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Doubt: A Startup Founder’s Greatest Threat
Part 2 of the Reinvention Series
When you’re doing a startup, something is always broken. There’s always a fire that threatens to destroy the beautiful but fragile empire you’ve started to build.
- The product crashes and users are pissed — or worse, no one really even notices
- A key hire doesn’t happen and you gotta keep interviewing
- One of your biggest customer churns, throwing off your revenue projections
- Your expensive marketing campaign launches with barely a peep
For all of the startups I’ve founded, the biggest problem was always that our growth was not good enough. Ridejoy was a ridesharing marketplace so we always needed more inventory (drivers to list their rides) because once the date passed, the ride was gone and our site looked empty.
When building Headlight, the tech hiring platform I built after leaving Etsy, we were B2B so there weren’t the same kind of dramatic network effects. But finding new customers and getting existing ones to keep using the product was always a struggle.
Pushing Through the Trough of Sorrow
Paul Graham calls this period, the trough of sorrow, because it can feel like a long slog where…
