Reel Lives: Jesse Learmonth On Startups, Awards Shows For Startups, And Fatherhood
The founder-turned-podcast-host talks about entrepreneurship from all different angles
7 min
Every gambler has a story to tell. And so does every person who chooses to make a living in this unique industry.
In our “Reel Lives” series, Casino Reports shines a spotlight on people working in the gaming business, from executives, to analysts, to media members and communications pros, and all points in between.
The subject in this interview: Jesse Learmonth, the Canada-based host of The Betting Startups Podcast and a multi-time starter-upper himself.
Casino Reports (CR): You don’t just host a podcast about betting startups; you are yourself a betting industry entrepreneur. What’s the no. 1 lesson from starting and running Bet Smart Media that you continue to carry with you?
Jesse Learmonth (JL): We operated Bet Smart Media for around five years before being acquired by Pinnacle in 2015, and to say those five years were a rollercoaster would be the understatement of the century. It feels like an impossible task to identify a top lesson from that ride, but I’ll try!
This sounds so obvious to say, but “stay alive” is my no. 1 lesson. Every startup has a finite runway to find the elusive “product-market fit,” and the name of the game is to extend that runway for as long as possible to buy enough time to find PMF.
In our case, we burned through all our investor capital before reaching profitability. We had an existential crisis, and could have easily thrown in the towel. But through some serendipity, we had an opportunity to do some custom development work for a large European sportsbook. We weren’t really in the work-for-hire business, but we saw it as a means to extend our runway, so we did it. Not only did it help us stay alive and buy time to find our place in the market, but it was a serious learning opportunity that also gave us instant credibility by being able to name them as a client.
I believe in those moments of existential crisis that all startups face at some point, there is always a path forward to ensure survival — but it requires a level of grit, perseverance, and humility that not all founders have.
CR: If someone has never listened to The Betting Startups Podcast, and you have one episode to hook them and make them a subscriber, which episode are you sending them the link to and why?
JL: Ooomph, we’re past 150 episodes now so there is a lot of gold (and some fluff) in that corpus of content. I’ll slightly dodge the question, and instead provide three of my “must-listen” episodes:
- Episode 142 with Nigel Eccles. He’s what I call a “builder’s builder.” He’s been at the bleeding edge of several new verticals over the last 20 years: exchanges, DFS (have you heard of FanDuel?), blockchain, and now crypto casinos. This episode provided an incredible window into how he thinks and operates.
- Episode 65 with Karolina Pelc (Part 1 & Part 2). I’m on record in several places saying that Karolina might be the most impressive founder I’ve met in gaming. She has this relentless drive to win, while also being very transparent about the challenges of founder life. Since this episode almost two years ago, she went on to sell her company to FanDuel, and remains a force for good in the industry.
- Episode 70 with Justin Park. This one was guest hosted by Benjie Cherniak, and really was the first time I’d heard the full arc of Justin’s story. He is a deeply strategic thinker and has world-class execution — a rare but powerful combo. I got more value from this episode than any other insofar as how it’s shaped my own thinking about my projects.
If you have insomnia and need episode recommendations to help you sleep, I can provide those too. (laughs)
CR: You recently announced the first-ever Starties are coming to New York in March. Give us the story of how the idea sprung up and what it took to go from “here’s a fun idea” to “OK, this is actually happening”?
JL: Like many good origin stories, it started over a couple drinks. I was with the WagerWire team last September in Lisbon, and Travis Geiger shared his idea for “an awards show for startups.” It was one of those tongue-in-cheek ideas that sounded so crazy that it just might work.
We let the idea sit for a while after Lisbon, then we synced back up in late November to ask whether it was mojito-fueled nonsense, or if it had legs. It was obviously the latter, so we immediately agreed to partner on the project, and then got to work.
That effort culminated with The Starties’ public launch on Jan. 27, and it’s been a wild ride since. We are calling it “the gaming industry awards by startups, for startups” — which is exactly what it sounds like.
Our inaugural event will be held March 12 during the NEXT.io Summit in Manhattan. Winners across nine award categories will be announced that evening at the event, which will have a much different look and feel than traditional industry award shows.
We’re thrilled to have the support of industry leading names such as Eberg Capital, Optimove, Sportradar Futures Hub, Defy the Odds, and more — this wouldn’t be happening without them.
There is a palpable enthusiasm for The Starties, so we’re pumped to deliver on this inaugural event and see where we can take it from there!
CR: You’re a new dad — at least according to your LinkedIn, maybe it hasn’t been updated recently and you were a new dad. Just how new a dad are you, and how has becoming a parent most impacted the way you approach your work?
JL: I should probably update that to say “new-ish” dad, as my baby has just about completed the first spin around the sun. But it’s been a profound experience in the best of ways, and has completely rewired me in terms of how I look at the world, life, and what really matters.
As it relates to my work, the obvious impact is that I have less available hours in the day to make things happen. This has been a good forcing function to work smarter than I did before — brute-forcing things for 10 hours a day is no longer an option. My answer to this new reality has been building a team around me, and trying to get better at the art of delegation (which doesn’t come easy, but it’s a huge unlock). Also trying to get better at saying “no” to things, which remains a work-in-progress.
CR: What are the best and worst (if there is a worst) thing about living in Curaçao?
JL: I didn’t have it on my life bingo card that I’d spend several years living on a small Caribbean island, but as part of our deal with Pinnacle, my co-founder and I packed our bags and moved there to work in the company’s head office. Life is very relaxed on the island, the people are awesome, and the white sandy beaches with bright blue water are exactly like the postcards we’ve all seen.
The best thing about living there was the friend group I made. There is something about a collective of expats ending up on an island together that sets the stage for lifelong friendships, which is exactly what Curaçao provided. Most of us have since left the island to our respective corners of the world, but we still see each other a few times a year and it’s like no time has passed.
Like anywhere, it also had a few downsides. The biggest one for me was simply the size — it’s small! You can drive from one end of the island to the other in under an hour, so after a while you run out of new places to check out. But a small drawback in the grand scheme of things.
CR: Having interviewed so many entrepreneurs in the space, do you feel you’ve developed a strong understanding of what makes the successful ones tick? And if so, what seems to be the one or two more important qualities for a successful founder to have?
JL: There are a few I reference regularly, but humility is right up there. Entrepreneurs by nature must have an almost delusional level of conviction about their idea, but that needs to be balanced with enough self-awareness to recognize when the market is saying that an idea isn’t quite right. There is lots of ego involved, and putting that ego aside can be challenging for many people. But it’s hard to deny that humility is a massive throughline with the most successful founders I’ve met. (Oh, and don’t be an a**hole to people!)
Reel fast
If I’m looking for you on a casino floor, what table or machine am I most likely to find you at?
Definitely at the roulette wheel, math and logic be damned.
Preferred podcast listening speed?
1.5x, much to the annoyance of my wife.
What’s your go-to movie theater snack?
Popcorn, and I’m not sharing.
There hasn’t been a Canadian Stanley Cup champion in 31 years. Set a fair over/under line for what year the drought ends.
Yikes, I’ll set it at 2029 (-130o).
What’s the streaming service you can’t live without?
Whichever one will let me watch Seinfeld reruns.
What’s an unusual talent or hobby you have that has nothing to do with gambling, business, podcasting, etc.?
Not unusual in absolute terms, but maybe unusual for an online gambling guy in his early forties: I’ve come to love gardening over the last few years, and playing in the dirt growing my own vegetables. Maybe I’ll launch a produce stand as my next endeavor!
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You can follow Jesse on LinkedIn and X/Twitter or keep tabs on The Starties at Instagram and elsewhere, but remember before you make any requests of him or his time: He’s trying to get better at saying “no” to things.
Previous installments of Reel Lives:
Kelly Kehn On Entrepreneurship, The Value Of Diversity, Paying It Forward, And Broadway
Gina Fiore On Gambling, Writing, Starring In A Documentary, And Explaining Her Job To Her Son
