Ryan Croft, few people have a background as diverse at the intersection of baseball and tech, from scouting baseball talent in the Dominican Republic to founding multiple tech companies. In 2013, Ryan co-founded TransitScreen, a mobility data platform that scaled across 40 plus cities in the United States.

Now he's back in the founder seat, building Pacto, an enterprise fintech startup in Mexico with backing from Dila Capital, Femsa Ventures, 500 Global, and several other prominent investors.

In our conversation, we'll explore the parallels between baseball scouting and startups, the challenges of building a company in Mexico as a foreigner, what it's like to be a second time founder, what's easier, harder, and why he wanted to build another company, and much more.

Chapters

00:00 Who is Ryan Croft?
00:46 Early Years
08:25 Parallels between MLB Scouting & Building a Startup
10:44 Building TransitScreen: The Intersection of Mobility and Technology
12:51 What is TransitScreen?
16:26 TransitScreens' Product Evolution
18:22 The TAM Wasn't Big Enough
19:17 Why Launch Another Startup? Why Mexico?
20:47 Pacto: The Toast / Square for LATAM?
22:02 Experience as a 1st vs. 2nd Time Founder
23:05 Nuances of Building in Mexico
25:09 Evolution of Leadership Style
26:07 Regulatory & Fx Challenges in Mexico
27:37 How do you Hire a Great Team?
29:03 Final Thoughts

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Cut The Check w/ Mack Meyer is a podcast about venture capital, startups, and entrepreneurship in Latin America and beyond.

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