⚡️ Founder Diaries Vol 1 Ch 7: Eliana Eskinazi, Co-Founder of Wagr - From Harvard Classroom Idea to Being Acquired by Yahoo
We celebrate the unfiltered BTS stories of today’s founders - from their highest highs to the lowest lows and how they powered through it all… or didn’t.
😊 Welcome to Volume 1 Chapter 7 of Founder Diaries. Now, Why Founder Diaries?
In an era where founders’ lives are glamorized and their stories are romanticized narratives of seemingly endless success, the behind-the-scenes reality of the highs and lows of being a founder often don’t come to light.
Alongside the startup with a high valuation is the string of risky decisions, maxed-out credit cards, and grueling late-night chats.
Alongside each polished story, there are real challenges, unsung heroes, and unique highs & lows that make every second of the founder's journey worth it. Or maybe not? We will let you decide.
These are the true, unfiltered short stories behind the founders of today. Enjoy :)
👋 Introducing Eliana Eskinazi, Co-Founder of Wagr - From Harvard Classroom Idea to Being Acquired by Yahoo
Wagr was on a mission to reinvent sports betting into a fun, social, and inclusive experience designed for all sports fans. They raised a $12M Series A, then were acquired by Yahoo Sports in 2023.
My entrepreneurship journey started before I even knew it. I worked as a Consultant at Accenture, and during weekly flights and train rides, I would think about ‘what ifs.’ What problem needed solving? Where could I find opportunities to help people, or create something meaningful? Ideas were always running through my head -- everything from an augmented reality educational tool for kids, to ways to improve the often terrible experiences at nursing homes.
I started spending so much time thinking about these ideas, and ultimately speaking about them with co-workers and friends, that I knew I wanted to start a company. I just didn’t have a strong enough conviction on what to start and with whom.
So, I applied to business school to give myself a two year playground to test ideas, learn about starting and running a business, and hopefully find a co-founder.
At Harvard Business School, I took a class called PM101 where small groups -- pretty much startup teams -- were tasked with validating an idea for a company and eventually starting to build it.
I joined Wagr with my co-founder Mario. It was 2019, the early days of sports betting becoming legalized in the US. We saw sports betting as an often solitary activity that didn’t need to be done in private. Sports are inherently social, as is betting. With Wagr, we wanted to create conversation, competition, and deep fandom.
We built a peer to peer betting app and ultimately ended up becoming the first social sports betting company to receive a license in the county. In the early days, Wagr was all about doing ‘things that don’t scale.’ We built an experience with Google Docs, Venmo, and text to simulate the experience of a peer-to-peer betting app. We wanted to run tests, get as much feedback as possible, and triple down on the things that worked and scrapped the things that didn’t. It was gritty. It wasn’t sexy, but I loved every second of it. People's eyes light up when they talk about sports and about betting against peers. Our ‘wizard of Oz’ tests were far from the platform we wanted to build, but they helped prove that we were on to something special.
When graduation was approaching, we made the decision to forgo “real jobs” and to pursue Wagr full time.
This was May 2020. Covid was in full force. Sports were cancelled. But…we were all in on starting a social sports betting company!
We joined Pear VC’s summer accelerator program and got to work.
In the early days, I think we were definitely naive about some things, and -- that honestly helped. Everything was ‘we’ll figure it out’ and, we did! But it wasn’t easy. And everything took longer and cost more than we thought!
Sports betting is a highly regulated industry with a complex infrastructure.
As one small example -- in order to even be allowed to operate, we were required to have physical servers up and running in the state where we were licensed. Remember the chip shortage? That provided a number of challenges -- amongst the fact that I had never ordered nor set up servers before so -- we learned a lot.
Then, we applied to Tennessee for a Sports Betting Operator’s License. It cost $750K per year, and required POUNDS of paperwork, and more caffeine than probably advisable.
We made it happen. With a small team of 8, we became the first and I believe smallest (!) team to receive a social sports betting license in the country. This was a huge accomplishment. We were off to the races.
As Wagr evolved, so did our need for a dream team—individuals who weren’t just looking for a job but were as passionate about our mission as we were. We spent hours and days convincing top-notch talent to not take the big tech jobs, but to believe in what we were creating and where we were going to go with it. And thankfully, it worked. Creating an all star team and culture within the company was as crucial as building the user base.
And…that was tough, too! We didn’t grow just via SEO or digital ads. We were on the ground. We partnered with Nashville Soccer Club and had a tent set up outside of every game. We offered promos, gave out Wagr foam fingers and t-shirts, and talked to anyone who would listen. We went to sports bars and interviewed fans. We spent months perfecting a referral program.
We had to get scrappy. I was on a flight from LA to Nashville, on my way home from a wedding. The flight was halfway through and then…redirected back to LA! During the unknown time when the airline was ‘figuring it out’ and everyone was frustratedly waiting around, I decided to do something fun. I bought two bags of Toblerone from the airport, convinced the person at the store to give me a piece of paper, and once we were back on the plane, I invited everyone to take a piece of chocolate and if they were a sports fan -- to sign up for Wagr! It was a simple gesture that 1) made people smile and 2) got us ~40 interested customers!
The startup life is crazy. For me -- I gained weight, I didn’t focus on making friends in a new city, and it was stressful. It was 100% intense, 100% meaningful, and 100% worth every second and every sacrifice.
We built something we were proud of, and I will forever be grateful to the Wagr team, our customers, our investors, partners, and everyone who believed in us and supported us.
After three years, we were acquired by Yahoo Sports.
In reflecting, I’ve come to fully appreciate what others always say -- entrepreneurship is truly about the journey. From the brainstorming sessions at Harvard, to navigating the complexities of the tech and legal world in sports betting, to building a team, finding customers, and finally, making the strategic decision to be acquired by Yahoo, the adventure has been anything but ordinary. It's about embracing the chaos, celebrating the small wins, and always, always betting on the power of community.
I will always celebrate the wild, winding road of building something up from zero. It’s exhilarating, terrifying, and filled with a million lessons.
-Eliana Eskinazi
Learn more about Eliana below:
If you know someone with a unique founder story who would like to share their BTS journey of founder life - the highest highs and the lowest lows - please feel free to refer them at diariesfounder@gmail.com.
— Michelle Kwok & Christine Lu Hong (The Founder Diaries Team)