Money, Startups, and Finding Sustainable Work

Guest: Chris Hutchins, host of All the Hacks

Episode theme: Building wealth with meaning—how to design a career (and life) you actually want, while optimizing the money side.

What we cover:

• Meaning > money-first: Chris didn’t start out chasing wealth; he chased options. Early jobs in consulting/banking felt misaligned (little meritocracy, lots of “performance”). That tension pushed him toward work that creates—startups, product, and eventually a podcast.
  
  
• From layoff to leverage: A 2008 layoff forced reinvention. He broke into tech by doing unglamorous, high-initiative work, learning in public, and obsessively networking. Key tactic: create value before you’re hired (he built a full market brief to win a BD role).
  
  
• Career as a cash-flow asset: Once he found work he loved, savings were easier because the job itself provided energy, purpose, and upside. That shift—liking the work—reduced the need to “buy happiness” elsewhere.
  
  
• Optimization without overwhelm: All the Hacks exists to find the 80/20 in money, travel, health, and life. You don’t need to become a points guru or biohacker; borrow Chris’s research and apply the simple levers.
  
  
• Counterintuitive insurance take: When he priced plans, the “best” (premium) plan cost ≈$24k/yr more than the “worst,” while the “worst” plan’s out-of-pocket max was less than that difference. With a real emergency fund and a strong stomach, a high-deductible plan can be rational. (Psychology is the hard part.)
  
  
• Prepay for joy: Pre-buying (subscriptions, passes, prepaid trips) can remove friction and guilt, increasing actual use and happiness.
  
  
• Know your enough: People who don’t know what money is for default to “more.” Define the life you want, price it, then fund that—not a moving target.
  
  
• Audience resonance: “Mini-retirements,” negotiation tactics, and insurance optimization were huge hits; even niche episodes can be life-changing for the right listener.
  
  

Actionable takeaways

1. Design a role you’ll keep doing. Treat your job like part of your portfolio’s fixed-income sleeve: dependable cash flow, lower stress, and compounding skills.
   
   
2. Front-load value. Pitch with a one-pager or mini-audit tailored to the company—proof you’ll do the work.
   
   
3. Run the insurance math (with your EF). Price premiums vs. out-of-pocket max; let your emergency fund shoulder higher deductibles if the numbers favor it.
   
   
4. Prepay strategically. Use prepayment to align behavior with values (fitness classes, transit, annual memberships).
   
   
5. Write money rules. E.g., “Invest 20% before lifestyle,” “Use points for intl. biz class only,” “If it saves 10+ hours/yr, buy it.”
   
   

Lightning-round fun

• Best <$100: Ultrasonic cleaner (for retainers/aligners)—tiny daily upgrade.
  
  
• Most overrated advice: Social-media tax “hacks” that cross legal lines.
  
  
• Apps he likes: A clean net-worth tracker + Copilot for spending (iOS).
  
  
• Guilty pleasure spend: Big annual fees on premium cards—only if the benefits net out.

Find Chris: All the Hacks (weekly deep dives). A great starting point: his “Top 50 Lessons” episode.