June 20, 2025

297: Grit, Mud & $400K | Jesse Phillips | Trustware Co-Founder & CEO

297: Grit, Mud & $400K | Jesse Phillips | Trustware Co-Founder & CEO

This week, I caught up with Jesse Phillips, co-founder and CEO of Trustware, and one of the most quietly determined founders I’ve ever backed.

I invested in Jesse and his co-founder Jonathan Frazier through the Techstars Web3 accelerator in 2023, and since then, Trustware have done what most early-stage startups only dream of—shipping a real product, signing real customers, and generating real revenue… all on just $400K in capital and a team of six.

In this conversation, Jesse and I get into what it really takes to build through the mud - when you’ve got more vision than runway, and the only way out of the mud is through the mud. We talk about the early decisions that shaped Trustware’s roadmap, the week Jesse had to tell his team he couldn’t promise their next paycheck, and why raising less money actually made them a stronger company.

Trustware is building what Jesse calls “a switchboard for crypto” - a way for wallets and apps to exchange any asset for any other asset(s) across chains and identity layers. It’s a big vision with a deeply pragmatic approach - and one that’s already helping crypto-native teams clean up the mess under the hood.

This one’s a masterclass in staying focused, tuning out the hype, and building for the long game.

  •  
  • The early decision to bootstrap and stay lean
  • How Trustware helps wallets and apps simplify cross-chain ops
  • Why team culture matters even more when the money’s tight
  • What Jesse learned about founder storytelling while fundraising
  • The value of persistence over polish in the early innings

LINKS:

Trustware:  Website  |  X/(Twitter)  |  LinkedInDiscord

Jesse Phillips:   X/(Twitter)  |  LinkedIn 

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Jesse Phillips Profile Photo

Jesse Phillips

Co-Founder & CEO, TrustWare