Fund/Build/Scale How to Build in a Market That Won’t Let You In
In most industries, if you’ve got a solid idea, a few engineers, and a working prototype, you can at least get in the game.
Professional sports is not one of those industries.
When Jordy Leiser co-founded Jump with Alex Rodriguez and Marc Lore, he wasn’t just building software — he was trying to rebuild the entire fan experience from the ground up, in a business dominated by legacy players like Ticketmaster.
Four years later, his company is powering the digital backbone for teams like the Minnesota Timberwolves and North Carolina Courage.
In this episode, Jordy explains what it actually takes to break into a closed industry, why he reverse-engineers every funding round before he raises it, and the biggest mistake he refused to repeat as a second-time founder.
RUNTIME 53:07 EPISODE BREAKDOWN(1:12) Breaking into pro sports, rebuilding fan experience, and reverse-engineering fundraising.
(2:03) How Stella Connect (customer service) laid the foundation for Jump (customer experience for fans).
(2:58) What Jump does today: a unified fan experience + data platform for teams.
(4:11) The unusual founding plan: 3-4 years of R&D, designed to launch with an NBA franchise from day one.
(5:46) Why sports is nothing like building a typical SaaS startup — more like a “car company” level of complexity.
(6:48)The true barrier: a near-monopoly in ticketing that stops innovation cold.
(7:59) Selling into a market where fans have low expectations — and why demand is obvious but still untapped.
(9:54) Early customers as classic early adopters — every team already knows the pain points intimately.
(11:25) The first hypothesis they had to kill: incumbents don’t want to integrate or share data. At all.
(12:32) Designing for the actual fan demographic: season ticket holders skew 50+, so “cutting-edge UX” isn’t always the answer.
(13:25) Jordy’s advice to founders: get out of the building, talk to insiders, but keep your “child’s mind.”
(15:06) Sports as an industry you can’t “hack into” — it works more like fashion or Hollywood.
(17:31) Moments when he realized he was losing stakeholders — and why being “comfortable in the uncomfortable” is essential.
(18:03) Early would-be partners who backed out, the impact on morale, and what they learned from those rejections.
(19:45) Jump’s origin as a “dynamic seating” idea — and why they had to build the entire platform instead.
(21:03) The “invisible platform” ethos: why Jump melts into the background so teams can own the fan relationship.
(23:10) Why NWSL teams and NBA franchises have surprisingly similar needs — and what that taught them about productizing.
(24:36) Jordy’s litmus test for platform vs. point solution: how many people in the org depend on you to do their job?
(27:01) Seed to Series A timeline — and how the Timberwolves sale collapsing delayed everything by a year.
(28:37HaHow Jordy processed a crisis that was public, sudden, and existential.
(31:13) The Long Beach pier walk: the moment he decided to pivot the GTM to a crawl-walk-run strategy.
(32:49) Effectuation theory, the “bird in hand,” and how it led to NCAA → NWSL → Timberwolves as a survival sequence.
(34:39) What he had to unlearn from Stella Connect: stop zooming in — zoom way out to a 10–20-year vision.
(37:05) The habit he kept: talent above all else — and why his first call was to a Chief People Officer.
(38:45) Minimum viable people function for early founders: fractional HR > junior recruiter.
(42:58) High performance without grind culture: intensity ≠ toxicity — and why durability matters more than speed.
(45:40) Hiring from big tech: what’s actually transferable, and the dangers of logo-blindness.
(50:55) The one answer Jordy would need from a founder-CEO before he’d join their startup.
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Delivering Happiness: A Path to Profits, Passion, and Purpose, Tony Shieh
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Effectuation — UVA Darden School of Business
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Thanks for listening!
– Walter