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Benjamin Gleason is the co-founder and CSO of Kamino, a financial operations platform serving over 1,500 Brazilian SMBs. Before founding Kamino, Benjamin co-founded GuiaBolso, one of Brazil's first open banking pioneers, which he successfully sold to PicPay after reaching 6 million active users. He also served as CFO at Groupon Brazil during its explosive growth phase and has been building businesses in Brazil for over 17 years. A Wisconsin native who moved to Brazil and never left, Benjamin has become a serial entrepreneur deeply embedded in the country's fintech ecosystem. In this episode, we discuss how Benjamin spotted massive opportunities in emerging markets, the unique challenges of building fintech infrastructure in Brazil, and the mindset shifts required to succeed as a repeat entrepreneur.
In this conversation, you'll learn:
1. Why you can solve much bigger problems in Brazil and emerging markets compared to Silicon Valley
2. How Benjamin bet his entire company on building "impossible" open banking technology before it was regulated
3. The story behind going from 10,000 to 1 million users in just six months through viral mobile growth
4. How GuiaBolso survived being sued by Brazil's biggest bank by creating an unbreakable shield of 6 million user supporters
5. Why Benjamin believes competing fintechs means both companies are probably screwed - and what market size really means
6. The three layers Kamino uses to transform SMB finances: efficiency, control, and visibility
7. How Kamino helped a Series B healthtech company go from being "completely underwater" to fully automated in just three weeks
8. Why 60-80% of Brazil's GDP is generated by SMBs still managing finances manually with Excel
9. The philosophy of "easy decisions, hard life, hard decisions, easy life" and why it guides every major business choice
10. Why you can't successfully launch in Brazil from outside the country - and the importance of boots on the ground in emerging markets
11. How Benjamin transitioned from a successful exit directly into co-founding Kamino with former Groupon colleagues
12. His contrarian prediction that traditional banks will become mere utilities in the next decade
Where to find Benjamin Gleason:
• LinkedIn: https://www.linkedin.com/in/benjamingleason/
Where to find Kamino:
• Website: https://www.kamino.com.br
• LinkedIn: https://www.linkedin.com/company/kaminolatam/
Where to find Tony Cueva Bravo:
• Newsletter: https://emergingfintech.co
• X: https://www.x.com/tonycueva
• LinkedIn: https://www.linkedin.com/in/tonycueva
In this episode, we cover:
(00:00) Introduction and Background
(06:12) Cultural Insights: Brazil vs. US
(07:11) Transitioning from Consulting to Fast-Paced Startups
(09:46) Challenges and Lessons from GuiaBolso
(12:36) Navigating Regulatory Challenges in Fintech
(15:35) Achieving Product-Market Fit at GuiaBolso
(18:14) Strategic Exit: Why Sell to PicPay?
(20:55) Founding Kamino: Lessons from GuiaBolso
(25:17) Initial Customer Engagement and Product Development
(29:10) Evolving Focus: From Startups to Medium-Sized Businesses
(31:49) Overcoming Adoption Challenges in Financial Solutions
(33:46) Navigating Brazil's Regulatory Landscape
(36:05) Financial Clarity for SMBs
(37:32) Case Study: Genial Care's Transformation
(39:46) Understanding ERP Adoption in Brazil
(41:32) Team Building and Company Culture Evolution
(43:58) Value Creation and Customer Retention
(46:48) Navigating Economic Volatility
(48:52) The Importance of Cash Flow Management
(50:26) Vision for Kamino's Future
(51:36) Strategic Considerations for Expansion
(53:47) The Future of Financial Management
(56:52) Differentiation in a Crowded Market
(58:45) Lessons from a Serial Entrepreneur
(01:02:33) Advice for Emerging Market Entrepreneurs
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