Latest Episode
022: Anne’s Finance Moves, Matt’s $500K Crypto Loss
Anne and Matt dig into how founders think about money, growth, and energy. Anne shares her recent dive into bonds, T-bills, and high-yield savings accounts—and why she treats checking accounts as “dead money.” Matt contrasts ...
Recent Episodes
Sept. 30, 2025
022: Anne’s Finance Moves, Matt’s $500K Crypto Loss
Anne and Matt dig into how founders think about money, growth, and energy. Anne shares her recent dive into bonds, T-bills, and high-yield savings accounts—and why she treats checking accounts as “dead money.” Matt contrasts ...
Sept. 25, 2025
021: The Planner vs. The Improviser - Travel, Poker, and Startup Pressure
Anne and Matt compare two founder mindsets: Anne thrives on preparation and systems, while Matt embraces last-minute decisions and unpredictability. From hunting flight deals to playing high-stakes poker, they unpack how diff...
Sept. 23, 2025
020: Before the Exit: Branding, Valuation, and the Hidden Runway
Anne checks in from rainy Times Square with stories of DIY travel hacks and pitching her new workshop to New York business owners. Along the way, she and Matt get into what it really takes to prepare a business for acquisitio...
Sept. 19, 2025
019: Risk, Reward, and the Hunt for the One Big Marketing Win
Anne and Matt dive deep into the messy, thrilling, and often contradictory world of growth hacking. From coworking space partnerships and unscalable local plays to billboard-style ads with QR codes, Matt shares how he’s testi...
Sept. 16, 2025
018: Momentum Means Sacrifice, or Death by a Thousand Cuts
Anne and Matt dive into the unspoken cost of being the momentum driver in your business. They wrestle with boundaries, burnout, and what it really means to keep growth alive when you’re the one with skin in the game. Anne ope...
Sept. 12, 2025
017: From Startup to Acquisition: Self-Care, 50 Employees, and Founder Lessons with Danika Brysha
Anne and Matt welcome their very first guest, longtime friend and self-care entrepreneur Danika Brysha. Together, they explore the unglamorous but transformative side of building both businesses and lives that actually work: ...