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Most startup founders don't make it past year three. Bo Jiang is entering year twelve. As the CEO and co-founder of Lithic, Bo has lived what feels like two completely different startup journeys in one company. He launched Privacy.com in 2014 as a consumer app helping people create virtual credit cards for safer online shopping. After issuing over 10 million cards, he hit a wall… legacy payment infrastructure couldn't keep up. So Bo did something radical: he built his own modern card processor from scratch. Then he opened it up to other companies. That pivot transformed Lithic into an $800M developer platform powering card programs for Mercury, Novo, Parker, and dozens of other next-generation fintechs. Today, Lithic processes over $1 billion in annual transactions and has raised $110M+ from top investors like Bessemer, Index, and Tusk Ventures. But this conversation isn't about the hockey stick growth or the impressive valuation. It's about what it actually takes to survive and evolve as a founder over more than a decade. In this episode, Brennan and Bo go deep on: → The real story behind Lithic's pivot from B2C to B2B infrastructure (and how other startups literally reverse-engineered their API before they officially launched it) → Why Bo believes burnout doesn't come from working hard… it comes from the "messy middle" of trying to control things you can't control → How your role as a founder completely transforms as you scale from 3 people to 130+ (and the inflection point where your individual output stops mattering) → The mental game of fundraising: why most rejections have nothing to do with you, and how stress literally shows up in your investor Zoom calls → Building high-trust, high-context culture while scaling beyond the small team magic of the early days → Competing against billion-dollar giants like Marqeta, Stripe, and legacy processors when you're the smaller player → Why Bo stayed private and played the long game while everyone else was chasing quick exits during the 2021 fintech boom → What it means to be "comfortable with extended periods of uncertainty" – and why that might be the most important founder skill → The future of fintech infrastructure: stablecoins, AI agents, and whether physical cards will become relics Bo is an MIT-trained engineer who spent years building in the unsexy world of payment infrastructure while everyone else chased shiny objects like crypto and neobanks. Turns out, fixing the pipes is where the real, sustainable value lives. If you're a founder, builder, or anyone playing the long game, this conversation is for you. Episode Timestamps 0:00 - Intro 1:34 - From Privacy.com to Lithic: building two startups in one decade 5:38 - Consumer vs. B2B 8:23 - How the CEO role changes as the company scales 15:07 - Raising capital without being an AI research lab 19:15 - Generalists vs. specialists 26:28 - Managing mental health & burnout over 12 years 36:43 - Choosing the right investors & advisors 43:06 - War stories: the fraud attack 51:58 - Where fintech infrastructure is headed in the next 5-10 years