In This Episode Jake Gibson, former investment banker, entrepreneur / co-founder NerdWallet, angel investor, now VC founder Better Tomorrow Ventures, who crossed career paths with host Jason Henrichs 10+ years ago, have an honest discussion about the twists and turns of co-founding a boot-strapping start-up particularly when you are young, on to something and quickly have to figure everything out. After years of hard work and being all-in, tough decisions needed to be made as NerdWallet continued to grow quickly. Jake knew it was time to move on, but so hard to do. The arrival of twins and focus on strengths, honesty, lessons learned, and giving advice to others in similar situations, helped Jake figure his calling and path forward, and has enabled him to keep many 'cards in his wallet'.  Read the entire transcript here. Podcast Content: Chapter 1: 00:00:00 - Introduction: Reinvention and Identity Setting the stage for Jake Gibson's journey, from Wall Street to co-founding NerdWallet, angel investing, and ultimately venture capital. Chapter 2: 00:04:30 - From Wall Street to Silicon Valley: The First Reinvention Jake shares his transition from a successful trading desk role at J.P. Morgan to joining Tim Chen on the early journey of NerdWallet. Chapter 3: 00:12:00 - Bootstrapping NerdWallet: The Rocky Early Days Insights into the early challenges of building NerdWallet, the struggles of SEO, and how Google’s algorithm updates became a turning point. Chapter 4: 00:22:45 - Growth Pains: Scaling Beyond Founders’ Capabilities The tough lessons in scaling NerdWallet, managing people, and navigating layoffs, despite the company’s upward revenue trajectory. Chapter 5: 00:35:00 - Leaving NerdWallet: Letting Go of Identity Jake opens up about the emotional difficulty of leaving NerdWallet, redefining his sense of self, and taking time to decompress. Chapter 6: 00:45:30 - Angel Investing: Paying It Forward The next phase for Jake—mentoring and investing in startups, building a network, and finding fulfillment through helping others succeed. Chapter 7: 00:52:00 - Commitment Issues: From Angel to VC with Better Tomorrow Ventures How Jake partnered with Sheel Mohnot, overcame hesitations, and co-founded Better Tomorrow Ventures (BTV) to support fintech innovation. Chapter 8: 01:05:30 - Facing Failure and Luck: Lessons for Founders Candid advice on preparing for potential failure, embracing identity shifts, and recognizing that success often requires persistence and luck. Chapter 9: 01:15:00 - Closing Reflections: The Founder’s Mentality Jake’s thoughts on unreasonable optimism, self-awareness, and how founders should approach reinvention and uncertainty. Related Content: Episode 44: Where Does The Money Go? - Angel Investing Episode 451: AWS Bets Big on Black and Women Founders & Harmonizing Taxes Episode 550: Cease and Desist Identities Merging Episode 551: This Spot Looks Soft https://youtu.be/aQnekFgirVU