Evan Dreyer’s Post

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Operator + Investor

After +3.4 years, today is officially my last atTola. I’m excited to turn the page on an influential chapter in my career as an operator + investor 📖In joining before we had a customer and supporting wind down, I’m grateful for a “full cycle” experience that will propel me personally and refine my approach to helping#founders. Sharing a few reflections in moving ⏩📞Take the call. In early stage investing, you meet a ton of people. Sometimes these calls lead no where. Other times they just lead to the next call. I metAlen Cvisic randomly through a friend of a friend of a friend. I was eager to back his andGuillaume Simard vision for US SMBs throughHalo Labs on the spot. At the time I had no idea this would set the stage for making the jump from +12 years atCredit Suisse toY Combinator#startups💸 SMBs aren’t as risky as they’re priced. We originated over $5.6mm in financing off our balance sheet with a default rate of 3.96%. While I’ll remain proud of our approach to#risk and#underwriting, our precision was unlocked by partners incl.Plaid,Lithic,Arva AI,Baselayer,TrueBiz andHeron Data. The market reality? Even SMBs that consistently generate profit face high financing costs. I’m hopeful modern approaches to#data and#compliance will drive down the cost of capital for all.🪨 Go, and stay, for the people. Its straightforward to chase opportunity, but as gravity pulls you back to earth - what makes the difference is who you’re working with and for. I will always be grateful to learn from so many incredible teammates at Tola, and to support +150 business owners. Its been beyond validating to see their successes. Even this week we watchedMaya Nazareth andAlchemize Fightwear make a deal onShark Tank ABC andSarah Jahnke andHomecourt announce a Series A!🧱 There’s no replacement for rolling up your sleeves. While I’ve invested in 60+ startups, there’s nothing like living and breathing company building. Its hard when times are good, and when times are bad. The highs touch the sky, and the lows - well, they hit different as personal referendums. All of it taken together has instilled a profound respect for those who dare to build something from scratch, and forever influenced how I think about investing.🔨You can just do stuff. Seriously. Get started. There’s less stopping you than it seems. If you’re looking for reasons why not - you’ll find them. My experience transformed how I think about taking on challenges, and empowered my ability to execute atTahoe Lead Removal Project and in public safety advocacy for Orinda.In closing, I’m grateful to everyone who supported our work at Tola as we facilitated over $30mm in payments. Every#fintech is a concatenation of partnerships, and this week atMoney20/20 was another reminder of how many tremendous people are in this industry. It’s been an honor to continue supporting the growth of SMBs atSquare and I’m increasingly excited for what my next chapter will bring in 2026.

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Will Messina, graphic

Congrats Evan, look forward to everything you go crush. Catch up soon

Christian Di Bratto, graphic
Christian Di Bratto

Founder @ Hat Tip. Helping startup founders generate pipeline from social.

5d

Congrats Evan!

Kate Volzer, graphic
Kate Volzer

Revenue Director Level20 @ Progressive | Exited Tech Founder

5d

Congratulations and so good seeing you this week! Excited for you and your new chapter!

Oleg Ivanov, graphic
Oleg Ivanov

Product Manager | Alternative Payment Methods & Solutions | Fintech | Cards | Payment Processing

1d

Great post! Thank you for sharing these reflections. It's very inspiring to see your journey and the lessons learned.All the best as you move forward into your next chapter!

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Tommy Mercein, graphic
Tommy Mercein

Vice Chair, Board Member at Homium | Ex-Vice Chairman, CIO at Credit Suisse | Former Global Head of Debt Capital Markets

1d

Great stuffEvan Dreyer ! Onwards ans upwards.

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Evan Dreyer

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