner with a lot of other venture capital firms, private equity firms, banks, law firms who have portfolios of companies who could use help in operating their business, and that's where we come in and support them. And then anyone listening who's building a SaaS business, a B2B software business that's where we are a seed stage, pre-seed stage investor, so we're a true investor. It's usually companies have found some initial traction or looking for a little bit of early growth capital to take it to the next level, but they want that capital amount just to be dumb money. With all respect, they want to actually help and resources and people have been there done that to support them, and that's what our 200 plus person infrastructure can help provide.

Speaker 1: 38:10

I know we've just barely touched the surface of what you do and your experience. How can people follow you directly or get in touch with you to learn more?

Speaker 2: 38:22

Yeah, that's great. I'm across all social channels at K York 20. That's my old football number. I've had that since AOL, instant messenger and like 93. So you can find us everywhere we're very accessible. I'm all over LinkedIn. You know you might have to mute me, you know, because I'm always putting out, you know, opining on the state of affairs in our world, right, so but I really appreciate you having me, Michael, it's been fun.

Speaker 1: 38:59

My pleasure. Well, I will say thank you for the throwback, because I'm not kidding you and you may have done this to some other people I forgot when I was a kid that we had to go to a local store to get the numbers ironed on our jerseys, get our shoes fitted. I forgot all about that because I've been so used to Amazon and Dick's and Academy and all these other stores, but it got so busy at that one store. You had to make an appointment, your team had to have an appointment, you had to go in between 2 and 4 on a Tuesday or something or you weren't getting your jersey in time. I forgot all about that.

Speaker 2: 39:35

Imagine the visceral reaction I have now when I have to go buy one of my three kids' sporting equipment. I just had to get lacrosse gear. My middle child wants to play lacrosse this year and so I had to buy him all this gear. And you know, it kills me that I can't just go to Indian Head, my dad's old store, and do it with that personal touch, where they actually know what they're talking about. They could fit you up and size you up and make sure you buy the right equipment for your performance level.

Speaker 2: 40:03

And you know I have to go kind of like through the commodity factory of Dick's to pick it all up.

Speaker 1: 40:08

Right it's just it is. It's a different world, but you're right.

Speaker 2: 40:15

A lot of a lot of these things are a kind of flashback and it's actually we do a lot of work in other like vertical industries that are like building software for a specific vertical, and so we get a lot of this throwback to like, oh, that's how it's done, pen and paper, or like in person, like no digital experience, you know, like so we, we we get this a lot in my world.

Speaker 1: 40:33

I bet. Well, I always end with a question, and that is if you're in a room full of business owners all sizes, different industries what's a something you could offer to all of them that's applicable? So it could be a quote, a book, some insight, something you learned along the way.

Speaker 2: 40:50

Yeah. So one thing I always talk about is in college I actually had in one of my classes you could get a guaranteed A if you brought in a notable guest speaker to class. So you get three big projects for the semester and you get one A if you bring in a guest speaker. So I brought in the founder and CEO of Total Gym.

Speaker 2: 41:11

Remember that, with Christie Brinkley and Chuck Norris, it was like the infomercial. He was a college teammate of mine's father and he came in and he told this amazing story about what made him successful and it was all around honesty, passion and persistence. And I remember just back then thinking to myself like he just had this great way of speaking because like he, he was almost like like an accidental success. He was like a bodybuilder who wanted to come out, who injured himself in his back and he wanted to come up with a, a way to um have like low resistance, um, working out. That didn't wasn't like heavy, heavy, uh, you know dead weight, you, you know working out. And it always stuck with me Always be honest, always be persistent, always be passionate, you know, I think that's what separates.

Speaker 1: 41:58

Yeah, that's great advice. Well, you've been a wealth of information and a blessing to many. I appreciate you, Kyle, for sharing with our audience today and wish you continued success.

Speaker 2: 42:08

You as well. Thanks for having me.

Speaker 1: 42:10

My pleasure. Thank you for listening to Small Business Pivots. This podcast is created and produced by my company, boss. Our business is growing yours. Boss, offers flexible business loans with business coaching support. Business loans with business coaching support Apply in minutes and get approved and funded in as little as 24 to 48 hours at businessownershipsimplifiedcom. If you're enjoying this podcast, don't forget to hit the subscribe button and share it as well. If you need help growing your business, email me at michael at michaeldmorrisoncom. We'll see you next time on Small Business Pivots.