Place good startup bets | Swizec Teller

• Your goal isn't to win every bet—it's to be slightly more right than wrong and keep playing (cap downside via salary, maximize upside via equity)
• Six pre-requisites for good bets: problem you can't stop thinking about, market you can reach, growing market, market worth chasing, unfair edge, and early traction evidence
• External signals to evaluate: employee growth rate on Crunchbase, quality of LinkedIn profiles, fundraising trajectory, and backchannel references from friends-of-friends
• What makes a bet "good" evolves with your career—indie money felt amazing 10 years ago, now the author needs bigger bets worth 5-10 years of effort
• Never join for no pay unless you're a student with support—early career capital from unpaid work can bootstrap bigger opportunities, but only if mom's filling the fridge

The author's framework for evaluating startups stems from his biggest career miss: turning down Shopify two years before IPO. While he doesn't regret avoiding Ottawa, he regrets missing the engineering lessons from a company now famous for their technical excellence. His evaluation framework has six pre-requisites: a problem you can't stop thinking about (if the core idea makes you tired, the inevitable bullshit will kill you), a market you know how to reach, a growing market (you can't beat the macro), a market big enough to justify 5-10 years of effort, an unfair edge (unique insight, market access, technique, capital, or talent), and evidence of early traction.

For external evaluation before you have database access, he recommends checking employee growth rate on Crunchbase, evaluating hire quality via LinkedIn profiles, analyzing fundraising trajectory (getting bigger with better investors vs. raised too much vs. too little), and conducting backchannel reference checks through friends-of-friends. Ask what people are excited about and whether the vibe is energized or tired. The key insight is looking for "slope"—the rate of change matters more than absolute size.

The meta-lesson is that evaluation criteria evolve with career stage. Ten years ago, any indie money felt like freedom. Now, just being self-employed isn't worth it—he'd rather be a "house-cat." The framework helps you assess whether the juice is worth the squeeze for YOUR current situation, not some generic standard. Never join for no pay unless you're a student with external support—he did this in college and it created career capital, but only because mom filled the fridge.