WORTH WATCHING:
The Most Risk-Averse Entrepreneur in the World
The Advantage · Mike Wystrach × Tobi Oluwole · ~53 min
This week's Worth Watching is my conversation with Tobi Oluwole, who runs Founder's Blueprint, a LinkedIn accelerator for founders. Tobi was born in Nigeria. At 15 his dad sent him to Canada, against his will, when the plan he had pitched his parents was to play for Arsenal.
He has started a business every year since he was 14. The first was lollipops at school, and the principal caught him three lollipops in. He was laid off from his first tech sales job and fired from his second. He applied to Shopify seven times, and on the seventh they let him in. In onboarding they taught him Freytag's Pyramid, a storytelling framework from the 1860s. He thought it was nonsense, so he tested it in a LinkedIn post. He had 1,000 followers and woke up to 200,000 impressions. He has posted every weekday since May 2020 and is now at about 400,000 followers.
WHAT I LOVED ABOUT IT:
Tobi calls himself the most risk-averse entrepreneur in the world. His rule: he will not quit his job until his side income has doubled his salary for at least six months. He calls it risk-free entrepreneurship.
Starting a company does not have to be binary. You can be a very good employee and build something of your own at the same time. It takes extra hustle. By Tobi's count, the founders in his program have done $40 million in the last four years.
On almost everything else, I am the exact opposite of Tobi. My alarm goes off at 4:15 every morning and I work seven days a week. Tobi has no alarm. He works Tuesday, Wednesday, and Thursday, takes eight weeks off every summer, and has said no to funding to keep it that way. There is no right or wrong. There is just your right and your wrong.
The danger is not building slowly. The danger is building a life you never wanted because it was somebody else's version of success.
THE LINE THAT STUCK
"It's your story. You can't be late for your story."
Tobi's answer to anyone racing to a million dollars this year: if it took four years, would you still be happy? Watch him explain it →
MY 20-SECOND RECAP
if you do not have the full 53 minutes
→Double it before you jump. Six months of side income at twice your salary is Tobi's line. Pick your own number now, before a bad week at work picks it for you.
→Your first job is still school. Tobi treated Shopify as his alternative to an MBA, a place to learn how to be a good entrepreneur while getting paid. Pick your next job for what it teaches you.
→Ten best, ten worst. Tobi starts with 20 stories, the ten best moments of your life and the ten worst. That is the first year of content. The best moments bring opportunities. The worst ones bring trust.
→Stay longer. "I haven't even gotten that much better. Right, I just stayed way longer than everybody else." Five days a week, 8 to 12 lines, one visual, posted between 9am and noon. Then do it again tomorrow.
→Share the blessing with the people who share the burden. That is a saying inside Tobi's company. If you want the upside, get in the trench.
PRO MOVE
Write down your salary and double it. That is the monthly side income Tobi would want to see for six months straight before he handed in his notice.
