Zero to $1B: 8 Lessons Scaling a Startup

Jonathan Swanson
Jan 16 · 11 min read

Lesson #1: If confidence + humility is a spectrum, you need to live on the extremes of both ends

Lesson #2: You must co-found a series of companies (not just one)

It’s important your companies are as symmetrical as these fields.

Lesson #3: Your happiness may have a .64 correlation with your startup success

I was an obsessive life tracker and this chart shows my weekly self-reported happiness (blue) and Thumbtack-bullishness (red) from 2011–2013 . The annotations are unedited notes from my lifelog. The highs and lows!

Lesson #4: The best companies win on product innovation AND business model innovation

Lesson #5: Culture is a self-fulfilling story designed to help you win

Create a story of where you want to go with your team. Then work endlessly to get there. Space suit optional.

Lesson #6: It’s helpful to have an irrational motivation

Startups can sometimes feel crazy. But if you’re climbing El Cap without ropes you’ve taken things too far.

Lesson #7: The unsung secret of scaling is a high tolerance for boredom

Someone needs to tell Keith Rabois he’s doing Barry’s Bootcamp wrong.

Lesson #8: Scaling a company requires scaling yourself (hire an EA early)

Running up the score is good. But you shouldn’t be the one dunking.

Jonathan Swanson

Written by

Co-founder & Executive Chairman at Thumbtack, former White House staffer, lover of life

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