Subscribe
Share
Share
Embed
Welcome to Cloudbreak, where breakthrough innovation meets breakthrough growth. In this podcast hosted by early stage VC firm Trilogy Equity Partners, we sit down with the brilliant minds and leaders building early stage startups to discuss the pivotal stories, insights, and hard-won lessons they've learned from the driver's seat of breaking innovation, company building, and scaling. They'll share what's working, what isn't, and what they'd wish they'd known earlier.
CLOUDBREAK PODCAST TRANSCRIPT
INTRO (00:00)
Welcome to Cloudbreak, where breakthrough innovation meets breakthrough growth.
Today, John Stanton of Trilogy Equity Partners chats with Ted Sullivan, co-founder and CEO
of Rollout. Rollout is a simple yet powerful mobile assistant for patrol officers, designed to
cut admin workload and improve information sharing, helping agencies be more efficient
and informed. Here's their conversation.
John Stanton (00:23)
Good morning, Ted. Such a pleasure to see you. How are you doing?
Ted Sullivan (00:27)
John, I'm thrilled to be here. Thank you so much for having me and thank you for being the
podcast host on this episode.
John Stanton (00:34)
I'm happy to do this. I think we'll get into it, it feels a little bit like the time I first met you,
fifteen years ago now. Once again, you're showing your entrepreneurial chops and tackling
a problem you've got a unique perspective on. I think it's going to be another great success
for Ted Sullivan and team.
Ted Sullivan (00:58)
I hope so, and I'm just really excited to be partnered with you and Trilogy again, excited to
run it back.
John Stanton (01:04)
You and I met at a baseball game, and we share a love of baseball. I was thinking, as an
opening question, talk about your journey: starting off as a kid playing baseball, playing at
Duke, playing for the Indians organization, and then becoming an entrepreneur. How did
that journey happen?
Ted Sullivan (01:26)
It's a good question, John, and those two paths were very much intertwined.
I was a ball player growing up in Washington, DC, and was fortunate to get recruited to play
at Duke. My brother was two years older and was playing at Stanford at the time. He was
drafted, and then I was drafted a few years after. During our college and minor league
careers, like most ball players, as you know, we didn't get paid much in the minor leagues,
we'd come back home to DC and need to make a buck during the off-season. We'd work
out in the mornings and coach kids in the afternoons. So, we started a business together
called Headfirst.
That business, which was really just a vehicle for us to make a few bucks during the off-
season and support ourselves while preparing for spring training, is still around 35 years
later. My brother runs it, it's been his entire career after baseball, and it's now impacted the
lives of tens of thousands of kids, thanks to him.
But that's where the entrepreneurial journey started. We looked at ourselves as players
and coaches helping local kids in the DC area. I got bitten by the entrepreneurial bug, the
business side of it. How do we market it? What products do we have? Even though at the
time I was really just giving pitching and hitting lessons or running the occasional clinic, I
realized: I'm actually running a business. All of a sudden, we'd created a business, and I
think we were both bitten by that bug from that point on.
John Stanton (03:19)
You and Brendan took somewhat different paths. I have to note, the first time we met was
at a Headfirst camp, and my son, who played baseball in college, benefited a lot from the
experience and advice he got from you and your brother.
While Brendan continued with Headfirst full-time for 30-plus years, you went off to that
little business school up in Boston. What caused you to leave your entrepreneurial journey
to devote yourself to business school?
Ted Sullivan (03:58)
When I stopped playing ball, there's a bit of an identity crisis that happens when a playing
career, or really any extended career, comes to an end or hits a pivot point. I didn't know
what I wanted to do. I thought I had some entrepreneurial skills, but I'd thought of myself
first and foremost as a baseball player since I was probably seven years old. And here I am,
23, 24 years old, getting that fateful phone call from the Cleveland Indians scouting
department telling me my career was over. They did offer me a job in the front office, but I
wasn't ready to take it. I remember hanging up the phone and taking several months to
figure out what I wanted to do, and I really didn't know the answer.
Business school ended up being a couple of years of reflection and learning. I knew that
despite whatever entrepreneurial instincts I had, I didn't really have business skills. I was
riding a bus in the minor leagues while my classmates from Duke were doing consulting or
banking, learning the real toolkit for business. I felt the best way to catch up was to go get
that foundation through an MBA.
John Stanton (05:29)
Harvard tends to send most of its graduates into Fortune 500 companies, investment
banking, and consulting. You were probably one of the few in your class who actually went
off and started a business. What accounts for that?
Ted Sullivan (05:47)
Good question. I think Harvard would like to believe that's different now, they've really
invested in supporting entrepreneurs, and I've seen some of that myself along the way. But
you're right, back then it was Fortune 500 executives, investment banking, private equity,
maybe real estate. I was a bit of a different candidate coming in, someone who'd started a
baseball camp business and played minor league baseball.
I got lucky in a sense. It was hard to resist the security that a lot of the banking and
consulting folks had by the first half of second year, with their jobs locked in. I didn't have
an idea yet for my own business, so I thought: let me go work for a venture-backed startup
and learn from the inside. I also wanted to move to New York, I'd never lived there, so I
basically said, "New York City, venture-backed startup, I'll take whatever job I can find just
to get in the mix."
That's what happened. I took a job at a company called RAVE, now called Rave Mobile
Safety, interestingly, in an industry tangentially similar to the one I'm back in now: law
enforcement. I had a great two years there. I graduated in 2006 and had the idea for
GameChanger around 2008 to 2009. But the real start came when I got laid off from the
startup, one of the great unfortunate-yet-fortunate events of my career. A lot of people can
probably relate to that: sometimes things that don't look like positives end up pointing you
in a positive direction.
In the second half of 2008, as you'll remember, there was a massive financial crisis. About
half the company got laid off, I was one of them. Getting another job wasn't a great option
in October, November, that Q4-2008 window. But I had this idea, and I thought, "I've got to
just go run with it." So, I started reaching out to friends and family, trying to scratch
together enough money to give me a few months to get it off the ground.
John Stanton (08:06)
Great story, and timing matters. For me, I got out of school in '79, which was a similarly bad
financial time, high interest rates, high unemployment. What was the core nugget of
GameChanger that you saw, and that you managed to turn into a dominant platform in
baseball scoring and communications?
Ted Sullivan (08:31)
There's always a number of nuggets that come together. Going back to that same timeline,
I'd moved to New York, I'm working at a startup. A friend of a friend has little-league-age
kids and hears that this former ball player has moved to town. The way I tell the story: he
probably thought he could get me as an assistant coach and win the league championship,
which absolutely did not happen. But I started volunteering in the downtown Little League
in the Battery Park/Tribeca area of Manhattan.
So here I am, leaving a tech, venture-backed mobile startup, taking the subway at 5, 6 p.m.
to practice or games, and now I'm coaching youth baseball. This is right around the time
Steve Jobs introduced us all to the iPhone and changed the world forever. My days were
filled with a front-row seat to what was happening in mobile, and my afternoons and
evenings were filled with an incredibly inefficient world of youth sports.
As a coach, all I wanted was to spend 100% of my time and effort on the kids, especially
since I didn't have a kid involved myself. I loved being on the field with them; I didn't want
anything else pulling my time, effort, or energy. But I found myself pulled into all this
administrative work. And I thought maybe the iPhone, what we were learning about the iOS
platform, could solve that problem.
It's a story as old as time: if you have a problem, that's a great way to start a business,
solve a problem you actually have. So, GameChanger solves the administrative side,
scorekeeping, stat management, reporting, for the coach and coaching staff. The second
side of GameChanger is that we take that data, collected through real-time scorekeeping,
and send it to parents and fans to keep them updated.
In lower Manhattan, there isn't a ton of room for baseball fields, but in the downtown Little
League we had two great fields right next to what's now One World Trade and the Goldman
Sachs headquarters, a magical spot. But there's not a lot of foul territory there. When I was
coaching, standing in the third-base coach's box, I was basically a step and a half from the
first row of the bleachers, so I could hear and see everything the parents were saying and
doing.
Having started Headfirst with my brother, I thought I understood youth sports, but I still
underestimated how deeply invested parents are in their kids' success, which of course I
understand now as a parent myself. I remember a routine ground-out to second base, and
whoever was in the bleachers would pick up their phone and call a spouse or grandma or
grandpa to explain what happened. I thought wow, this is incredible, that much desire to
report to loved ones who can't be there.
So those are the two "aha" moments: the administrative problem I was feeling myself, and
standing feet away from parents who were so deeply invested in their 10-, 11-, 12-year-
olds' success on the field. Those two things came together to create GameChanger.
John Stanton (12:14)
What was the process from there? You had to find a partner; you seem to have a repeat
partner in this and your next venture and then hire people. How did you go from a great idea
to an established business?
Ted Sullivan (12:30)
It was a long and winding road, as it always is. The most fortunate thing that happened is
that Kirill and I met through what we call a "founder blind date." I had this idea, but I'm not
an engineer, not capable of writing software code, though I sometimes wish I could (these
days maybe it's not as necessary). But back in 2008 to 2009 it certainly was. So, I was
looking for a co-founder to help build this concept. I don't think I had any idea how hard it
would be. We were thinking about the iOS platform, which was extremely early-stage at the
time.
John Stanton (13:10)
Brand new, at that point.
Ted Sullivan (13:11)
Brand new. In fact, and this'll date both me and the idea, I remember after connecting with
Kirill, my co-founder, we had a legitimate decision to make: build this for iOS or build it for
BlackBerry. That gives you a sense of the timing. Everybody had BlackBerries; almost
nobody had iOS. But you could start to see where iOS was going in terms of engaging
interfaces.
I had a Harvard Business School classmate who knew Kirill, told him about my idea, and
connected us. We met for lunch in Manhattan one day. The way Kirill tells it, which I think is
funny, is that he had his own ideas he was excited about. He wasn't told our mutual friend
had set this up because I was pitching an idea; he thought he was coming to pitch me, the
"business guy," on his idea. We got to lunch, he talked about his idea, I talked about mine,
GameChanger. The way he tells it: "Of course Ted, the sales guy, gives the better pitch."
So, we decided to do GameChanger, and we were off to the races from there.
John Stanton (14:18)
It wasn't a better idea; it was a better pitch.
Ted Sullivan (14:21)
Who knows, honestly, you never know. Ideas, as you know, aren't worth anything on their
own. It's all about execution. So, the two of us joined together to try to build this thing.
John Stanton (14:32)
You self-funded, or funded with friends and family for a while, before raising money and
increasing your trajectory. Talk a little about that process, for those listening, about how
you identified the point when you needed additional money, and what you did to get it.
Ted Sullivan (14:52)
I felt like we always needed more money. This was a bit before Trilogy came in, when we
had real traction to speak of. But in that era, youth sports tech wasn't really a thing, there
weren't a lot of successes to point to, and it wasn't an area venture firms were interested
in. So, we were scratching and clawing to raise money. We didn't raise in the traditional
sense, a clean seed round, then a Series A, the kind of trajectory you'd read about in
TechCrunch. That wasn't our story. It was literally $10,000 here, $50,000 there, maybe
$100,000, several angel rounds just to buy us another three to six months and a little more
traction.
It was a real grind. The evidence: I still have the spreadsheet listing every investor I ever
pitched, from the very beginning. By the time you guys were involved, we probably had 25
or 30 different individuals or entities on the cap table. That spreadsheet has 425 lines on it.
A lot of "no's." A lot of "you're crazy." A lot of "this market isn't really a market." A lot of "this
isn't going to be big enough." Dozens and dozens of people said this would never work.
So maybe that's a takeaway for entrepreneurs, not to say just bang your head against the
wall, but we had enough conviction. Our customers were telling us it was going to work.
The investors weren't.
John Stanton (16:48)
As someone who believed in your story, I think the persistence and grit that you and Kirill,
and particularly you, demonstrated is the critical ingredient in your success. If you hadn't
been that persistent, that willing to hear people say no, you probably wouldn't have
succeeded. I attribute some of that to baseball, it's a game of failure. You'd excelled there,
and I think that carried over to how you excelled as an entrepreneur.
Ted Sullivan (17:24)
I'd like to think there's some connection. Failure wasn't an option for me, maybe it should
have been. People say "fail fast" and all that, but I was convinced it was going to work. We
had enough traction and enough "ahas" and "wows" from customers that it fueled us. We
spent so much time in the early days getting close to customers, flying all over the country
to coaches' conventions just to be in a room with dozens or hundreds of coaches we could
show the product to. Coaches would tell us, "This is going to change everything. This is
incredible. This is too good, what's the catch?" That fueled us.
The challenge was that the business itself was particularly hard to build, the industry is
hard. As much as I love youth sports, and I love that it's become a real industry with lots of
businesses and smart entrepreneurs going into it, there are underlying, foundational
factors that make it very hard to build big, fast-growing businesses in that space. We
fought those headwinds at GameChanger.
There are three factors, I think listeners would find this interesting, and it's what I tell other
youth sports entrepreneurs who come to me for advice, any one of which can kill a
business. All three exist in this market.
The first is hyper-fragmentation. People think youth sports is a $30 to 50 billion industry.
That's complete BS, because high school varsity football looks totally different from nine-
and-under volleyball, which looks totally different from club soccer, different products,
different culture, different seasons, different cadence, different everything. The fact that
it's all under one "sports" umbrella is the only thing they have in common. That
fragmentation makes it hard to scale, because the actual market you're going after within
any one niche is relatively small.
The second is seasonality. One of the hard things about growing GameChanger specifically
was that, in the beginning, we were only in baseball and softball, and with a scorekeeping
product, you're not going to start using it midway through the season, you need a full
season's worth of stats. So, we had 90 days to grow each year, and it wasn't the same 90
days everywhere, it followed everyone's opening day as the weather warmed across the
country. Once that window closed, our growth for the year was essentially done, and we'd
hunker down and generate as much revenue as we could.
The third is natural churn. You could have a genuinely happy customer, but their kid
graduates, or decides to stop playing, and they're gone. So, we had to grow equal to our
natural churn every year just to break even, and then grow on top of that to actually grow
the business.
A lot of youth sports businesses fight all three of those. When I see one struggling, it's
usually because they haven't designed the business to overcome one or more of them.
John Stanton (20:42)
Do you think those same challenges became a moat for GameChanger once you'd
conquered them?
Ted Sullivan (20:52)
It's certainly become helpful. I'm not involved with the business anymore, but there's no
doubt, a great product with incredible traction, and everyone else is still facing those same
three challenges. Throw in a huge, established competitor as a fourth challenge, and it
becomes nearly impossible for a new business to chip away. So, a hundred percent.
John Stanton (21:14)
After eight years, you decided to sell GameChanger to Dick's Sporting Goods, an
established company. What were the elements that made you willing to do that? When we
sold our business, it felt like selling my baby, my children. What made you willing to sell
GameChanger?
Ted Sullivan (21:33)
A number of factors. The business has been so successful since, I always get asked, "Was
it the right time? Do you regret it?" I don't have any regrets. It was the right time for us, the
right time for our investors, and I think the right time given how the industry was evolving, it
was consolidating a lot. Without getting into all the details, I think it was the right time for
the business, and Dick's ended up being a great home for it.
It's always a challenge, I do think of GameChanger as my firstborn. I have two kids now,
born not long after we founded the company, but I still think of GameChanger as my
firstborn. So it's always hard to hand over the reins, like sending a kid to college, I imagine.
I feel really grateful that Dick's has done a great job managing it, and that a lot of our
talented, long-tenured team is still there, still building the same customer-focused,
product-focused culture. I think that's what's driven the success. I joke with them; I spoke
at a GameChanger fireside chat last year and told them I keep getting all this credit for
what the business has become without having to do any of the work. It's honestly the best
combination. It helps that I now have a 12-year-old son playing baseball, so I'm a customer
myself now, I truly understand all our engagement metrics because I'm contributing to
them.
John Stanton (23:12)
Life goes full circle, both the baseball player becoming a future baseball prodigy's dad, and
the entrepreneur. I think of Headfirst as your first child and GameChanger as your second,
but you're having a third entrepreneurial experience now with Rollout.
Ted Sullivan (23:26)
You might be right.
John Stanton (23:27)
Tell us where that idea came from.
Ted Sullivan (23:36)
It's such a great transition from the GameChanger origin story. After GameChanger, I took
some time off with my family, did some traveling, caught my breath. Then I decided I
wanted to work at a bigger company, joined IMG Academy and was an executive there for
four years, within the Endeavor portfolio, and then it was acquired by BPEA EQT, a great
experience. I left after about four years without knowing exactly what I wanted to do next,
but I had that urge again to build something from scratch.
I was looking at different areas when I got a cold LinkedIn message from a woman named
Emily McKinley, the Deputy Chief of Police in Louisville, Kentucky. Long story short, Emily
happens to be a longtime GameChanger user: a team scorekeeper and team mom with
kids who played baseball and softball, in addition to her job as second-in-command at
Louisville Metro Police, overseeing 1,300 officers.
She wrote me a thoughtful, compelling note on LinkedIn that essentially said: the problems
GameChanger solves in youth sports, the administrative burden that coaches and
scorekeepers deal with, which isn't what they signed up for, those same kinds of problems
exist in policing. Patrol officers don't sign up to be swamped with paperwork; they want to
keep their communities safe. It was almost like a cry for help, she was reaching out to the
founder of GameChanger, essentially asking, "If you solved this for GameChanger, could
you solve it for policing?"
John Stanton (25:51)
As you began this journey, you had to find a technical co-founder. Where did you find
someone to partner with on this venture?
Ted Sullivan (26:03)
I told you, running it back! Kirill Savino, my co-founder from GameChanger, we'd stayed
close, kept each other updated on our careers since then. After Emily reached out, I spent
several months trying to better understand the problem. With GameChanger, I had the
sports background and had lived the problem as a Little League coach myself. I didn't have
that firsthand experience in policing, so even though Emily made a compelling case, my
first reaction was: I need to see this in person.
She invited me to Louisville, and I started doing ride-alongs, riding shotgun with patrol
officers in Louisville Metro, who were incredibly gracious in letting me tag along as they did
their jobs, which were unbelievably impressive. But I also saw firsthand how swamped
they were with paperwork. After several months digging into the problem, once I was
convinced it was exactly as painful as Deputy Chief McKinley had described, I thought
okay, we should try to start a company to solve this.
My first call was to Kirill. We joined forces again, and we've been at it for about a year now,
building a prototype and running a pilot with Louisville Metro. We also work with
Haverstraw, New York, a much smaller agency about an hour north of where we live. We've
been chugging away, and just recently we fully brought the band back together by bringing
Trilogy in as our seed investor.
John Stanton (27:41)
We're flattered to be your partner again. One thing we hear from entrepreneurs who started
companies three to seven years ago is that they wish AI had existed when they were
starting out. You have that luxury now. Do you have a sense of the role AI is likely to play in
Rollout's development, compared to GameChanger's?
Ted Sullivan (28:05)
It's night and day, in two ways. First, our product is very much an AI product. Let me step
back and explain: we're building an AI-powered assistant for the patrol officer. We may
expand to other roles in law enforcement or emergency management generally, but we're
focused specifically on the patrol officer, roughly half of every police department. There
are about 18,000 police departments in America, and roughly 900,000 to a million patrol
officers. They're the ones you see driving around in the cars, and they're the most
overwhelmed with paperwork because they handle such a high volume of incidents.
Our product is an iOS mobile app and a Windows app that runs on the in-car laptop.
Between the two, we use AI, camera, and voice to massively decrease the administrative
burden on patrol officers. So, there's AI embedded directly in the product, it wouldn't exist
without AI.
The second way is in how we build it. Kirill would say he's not really writing much software
code himself anymore; he's using his experience to direct coding assistants to write the
code, and doing quite a bit of debugging. It's not totally smooth yet. Some weeks you look
back and think, "Holy crap, we accomplished an amazing amount this week," given that
Kirill is one engineer, and a particularly capable one. Other weeks you're running in circles
a bit because the AI-generated code needs more debugging than if he'd written it himself.
Net-net, it's absolutely an advantage, absolutely positive, but it isn't always smooth
sailing. I suspect that'll keep improving; it's already improved a lot in the last six months.
We feel fortunate to have started this business when we did, because even businesses in
this space that are five or ten years old, and there are plenty of 20-plus-year-old
businesses here, aren't nearly as able to leverage these tools, since we built this with AI as
part of the foundation from day one.
John Stanton (30:47)
The pace of change is accelerating, fascinating to watch how far it continues to go. We're
reaching the end of our time, but I've got a few speed-round questions for you. What's
something founders spend too much time on?
Ted Sullivan (31:07)
Great question. I'd say founders spend too much time on everything until they deeply
understand the problem they're trying to solve. So often, entrepreneurs are building a
product, creating a name and a brand, and all this stuff, but if you really ask them whether
they deeply understand the problem, whether it actually exists the way they're imagining it,
the answer isn't always yes. Deeply understanding the problem before doing anything else,
before wasting time on anything else, is a common error I see.
John Stanton (31:49)
Someone, dead or alive, you'd like to have dinner with someday?
Ted Sullivan (31:56)
My entrepreneurial mentor and idol is someone you know, Morgan O'Brien. He's my
godfather, my mom's brother, my uncle. You know his career probably as well as I do, he
was very successful in wireless, founded Nextel, and did a number of other things. The
reason I look up to Morgan is that he's an incredibly big thinker, incredibly ambitious, but
balanced with being a business leader who's truly beloved by everyone who's worked for
and with him.
Maybe the headlines deceive us, John. But Morgan is rare in that he's both super ambitious
and a big thinker and also beloved by everyone he's worked with.
John Stanton (33:05)
As you know, he was the first person I met in Washington, DC, in 1982, when I was trying to
figure out how to get into the wireless business. And I think he was the one who vouched
for me to you, back when you were running your background check on me, you called me
up and said, "Are you the same John Stanton who worked in wireless? My uncle says we
should do business together."
Ted Sullivan (33:32)
It's incredible, we met at a baseball camp but then had that connection where your career
and Morgan's career were so aligned. He's been my entrepreneurial mentor from the very
beginning.
I'll tell you a story you'll appreciate. We were running Headfirst, and something wasn't
going well, one of the first times we'd paid in advance to reserve a field, and we had costs
that weren't being covered by enough customers. My mom, Morgan's sister, told me the
story of the early days of Morgan building Nextel and the massive risks he took. I never
forgot that, I thought, if he could withstand that, I could certainly withstand the risks I've
taken throughout my career, whether it was building a camp where you have to pay for the
field in advance, or starting a business in the middle of the financial crisis, or whatever it
might be.
John Stanton (34:28)
He's one of the great people God put on this earth. Nextel was actually his third venture,
the first two attempts at building an Enhanced Specialized Mobile Radio (ESMR) business
failed. He's got the same persistence and grit, must run in the family.
Two more questions: what are you reading these days? What are you listening to?
Ted Sullivan (34:48)
Two books. One I just finished is Founding Brothers by Joseph Ellis, I'm not sure if I picked it
up because of the 250th anniversary, but it feels timely at all times, so I'd recommend it.
And I'm currently halfway through 1929 by Andrew Ross Sorkin, which is also quite good.
Loved Founding Brothers and loving the Sorkin book.
John Stanton (35:15)
Ted, your success as an entrepreneur, three times over, speaks for itself. What folks may
not know is your success as a husband, father, son, and brother, and your commitment to
family. That's one of the things that makes us very happy to be your partners. Thank you
very much, and thanks for participating today.
Ted Sullivan (35:42)
John, I should mention, when you asked who I'd want to have dinner with, dead or alive,
what I'd actually love is dinner with you and Morgan. Two of my entrepreneurial idols. Let's
make that happen, okay?
John Stanton (35:55)
You may not get a word in edgewise if Morgan and I start telling stories.
Ted Sullivan (35:58)
I shouldn't, I should just be listening and learning. But thank you, thank you to the team.
John Stanton (36:05)
Looking forward to that dinner soon. Thank you.
OUTRO (36:08)
That's a wrap on today's episode of Cloudbreak. To learn more about Rollout, visit
rolloutpolice.com. If you're building something amazing and want to learn more about
Trilogy Equity Partners, visit us at trilogyequity.com. Until then, subscribe, rate, review, and
share this podcast with fellow entrepreneurs.