Aug. 10, 2025

002: “Reverse Ranking Imperfection”: Why Founders Should Embrace the Mess

002: “Reverse Ranking Imperfection”: Why Founders Should Embrace the Mess

Anne and Matt dive deep into the messy reality of mixing friendship and business—and why it usually doesn’t work. They unpack the emotional landmines of hiring friends, share raw confessions about sacrificing pay, and debate when founders should actually start paying themselves. Matt opens up about bootstrapping ChipBot through years of near-zero revenue and how table tennis taught him resilience. Anne drops a truth bomb about trading self-worth for runway—and what it costs. This one's for the founders running lean, playing the long game, and learning the hard way.

🚨 Stuff You’ll Want to Remember:

  • Hiring friends almost always complicates performance and accountability—think twice.
  • Bootstrapping means sacrificing pay, time, and sometimes your damn soul.
  • Founders often grow closest to the people they start working with—not lifelong friends.
  • If your company can’t pay you for three years, you better have a backup plan (consulting, savings, etc.).
  • You need the same energy for 4 views as you would for 4 million—every single day.

💣 Sh*t Only Founders Say:

  • “If you hire friends and performance hits, you can’t fire them.” — Matt
  • “I’m tired of doing all the bullshit, but I’m still sacrificing owners pay to grow.” — Anne
  • “If you want to build something huge, be ready to give up your time, money, and a little bit of your soul.” — Matt
  • “Your 20% is still better than most people’s 80%.” — Anne
  • “Founders need to get real about what ‘no money’ actually means.” — Matt

💬 Lines That Slap:

“We’re not just talking about Matt playing table tennis. He goes all around the world. That’s a big deal.” — Anne

“If you're always perfect the first time, there’s nothing to look forward to.” — Matt

“Sometimes I forget to say good morning—I just get right into the sh*t.” — Anne

“Reverse ranking: if they comment that it’s bad, the algorithm thinks it’s good.” — Matt


📡 Where to Find Us