🎙️ How Kyle York Built a $100M Revenue Engine and Created York IE’s Revolutionary Advisory Model
In this compelling episode, Kyle York, CEO and co-founder of York IE, shares his remarkable journey from middle son of five boys in New Hampshire to building a venture capital and advisory firm that’s revolutionizing startup support. Through candid stories of scaling Dyn from $3M to $100M in revenue, battling debilitating migraines during high-pressure growth phases, and ultimately creating a unique dual model combining investment with hands-on operational support, Kyle reveals how authentic leadership emerges from embracing both ambition and vulnerability. From his unexpected connection to Ohio State’s Coach Ryan Day to building a 225-person global team with operations in India, Kyle demonstrates how staying true to family business values can drive innovation in the venture capital world.
✨ Key Insights You’ll Learn:
Building from middle child competitive spirit into sales and deal-making expertise
Scaling revenue from $3M to $100M through inside sales and digital demand generation
Creating integrated advisory and investment model serving 250+ clients globally
Founder-market fit importance over product-market fit in early stage investments
Mental health challenges of high-pressure leadership and coping strategies
Bootstrapping businesses versus venture capital growth-at-all-costs mentality
Building sustainable “pragmatic growth” companies in secondary markets
Leveraging global talent through strategic offshore operations centers
🌟 Kyle’s Key Mentors:
Frank (High School Athletic Director): Recognized his natural selling and political abilities, encouraging authentic leadership approach
Whipple Hill CEO and Head of Sales: Pushed him into sales role despite initial resistance, accelerating career trajectory
Dyn Co-founder (High School Classmate): Recruited him as “co-founder they never had” to build enterprise sales engine
Various Therapists: Provided mental health support during high-pressure growth phases, including life-changing post-it note advice
Adam (Co-founder and CMO): Childhood best friend and high school quarterback who suggested naming company after Kyle’s existing brand
👉 Don’t miss this powerful conversation about building companies with family business values, the importance of founder-market fit, and how personal struggles can fuel professional resilience in the high-stakes world of venture capital.
LISTEN TO THE FULL EPISODE HERE
Transcript
Anthony Codispoti : Welcome to another edition of the Inspired Stories podcast where leaders share their experiences so we can learn from their successes and be inspired by how they’ve overcome adversity. My name is Anthony Codispoti and today’s guest is Kyle York, CEO and managing partner and co-founder of York IE, an advisory and venture capital firm based in Manchester, New Hampshire. York IE works with early stage B2B SaaS startups focusing on sustainable growth and building strong community impact. They offer advisory services and selective investments to help tech companies scale effectively, creating jobs and generating wealth in the process. Kyle has an impressive background, having previously helped grow revenue from $3 million to $100 million at a prior company and has been recognized for his innovative strategies in the tech sector. Under his leadership, York IE has supported many emerging ventures, developed new market research tools and shared leading insights on industry trends. He also wrote articles on industry trends and best practices demonstrating his commitment to sharing expertise with the broader community. With hands-on experience in consulting, building technology stacks and optimizing operations, Kyle brings a wealth of knowledge to our show. Now, before we get into all that good stuff today, our episode is brought to you by my company, Add Back Benefits Agency, where we offer very specific and unique employee benefits that are both great for your team and fiscally optimized for your bottom line. One recent client was able to add over $900 per employee per year in extra cash flow by implementing one of our innovative programs. Results vary for each company and some organizations may not be eligible.
To find out if your company qualifies, contact us today at addbackbenefits.com. All right, back to our guest today, the CEO of York IE, Kyle York. I appreciate you making the time to share your story today. Yeah, I appreciate you having me Anthony. Okay, so before we get into talking about York IE, I’m going to talk just a little bit about sort of your past leading up to this. You held a variety of roles, different companies. And I guess before we even get into some of that, maybe you can help frame for us what is Kyle’s superpower? What are your strengths that have allowed you to be successful?
Kyle York : Yeah, so thanks. Great question to start it off. And I appreciate the background. I was sitting here. Sometimes it’s interesting to reflect when you’re getting kind of introduced and to think about the long journey you have to get to where you are in your career.
So I think superpower wise, I’m an interesting character. I was the middle son of five boys. I grew up in a sports competitive household here in New Hampshire, Southern New Hampshire. My parents actually owned a Main Street small business that was a sporting goods retail and team outfitter. So I’ve kind of, if you think about that, middle son, five boys, athlete, I played college football at the university for four years, division two. All these things kind of lead to the fact that my superpower has really been about being competitive and aggressive and ambitious. And I’ve just channeled that into a sales and marketing career, evangelizing my companies and my technology and my customers and my industries and doing deals, right?
Being a business development sales oriented deal maker. And that’s been the commonality and common thread throughout my career. In the beginning of my career, I kind of shied away from it. I thought sales and deals were sort of like snake oily and I don’t want to be pushy. But when you really find your hooks and the companies you work for and you believe in the technologies or the services or the offerings you have becomes a heck of a lot easier for you.
Anthony Codispoti : Yeah, let’s explore this a little bit because I’ve run into lots of people who have found themselves in a similar position. I earlier in my career felt the same way. Like, I don’t know if I’m like a very good salesman because, you know, I had this sort of, I don’t know, stereotype in my head of like a used car salesman is sort of the good sit, like he’s just pushing and he’s like over the top and, you know, not like super authentic. What was it for you that kind of like flipped that around and said, no, I’m actually good at this. Like I’ve got the skills for this. I need to think about it differently.
Kyle York : Well, I think it was honestly the juxtaposition of like, I thought of like sales careers as like corporate, you know, and I grew up in a very entrepreneurial, you know, stick it to the man, you know, how hard you work and, you know, how well you do, you know, dictates your future, right? And that’s how my parents running a small family business operated, right? If you didn’t make a profit, you didn’t get to go to dinner or go on vacation or, you know, get some, get to be able to buy the new car that you need for the family, right? And, you know, I don’t think that’s like necessarily fully translatable to venture capital in the tech landscape.
It’s not how it has sort of been built. So I always looked at it like, like sales jobs as like guys in a suit with a briefcase, you know, and being very corporate. And early on, I got internships and startups and tech startups. And here we are 20 plus years later, and that’s the career I had. And then what I realized in startups is they were kind of like the main street small business. They were very entrepreneurial. And, you know, a lot of startups, you know, especially in the early 2000s, you were wearing jeans and a t-shirt to the conferences, right? And, and it was actually a mentor of mine, really early on, who kind of like, you know, basically, he was actually the athletic director of my high school who looked at me and he said, York, you’re a natural seller, you know, he’s like, you’re a politician, you know, you’re, you’re, he’s like, his name is Frank Harlan.
He was in the halls of West High School in Magisteria, Hampshire. And, and he’s like, and I was like, I don’t want to be any of those things. And he’s like, you know, if you have like, if you’re rooted in integrity and you follow your passions, like you can do that really authentically and have a great, you know, life and whatever. And I, that actually led me to, I was student council president of my high school and, you know, I got internships and I majored in marketing and I was doing marketing jobs and, you know, writing content and doing programs and marketing and events. And I kept going to these shows and I’m like, I’m better than all the salespeople at evangelizing our story and building relationships and sharing the value of our solutions. And, and finally, the CEO and founder of that company and the head of sales of that company just pushed me in the pool and were like, you got to just follow what you’re really, really good at. And so it kind of was a natural evolution for me, but it kind of went back to kind of early days and, you know, just realizing that I had that natural, you know, natural salesman sort of evangelist, curbed deal making DNA mixed with the entrepreneurial spirit, you know, that’s the beauty of a sales rep, right? I mean, a lot of times you’re kind of independent to, you know, it’s kind of like running your own micro business. And that’s how I viewed the beginnings of my career.
Anthony Codispoti : And so that company that you were just referring to where they kind of said, hey, go get in the pool, Kyle, like you can do this. Was that, and I don’t know if I pronounce it din or dy.
Kyle York : No, it was actually before that I was dying is the name of that company. We’ll get to that one. But it was actually a company called Whipple Hill. What happened to me is I went to school at Bentley University at Walt Van Mass. And I wanted to get internships. And it’s right outside Boston. And I thought, oh, let’s get internships at Boston.
And my oldest brother, he’s built a phenomenal career in advertising. And so I wanted to go into like an Arnold or a holiday or an agency for the summer. And it turned out they didn’t offer any paid internships. And so I was like, I can’t afford to live in the city and supplement the apartment. So I moved back to New Hampshire.
When I looked in New Hampshire, there was no agencies. So I said, oh, maybe I’ll go in house. And I looked at a bunch of companies. And I just so happened to apply for internships to a bunch of tech businesses.
And I found this company called Whipple Hill that had, you know, mid 20 year old mid 20 year old founder, and they actually built a software solution for prep schools, K to 12 private schools. So there’s plenty in Columbus and in Ohio. And I spent a lot of time there. But you know, it was it was really, it was a it was a complete system operating platform to run your K to 12 private school. And that was the company. And I started as an intern spent seven years there climbing the ladder doing every, you know, crappy low level marketing job sales job. And just kind of they threw me in the pool and said go for it.
And it was it was incredible. They even offered me an opportunity to move to California. I moved to California for that company. I always say that move sort of accelerated my career five to 10 years, because I just took a leap and went remote as a remote seller to build a market in the West Coast that didn’t exist for the company. And it was a heck of an experience.
Anthony Codispoti : It really accelerated your career because you sort of develop these skills in terms of like, how to sell remotely? Is that sort of the
Kyle York : No, it was more than I took the risk and bet on myself, right? Like, I think, I think what a lot of people don’t realize about startups is that the earlier you go into a startup, you really need to be a builder yourself. And you’re you’re betting on yourself just as much as you are the startup at the earliest stages of startup. And, you know, that company was quite small. And, you know, I took a leap, I had belief in myself, they had belief in me.
And yeah, also the skills and the accelerated skills I was able to learn as a young person given that opportunity, it sort of forced me to grow up, mature and deliver, right? Because in sales, like there’s no hiding, right? Like, you know, you have a quota, you have numbers to hit, you’re paid in your base salary, plus your variable that gives you your on target earnings, like, if you don’t sell, you don’t have a job, if you don’t hit your numbers, you’re not making the compensation that you think you should make, right?
So it’s just a pressure cooker at the very beginning. And for me, especially as a remote seller, you kind of have your own book of business, your own targets, it’s almost like your own P &L to manage, right? And that really helped me, like, take business seriously and understand that like what I put in is going to dictate what I get out.
And again, that goes all the way back to my family business values. But it was like an environment that allowed me to do that and do that very young. I mean, I was 23 to 26 when I ran the West Coast Territory. I mean, this is wildly young. And the person I replaced was 45 years old, right?
With 20 years of sales experience. So, so, you know, it could have gone the other direction, right? I could I could have failed. And there was, you know, micro failings and issues and things that didn’t go perfect, of course, along the way. But in the end, it led it led to the next tracks of my career.
Anthony Codispoti : So one of those tracks I want to talk about is this company, Den, because I understand why you were there revenue grew from 3 million to 100 million. And I think you were there over the period of 11 years. First, before you explain how you helped accomplish that, explain what the company did or what it still does today.
Kyle York : Yeah, sure. So it’s Dyn and it’s short for dynamic network services. And Dyn became the world’s leader in managed domain name system services, so DNS. In essence, in layman’s terms, you know, when you type in a domain name into a browser, and are being served up content, the domain name system is what’s telling you where that content resides or what IP addresses live behind that website. So it’s almost like the phone book of the internet is a good way to think about it.
Anthony Codispoti : So is there just one company that provides that service?
Kyle York : No, I mean, you can get these, you can get DNS with, you know, your domain you buy at GoDaddy or network solutions or whatever your domain registrar choices, your ISPs provide some level of free or basic DNS. And then there’s, there’s been over the years of the internet, there’s been managed DNS providers who are third party, more highly performant, more secure, more reliable.
Anthony Codispoti : Like a cloud flare would be an example. Yeah, cloud flares a good example. Cloud flares does DNS and they do content delivery. So they actually serve the content as well. So they have both the pipes and the naming and the routing, but they also have caching and content servers on the backend.
But all the cloud platforms now from AWS, the Oracle, to Google, to Microsoft, Azure all have now DNS capabilities and the types of capabilities that Dyn made its hay around. But I was actually recruited to that company, the quick story there of how I went from Whipple Hill there as I was living in California with my now wife, Katie, and all pre kids, we were out there having a great time. She was working, I was working that job for Whipple Hill and actually high school classmate called me and he was one of the co-founders of Dyn. And he was moving the company from Worcester, Massachusetts, they founded it in the dorm room at Worcester Polytechnic Institute.
And they were moving it back up to our hometown, home city of Manchester, New Hampshire. Again, not exactly the tech mecca, right? It’s not Silicon Valley, right? Not New York.
I’m not even Boston, right? Moving it, choosing to locate it up here. And he called and he’s like, Hey, we’re looking for a co-founder we never had.
We’re a bunch of engineers. We know how the internet protocol of DNS works, you know, we’ve, they had built the three million a revenue was a very consumer oriented DNS service that allowed you to name your home network or your lake house through your vacation home or your, you know, computer lab machines. You could have like Anthony’s lakehouse.com and you could access your cameras back in the day or your music back in the day. Again, think of this all before IoT and, you know, every year was this what timeframe are we talking about?
Kyle York : Kyle, they started the business as a community project in 98 and then they launched the con. Yep, they launched the company as a, as a, you know, Massachusetts LLC first in 2001. And then I joined in 2008. So from 01 to eight, they went, they brought the three million dollars and it was all self-serve e-commerce for the home user, the kind of geek at home who was trying to remote access their home machines. I mean, I was not going to be a client, right?
I couldn’t even like, you know, understand it back then, right? But they had this vision that, Hey, as the internet becomes more prolific as websites and apps become more global and have user bases and audiences around the world. And as manage hosting and cloud emerges, you’re going to need to name those things too, right? And that was the, the genesis of time, but they built the tech and they had no idea how to market how to sell it. And that’s where I got recruited in.
Anthony Codispoti : And so did you come into market and sell increasingly to the same consumers that they already were? Or did you take more of like a business approach?
Kyle York : Yeah, so that’s a great question. They, they thought because of the internet of things and because of mobile devices and the emergence of mobile apps and, you know, every single one of us have one of these phones right in our pocket at that point in time, that, that the consumer business was actually going to slowly die. It was going to be like a boil the frog type of situation. And so the, the, the idea that business was the pivot entirely to B2B enterprise. And that’s what I had been doing.
And again, I’ll be in a different market, but I’ve been selling subscription, you know, services to schools. And at that point in time, I kind of felt like I hit a glass ceiling, you know, there was a head of marketing and a head of sales at the company I was at that were founding team members, they weren’t going anywhere. I was kind of feeling like an island Katie and I were getting married back in Boston. It was like, Hey, it’s now the time to think about moving back, maybe buying a home, maybe, you know, starting a family, we’re getting married back here.
And it was just, it was another one of those leaps, right? You take and I remember my wife thinking it was a terrible job. She’s like, you know, she just like, what do you mean this little tidy company and you don’t understand what they do.
And these guys are all introverted, you know, nerdy engineers, like, are you sure it’s like, you can even do that, like learn that, sell that. I’m damn glad I did. And, and, you know, again, obviously she believed in me, don’t get me wrong. But it was like, are we really want to leave the palm trees and the beaches and, you know, head home? Like, we will eventually back to Coleradors.
Yeah, exactly. So it’s really, it became, we scaled to 100 million. You mentioned that earlier, it became 70 million or so of B2B.
And we still scaled the kind of self service, it became both SMB and, you know, consumer to, you know, around 30 million. So it was a, it was a, it was an unbelievable journey. And the only reason that journey ended, by the way, is we actually sold the company to Oracle for $600 billion. So it wasn’t like we, you know, we gave up, we, we, you know, power very successful conclusion.
Anthony Codispoti : Yeah, very successful conclusion. And I ended up staying at Oracle for three full years after the deal and ran the whole business unit and helped drive strategy and M &A and partnerships for all of Oracle Cloud, which is, you know, now tens of billions of revenue and, you know, is that kind of where you cut your teeth in the M &A and the funding world?
Kyle York : Yeah, a little bit. I mean, I think Dyn was interesting in that we actually bootstrapped the business, the beauty of that initial three million of revenue when I showed up is it was very profitable revenue, right? Because it was sold with a credit card on the internet, right? And had like, you know, hundreds of thousands of users to make up that three million of revenue. And so when we went upmarket, we were actually able to bootstrap our business and not raise outside funding to about 30 million of revenue. And that really, you know, if you think about tracking back all the way to everything I’ve talked about selling private schools, by the way, self-funded business down to my home, you know, my home wife and my parents’ family business, right? Kind of bootstrapped, self-funded, all that.
That was kind of the way I thought about it. But along the way of Dyn, we did end up raising 100 million of private equity as we grew and as we founders left and as we needed to do acquisitions and fund growth. And we also acquired 11 companies, during the Dyn journey that I helped lead those acquisitions. And we even- Prior to being acquired by Oracle? Prior to being acquired by Oracle, everything from the 50k tuck-in of some IP, all the way to we did a 30 million dollar acquisition ourselves. And we even divested four of our technologies that we were not, you know, bringing to market that others wanted to, you know, we had a SSL, you know, product. We had our own little web hosting product.
We would sold these things off to partners that they could do a better job stewarding and scaling those types of businesses. So, like when I talked earlier about like core skill, like it’s deal-making, right? It’s building partnerships, it’s building connection, it’s finding unique value between two parties and helping get deals done. That wasn’t just in selling products that was always in, you know, building partnerships and, you know, divesting technologies or acquiring assets and building Dyn up to scale. In Oracle, yeah, I mean, that was like the MBA of this, right?
I mean, all of a sudden you have real budgets. You’re writing, you’re doing months and months of discovery and analysis that bring strategic rationales all the way up to Larry Ellison himself. I mean, he is like the chairman, executive founder, you know, he owns just south of 50%. I still believe of Oracle. You know, and we brought, we ended up doing four acquisitions while we were there, dozens of partnerships and investment off balance sheet. And, you know, really, really Oracle is a machine at M &A, right? We took all the goods of those, of what they do at M &A and investments.
I mean, sort of, in what I do now, I’ve kind of like, you know, downscoped it, made it more urgent, made it less corporate, right? But it’s a lot of, a lot of really where I got that muscle.
Anthony Codispoti : I want to hear more about that muscle. But I’m kind of curious, biggest lever you pulled while with Dine to help fuel that growth?
Kyle York : Yeah, our biggest thing was the engine. And I think what gets a lot of the glamour is when I rattle off the clients, the big clients we won, right? The Amazons, the Salesforce, the Facebooks, the Twitters, the Airbnb’s, the Pandora’s, the Spotify, the New York Times, the CNN.
Like, that’s what, like, if you go to the Wikipedia, the entry I died, it will say we powered all those websites. But, and by the way, those are big clients, right? Like, out, but those were outliers. And I think the world I live in in tech talks all the time about the outliers. But it’s really the grit and grind that makes these businesses happen, right? And what we got really, really good at is sort of inbound marketing, digital demand generation and inside sales. Like, we really built the machine to transact tons of deals at once through the inside sales engine, as well as through the e-commerce engine. And it turned out that the e-commerce engine ended up being the best place to farm leads, because they were paying clients through the e-commerce engine that we could look and say, oh, there’s Twitter, there’s Subway, there’s Breitling watches, there’s Beanie Babies, right? And we would actually pull out the self-serve clients, we’re paying us for lightweight services and upsell, cross-sell them into the enterprise accounts, right?
Anthony Codispoti : So that was really an example of a lightweight service that they sort of come in the door with. And then what’s the sort of the premium service?
Kyle York : As simple as Twitter was the best example. Twitter, Evan Williams, the founder of Twitter with Jack Dorsey, he bought his domain names from Dine. He wanted more technical partner than a GoDaddy or network solutions.
We were like a more serious premium domain registrar, and we brought about some of these DNS tricks and routing technologies. And so he just came in and he bought every variation. He spun Twitter out of Odeo, which was a podcasting platform, if you can believe it or not, back in the kind of early 2000s. And he bought everything, like Twitter without vowels, Twitter, Twitter, TWTR, everything’s short.
It was all these versions of it. And we would just mine the database of all the customers and we would look for the non-home use cases and look for the more… We had this assumption that if you were a technical person, you probably had a technical job, and you were probably using us in your company, and we would mine that database and then call and say, hey, we have a better solution. And the better solution was the enterprise platform we built that was more globally distributed, had service level agreements, had acceptable use policies, you could get into a contract, you could have an account manager, you could get concierge services. It was just a heck of a lot better of a technology network in architecture than the very basic versions we sold through the web, and that really carried us.
Anthony Codispoti : I feel like we could talk all day about some of the things that you’ve done before starting your IE, but that’s really, I think we should really focus the bulk of our time.
And if there’s enough time at the end, folks, we’re going to talk about his relationship with Ryan Day, National Championship Football Coach at Miami-Modern Ohio State. But before we talk about the inspiration for starting your new company, I want to talk about the name for a moment, York IE, because when we were first communicating and I saw your domain, York.ie, I thought, well, I’m not sure if this is going to be a good fit because most of our audience and the folks that we interview are based here in the US and .ie is Ireland. So explain what is the name?
Kyle York : Yeah, it’s a great question. So York IE stands for York Investment Enterprise. Really early on in my dine days, I would write a lot of content blogs, tweets, LinkedIn posts about how to scale a technology company in the era of venture capital and do that with family business values and family business characteristics. And really all that was was like business fundamentals, 101, build a good healthy business. And that actually gained me a reputation in the family business space as a thought leader. And it was kind of a unique one because it wasn’t like I was a multi-generational kid who inherited wealth or some giant multi-generational family business.
I was using the foundation of my local family business that gave me a great life. And now trying to drive wealth and impact on all these different things in the world. And I learned about this concept called the family business enterprise, which is that the first generations of businesses don’t necessarily look exactly like the generations 2, 3, 4, and 5. And I thought this concept of investment enterprise was kind of a cool name. And so we all know there’s an air conditioning company called York. They own York.com.
So you’re not going to get that. You look out every window of every major office building and you’re going to see York air conditioning units and condensers. And so I was thinking like I wanted to have a personal blog for myself and a personal website and a personal portfolio because I started to do a lot of angel investing. I started to create a lot of this content. And so I actually went to one of our clients at Dine and I said who was .ie, IEDR, the country registry for those domain names and that infrastructure. And they were a client of ours. And I was spending tons of time in Ireland because the biggest web brands in the world actually put their infrastructure teams in Dublin. So Amazon, Facebook, HubSpot, they all have hundreds and hundreds if not thousands of people working on the infrastructure plug.
Anthony Codispoti : Good cost of labor, good tax incentives for being there, kind of a low tax rate.
Kyle York : Outstanding. And also just if you think about the globe, right, if you have global audiences, if you have a global client base, especially for a lot of these West Coast brands, putting something in Europe makes a heck of a lot of sense. Where in Europe, it’s a very easy flight from New York, Boston, East Coast especially.
I mean, it’s pre-customs for Boston as an example. And so I was there all the time and I ended up convincing a registrar there called Black Knight, McKaylee Nailin was the CEO founder who was also a client. Hey, can I get my hands on an IED domain name? And he said, well, you have to, the only way you can get one is in there, by the way, way more expensive than a regular name that wasn’t taken. You have to do business in Ireland. And I said, well, look, I have all these clients.
I’m here all the time. Look at my passport. And I got some letters of recommendation from some clients. And at this time, I had also been using my insights into infrastructure and web traffic, as well as my expertise in go-to-market.
And I started to build a portfolio of angel investments and independent board roles and advisor gigs of dine clients. And some of them were in Ireland as well. So I just thought it was a cool tie and a cool domain name. And we ran that for many years. I probably picked that up and I have to look at the registrar notes, but I probably created that in 2014, 2015. And then when we sold the company to Oracle, spent the few years there, cut our teeth there, got our MBA and business and deal making and big enterprise and cloud computing. And we decided to build this firm York IE. It was on that foundation of angel investments advising, operational understanding and expertise. And we were coming up with all these cheeky names, Anthony. Like any name you would think of of like a growth firm for startups, rocket ship this and fuel this and whatever, whatever. And then my co-founder and CMO Adam, who’s my child and best friend, he was actually my high school quarterback. Adam’s like, he worked with me at Dine and Oracle for years.
Like you already have web traffic, you’re already getting pitch deals, you already have a portfolio. Why don’t we just name the brand after you? And if you think of the McKinsey’s and the Andreessen Horowitz’s and the Banes and the Gartner’s, they’re named after some patriarch or founder or CEO back in time. Let’s go create our own version of Deloitte.
And so that’s how this all kind of came to be and how the name that connected it. And over time, I plan when I enter Europe and scale my business, I plan on hunkering down and putting our offices in Dublin and again, doing the same playbook that we once saw a lot in our tech company’s career.
Anthony Codispoti : So in layman’s terms, Kyle, explain what it is that you guys are doing there at York Eye. Yeah.
Kyle York : So we’re an advisory and investment firm for technology companies. We have two sides of our business that are fully integrated. We have an advisory platform we’ve created that is really tech enabled services for startups. So any startup who needs operational support and scaling their business, we’ve built out a tech enabled AI enabled onshore, offshore subscription based business that can help you with app development, mobile development, UI UX work, RevOps systems, marketing, bookkeeping, FB and A. So we’ve been building this integrated stack of R &D, go to market and G &A services that help startups with growth. And the way we go to market on that side of the house is we partner with a lot of other venture firms and growth equity firms and private equity firms and banks and other service providers to help support their portfolios and clients with growth based on all the experience and learnings we have and playbooks and templates and tools we’ve created. And then the other side of the house, we run a pre seed seed investment fund that specializes and invest in the earliest stages of tech startups and B2B software and B2B SaaS. So we’ve actually got a portfolio of about 60 companies, some real high flyers in there. We do 10 to 15 deals a year investments out of our funds.
That’s run by my other co-founder, Joe Raskha. And we’ve serviced over 250 clients in the advisory business and have about 225 employees globally now in New York, IE, and then and
Anthony Codispoti : just in New York, IE are also in the portcos.
Kyle York : Just in New York, IE and the port and the portcos we’re in the thousands now, you know, because you know, we’ve been doing, we launched the firm in late 2019.
We launched the services arm in late 2020. You know, the portfolio is now maturing. The client base is now maturing, right? So, you know, we’ve got, I mean, I haven’t, that’s a great, that’s gonna be a great fact to have is like how many jobs have been created across the entire ecosystem?
Because it’s probably, I mean, there’s some huge companies that have been created, like 500 people already out of this model. So, you know, it’s in York, IE proper though, we have about 225. We’ve got about 35 or 40 here in the States out of our Manchester, New Hampshire headquarters with a few remote people around the country. But the crux of our team is we actually launched York IE APAC Limited in Omdebag, Gujarat, India. And we have an operation center that’s made up of, you know, technology folks and revenue operations folks and back office folks that are building technology and tools and automation as well as putting hands on keyboards and doing coding and doing marketing and doing back office with a front of our strategists and account managers here in America.
So, it’s a little bit of a growth hack. You know, we got a pretty big head count over there. It’s already up to about 190 full time people. And we have a revolving class of about 15 to 20 interns. I just went in February, it’s insane to see your name on a building and that far flung across the world.
Anthony Codispoti : So, you’re not just sort of making investments in these companies, you’re getting very involved in the operations to the point where you’ve got nearly 200 folks in India that they’re handling, I don’t know, sales, marketing, probably, you know, tech support. Yes.
Kyle York : Yeah, exactly. I think, yeah, the vision for the firm was that, you know, not since the late 70s was something like a Bain created that had Bain consulting and Bain capital, right? And but the issue with those types of firms is they’re doing like public company clients and public company buyouts, right? So, like where do you go in the early days of startup building to get support? And really what you do is you get fractional lists, consult with this, boutique agency lists, boutique dev firm lists, but you know, fractional CFO lists, right?
And they’re all disparate and scattered. So, we thought, could we build a platform for the startup industry that could help them with growth along the way? And what it’s really done as we’ve grown is it drives incredible deal flow, right? Because, you know, we partner with a lot of other funds to support their portfolios. So, we don’t only provide these services to our portfolio companies, we provide them to the market and to the industry. And what that does is it drives incredible deal flow and access that clearly will want to have capital pools to get skin in the game and be owners of these businesses alongside these wonderful founders.
Anthony Codispoti : Oh, that’s really fascinating. Okay, so I’m starting to connect the dots here.
Kyle York : Yeah, there’s VC firms and especially private equity firms like big private equity firms, ThinkVista or, you know, ThinkLike, Toma Brava or Andreessen Horowitz or JMI or Summit Partners. Like they all have operating partners or value creation teams or things like that. But the model of those funds is they’re not necessarily operators, right? They’re financial managers, they’re really big.
They become big banks, right? What we know how to do is really help operate and scale businesses and see patterns and help founders with the challenges around the corner. And so, there are a lot of funds that provide value just to their investments, right? Insight venture partners out of New York made this famous.
They have Insight on site. But again, they’re all huge funds for later stage companies and only for their portfolio. And we thought like, well, let’s build the value platform, the operating partner platform for the space that everybody can leverage. And then obviously, if we do that really, really well, and we have a lot of clients and founders who love us and other investors who love us that will drive investment opportunities all day, every day. And that’s what we’ve been capitalizing on.
Anthony Codispoti : So I was gonna ask why focus exclusively on tech companies, but now understanding that you’re providing the back office as well, it makes a lot more sense because the playbooks are gonna be very similar in terms of how do we scale this? How do we market it? What are the channels that we have?
Kyle York : Yeah, but you make a great point. But I mean, I think on the investment side, we have LPs or right now, individual investors who invest in our funds to go put money into startups, right? So we have to give them a thesis. Like where do we focus our energy and effort and what portfolio of companies are we gonna provide to you that’s different than everybody else, right?
So it’s not generic, right? So B2B Software, SaaS, Subscription, Tech is where we focus and it’s exclusive to that in our investments business. I will say in our advisory business, it is a broader set of empathy to your point. Like, for example, we work with the American Cornhole League. We work with Internet Society and nonprofit. We work with district real estate advisors, a real estate brokerage and investment firm. So I kinda look at it as like in the year 2025, every company’s like tech enabling themselves or even that that’s internal apps or internal systems or website and digital presence, right? Everyone needs help. So we kinda look for like tech enabled, growth oriented, looking at unique subscription models, again for stickiness and repeatability and sustainability, their models.
Anthony Codispoti : You’re looking for these criteria in the companies that you invest in or just in the companies that you’re providing the back office services?
Kyle York : This is what I’m saying also for the back office services. It’s just, and again, and so those don’t have to be tech or have to be B2B SaaS and there’s a broader swap.
Like we even work with consumer tech and marketplace tech and hardware tech, right? Like, and those aren’t types of companies that I would put money in out of my funds today. Now, maybe someday I have a marketplace fund or maybe someday I have a tech enabled services fund, right? But today it’s very focused on the B2B SaaS and the investments, but the advisory business is open for business for anyone.
Anthony Codispoti : Okay, so the reason that you’re really more focused in tech on your investments is because that’s what, you had to sort of pick a niche for your investment.
Kyle York : Yeah, and it’s exactly, yeah, and it’s the most of what we do and what we know and where we’re the biggest experts and the majority of our content and curriculum is around that. But there isn’t a company I meet nowadays. It isn’t trying to figure out how to get longer term contracts, more consumption based pricing models, higher margin service delivery, especially in the age of AI. And, you know, like we know how to do that, right? And even if you’re building a real estate business or even if you’re building a nonprofit, you’re all trying to get more predictable, sustainable and create more value and we can help, right?
And so, you know, that’s a tough balance, right? Of course, in our own messaging and communication and demand gen, but the way that we really do it is, you know, we focus on that top of funnel and we try to drive community and brand and that leads to lots of great opportunities for all sides of the business.
Anthony Codispoti : You know, and doing a little bit of research, so I understand that at York, I, you guys really want to emphasize building good companies that create jobs, wealth and community impact. Is there maybe a real world example of how this mission has kind of shown up in a decision or an investment?
Kyle York : Yeah, I mean, I think we talk a lot about like pragmatic growth versus growth at all costs. And if you follow like the headlines, I mean, think about even all the movies that are created about tech companies, right? It’s like, it’s either like the Facebook movie about a roaring success or it’s the WeWork movie or the Theranos documentary series, you know, about epic fails, right? And I think in the world of tech and the world of Silicon Valley venture, we call it growth at all costs or VC power law, you know, it sort of celebrates this concept that like nine of 10 startups might fail, but the one that emerges, the Uber that emerges might cover all the sins or all the losses. And I just think that’s a shitty thing for founders honestly, right? Like you have backers of your company who expect one of 10 of you to fail or maybe they don’t expect it when they initially invest but are okay with it in the end.
And I think that’s a really challenging thing. I also think venture capital plays to the coast, especially New York and Silicon Valley, San Francisco more and in places like Manchester and Columbus and Minneapolis and Atlanta and Denver and you know, Salt Lake City. There’s also really, really good startups that are emerging that are good, healthy business models solving real world challenges for customers. And sometimes the good companies aren’t the ones that are gonna get, you know, Sequoia or Benchmark or Bessemer and A16Z or General Catalyst to invest. And so there’s a whole world out there of great companies, of good exits into the future. They don’t all need to be dines at 600 million or all need to be, you know, open AI at whatever the hell, you know, billion, tens of billions they’re now saying their worth, right? There’s a lot of good to be had in the market with good, healthy businesses and that’s where we like to focus.
So there’s tons of examples in that, you know. I mean, I have companies in all facets, you know, Ovation’s one in Salt Lake City. It’s, you know, it’s a great company that does restaurant reviews, right?
We have a company called Canvas that’s, you know, remote entirely across the country. And it’s a text analysis platform for the market research in consumer brands, right? Like, you know, these are companies that are good, healthy companies that will change founders lives and change their employees’ lives along the way and upon exit. And they’ll operate in communities where they can make a real debt like you can in Columbus and I can in Manchester, where, you know, if I’m down in New York or if I’m in San Jose or, you know, I might just be one of many and get lost in the shuffle. And I think that’s unfortunate for many.
Anthony Codispoti : So what is it that you’re looking for in a potential investment? You said you’ll make, you know, 10 to 15 investments a year. What’s kind of the common threads between them?
Kyle York : Yeah, so we look at about 600 deals a month that come to us raising their hand, saying they’re looking to raise money. Pretty quickly at the top, we can tell what’s a B2B software company at the stage that we invest, right? We invest very early, think sub one million of revenue companies that we call pre seed seed stage. Sometimes it might even be pre revenue, it might even be an idea in a founder that we’ve worked before that we really love. And so it’s again, it’s B2B SaaS, you know, growth oriented really, really early. We love, we’ve done a lot obviously in infrastructure and cyber in the areas we came from, but we do a lot now in data platforms and a lot of vertical industry apps.
Like that’s really hot for us right now. Like, you know, pick your random industry that hasn’t, you know, had great software or great automation or great efficiency, manufacturing as a good example, or supply chain or, you know, meat butchering, you know, we have literally some of the most random companies you’ve ever seen.
Anthony Codispoti : Meat butchering plus SaaS?
Kyle York : Yeah, it’s literally, it’s an optimization platform called VOLAR that is actually founded out of Nordics. And they’ve built this AI platform to help, you know, butchers not have so much waste in the animals that they’re butchering.
It’s incredible, right? And so we have everything from that, Blue Trace out of Portland, Maine’s a great example. I mean, Blue Trace is a shellfish traceability company from the, you know, fishermen to the Whole Foods and making sure that the, you know, halibut you think you’re eating is halibut and that, you know, it was actually caught in a time period and it says it was caught and it’s fresh.
Anthony Codispoti : And these are, are they barcoding the actual fish it’s for?
Kyle York : They are, they’re literally, they’re packaging, they’re from the, from the docs. They’re literally in the supply chain. They built the SaaS system to kind of track, you know, the, the captures along the way.
Anthony Codispoti : So the fish comes off the boat. It’s immediately getting packaged and that there’s some sort of a barcode tracking mechanism or RFID that goes on it.
Kyle York : And a system that gets put into a operating system just like you’d expecting kind of anything that, you know this industry was left behind and everything was physical and manual and not digitized. And that’s the examples that we love, right? Like tell us an industry that hasn’t been, you know how to solution. And so we’re seeing a lot of these industry experts who come from these spaces saying, Hey, I think I can solve that with technology. And then in the year we’re in, you know it’s easier than ever to build great tech.
Anthony Codispoti : What’s the common thread in a successful starter? What’s something that you’re looking for?
Kyle York : Or you’re like, ah, this guy or gal has it. We index like so hard right now on the person, right? Like everyone, I got asked this. I spoke at an event in Boston the other night to a group of young, you know, 30 year old professionals and they were asking that, but like what’s the DNA?
What’s the difference? Whatever. And it’s like, listen, you know you can have the best idea in the world. You can be in the biggest market in the world. You can, you know, be super tech geek and have some cool app you’ve already developed an MVP for. At the end of the day, we talk a lot about like founder market fit. Like why are you Anthony, the most unique person or the right person to attack that market problem, to build technology solutions, to deliver value to that industry.
And I think it’s kind of starts there. Like what’s the founder market fit? You know, people talk a lot about product market but that comes a little later. And so we look for that a lot.
And then we look for the founding team, you know like to do a startup like, and I’m building a startup helping startups and I’ve been in startups my whole life. Like you need really thick skin and you need to deal with like 99% of things going wrong or bad or negative. And somehow through all of that still push forward. And so that’s a lot of like the push on these like what’s your ambition?
What are you looking to do? What’s your philosophy on business scaling? Like how do you, what’s your capital strategy? How do you plan on being efficient? How do you plan on like, you know getting proof from customers? We call it the market in approach to company building, right? Like don’t just build an app and hope the world finds it. You know, are you out there getting feedback?
Are you right? So these are the types of things we really push for. And, you know, of course we look at financials and we look at tech and we look at market and total addressable market and competitive landscape. But in the end it’s really about who’s delivering it and their conviction and their commitment and the kind of aligned philosophies that we can share together.
Anthony Codispoti : So you’re evaluating 600 deals a month. Obviously there’s no headspace or time to talk to 600 founders. So you’ve got some mechanism for funneling that down. And I know one of the things you said is, hey, pretty quickly we can see if it’s in sort of the tech SaaS space that we’re interested in. From there, how many are left over and how do you begin to kind of sift through those?
Kyle York : Yeah, it’s probably about half, you know I think founders are getting a little bit better and actually doing a slight amount of research of the investors they’re pitching before they reach out.
But it’s probably about half end up kind of in the lane that end up in our funnels. And we’ve created a bunch of technology and integration with our HubSpot CRMs and our own. We have a platform called Fuel, which is fuel.york .ie that’s free and available. But it’s a market research platform to do analysis on companies and get information quickly on them.
Think of it like a CrunchBase or a PitchBook type solution. And we’ve created a lot of that, the filter, right? And then obviously humans come into the mix, right? We have a team of analysts, they come in, they look for deals, they evaluate, okay, now does it fit our stage?
That’s a big deal, right? Like we don’t invest in companies doing more than a million and there are or so, right? Or most of the rounds we’re investing in are, three to $5 million rounds.
So there’s all these little mechanisms that it’s like check, check, check, does it fit, does it fit? And then if it gets all the way through that, let’s say that’s now down to 100 deals a month. Now you’re probably doing, trying to do first calls or some follow up on email we have form submissions, we’re looking for pitch decks. We’re kind of giving a quick look and glance. We might have competitive companies in our portfolio already. We might have made investments as angels a decade ago and like not had some spaces really, not a huge fan of HR tech. I don’t love human resource tech.
I don’t love it, I just don’t love it, right? Like, and there’s reasons for it or ad tech, very hard, or marketplaces, very difficult, like require lots of capital. So you kind of pattern map a bunch of these things and we run it like a company though, right? Like so we run through our processes, different members of the team in seniority get pulled into the deals as they move their way through the gauntlet, through our pipeline.
We have weekly pipeline reviews, we have Friday updates to the whole leadership team. And then they bring the deals most of the time that they want to do the investments team to me when they want to do them, right? And because we’ve all worked together so long and home this process through Dine and Oracle. And by the way, I didn’t mention this, but moonlighting I made 60 investments in B2B software companies before we launched ShorqAE and now we’ve made 64, right? So, it’s a decade of doing this with different vehicles and in different time and different value that really led to us to the day to make the decisions we make. We just got a term sheet signed last night.
It’s a kind of always on, right? It’ll be announced probably within a month. Hope we can close that quickly. That’s a company out of Charlotte, North Carolina. So we invest everywhere too, right? We have companies all over the globe.
Anthony Codispoti : And so what’s the typical life cycle from the deal shows up in the pipeline to signing wet ink on paper?
Kyle York : It depends on where the startup is in their fundraising process. Like sometimes we’re at the end, right? They’ve already got a lead investor. They’re looking to fill out the rest of the round. Heck, we might even know the lead investor and give them a quick call and say, hey, why do you like this company?
Give us all your diligence materials, right? Other times they’re just kicking off a process, right? And depending upon the company, it can be a two week process for the company or it can be a six to nine month process for the company. I think the earliest stage again is about founder market fit.
It’s about feel between us. Think about how much time founders spend like deciding who their co-founders are, right? And who’s gonna own what and all that. Well, you gotta remember when you’re raising money from whether even if it’s just angel investors or funds, you’re selling a piece of your company to someone and you’re going into business, it’s a marriage. And startups take a while, right?
They take seven to 12 years, most of the time when a good outcome happens. And so you’re going into a long-term partnership. You should take it seriously and make sure you’re pretty well aligned.
Anthony Codispoti : Kyle, you said something a moment ago about what you look for in an entrepreneur. You’re like, hey, thick skin, 99% of things are gonna go wrong and how do you handle that and bounce back? I’d like to hear a story about something that you had to bounce back from, a serious challenge, whether it was on the personal or professional side and how you got through it and what you learned.
Kyle York : Yeah, so in the meteoric rise of Dine, where I was chief revenue officer for my 26th birthday to my 33rd birthday when we sold the Oracle, I was a young first-time executive, right? And it was an incredibly hard ride. And as we scaled from three to 10 to 20 to 40 to 50 and raised private equity and created a board, a lot of those older private equity investors who were very experienced in doing it a long time didn’t think that myself and or our leadership team had the chops to take it to the next level. And that created an unbelievable amount of pressure, self-doubt, fear, right? Because I had a great upbringing, but I wasn’t independently wealthy by any stretch.
And if you think about when you’re scaling a startup and it starts to grow and get valued higher, your net worth might be growing, but it’s very illiquid. So I knew that I was gonna be set for life as long as this thing didn’t implode and tip over. And what happened was other founders, other executives, there was a core five of us who built Dine, started to either burn out, quit, get fired. And I kept looking around and saying, hey, like I have to steward this to some outcome someday or else none of us are making any money, right?
And none of us are gonna have the life changing outcome that we all hope for. And I wore all that, right or wrong. I wore it, I felt the pressure. I felt like I was doubted.
That inspired me in many ways to persevere and power through, but it actually led me to incredibly poor mental health and incredibly poor physical health. I started to manifest, this is like 2015 time period, we sold the end of 2016 early 17. I started to manifest the worst migraines I ever had. Actually, I never had a migraine before that. And I never have had one since actually. It’s kind of a, there was a stretch of time that were, it was so debilitating that if I would get a migraine at eight in the morning, I had to go to bed till the next day. And so, I was getting MRI scans, my brain, I was convinced I had a brain tumor and that I was gonna be six feet under soon. And I was updating my estate plans, my trusts and wills.
It was dark and I was dark. And, but I powered through because of, when you build a company in your hometown and you, we’ve got the 500 global employees, I actually recruited a lot of people who had moved away to New York or the West Coast or Boston. And I felt responsible and accountable to all of them and myself and my family and my future family.
And the pressure just mounted and mounted and mounted. And what I realized about myself is that I do really well but I’m in control. If I feel like I’m in control, I can handle the stress and the anxiety that comes with the career path in life I’ve chosen. I work in a very high risk, high reward climate. And that’s, you can correlate that to Ryan Day. It’s a high risk, high reward career and profession.
And now York, I need business I’ve decided to create. But if I feel like I’ve got a hand at the wheel and that, I’m calling the shots with my team in collaboration and I don’t have people pulling puppet strings up here around me, telling me what I can and cannot do. I found methods through visiting therapists and different things that deal with that over time. And I just don’t think a lot of people talk about this type of stuff, by the way, like it’s more and more in the last several years of like mental health and physical health and how that affects you as an entrepreneur. But I don’t think people like really talk about like the actual issues they’ve dealt with. And I remember a therapist once wrote down in a post-it note and I haven’t saved somewhere, it might be in here, but they wrote in a post-it note, I can’t remember, it’s right here actually.
It was like write things down to get out of your head and then see and feel your accomplishments. Cause it’s funny, to me, I sometimes think I’m an aunt and maybe part of that’s that I wouldn’t work in an Oracle and sold my company there and I’ve been around tech founder billionaires, that was our clients that died and these are people I’ve interfaced with or sat on panels with and I think of myself as like a cute successful person, but not relatively, there’s a spectrum of all this. And sometimes you just have fear and self doubt and challenge yourself and think differently. But again, you just gotta remind yourself what you’re playing for, like play the long game, be loyal to yourself, keep your integrity, be loyal to your team and the people around you. And if you can power through the tough times, hopefully you can reach some relative map and top for yourself as you progress.
Anthony Codispoti : Yeah, I do appreciate you giving voice to this cause I think you’re right Kyle, this is the kind of thing that doesn’t really get a lot of attention and people might give it sort of a passing mention of, oh yeah, that was a really difficult time, but that kind of glosses over like, man, really struggling the migraines, you know, put me out of commission for a full day, have to go to bed. And, you know, the therapy that you saw, sounds like it helped a lot that posted note there, clearly means a lot to you, you’ve kept it over the years, those two different messages. Anything else that might be helpful for folks who are listening, going through their own struggle that you might wanna pass along to them?
Kyle York : Yeah, talk about it. I think there are resources available to people, but I also think founders tend to, like lonely is the head that wears the crown, right? And they tend to keep a lot of stuff hidden and try to avoid a lot of things. There’s a great, great figure, a friend of mine named Dr. Julie Gerner on X and Twitter. She’s so good. She’s like coined the Wendy Rhodes from Billions of Tech and she just always has these perspectives and a lot of it comes down to like, actually talking about things and not avoiding the things that are actually hard and challenges. And, you know, again, I just take all the, I listen to podcasts like this, I read blogs or articles or interviews, like I try to just take little nuggets, like see public speakers, like I’m always trying to like, learn, get better, enhance my own worldview and perspectives. And I think that’s something that everybody can control.
Anthony Codispoti : You know, and you made that connection to Ryan Day there a moment ago, high risk, high reward. And, you know, kind of another tie in with him is sort of the importance that, and the spotlight that he’s shown on the importance of mental health. And maybe you could say a little bit more about, you know, how you know him and you know, what he kind of went through as a kid.
Kyle York : Yeah, I mean, the correlation there is Anthony is based in Columbus, Ohio. So I asked if he was a Buckeyes fan. And of course he’s not just a Buckeyes fan, he’s also an alum and a diehard fan, right? And so Ryan Day actually grew up in New Hampshire. Our headquarters are Manchester, New Hampshire. I went to Manchester West High School. Ryan Day went to Manchester Central. By the way, fun fact, Adam Samler also went to Manchester Central and Sarah Silverman went to West. So there’s like, there’s comedians, there’s Chip Kelly as well, went to Manchester Central High School, Dan Mullen went to Manchester Trinity High School. He was like a weird coaches and comedians track out of this place.
But yeah, Ryan was a competitor. You know, he was a few years older than me. I played football against his younger brothers.
He went on to UNH, you know, my older brothers played against him. And he had up, he has, he has let him tell his own story of dealing with mental health and mental health in his family. And he and his wife, Nina are big supporters of mental health. We do some big initiatives in the state of Ohio, you know, and I’ve stayed in touch a bit with Ryan over the years as we’ve been on our own different careers, but trajectories, right? We both kind of had relatively young, success young in our lives, right?
And neither came from big money or anything. And all of a sudden you start to make money and have more eyeballs on you and your name’s more in lights. And again, I’m not comparing myself to a, you know, the fire Ryan Day challenges.
He’s had the weather until he finally won the big chip this year, which is outstanding for him. But you know, I’ve stayed in touch because he’s actually married to a twin, Nina and Kelly Spiro. It’s now Kelly Burnett, Nina Day, our twin girls who Ryan’s dated Nina since high school. And they’re actually my next door neighbors. Ryan’s sister-in-law and her husband, Mike, and their family. So they’re around a lot, you know, and they’re big supporters of New Hampshire football and obviously football everywhere. And I just appreciate that they’ve, you know, opened up a lot about this as well over the last several years when, you know, kind of Ryan didn’t talk or need to talk as much about it historically.
Last quick thing on Ryan too is he actually married Nina and Kelly and their family. And actually coach Spiro, Stanley Spiro is an absolute legend with the high school with my mother. And, you know, he was a legend. He was a maybe 45, 50 year coach of Southern New Hampshire University’s basketball program and a real coaching mentor and supporter, obviously, of Ryan. And, you know, father figured Ryan his whole life. And I see Stan all the time.
He’s just a, he’s a larger than life character. He plays golf at the same country club I go to. And he’s always out in Ohio. So look for him, look for him at games and, you know, go Buckeyes.
Anthony Codispoti : Go Buckeyes is right. Yeah, I appreciate you sharing all that on Ryan Day, you know, as a Buckeye fan, big Ryan Day fan, you know, watching what he endured with, you know, some of the fan backlash and then, you know, the ultimate resiliency that he showed. But, you know, even aside from that, again, the involvement and the voice that he’s given to the importance of mental health, you know, especially when some of his players have been in a rough spot and, you know, he’s put them first over, you know, the importance of the game, which is the right thing to do. And so, yeah, I’m glad we gave a little voice to that. Yeah, that’s great. Yeah, I’m extending. I’ve just got one more question for you, Kyle.
But before I ask it, I want to do a couple of things. I’m going to invite everybody listening. Go ahead and hit the follow button on your favorite podcast app. Let’s continue to get more great interviews like we’ve had today with Kyle York from Yorkie. Kyle, I also want to let people know the best way to either get in touch with you directly or to follow your story. What would that be?
Kyle York : Yeah, that’s great. So you heard our website, Yorkie. There’s tons of resources there available to all types of founders, startups, operators, investors. So please engage. We’re also at York Growth across all social channels. And I’m K York 20 across all social channels. The 20 is my football member. My favorite player of all times, the Great Barry Sanders out of Detroit. Sorry about that. You know, Ohio fans, but you know, Oh, Big Barry Sanders fans.
Anthony Codispoti : Yeah, Big Barry Sanders fans. Yeah, yeah, great athlete. So I wore his number from youth all the way through college football and kept it. It was my AOL instant messenger screen name and I’ve kept it all these years later. But yeah, feel free to connect, look us up, follow along, and we’re here to support you. So last question for you, Kyle, as you look in your industry things, evolve pretty quickly, but maybe over the next two to three years, what are some of the trends, investment trends, business trends, tech trends that you’re most excited to kind of see unfold and be a part of?
Kyle York : Yeah, listen, I think I’ve talked a bit about it today. I think there’s been a somewhat of a correction back to healthier business models and more sustainability and, you know, less burn as you, in this capital may be required to scale some of these companies. I think that’s number one. I think number two, I’m all about these vertical industry solutions. I think, you know, there’s a lot of horizontal software, you know, in big tech, but what about these underserved industries?
I think is really, really, really happy to see. And I also think post pandemic, pandemic especially, you know, Steve Case from AOL has this thing called the rise of the rest and it’s about, you know, secondary tertiary cities and the ecosystems and entrepreneurial mindedness that can come from them. And many of these places are very entrepreneurial. It’s just been more main street, small business or small business oriented. And you’re seeing tech companies be able to be built anywhere.
So, you know, I’m big about those three things. Obviously there’s an overarching AI hype cycle and overall, you know, cybersecurity, internet security, nation state conflict, crazy stuff going on in the world. These are things where we’re keeping our eye on.
That’s the more kind of technical answer. But, you know, we believe there’s, that’s going to impact every sector. And, you know, we’re just running off the cliff to chase that stuff. You know, we’re trying to be really thoughtful about everything we’re doing.
Anthony Codispoti : Kyle York, I want to be the first to thank you for sharing both your time and your story with us today. I really appreciate it. Thank you. Folks, that’s a wrap on another episode of the Inspired Stories podcast. Thanks for learning with us today.
REFERENCES
Personal Social: @KYork20 (across all platforms)
Company Social: @YorkGrowth
Website: york.ie
Free Platform: fuel.york.ie