Latest / The Inspired Stories Podcast / Founder-Market Fit First: Kyle York's Investment Philosophy That's Changing Startups

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Founder-Market Fit First: Kyle York's Investment Philosophy That's Changing Startups · The Inspired Stories Podcast

• 0:04
  Welcome to another edition of the Inspired Stories podcast,
• 0:08
  where leaders share their experiences so we can learn from
• 0:11
  their successes and be inspired by how they've overcome
• 0:14
  adversity. My name is Anthony Kotaspodi and
• 0:16
  today's guest is Kyle York, CEO and Managing Partner and Co
• 0:21
  Founder of York IE, an advisory and venture capital firm based
• 0:26
  in Manchester, NH. York IE works with early stage B
• 0:30
  to B SAS start-ups focusing on sustainable growth and building
• 0:34
  strong community impact. They offer advisory services and
• 0:38
  selective investments to help tech companies scale
• 0:41
  effectively, creating jobs and generating wealth in the
• 0:44
  process. Kyle has an impressive
• 0:47
  background, having previously helped grow revenue from
• 0:50
  3,000,000 to $100 million at a prior company and has been
• 0:54
  recognized for his innovative strategies in the tech sector.
• 0:58
  Under his leadership, York IE has supported many emerging
• 1:01
  ventures, developed new market research tools and shared
• 1:05
  leading insights on industry trends.
• 1:08
  He also wrote articles on industry trends and best
• 1:11
  practices, demonstrating his commitment to sharing expertise
• 1:14
  with the broader community. With hands on experience in
• 1:17
  consulting, building technology stacks and opera optimizing
• 1:22
  operations, Kyle brings a wealth of knowledge to our show.
• 1:25
  Now before we get into all that good stuff, today our episode is
• 1:29
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• 1:32
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• 1:56
  All right, back to our guest today, the CEO of York, IE Kyle
• 2:00
  York. I appreciate you making the time
• 2:02
  to Share your story today. Yeah, I appreciate you having
• 2:04
  me, Anthony. OK.
• 2:06
  So before we get into talking about York IE, I'm going to talk
• 2:09
  just a little bit about sort of your past leading up to this
• 2:12
  held a variety of roles, different companies.
• 2:16
  And I guess before we even get into some of that, maybe you can
• 2:19
  help frame for us what is Kyle's superpower?
• 2:23
  What are your strengths that have allowed you to be
• 2:25
  successful? Yeah, so thanks.
• 2:28
  Great question. To start it off, you know, and I
• 2:31
  appreciate the background. I was sitting here.
• 2:33
  Sometimes it's interesting to reflect when you're getting kind
• 2:36
  of introduced and to think about, you know, the long
• 2:39
  journey you have to get to where you are in your career.
• 2:43
  So, you know, I think superpower wise, you know, I'm an
• 2:46
  interesting character. You know, I, I was the middle
• 2:48
  son of five boys. I grew up in a sports
• 2:52
  competitive household here in New Hampshire, Southern New
• 2:54
  Hampshire. My parents actually owned a Main
• 2:57
  Street small business that was a sporting goods retail and team
• 3:02
  outfitter. So, you know, I, I've kind of,
• 3:05
  if you think about that middle son, you know, five boys
• 3:09
  athlete, I played college football at the university for
• 3:11
  four years, division two. You know, all these things kind
• 3:15
  of lead to the fact that like my superpower has really been about
• 3:19
  being, you know, competitive and aggressive and ambitious.
• 3:22
  And I've just channelled that into a sales and marketing
• 3:25
  career, you know, evangelizing my companies and my technology
• 3:30
  and my customers and my industries and, you know, doing
• 3:33
  deals right, being a, a business development sales oriented deal
• 3:37
  maker. And that's been the commonality
• 3:40
  and common thread throughout my career.
• 3:42
  In the beginning of my career, I kind of shield away from it.
• 3:44
  I shot, I thought sales and deals were sort of like snake
• 3:47
  oily. And you know, I don't want to be
• 3:49
  pushy and you know, but you know, when you really find your
• 3:51
  hooks in in the companies you work for and you believe in the
• 3:55
  technologies or the services, the offerings you have becomes a
• 3:58
  heck of a lot easier for you. Yeah, let's explore this a
• 4:01
  little bit because I've run into lots of people who who have
• 4:05
  found themselves in a similar position.
• 4:06
  I earlier my career felt the same way.
• 4:08
  Like, I don't know if I'm like a very good salesman because, you
• 4:12
  know, I had this sort of, I don't know, stereotype in my
• 4:15
  head of like a used car salesman is sort of the good sit.
• 4:18
  Like he's just pushing. He's like over the top and, you
• 4:21
  know, not like super authentic. What was it for you that kind of
• 4:25
  like flipped that around and said, no, I'm, I'm actually good
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  at this. Like I, I've got the skills for
• 4:31
  this. Yeah.
• 4:32
  I need to think about it differently.
• 4:33
  Well, I think it was honestly the juxtaposition of like, I
• 4:37
  thought of like sales careers as like corporate, you know, and I
• 4:41
  grew up in a very entrepreneurial, you know, stick
• 4:44
  it to the man. You know how hard you work and
• 4:47
  you know how well you do, you know, dictates your future,
• 4:51
  right? And and that's how my parents
• 4:53
  running a small family business operated, right?
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  If you didn't make a profit, you didn't get to go out to dinner
• 4:58
  or go on vacation or, you know, get some, get to be able to buy
• 5:01
  the new car that you need for the family, right.
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  And, you know, I don't think that's like necessarily fully
• 5:07
  translatable to venture capital in the tech landscape.
• 5:10
  It's not how it has sort of been built.
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  So I always looked at it like like sales jobs as like guys in
• 5:16
  a suit with a briefcase, you know, and being very corporate.
• 5:20
  And early on, I got internships in start-ups and tech start-ups.
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  And here we are 20 plus years later.
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  And that's the career I had. And what I realized in start-ups
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  is they were kind of like the Main Street small business.
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  They were very entrepreneurial and you know, a lot of
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  start-ups, you know, especially in the early 2000s, you were
• 5:37
  wearing jeans and AT shirt to the conferences, right.
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  And, and it was actually a mentor of mine really early on
• 5:44
  who who kind of like, you know, basically he was actually the
• 5:48
  athletic director of my high school who looked at me and he
• 5:50
  said, York, you're a natural seller.
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  You know, he's like, you're a politician.
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  You know, you're, you're he's like, his name is Frank Harlan.
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  He was in the halls of West High School in Manchester, NH.
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  And, and he's like, and I was like, yeah, I don't want to be
• 6:01
  any of those things. And he's like, you know, if you
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  have like if you're rooted in integrity and you follow your
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  passions, like you can do that really authentically and have a
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  great, you know, life and whatever.
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  And I, that actually led me to, I was student council president
• 6:13
  of my high school and, you know, I got internships and I, I
• 6:17
  majored in marketing and I was doing marketing jobs and, you
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  know, writing content and doing programs and marketing and
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  events. And I kept going to these shows
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  and I'm like, I'm better than all the salespeople at
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  evangelizing our story and building relationships and
• 6:31
  sharing the value of our solutions.
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  And, and finally, the, the CEO and founder of that company and
• 6:37
  the head of sales of that company just pushed me in the
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  pool. And we're like you, you got to
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  just follow what you're really, really good at.
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  And so it kind of was a natural evolution for me, but it kind of
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  went back to the kind of early days and, you know, just
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  realizing that I had that natural, you know, natural
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  salesman, sort of evangelist, sort of deal making DNA mixed
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  with the entrepreneurial spirit. You know, that's the beauty of a
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  sales Rep, right? I mean, a lot of times they're
• 7:03
  kind of independent to, you know, it's kind of like running
• 7:06
  your own micro business. And that's how I viewed the
• 7:08
  beginnings of my career. And so that company that you
• 7:11
  were just referring to where they kind of said, hey, go get
• 7:14
  in the pool, Kyle, like you, you can do this was that.
• 7:17
  And I don't know if I pronounce it Din or DY.
• 7:20
  No, it was actually before that. It was 9 is the name of that
• 7:22
  company and we'll get to that one.
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  But it was actually a company called Whipple Hill.
• 7:26
  What happened to me is I went to school at Bentley University in
• 7:29
  Waltham, Mass, and I wanted to get internships.
• 7:31
  And I, it's right outside Boston and I thought I was getting
• 7:34
  internships in Boston. And my oldest brother, he's
• 7:37
  built a phenomenal career in advertising.
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  And so I wanted to go into like an Arnold or a Hill Holiday or
• 7:43
  an agency for the summer. And it turned out they didn't
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  offer any paid internships. It sounds like I can't afford to
• 7:48
  live in the city in Subwadin apartment.
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  So I moved back to New Hampshire.
• 7:52
  When I looked in New Hampshire, there was no agencies.
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  So I said, oh, maybe I'll go in house.
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  And I looked at a bunch of companies and I just so happened
• 7:59
  to apply for internships to a bunch of tech businesses.
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  And I found this company called Whipple Hill that had, you know,
• 8:05
  mid 20 year old, mid late 20 year old founder.
• 8:08
  And they actually built a software solution for prep
• 8:11
  schools, K to 12 private schools.
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  So there's plenty in Columbus and in Ohio.
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  And I spent a lot of time there. But you know, it was, it was
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  really, it was a, it was a complete system operating
• 8:21
  platform to run your K to 12 private school.
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  And that was the company. And I started as an intern,
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  spent seven years there climbing the ladder, doing every, you
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  know, crappy low level marketing job, sales job and just kind of
• 8:35
  they threw me in the pool and said go for it.
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  And it was, it was incredible. They, they even offered me an
• 8:41
  opportunity to move to California.
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  I moved to California for that company.
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  I always say that move sort of accelerated my career 5 to 10
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  years because I just took a leap and went remote as a remote
• 8:52
  seller to build a market in the West Coast that didn't exist for
• 8:55
  the company. And it was a heck a heck of an
• 8:58
  experience. It really accelerated your
• 9:00
  career because you sort of developed these skills in terms
• 9:03
  of like how to sell remotely. Is that sort of the?
• 9:07
  No, it's more that I took the risk and bet on myself, right?
• 9:10
  Like I think, I think what a lot of people don't realize about
• 9:13
  startups is that the earlier, if you go into a start up, you
• 9:17
  really need to be a builder yourself.
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  And you're, you're betting on yourself just as much as you are
• 9:21
  the start up at the earliest stages of start up.
• 9:24
  And, you know, that company was quite small and, you know, I
• 9:28
  took a leap. I had belief in myself, They had
• 9:29
  belief in me. And yeah, also the skills and
• 9:33
  the accelerated skills I was able to learn as a young person,
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  given that opportunity, it sort of forced me to grow up, mature
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  and deliver, right? Because in sales, like there's
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  no hiding, right? Like, you know, you have a
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  quota, you have numbers to hit your paid and your base salary
• 9:50
  plus your variable that gives you your on target earnings.
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  Like if you don't sell, you don't have a job.
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  If you don't hit your numbers, you're not making the
• 9:57
  compensation that you think you should bake, right?
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  So it's just a pressure cooker in the very beginning.
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  And, and for me, especially as a remote seller, you kind of have
• 10:07
  your own book of business, your own targets.
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  It's almost like your own PNL to manage, right?
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  And that really helped me like take business seriously and
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  understand, understand that like what I put in is going to
• 10:19
  dictate what I get out. And again, that goes all the way
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  back to my family business values.
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  But it was like a environment that allowed me to do that and
• 10:26
  do that very young. I mean, I was 23 to 26 when I
• 10:30
  ran the West Coast territory. I mean, this is wildly young.
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  And the person I replaced was 45 years old, right, with 20 years
• 10:37
  of sales experience. So, so, you know, it could have
• 10:40
  gone the other direction, right? I could, I could have failed.
• 10:42
  And there was, you know, micro failings and, and issues and
• 10:45
  things that didn't go perfect, of course, along the way.
• 10:48
  But in the end, it LED it LED to the the next tracks of my
• 10:51
  career. So one of those tracks I want to
• 10:53
  talk about is this company Din, because I understand why you
• 10:56
  were there. Revenue grew from 3 million to
• 11:00
  100 million and I think you were there over the period of 11
• 11:03
  years. First, before you explain how
• 11:07
  you helped accomplish that, explain what the company did or
• 11:11
  what it still does today. Yeah, sure.
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  So that it's Dine and it's short for dynamic Network Services and
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  Dime was the became the world's leader in manage Domain Name
• 11:23
  System services. So DNS in essence, in layman's
• 11:27
  terms, you know when you type in a domain name into a browser and
• 11:32
  are being served up content, the Domain Name System is what's
• 11:36
  telling you where that content resides or what IP addresses
• 11:40
  live behind that website. So it's almost like the phone
• 11:43
  book of the Internet is a good way to think about.
• 11:45
  It so is there just one company that provides that?
• 11:47
  Service. No, I mean you can get these,
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  you can get DNS with, you know, your, your domain, you buy at
• 11:53
  GoDaddy or Network Solutions or whatever, your domain registrar
• 11:56
  of choices, your ISPs provide some level of free or basic DNS.
• 12:02
  And then there's there's been over the years of the Internet,
• 12:06
  there's been managed DNS providers who are third party,
• 12:10
  more highly performant, more secure, more reliable.
• 12:13
  Yeah, Cloudflare is a good example.
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  Cloudflare does DNS and they do content delivery.
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  So they actually serve the content as well.
• 12:20
  So they have the both the pipe and the naming and the routing,
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  but they also have caching and content servers on the back end.
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  But all the cloud platforms now from AWS to Oracle to Google to
• 12:31
  Microsoft Azure all have now DNS capabilities and the types of
• 12:35
  capabilities that Dine made a Tay around.
• 12:39
  But I was actually recruited to that company.
• 12:40
  The quick story there of how I went from Whipple Hill there as
• 12:43
  I was living in California with my now life Katie and all pre
• 12:47
  kids, we were out there having a great time.
• 12:49
  She was working, I was working that job for Whipple Hill and
• 12:53
  actually a high school classmate called me and he was one of the
• 12:56
  Co founders of that and he was moving the company from
• 12:59
  Worcester, MA. They had founded it in the dorm
• 13:02
  room at Worcester Polytechnic Institute and they were moving
• 13:04
  it back up to our hometown home City of Manchester, NH.
• 13:07
  Again, not exactly the tech Mecca, right?
• 13:10
  It's not Silicon Valley, right? Not New York.
• 13:12
  I'm not even Boston, right? Moving it, choosing to locate it
• 13:16
  up here and he called and he's like, hey, we're looking for a
• 13:19
  Co founder. We never had.
• 13:20
  We're a bunch of engineers. We we we know how the Internet
• 13:23
  Protocol of DNS works. You know, we've they had built
• 13:27
  the the the 3 million of revenue was a very consumer oriented DNS
• 13:31
  service and allowed you to name your home network or your lake
• 13:34
  house or your vacation home or your, you know, computer lab
• 13:38
  machines. You could have like Anthony's
• 13:40
  lakehouse.com and you can access your cameras back in the day or
• 13:44
  your music back in the day. Again, think of this all before
• 13:46
  IoT and you know everything. And So what year was this?
• 13:49
  What time frame are we talking about?
• 13:50
  Kyle, they started the business as a community project in 98 and
• 13:53
  then they launched, they launched the con Yep, they
• 13:56
  launched the, the company as a, as a, you know, Massachusetts
• 14:00
  LLC first in 2001 and then I joined in 2008.
• 14:05
  So from 01 to 08 they went, they brought the $3,000,000 and it
• 14:08
  was all self-serve e-commerce for the home user, the kind of
• 14:12
  geek at home who was trying to promote access their home
• 14:16
  machines. I mean, I was not going to be a
• 14:17
  client, right? I couldn't even like, you know,
• 14:19
  understand it back then, right? But they had this vision that,
• 14:23
  hey, as the Internet becomes more prolific, as websites and
• 14:27
  apps become more global and have user bases and audiences around
• 14:31
  the world, and as managed hosting and cloud emerges,
• 14:34
  you're going to need to name those things too, right?
• 14:36
  And that was the, the genesis of that.
• 14:39
  But they built the tech and they had no idea how to market, how
• 14:41
  to sell it. And that's where I got recruited
• 14:43
  in and. So did you come in to market and
• 14:46
  sell increasingly to the same consumers that they already were
• 14:49
  or did you take more of like a business approach?
• 14:52
  Yeah. So that's a great question.
• 14:54
  They, they thought because of the Internet of Things and
• 14:57
  because of mobile devices and, and the emergence of mobile apps
• 15:01
  and, you know, every single one of us have one of these phones
• 15:03
  right in our pocket at that point in time that, that the
• 15:06
  consumer business was actually going to slowly die.
• 15:08
  It was going to be like a boiled frog type of situation.
• 15:11
  And so the, the, the idea that business was to pivot entirely
• 15:15
  to B2B enterprise. And that's what I have been
• 15:18
  doing. And again, I'll be in a
• 15:20
  different market, but I've been selling subscription, you know,
• 15:22
  services to schools. And at that point in time, I
• 15:25
  kind of felt like I had a last ceiling.
• 15:27
  You know, there was a head of marketing and a head of sales at
• 15:30
  the company I was at that were founding team members.
• 15:32
  They weren't going anywhere. I was kind of feeling like an
• 15:35
  Highland Katie and I were getting married back in Boston.
• 15:38
  It was like, hey, is now the time to think about moving back,
• 15:40
  maybe buying a home, maybe, you know, starting a family.
• 15:43
  We were getting married back here and it was just it was
• 15:46
  another one of those leaps, right?
• 15:47
  You take and, and I remember my wife thinking it was a terrible
• 15:50
  job to take. She like, you know, she's just
• 15:51
  like, what do you mean this little tiny company?
• 15:54
  And you don't understand what they do.
• 15:55
  And these guys are all introverted, you know, nerdy
• 15:58
  engineers. Like, Are you sure?
• 15:59
  It's like, you can even do that And like, learn that, sell that.
• 16:04
  I'm damn. I'm damn glad I I did.
• 16:06
  And and, you know, again, obviously she believed in me,
• 16:08
  don't get me wrong. But it was like, I really want
• 16:10
  to leave the palm trees and the beaches and, you know, head
• 16:13
  home. Like, I don't.
• 16:14
  We will eventually. Yeah, exactly.
• 16:18
  So it's really it became, we scaled to 100 million, you
• 16:22
  mentioned that earlier it became 70 million or so of B to B and
• 16:28
  we still scaled the the kind of self-service.
• 16:31
  It became both SMB and you know, consumer to you know, around 30
• 16:36
  million. So it was a, it was a, it was an
• 16:38
  unbelievable journey. And the only reason that journey
• 16:41
  ended, by the way, is we actually sold the company to
• 16:43
  Oracle for $600 billion. So it wasn't like we, you know,
• 16:47
  we gave up. We, we, you know, power, Yeah,
• 16:51
  very successful conclusion. And I ended up staying at Oracle
• 16:54
  for three full years after the deal and ran the whole business
• 16:58
  unit and helped drive strategy and M&A and partnerships for all
• 17:01
  of Oracle Cloud, which is, you know, now 10s of billions of
• 17:05
  revenue. And you know and and is that.
• 17:07
  Kind of where you cut your teeth in the M&A in the funding world?
• 17:11
  Yeah, a little bit. I mean, I think Dime was
• 17:12
  interesting in that we actually bootstrapped the business that
• 17:15
  the beauty of that initial 3 million of revenue when I showed
• 17:18
  up as it was very profitable revenue, right, because it was
• 17:20
  sold with a credit card on the Internet, right.
• 17:23
  And had like, you know, hundreds of thousands of users to make up
• 17:26
  that 3 million of revenue. And so when we went upmarket, we
• 17:30
  were actually able to bootstrap our business and not raise
• 17:33
  outside funding to about 30 million of revenue.
• 17:36
  And that really, you know, if you think about it, tracking
• 17:39
  back all the way to everything I've talked about from selling
• 17:41
  private schools, by the way, self funded business down to my
• 17:44
  home, you know, my, my home life and my parents family business,
• 17:48
  right? Kind of bootstrapped, self
• 17:50
  funded all that, that was kind of the, the, the way I thought
• 17:53
  about it. But along the way of dying, we
• 17:55
  did end up raising 100 million of private equity as we grew and
• 18:00
  as we founders left and as we needed to do acquisitions and
• 18:03
  fund growth. And we also acquired 11
• 18:07
  companies during the dime journey that I helped lead those
• 18:10
  acquisitions prior. To being acquired by.
• 18:13
  Prior to being acquired by Oracle, everything from the 50K
• 18:16
  tuck in of some IP all the way to we did a $30 million
• 18:20
  acquisition ourselves and we even divested four of our
• 18:25
  technologies that we were not, you know, bringing to market,
• 18:29
  market that others wanted to, you know, we had an SSL, you
• 18:32
  know, product, we had our own little web hosting product that
• 18:36
  we would sold these things off the partners that they could do
• 18:39
  a better job stewarding and scaling those types of
• 18:41
  businesses. So, so like when I talked
• 18:44
  earlier about like core skill, like it's deal making, right?
• 18:47
  It's, it's, it's building partnerships, it's building
• 18:49
  connection, it's finding unique value between two parties and
• 18:53
  helping get deals done. That wasn't just in selling
• 18:56
  products. That was always in, you know,
• 18:58
  building partnerships and, you know, divesting technologies or
• 19:02
  acquiring assets and building dine up to scale in Oracle.
• 19:08
  Yeah. I mean, that was like the MBA of
• 19:10
  this, right? I mean, all of a sudden you have
• 19:12
  real budgets. You're you're writing, you're
• 19:15
  doing months and months of discovery and analysis to bring
• 19:19
  strategic rationales all the way up to Larry Ellison himself.
• 19:22
  I mean he is like the Chairman executive founder, you know, he
• 19:26
  owns just South of 50% I still believe of Oracle, you know,
• 19:32
  and, and we brought, we did end up doing 4 acquisitions while we
• 19:34
  were there, dozens of partnerships and investment off
• 19:38
  balance sheet. And you know, really, really
• 19:42
  Oracle's a machine at M&A, right.
• 19:44
  We took all the goods of those of what they do in M&A and
• 19:48
  investments and we sort of in what I do now it's kind of like,
• 19:51
  you know, down scoped it made it more urgent, made it less
• 19:55
  corporate, right. But it's a lot of a lot of
• 19:58
  really where I got that muscle. I want to hear more about that
• 20:01
  muscle, but I'm kind of curious, biggest lever you pulled while
• 20:06
  with Dine to help fuel that growth?
• 20:09
  Yeah, our biggest thing was the engine.
• 20:11
  And I think what gets a lot of the the glamour is when I rattle
• 20:15
  off the clients, the big clients.
• 20:17
  We won, right? The Amazons, the sales forces,
• 20:20
  the Facebooks, the Twitters, the Airbnb's, the Pandora's, the
• 20:24
  Spotify, the New York Times, the CNN.
• 20:27
  Like that's what like if you go to the Wikipedia entry, I died,
• 20:30
  it will say we powered all those websites and and by the way,
• 20:33
  those are big clients, right? Like out, but those are
• 20:35
  outliers. And I think the world I live in,
• 20:37
  in tech talks all the time about the outliers, but it's really
• 20:40
  the grit and grind that makes these businesses happen, right?
• 20:43
  And what we got really, really good at is sort of inbound
• 20:47
  marketing, digital demand generation and inside sales.
• 20:51
  Like we really built the machine to transact tons of deals at
• 20:55
  once through the inside sales engine as well as through the
• 20:58
  ecommerce engine. And it turned out that the
• 21:01
  ecommerce engine ended up being the best place to farm leads
• 21:04
  because they were paying clients through the ecommerce engine
• 21:08
  that we could look and say, oh, there's Twitter, there's Subway,
• 21:10
  there's Breitling watches, there's beauty babies, right?
• 21:13
  And we would actually pull out the self-serve clients were
• 21:17
  paying us for lightweight services and upsell cross sell
• 21:21
  them into the enterprise accounts, right.
• 21:23
  So that was really been an example.
• 21:25
  Of a lightweight service that they sort of come in the door
• 21:27
  with and then what's the sort of the premium as?
• 21:30
  Simple as Twitter was the best example Twitter Evan Williams,
• 21:34
  the founder of Twitter with Jack Dorsey, he bought his domain
• 21:38
  names from dine. He wanted more technical partner
• 21:41
  than a GoDaddy or Network Solutions.
• 21:44
  We were like a see more serious premium, you know, domain
• 21:47
  registrar and we brought about some of these DNS tricks and
• 21:51
  routing technologies. And so we just came in and he
• 21:53
  bought every variation. He's fun.
• 21:55
  Twitter out of Odeo, which was a podcasting platform, if you can
• 21:59
  believe it or not, back in the, you know, kind of early 2000s.
• 22:03
  And he bought everything like Twitter without vowels, you
• 22:06
  know, Twitter T TWTR, you know, like everything's short, like it
• 22:10
  was all these versions of it. And and we would just mine the
• 22:14
  database of all the customers and we would look for the non
• 22:17
  home use cases and look for the more, you know, we had this
• 22:20
  assumption that if you were a technical person, you probably
• 22:24
  had a technical job, right? And you were probably using US
• 22:27
  in your company. And we would mine that, mine
• 22:29
  that database and then call and say, hey, you know, we have a
• 22:32
  better solution. And the better solution was the
• 22:34
  enterprise platform we built that was more globally
• 22:36
  distributed. It had, it had service level
• 22:39
  agreements, had acceptable use policies, you could get into a
• 22:42
  contract, you could have an account manager, you could get
• 22:45
  concierge services. It was just a heck of a lot
• 22:47
  better of a technology network in architecture than the very
• 22:52
  basic versions we sold through the web and and that really
• 22:55
  carried us. I feel like we could talk all
• 22:59
  day about some of the things that you've done before starting
• 23:03
  York, IE. But that's really, I think we
• 23:05
  should really focus the bulk of our time.
• 23:07
  And if there's enough time at the end, folks, we're going to
• 23:11
  talk about his relationship with Ryan Day, national championship
• 23:16
  football coach at my alma mater, Ohio State.
• 23:18
  But before we talk about sort of the, the inspiration for
• 23:23
  starting your new company, I want to talk about the name for
• 23:27
  a moment. York IE, because you know, when
• 23:30
  I was first, when we were first sort of communicating and I saw
• 23:33
  your domain York dot IEI thought, well, I'm not sure if
• 23:37
  this is going to be a good fit because, you know, most of our
• 23:41
  audience and, and the folks that we interview are based here in
• 23:44
  the US and dot IE is, you know, Ireland.
• 23:47
  So explain what? What is the name?
• 23:50
  Yeah, it's a great question. So York, IE stands for York
• 23:53
  Investment Enterprise. Really early on in my dying
• 23:57
  days, I would write a lot of content, blogs, tweets, LinkedIn
• 24:01
  posts about how to scale a technology company in the era of
• 24:07
  venture capital and, you know, do that with family business
• 24:11
  values and family business characteristics.
• 24:13
  And really all that was was like business fundamentals,
• 24:16
  one-on-one, right, build a good healthy business, right.
• 24:19
  And that that actually gained me a reputation in the family
• 24:23
  business space as a thought leader.
• 24:26
  And it was kind of a unique one because it wasn't like I was a
• 24:28
  multi generational kid who inherited wealth or some giant,
• 24:32
  you know, multi generational family business.
• 24:33
  I was using the foundation of my local family business that gave
• 24:36
  me a great life and, you know, now trying to drive wealth and
• 24:41
  impact and all these different things in the world.
• 24:43
  And, and I learned about this concept called the family
• 24:45
  business enterprise, which is that, you know, the first
• 24:48
  generations of businesses don't necessarily look exactly like
• 24:53
  the generations 234 and five. And I thought this concept of
• 24:57
  investment enterprise was kind of a cool name.
• 25:00
  And so, you know, we all know there's a air conditioning
• 25:04
  company called York, right? They own york.com.
• 25:07
  So you're not going to get that. You look out every window of
• 25:10
  every major office building, you're going to see York air
• 25:12
  conditioning units and condensers, right?
• 25:15
  And so I was thinking like, you know, I wanted to have a
• 25:17
  personal blog for myself and a personal website and a personal
• 25:21
  portfolio because I started to do a lot of Angel investing and
• 25:23
  I started to create a lot of this content.
• 25:25
  And so I actually went to one of our clients at Dine and I said
• 25:31
  who was dot i.e. i.e. Dr. the country registry for
• 25:36
  those domain names and that infrastructure and they, they
• 25:39
  were a client of ours and I was spending tons of time in Ireland
• 25:43
  because the biggest web brands in the world actually put their
• 25:47
  infrastructure teams in Dublin. So Amazon, Facebook, HubSpot,
• 25:53
  they all have hundreds and hundreds, if not thousands of
• 25:56
  people working on the infrastructure plug.
• 25:58
  Cost of Labor, good tax incentives for being there, kind
• 26:02
  of a low tax rate, right? Outstanding.
• 26:04
  And also just, if you think about the globe, right, if
• 26:07
  you're have global audiences, if you have a global client base,
• 26:11
  especially for a lot of these West Coast brands, putting
• 26:14
  something in Europe makes a heck of a lot of sense.
• 26:16
  Where in Europe it's a very easy flight from New York, Boston,
• 26:19
  East Coast especially. I mean, it's pre customs for
• 26:22
  Boston as an example. It's I was there all the time
• 26:24
  and I, I ended up convincing A registrar there called Black
• 26:28
  Knight. Michaela Nayland was the CEO
• 26:30
  founder who's also a client. Hey, can I get my hands on an IE
• 26:33
  domain name? And he said, well, you have to,
• 26:35
  the only way you could get one is it.
• 26:37
  And they're by the way, way more expensive than, you know,
• 26:39
  regular name that wasn't taken. You, you have to do business in
• 26:44
  Ireland. And I said, well, look, I have
• 26:45
  all these clients, I'm here all the time.
• 26:47
  Look at my passport. And I got some letters of
• 26:50
  recommendation from some clients.
• 26:52
  And at this time I had also been using my insights into
• 26:55
  infrastructure and web traffic as well as my expertise in go to
• 26:59
  market. And I started to build a
• 27:01
  portfolio of Angel investments and independent board roles and
• 27:05
  advisor gigs of dime clients. And some of them were in Ireland
• 27:09
  as well. So I just thought it was a cool
• 27:11
  tie and a cool domain name and, and we ran that for many years.
• 27:15
  I, I probably picked that up and I have to look at the registrar
• 27:18
  notes, but I probably created that in 20/14/2015.
• 27:22
  And then when we, you know, sold the company to Oracle, spent a
• 27:25
  few years there, cut our teeth there, got our MBA and business
• 27:29
  and deal making and big enterprise and cloud computing,
• 27:32
  and we decided to build this, this firm York, IE it was on
• 27:35
  that foundation of Angel investments, advising
• 27:38
  operational understanding and expertise.
• 27:41
  And we are coming up with all these cheeky names, Anthony,
• 27:43
  like any name you would think of, like a growth firm for
• 27:46
  startups, rocket ship this and fuel this and whatever,
• 27:49
  whatever. And then my Co founder in CMO,
• 27:52
  Adam, who's my childhood best friend.
• 27:53
  He was actually my high school quarterback.
• 27:55
  Adam's like he worked with me at Dine and Oracle for years.
• 27:58
  Like you already have web traffic, you're already getting
• 28:00
  pitch deals, you already have a portfolio.
• 28:03
  Why don't we just named the brand after you?
• 28:05
  And if you think of the Mckenzie's and the Andreessen
• 28:08
  Horowitz's and the Baines and the Gartner's, they're all named
• 28:11
  after some patriarch or founder or CEO back in time.
• 28:16
  Let's go create our own version of Deloitte, right?
• 28:18
  And so that's how this all kind of came to be and have a name
• 28:22
  that connected. And over time I plan when I
• 28:24
  enter your up and scale my business, I plan on hunkering
• 28:28
  down and putting our offices in Dublin and again doing the same
• 28:32
  playbook that we once saw a lot in our tech companies career.
• 28:37
  So in layman's terms, Kyle, explain what it is that you guys
• 28:41
  are doing there at York IE. Yeah.
• 28:43
  So we're an advisory and investment firm for technology
• 28:46
  companies. We have two sides of our
• 28:48
  business that are fully integrated.
• 28:50
  We have an advisory platform we've created that is really
• 28:53
  tech enabled services for start-ups.
• 28:55
  So any start up who needs operational support and scaling
• 28:59
  their business, we've built out a tech enabled, AI enabled,
• 29:02
  onshore, offshore subscription based business that can help you
• 29:06
  with app development, mobile development, UIUX work, Rev OPS,
• 29:11
  systems, marketing, bookkeeping, FBNA.
• 29:15
  So we've been building this integrated stack of R&D go to
• 29:18
  market and G and a services that help startups with growth.
• 29:22
  And the way we go to market on that side of the house is we
• 29:25
  partner with a lot of other venture firms and growth equity
• 29:28
  firms and private equity firms and banks and other service
• 29:31
  providers to help support their portfolios and clients with
• 29:36
  growth based on all the experience and learnings we have
• 29:39
  and playbooks and templates and tools we've created.
• 29:41
  And then the other side of the house, we run a, a a pre seed
• 29:45
  seed investment fund that specializes in invest in the
• 29:48
  earliest stages of tech startups in, in B to B software and B to
• 29:53
  B SAS. So we've actually got a
• 29:55
  portfolio of about 60 companies, you know, some real high Flyers
• 30:00
  in there. We do 10 to 15 deals a year
• 30:03
  investments out of our funds. That's run by my other Co
• 30:07
  founder Joe Rasca. And you know, we've serviced
• 30:10
  over 250 clients in the advisory business and have about 225
• 30:14
  employees globally now in in New York, IE end to end.
• 30:18
  Just in New York, IE are also in the port coast.
• 30:21
  Just in New York, IE in the port and the port goes, we're in the
• 30:23
  thousands now. You know, because you know, we
• 30:26
  been, we, we launched the firm in late 2019, we launched the
• 30:29
  services arm in late 2020. You know the, the portfolio is
• 30:34
  now maturing, the client base is now maturing, right.
• 30:37
  So, you know, we've got, I mean, I, I haven't, that's a great,
• 30:40
  that's gonna be a great fact to have is like how many jobs have
• 30:43
  been created across the entire ecosystem?
• 30:46
  Because it's probably, I mean, there's some huge companies that
• 30:48
  have been created like 500 people already out of this
• 30:51
  model. So, you know, it's in York, IE
• 30:53
  proper though we have about 225, we've got about 35 or 40 here
• 30:59
  in, in the states out of our Manchester, NH headquarters with
• 31:02
  a few remote people around the country.
• 31:05
  But the the crux of our team is we'll actually launched York IE
• 31:08
  8 Pack Limited in Ahmedabad, Gujarat, India.
• 31:13
  And we have an operation center that's made-up of, you know,
• 31:16
  technology folks and revenue operations folks and back office
• 31:20
  folks that are building technology and tools and
• 31:24
  automation, as well as putting hands on keyboards and doing
• 31:27
  coding and doing marketing and doing back office with a front
• 31:31
  of our strategists and account managers here in America.
• 31:35
  So it's a little bit of a growth hack.
• 31:36
  You know, we get the, we get a pretty big head count over
• 31:38
  there. It's, it's already up to about
• 31:40
  190 full time people. And we have a revolving class of
• 31:43
  about 15 to 20 interns. I just went in February.
• 31:47
  It's it's insane to see your name on a on a building and that
• 31:50
  that far flying across the world.
• 31:52
  So you're not just sort of making investments in these
• 31:55
  companies, you're getting very involved in the operations to
• 31:59
  the point where you've got nearly 200 folks in India that
• 32:03
  they're handling, I don't know, sales, marketing, probably, you
• 32:07
  know, tech support. Yes, yeah, exactly.
• 32:10
  I think, yeah, the vision for the firm was that, you know, not
• 32:14
  since the late 70s was something like a Bain created that had
• 32:17
  Bain Consulting and Bain Capital, right.
• 32:20
  And but the issue with those types of firms is they're doing
• 32:22
  like public company clients and public company buyouts, right.
• 32:26
  So like where do you go in the early days of start up building
• 32:29
  to get support? And and really what you do is
• 32:31
  you you, you get fractional this consultant, this boutique
• 32:34
  agency, this boutique dev firm, this but you know, fractional
• 32:37
  CFO this right. And they're all disparate and
• 32:40
  scattered. So we thought could we build a
• 32:42
  platform for the startup industry that could help them
• 32:46
  with growth along the way. And, and what it's really done
• 32:48
  as we've grown is, is it drives incredible deal flow, right?
• 32:52
  Because you know, we partner with a lot of other funds to
• 32:55
  support their portfolios. So we don't only provide these
• 32:58
  services to our portfolio companies, we provide them to
• 33:01
  the market and to the industry. And what that does is it drives
• 33:04
  incredible deal flow and access that clearly will want to have
• 33:07
  capital pools to get skin in the game and be owners of these
• 33:10
  businesses alongside these wonderful founders.
• 33:13
  Oh, that's really fascinating. OK, so I'm starting to connect
• 33:15
  the dots. Here, yeah, there's, there's,
• 33:17
  there's VC firms and especially private equity firms like big
• 33:20
  private equity firms, Thinkvista or you know, think like Tomo
• 33:24
  Bravo or Andreessen Horowitz or JMI or Summit Partners, like
• 33:28
  they all have operating partners or value creation teams or
• 33:32
  things like that. But the model of those funds is
• 33:35
  they're not necessarily operators, right?
• 33:37
  They're, they're financial managers.
• 33:39
  They're, they're, they're really big.
• 33:41
  They become, they become big banks, right?
• 33:44
  What we know how to do is really help operate and scale
• 33:46
  businesses and see patterns and, you know, help help founders
• 33:49
  with the challenges around the corner.
• 33:51
  And so there are a lot of funds that provide value just to their
• 33:56
  investments, right? Insight Venture Partners out of
• 33:58
  New York made this famous. They have Insight on site.
• 34:01
  But again, they're all huge funds for later stage companies
• 34:06
  and only for their portfolio. And we thought like, well, let's
• 34:09
  build the value platform, the operating partner platform for
• 34:12
  the space that everybody can leverage.
• 34:14
  And then obviously, if we do that really, really well and we
• 34:17
  have a lot of clients and founders who love us and other
• 34:20
  investors who love us, that will drive investment opportunities
• 34:23
  all day, everyday and that's what we've been capitalizing on.
• 34:26
  So I was going to ask why focus exclusively on tech companies,
• 34:30
  but now understanding that you're providing the back office
• 34:34
  as well, it makes a lot more sense because the playbooks are
• 34:37
  going to be very similar in terms of how do we scale this,
• 34:40
  how do we market it? What are the channels that?
• 34:42
  We. Yeah, but you make a great
• 34:43
  point. But I mean, I think on the
• 34:46
  investment side, you know, we have LP's or you know, right now
• 34:49
  individual investors who invest in our funds to go put money
• 34:52
  into startups, right? So we have to give them a thesis
• 34:55
  like where do we focus our energy and effort and, and what
• 34:59
  portfolio of companies are we going to provide to you that's
• 35:01
  different than everybody else, right?
• 35:03
  So it's not generic, right? So B2B software, SAS
• 35:06
  subscription tech is where we focus and it's exclusive to that
• 35:10
  in our investments business. I will say in our advisory
• 35:13
  business, it is a broader set. Anthony, to your point, like,
• 35:16
  you know, for example, we work with the American Cornhole
• 35:20
  League, we work with Internet Society, a non profit, you know,
• 35:24
  you know, we have, we work with District real estate advisors, a
• 35:27
  real estate brokerage and investment firm.
• 35:29
  Like, so I kind of look at it as like in the year 2025, every
• 35:33
  company's like tech enabling themselves or trying to even if
• 35:37
  that's internal apps or you know, or internal systems or you
• 35:42
  know, and website and digital presence, right, Everyone needs
• 35:45
  help. So we kind of look for like tech
• 35:46
  enabled, growth oriented, looking at unique subscription
• 35:51
  models again for stickiness and repeatability and
• 35:55
  sustainability. They're you're.
• 35:56
  Looking for these criteria in the companies that you invest in
• 35:59
  or just in the companies that you're providing the back office
• 36:01
  services? This is what I'm saying also for
• 36:03
  the back office services, it's just, and again, it's and so
• 36:05
  those don't have to be tech or have to be B2B SaaS.
• 36:08
  And there's a broader swap like we even work with consumer tech
• 36:12
  in marketplace tech and hardware tech, right?
• 36:14
  Like, and those aren't types of companies that I would put money
• 36:17
  in out of my funds today. Now maybe someday I have a
• 36:20
  marketplace fund or maybe someday I have a tech enabled
• 36:23
  services fund, right? Like, but today it's very
• 36:25
  focused on the BDBSS on the investments, but the advisory
• 36:28
  business is open for business for anyone.
• 36:30
  OK. So the reason that you're really
• 36:31
  more focused in tech on your investments is because that's
• 36:35
  what you had to sort of pick a niche for your investment.
• 36:39
  Yeah. And it's exactly yeah.
• 36:40
  And it's the most of what we do and what we know and where we're
• 36:43
  the biggest experts and the majority of our content and
• 36:45
  curriculum is around that. But but there isn't a company I
• 36:48
  meet nowadays, it isn't trying to figure out how to get longer
• 36:52
  term contracts, more consumption based pricing models, you know,
• 36:56
  higher margin service delivery, especially in the age of AI.
• 37:00
  And you know, like we know how to do that, right?
• 37:03
  And even if you're building a real estate business or even if
• 37:05
  you're building a non profit, you're all trying to get more
• 37:07
  predictable, sustainable and create more value.
• 37:10
  And we can help, right? And so, you know, it, it, that's
• 37:12
  a tough balance, right? Of course, to, to in our own
• 37:15
  messaging and communication and demand Gen.
• 37:17
  But the way that we really do it is, you know, we, we focus on
• 37:20
  that top of funnel and, and we try to drive community and brand
• 37:23
  and that leads to lots of great opportunities for all sides of
• 37:26
  the business. You know, in doing a little bit
• 37:28
  of research, I understand that York, IE you guys really want to
• 37:33
  emphasize building good companies that create jobs,
• 37:37
  wealth and community impact. Is there maybe a real world
• 37:41
  example of how this mission has kind of shown up in a decision
• 37:46
  or an investment? Yeah.
• 37:48
  I mean, I think we talk a lot about like pragmatic growth
• 37:53
  versus growth at all costs. And if, if you follow like the
• 37:56
  headlines, I mean, think about even all the movies that are
• 38:00
  created about tech companies, right?
• 38:01
  It's like, it's either like the Facebook movie about a roaring
• 38:04
  success, or it's the Wework movie or the Theranos
• 38:08
  documentary series, you know, about epic fails, right?
• 38:12
  And I think in, in the world of tech, in the world of Silicon
• 38:16
  Valley venture, we call it growth at all costs or, or VC
• 38:19
  power law. You know, it's sort of
• 38:22
  celebrates this concept that like 9 of 10 startups might
• 38:24
  fail, but the one that emerges, the Uber that emerges might
• 38:29
  cover all the sins or all the losses.
• 38:32
  And I just think that's a shitty thing for founders, honestly,
• 38:35
  right? Like you have backers of your
• 38:37
  company who expect one of 10 of you to fail or, or maybe they
• 38:41
  don't expect it when they initially invest, but are OK
• 38:44
  with it in the end. And I think that's a really
• 38:46
  challenging thing. I also think venture capital
• 38:48
  plays to the coasts, especially New York and Silicon Valley, San
• 38:52
  Francisco more and in in places like Manchester and Columbus and
• 38:56
  Minneapolis and Atlanta and Denver and you know, Salt Lake
• 39:01
  City. There's also really, really good
• 39:03
  startups that are emerging that are good healthy business models
• 39:07
  solving real world challenges for customers.
• 39:09
  And sometimes the good companies aren't the ones that are going
• 39:13
  to get, you know, Sequoia or Benchmark or Bessemer and A16Z
• 39:17
  or General Catalyst to invest. And so there's a whole world out
• 39:20
  there of great companies of good exits into the future.
• 39:24
  They don't all need to be Dines at 600 million or all need to
• 39:27
  be, you know, you know, open AI at whatever the hell, you know,
• 39:32
  billion 10s of billions, They're now saying they're worth, right?
• 39:36
  There's a lot of good to be had in the market with good healthy
• 39:38
  businesses. And that's we like the focus.
• 39:41
  So there's tons of examples in that.
• 39:42
  You know, I mean, I, I have companies and all, all facets,
• 39:46
  you know, ovations one in Salt Lake City, it's, you know, it's
• 39:49
  a great company that does restaurant reviews, right?
• 39:53
  We have a company called canvas. That's, you know, remote
• 39:58
  entirely across the country and it's a text analysis platform
• 40:03
  for the market research in in consumer brands, right?
• 40:06
  Like, you know, these are companies that are good, healthy
• 40:09
  companies that will. Change founders lives and change
• 40:13
  their employees lives along the way and upon exit.
• 40:17
  And they'll operate in communities where they can make
• 40:19
  a real dent, like you can in Columbus and I can in Manchester
• 40:23
  where, you know, if I'm down, down in New York or if I'm in
• 40:25
  San Jose or, you know, I, I might just be one of many and
• 40:29
  get lost in the shuffle. And I think there's that's
• 40:30
  unfortunate for for many. So what is it that you're
• 40:33
  looking for in a potential investment?
• 40:36
  You said you'll make, you know, 10 to 15 investments a year.
• 40:38
  What's kind of the common threads between them?
• 40:40
  Yeah. So we look at about 600 deals a
• 40:42
  month that come to us raising their hand, saying they're
• 40:45
  looking to raise money pretty quickly at the top.
• 40:50
  We can tell what's AB to B software company at the stage
• 40:52
  that we invest, right? We invest very early, think sub
• 40:55
  1,000,000 of revenue companies that we call pre seed, seed
• 40:59
  stage. Sometimes it might even be pre
• 41:01
  revenue. It might even be an idea and a
• 41:03
  founder that we've worked with before that we really love.
• 41:06
  And so it's again, it's B to B SaaS, you know, growth oriented
• 41:09
  really, really early. We love.
• 41:12
  We've done a lot obviously in infrastructure and cyber in the
• 41:15
  areas we came from, but we do a lot now and data platforms and a
• 41:20
  lot of vertical industry apps Like that's really hot for us
• 41:23
  right now. Like, you know, pick your random
• 41:26
  industry that hasn't, you know, had great software or great
• 41:29
  automation or great efficiency manufacturing is a good example
• 41:33
  or supply chain or you know, you know, meat butchering.
• 41:40
  You know, we have literally some of the most random companies
• 41:42
  you've ever seen. Meat Meat butchering plus SAS.
• 41:46
  Yeah, it's literally, it's an optimization platform called
• 41:50
  Boler that is actually founded out of the Nordics and they've
• 41:56
  built this AI platform to help, you know, butchers not have so
• 42:00
  much waste in the in the animals that they're, you know,
• 42:04
  butchering. It's incredible, right?
• 42:06
  And and so we have everything from that Blue Trace out of
• 42:08
  Portland, ME's a great example. I mean, Blue Trace is a
• 42:13
  shellfish traceability company from from the, you know,
• 42:17
  fishermen to the Whole Foods and making sure that the, you know,
• 42:21
  halibut you think you're eating is halibut and that, you know,
• 42:24
  it was actually caught in a time period and it says it was caught
• 42:27
  and it's fresh and, and these are.
• 42:29
  That are they bar coding the actual fish that they are.
• 42:32
  They are, they're literally, they're packaging, they're from
• 42:35
  the, from the docks. They're literally in the supply
• 42:39
  chain. They've built the SAS system to
• 42:41
  kind of track, you know, the that captures along the way, so.
• 42:45
  The fish, the fish comes off the boat, it's immediately getting
• 42:48
  packaged and that Yep, there's some sort of a barcode tracking
• 42:51
  mechanism, RFID that goes on. It and, and a system that gets
• 42:55
  put into a operating system just like you'd expect in kind of
• 42:59
  anything that, you know, this industry was left behind and
• 43:01
  everything was physical and manual and not digitized.
• 43:04
  And and that's the examples that we love, right like tell us an
• 43:06
  industry that hasn't been, you know, had a solution.
• 43:10
  And so we're seeing a lot of these industry experts who come
• 43:12
  from these spaces saying, hey, I think I can solve that with
• 43:14
  technology. And then in the year we're in,
• 43:17
  you know, it's easier than ever to build great time.
• 43:20
  What's the common thread in a successful starter?
• 43:25
  What's something that you're looking for?
• 43:28
  I mean, we, we index like we index like so hard right now on
• 43:33
  the person, right, like everyone, I got asked this.
• 43:35
  I spoke at an event in Boston the other night to a group of
• 43:38
  young, you know, 30 year old professionals and, and they're
• 43:41
  asking that they're like, what's the DNA?
• 43:42
  What's the difference? Whatever.
• 43:43
  And it's like, listen, you know, you can have the best idea in
• 43:47
  the world. You can be in the biggest market
• 43:48
  in the world. You can, you know, be super tech
• 43:51
  geek and have some cool app you've already, you know,
• 43:54
  developed an MVP for. At the end of the day, we talk a
• 43:56
  lot of it like founder market it fit like why are you Anthony,
• 44:00
  the most unique person or the right person to attack that
• 44:04
  market problem to build technology solutions to deliver
• 44:07
  value to that industry? And I think it's kind of starts
• 44:10
  there, like what's the founder market fit?
• 44:12
  You know, people talk a lot about product market fit, but
• 44:14
  that comes a little later. And so we look for that a lot.
• 44:17
  And then we look for the founding team, you know, like to
• 44:20
  do a start up like, and I'm, I'm building a start up, helping
• 44:23
  start-ups and I've been in start-ups my whole life.
• 44:25
  Like you need really thick skin and you need to deal with like
• 44:28
  99% of things going wrong or bad or negative and somehow through
• 44:35
  all of that, still push forward. And so there's a lot of like the
• 44:39
  push on these. Like what's your ambition?
• 44:40
  What are you looking to do? What's your philosophy on
• 44:43
  business scaling? Like how do you, how are you
• 44:45
  going to what's your capital strategy?
• 44:46
  How do you plan on being efficient?
• 44:48
  How do you plan on like, you know, getting proof from
• 44:51
  customers? We call it the market in
• 44:52
  approach to company building, right?
• 44:54
  Like don't just build an app and hope the world finds it.
• 44:56
  You know, are you out there? They're getting feedback or so
• 44:59
  these are the types of things we really push for.
• 45:01
  And you know, of course we look at financials and we look at
• 45:04
  tech and we look at market and total addressable market and
• 45:08
  competitive landscape. But in the end, it's really
• 45:10
  about who's delivering it and and their conviction and their
• 45:13
  commitment and the kind of aligned philosophies that we can
• 45:16
  share together. So you're evaluating 600 deals a
• 45:19
  month. Obviously, there's no headspace
• 45:21
  or time to talk to 600 founders. So you've got some mechanism for
• 45:25
  funneling that down. And I know one of the things you
• 45:28
  said is, hey, pretty quickly we can see if it's in sort of the
• 45:31
  tech SAS space that we're interested in From there, how
• 45:34
  many are leftover and how do you begin to kind of sift through
• 45:39
  those? Yeah, it's probably about half.
• 45:42
  You know, I think, I think founders are getting a little
• 45:44
  bit better and actually doing a slight amount of research of the
• 45:47
  investors they're pitching before they reach out.
• 45:50
  But it's probably about half end up kind of in the lane that end
• 45:54
  up in our funnels. And we've created a bunch of
• 45:56
  technology and integration with our HubSpot CRMS and our own.
• 45:59
  We have a platform called Fuel, which is Fuel dot York dot IE
• 46:03
  that's free and available, but it's a market research platform
• 46:06
  to do analysis on companies and get information quickly on that.
• 46:10
  Think of it like a Crunchbase or a pitch book type solution.
• 46:14
  And we've created a lot of that the filter, right?
• 46:16
  And then obviously humans come into the mix, right?
• 46:19
  We have a team of analysts, they come in, they look at deals,
• 46:22
  they evaluate. OK, now does it fit our stage?
• 46:24
  That's a big deal, right? Like we don't invest in
• 46:27
  companies doing more than a million and there are or so
• 46:30
  right or, or, you know, most of the rounds we're investing in
• 46:34
  our, you know, 3 to $5,000,000 rounds.
• 46:36
  There's all these little mechanisms and it's like check,
• 46:38
  check, check. Does it fit?
• 46:39
  Does it fit? And then if it gets all the way
• 46:41
  through that, let's say that's now down to 100 deals a month.
• 46:44
  Now you're probably doing trying to do first calls or some follow
• 46:47
  up on e-mail. We have form submissions, you
• 46:51
  know, we're looking for pitch decks.
• 46:52
  We're kind of giving a quick look and glance.
• 46:54
  You know, we might have competitive companies in our
• 46:57
  portfolio already. We might have made investments
• 47:00
  as angels a decade ago and like not, you know, had some spaces.
• 47:04
  Really. I'm not a huge fan of in HR
• 47:07
  tech. I don't love human resource
• 47:08
  tech. I don't love it.
• 47:09
  I just don't love right like and there's reasons for it or ad
• 47:12
  tech very hard, you know, or marketplaces very difficult, you
• 47:15
  know, like require lots of capital.
• 47:17
  So you kind of pattern map a bunch of these things and and we
• 47:20
  run, we run it like a company though, right?
• 47:22
  Like so it runs through our processes, different members of
• 47:26
  the team and seniority get pulled into the deals as they
• 47:29
  move their way through the gauntlet, you know, through our
• 47:31
  pipeline. We have weekly pipeline reviews.
• 47:35
  We have Friday updates to the whole leadership team.
• 47:38
  And then, you know, they bring the deals most of the time that
• 47:42
  they want to do the investments team to me when they want to do
• 47:45
  that, right. And because we've all worked
• 47:47
  together so long and known this process through Dine and Oracle
• 47:51
  and you know, by the way, I didn't mention this, but
• 47:54
  Moonlighting, I made 60 investments in B2B software
• 47:57
  companies before we launched short IE and now we've made 64,
• 48:00
  right? So, you know, it's a decade of
• 48:02
  doing this with different vehicles and, and, and, and
• 48:06
  different, you know, time and different value that really led
• 48:10
  to us to today to, to make the decisions we make.
• 48:12
  We just got a term sheet signed last night.
• 48:14
  It's a kind of always on, right? It's a, it'll be announced
• 48:18
  probably within a month. Hopefully we can close that
• 48:20
  quickly. That's a company out of
• 48:22
  Charlotte, NC. So we invest everywhere too,
• 48:24
  right? We have companies all over the
• 48:26
  globe. And so what's the typical life
• 48:29
  cycle from the deal shows up in the pipeline to signing the, you
• 48:35
  know, wet ink on paper? It depends on where the startup
• 48:39
  is in their fundraising process. Like sometimes we, we're at the
• 48:43
  end, right? They, they, they've already got
• 48:45
  a lead investor. They're looking to fill out the
• 48:46
  rest of the round. Heck, we might even know the
• 48:49
  lead investor and give them a quick call and say, Hey, why do
• 48:51
  you like this company? Give us all your diligence
• 48:52
  materials, right? Other times they're just kicking
• 48:55
  off a process, right? And depending upon the company,
• 48:58
  it can be, you know, a two week process for the company, or it
• 49:01
  can be a six to nine month process for the company.
• 49:05
  You know, I think the earliest stage again, is, is about
• 49:08
  founder market fit. It's about feel between us, you
• 49:11
  know, like think about how much time founders spend, like like
• 49:15
  deciding who their Co founders are, right and who's going to
• 49:19
  own what and all that. Well, you got to remember when
• 49:22
  you're raising money from whether even if it's just Angel
• 49:24
  investors or funds, you know, you're selling a piece of your
• 49:27
  company to somebody and you're going into business.
• 49:29
  It's a marriage and you know, start-ups take a while, right?
• 49:32
  They take 7 to 12 years, you know, most of the time when a
• 49:35
  good outcome happens. And so you know you're going
• 49:38
  into a long term partnership, you should take it seriously and
• 49:41
  make sure you're pretty well aligned.
• 49:43
  Kyle, you said something a moment ago about what you look
• 49:45
  for in an entrepreneur. You're like, hey, thick skin,
• 49:49
  99% of things are going to go wrong and how do you, you know,
• 49:53
  how do you handle that and bounce back?
• 49:55
  I'd like to hear a story about something that you had to bounce
• 49:59
  back from a serious challenge, whether it was on the personal
• 50:01
  or professional side, and how you got through it and what you
• 50:04
  learned. Yeah.
• 50:06
  So in the meteoric rise of Dine where I was Chief Revenue
• 50:11
  Officer for my 26th birthday to my 33rd birthday when we sold
• 50:15
  the Oracle, I was a young first time executive, right And it was
• 50:23
  an incredibly hard ride. And as we scaled from three to
• 50:28
  10 to 20 to 40 to 50 and raise private equity and created a
• 50:33
  board, a lot of those older private equity investors who
• 50:36
  were very experienced and doing it a long time, didn't think
• 50:38
  that myself and, or our leadership team had the chops to
• 50:41
  take it to the next level. And that created an unbelievable
• 50:44
  amount of pressure, self doubt, you know, fear, right?
• 50:49
  Because, you know, I I had a great upgrade bringing, but you
• 50:54
  know, I wasn't independently wealthy by any stretch.
• 50:57
  And if you think about when you're scaling a start up and it
• 50:59
  starts to grow and get valued higher, your net worth might be
• 51:03
  growing, but it's very illiquid, you know, so I knew that I was
• 51:08
  going to be set for life as long as this thing didn't implode and
• 51:10
  tip over. And what happened was other
• 51:14
  founders, other executives, there was a core five of us who
• 51:17
  built dine, you know, started to either burn out, quit, get
• 51:22
  fired. And I kept looking around and
• 51:25
  saying, Hey, like, I have to steward this to some outcome
• 51:28
  someday or else none of us are making any money, right?
• 51:31
  And none of us are going to have the life changing outcome that
• 51:33
  we all hope for. And, and I wore all that, you
• 51:36
  know, right or wrong, you know, I, I, I wore it.
• 51:39
  I felt the pressure, I didn't, I, I felt like I was doubted.
• 51:42
  That inspired me in many ways to persevere and power through, but
• 51:46
  it actually led me to incredibly poor mental health and
• 51:50
  incredibly poor physical health. I started to manifest.
• 51:54
  This is like 2015 time period. We sold the end of 16, early 17.
• 51:58
  I started to manifest the worst migraines I ever had.
• 52:02
  I have actually, I've never had a migraine before that and I
• 52:06
  never have had one since. Actually.
• 52:07
  It's kind of a, there's a stretch of time that we're, it
• 52:11
  was so debilitating that if I would get a migraine at 8:00 in
• 52:13
  the morning, I had to go to bed till the next day.
• 52:16
  And so, you know, I was getting MRI scans, my brain, I was
• 52:20
  convinced I had a brain tumor and that I was going to be 6
• 52:24
  feet under soon. And you know, I was updating my
• 52:26
  estate plans, my trust and wills.
• 52:30
  You know, it was, it was dark and I was dark and, you know,
• 52:34
  but I powered through because of, you know, when you build a
• 52:37
  company in your hometown and you, you know, we've got the 500
• 52:40
  global employees. I actually recruited a lot of
• 52:43
  people who had moved away to New York or the West Coast or
• 52:45
  Boston. And I felt, I felt responsible
• 52:48
  and accountable to all of them and myself and my family and my
• 52:52
  future family. And the pressure just mounted
• 52:55
  and mounted and mounted. And what I realized about myself
• 52:58
  is that I do really well when I'm in control.
• 52:59
  You know, if I, if I feel like I'm in control, I can handle the
• 53:03
  stress and the anxiety that comes with the, the career path
• 53:07
  and life I've chosen. I, I work in a very high risk,
• 53:09
  high reward climate, right? And that's, you know, we can
• 53:13
  correlate that to Ryan Day, right?
• 53:14
  I mean, it's a high risk, high reward career and profession.
• 53:18
  And now York, IE business I've decided to create.
• 53:21
  But if I feel like I've got a hand at the wheel and that, you
• 53:24
  know, I'm calling the shots with my team in collaboration and and
• 53:29
  I don't have people pulling puppet strings up here around me
• 53:33
  telling me what I can and cannot do.
• 53:36
  Yeah, I found methods through visiting therapists and
• 53:40
  different things to deal with that over time.
• 53:41
  And I just don't think a lot of people talk about this type of
• 53:43
  stuff, by the way, like, you know, it's more and more in the
• 53:47
  last several years of like mental health and physical
• 53:50
  health and how that affects you as an entrepreneur.
• 53:52
  But I don't think people like like really talk about like the
• 53:56
  actual issues they've dealt with.
• 53:57
  And I remember a therapist once wrote down in a post it note and
• 54:02
  I haven't saved somewhere. It might, it might be in here,
• 54:05
  but they wrote in a post it note.
• 54:06
  I can't remember. It's right here.
• 54:07
  Actually. It was like write things down to
• 54:12
  get out of your head and then see and feel your
• 54:15
  accomplishments, right? Because it's like, it's funny,
• 54:18
  like, you know, to me, like I sometimes think I'm an aunt and,
• 54:24
  you know, like, maybe part of that's that I went and worked in
• 54:26
  an Oracle and sold my company there.
• 54:27
  And, you know, I've been around your tech founder billionaires,
• 54:31
  you know, like that was our clients at Dine.
• 54:33
  And, you know, these are people I've interfaced with or sat on
• 54:36
  panels with. And and I think of myself as
• 54:38
  like a cute, you know, like, yeah, successful person, but not
• 54:41
  relatively. You know, there's a spectrum of
• 54:43
  all this, right? And, and sometimes you just, you
• 54:45
  just have fear and self doubt and, you know, challenge
• 54:48
  yourself and think differently. And, but again, you just going
• 54:51
  to remind yourself what you're playing for, like, you know,
• 54:55
  play the long game, be loyal to yourself, you know, keep your
• 54:58
  integrity, be loyal to your team and the people around you.
• 55:01
  And you know if, if, if you can power through the tough times,
• 55:05
  you know, hopefully you can reach some relative mountaintop
• 55:08
  for yourself as you progress. Yeah, I do appreciate you giving
• 55:11
  voice to this because I think you're right, Kyle, this is the
• 55:13
  kind of thing that doesn't really get get a lot of
• 55:16
  attention and people might give it sort of a passing mention of
• 55:21
  oh, yeah, that was a really difficult time.
• 55:23
  But that kind of glosses over like, man, really struggling,
• 55:27
  the migraines, you know, put me out of Commission for a full
• 55:29
  day, have to go to bed. And you know, the the therapy
• 55:33
  that you sought sounds like it helped a lot that that post it
• 55:36
  note there clearly means a lot to you.
• 55:39
  You've kept it over the years. Those two different messages.
• 55:42
  Anything else that might be helpful for folks who are
• 55:44
  listening, going through their own struggle that you might want
• 55:48
  to pass along to them? Yeah, talk about it.
• 55:51
  I think the there are resources available to people, but I also
• 55:55
  think like founders tend to like lonely is the head that wears
• 55:58
  the crown, right? And they tend to keep a lot of
• 56:00
  stuff hidden and, you know, try to avoid a lot of things.
• 56:05
  Is a great, great figure. A friend of mine named Doctor
• 56:08
  Julie Gerner on X and Twitter. She's so good.
• 56:11
  She's like coined the Wendy Rhodes from billions of tech
• 56:14
  and, and she just always has these perspectives.
• 56:16
  And a lot of it comes down to like actually talking about
• 56:19
  things and not avoiding the things that are actually hard
• 56:22
  and challenges. And, you know, and again, I, I
• 56:25
  just take all the, I, I, I'm, I listen to podcasts like this.
• 56:29
  I, I read blogs or articles or interviews, like, I try to stick
• 56:33
  little Nuggets like see public speakers, like I'm always trying
• 56:36
  to like learn, get better, enhance my own world view and
• 56:39
  perspectives. And I think that's something
• 56:42
  that everybody can control. You know, and you made that
• 56:45
  connection to Ryan Day there a moment ago, high risk, high
• 56:48
  reward. And, you know, kind of another
• 56:50
  tie in with him is sort of the importance that in the spotlight
• 56:55
  that he's shown on the importance of mental health.
• 56:58
  And you could say a little bit more about, you know, how you
• 57:01
  know him and you know what he kind of went through as a kid.
• 57:04
  Yeah, the, I mean, the correlation there is Anthony's
• 57:06
  based in Columbus, OH. So I asked if he was a Buckeyes
• 57:09
  fan. And of course, he's not just a
• 57:10
  Buckeyes fan. He's also an alum and a die hard
• 57:14
  fan, Right. And so Ryan Day actually grew up
• 57:16
  in New Hampshire. Our headquarters are in
• 57:18
  Manchester, NH I went to Manchester West High School.
• 57:21
  Ryan Day went to Manchester Central, by the way.
• 57:23
  Fun fact, Adam Sandler also went to Manchester Central and Sarah
• 57:28
  Silverman went to West. So there's like there's
• 57:30
  comedians, there's Chip Kelly as well, went to Manchester Central
• 57:33
  High School. Dan Mullen went to Manchester.
• 57:35
  Trinity High School is like a weird coaches and comedians
• 57:39
  track out of this place. But yeah, Ryan was a competitor.
• 57:43
  You know, he's a few years older than me.
• 57:45
  I played football against his younger brothers.
• 57:48
  He went on to UNH, you know, my older brothers played against
• 57:52
  them. And he end up, he has a, he has
• 57:55
  a, let him tell his own story of, of dealing with mental
• 57:58
  health and mental health in his family.
• 58:00
  And he and his wife Nina are big supporters of mental health.
• 58:05
  We do some big initiatives in in the state of Ohio, you know, and
• 58:09
  and and I've stayed in touch a bit with Ryan over the years as
• 58:13
  we've been on our own different careers, but trajectories,
• 58:17
  right? We both kind of had relatively
• 58:19
  young success young in our lives, right, And neither came
• 58:24
  from big money or anything. And all of a sudden you start to
• 58:26
  make money and have more eyeballs on you and your name's
• 58:30
  more in lights. And again, I'm not comparing
• 58:32
  myself to a, you know, the fire Ryan day challenges He's had the
• 58:36
  he's had the weather until he finally run the big chip this
• 58:38
  year, which is outstanding for him.
• 58:41
  But you know, I've stayed in touch because he's actually
• 58:43
  married to a twin Nina and and Kelly Spiro.
• 58:47
  That's now Kelly Burnett Nina Day are twin girls who Ryan's
• 58:51
  dated Nina since high school. And and they're actually my next
• 58:54
  door neighbors. Ryan's Ryan's sister-in-law and
• 58:58
  her husband Mike and and their family.
• 58:59
  So they're around a lot, you know, and they're big supporters
• 59:03
  of New Hampshire football and obviously football everywhere.
• 59:06
  And, and I just appreciate that they've, you know, opened up a
• 59:09
  lot about this as well over the last several years when, you
• 59:12
  know, kind of Ryan didn't talk as or need to talk as much about
• 59:15
  it historically. Last quick thing on Ryan too, is
• 59:18
  he actually married Nina and Kelly and their family and, and
• 59:22
  actually coach Spiro Stanley. Spiro is an absolute legend with
• 59:26
  the high school with my mother and, and you know, he was a
• 59:29
  legend. He was a maybe 4550 year coach
• 59:32
  of Southern New Hampshire University's basketball program
• 59:35
  and a real coaching mentor and supporter obviously, of Ryan and
• 59:40
  you know, father figure to Ryan his whole life.
• 59:42
  And and I see Stan all the time. He's just a he's a larger than
• 59:45
  life character. He plays golf at the same
• 59:47
  Country Club I go to and he's always out in Ohio.
• 59:50
  So look for him, look for him at games and you know, go Buckeyes,
• 59:54
  go. Buckeyes is right.
• 59:55
  Yeah. I appreciate you sharing all
• 59:56
  that on Ryan Day. You know, as a Buckeye fan, big
• 1:00:00
  Ryan Day fan. You know, watching what he
• 1:00:03
  endured with, you know, some of the fan backlash and then, you
• 1:00:06
  know, the, the ultimate resiliency that he showed.
• 1:00:09
  But you know, even aside from that, again, the involvement
• 1:00:13
  and, and the voice that he's given to the importance of
• 1:00:15
  mental health, You know, especially when some of his
• 1:00:18
  players have been in a rough spot and you know, he's he's put
• 1:00:22
  them first over, you know, the importance of the game, which is
• 1:00:25
  is the right thing to do. And so I'm glad, glad we gave a
• 1:00:27
  little voice to that. Yeah, that's great.
• 1:00:29
  Yeah, I was standing. I just got one more question for
• 1:00:32
  you, Kyle, but before I ask it, I want to do a couple things.
• 1:00:34
  I'm going to invite everybody listening.
• 1:00:35
  Go ahead and hit and hit the follow button on your favorite
• 1:00:38
  podcast app. Let's continue to get more great
• 1:00:40
  interviews like we've had today with Kyle York from York, IE.
• 1:00:44
  Kyle, also want to let people know the best way to either get
• 1:00:47
  in touch with you directly or to follow your story.
• 1:00:49
  What would that be? Yeah, that's great.
• 1:00:51
  So you heard our websites York dot IE there's tons of resources
• 1:00:55
  there available to all types of founders, start-ups, operators,
• 1:00:58
  investors. So please engage.
• 1:01:00
  We're also at York growth across all social channels and I'm K
• 1:01:05
  York 20 across all social channels.
• 1:01:07
  The 20 is my football number. I my my best, my favorite player
• 1:01:11
  of all time is the great Barry Sanders out of Detroit.
• 1:01:15
  Sorry about that. You know Ohio fans, but you
• 1:01:17
  know. Big Barry Sanders.
• 1:01:19
  Yeah, big Barry Sanders fan. Yeah.
• 1:01:21
  Yeah. Great athlete.
• 1:01:22
  And, you know, so I wore his number from, you know, youth all
• 1:01:25
  the way through college football and, you know, kept it.
• 1:01:27
  Kept it. It was my AOL Instant Messenger
• 1:01:29
  screen name. And I've kept it all these years
• 1:01:31
  later. But yeah, feel free to connect.
• 1:01:33
  Look us up, follow along, and we're here to support you.
• 1:01:37
  So last question for you, Kyle. As you look, you know, in your
• 1:01:40
  industry, things you know evolve pretty quickly, but maybe over
• 1:01:43
  the next two to three years, what are some of the trends,
• 1:01:46
  investment trends, business trends, tech trends that you're
• 1:01:49
  most excited to kind of see unfold and be a part of?
• 1:01:53
  Yeah. Listen, I think I talked a bit
• 1:01:54
  about it today. I think there's been a somewhat
• 1:01:58
  of a correction back to healthier business models and
• 1:02:01
  more sustainability and you know, less burn as you and less
• 1:02:06
  capital may be required to scale some of these companies.
• 1:02:09
  I think that's number one. I think #2 I'm all about these
• 1:02:12
  vertical industries solutions. I think, you know, there's a lot
• 1:02:16
  of horizontal software, you know, in big tech, but what
• 1:02:20
  about these underserved industries?
• 1:02:22
  I think is really, really, really happy to see.
• 1:02:25
  I also think post pandemics, pandemic especially, you know,
• 1:02:29
  Steve Case from AOL has this thing called the rise of the
• 1:02:32
  rest and it's about, you know, secondary tertiary cities and
• 1:02:36
  the ecosystems and entrepreneurial mindedness that
• 1:02:39
  can come from them. And many of these places are
• 1:02:41
  very entrepreneurial. It's just been more Main Street
• 1:02:43
  small business or small business oriented.
• 1:02:45
  And you're seeing tech companies be able to build, be built
• 1:02:47
  anywhere. So, you know, I'm, I'm big about
• 1:02:50
  those three things. Obviously there's an overarching
• 1:02:54
  AI hype cycle, an overall, you know, cyber security, Internet
• 1:03:00
  security, you know, nation state conflict, crazy stuff going on
• 1:03:04
  in the world. These are things where we're
• 1:03:06
  keeping our eye on. That's the more kind of
• 1:03:08
  technical answer. But you know, we believe there's
• 1:03:11
  that's going to impact every sector and you know, we aren't,
• 1:03:13
  we're just running off the Cliff to chase that stuff.
• 1:03:15
  You know, we're, we're trying to be really thoughtful about
• 1:03:17
  everything we're doing. Kyle York, I want to be the
• 1:03:19
  first to thank you for sharing both your time and your story
• 1:03:22
  with us today. I really appreciate it.
• 1:03:24
  Thank you. Folks, that's a wrap on another
• 1:03:26
  episode of the Inspired Stories podcast.
• 1:03:29
  Thanks for learning with us today.