Founder dilemmas · Breaking point
What would you have done?
Six founders who hit a wall. The side of famous companies that never makes the highlight reel. Pick what you'd do, then see what they actually did.
6 rounds · about 3 minutes · one tap each
Real moments from famous companies. Pick what you'd do, then see the call the founders actually made.
- HuffPost
- Moz
- Tesla
- Gumroad
- Flatiron Partners
- Bumble
All 6 stories and what really happened (spoilers)
What did Arianna Huffington do after collapsing from exhaustion?
The Huffington Post, 2007
The situation: Two years after launch, you're working 18-hour days to grow your site. One morning you collapse from exhaustion at your desk, breaking your cheekbone on the way down. The doctors find nothing wrong except exhaustion.
What they did: Arianna Huffington rebuilt her life around rest and wrote two bestsellers about it, Thrive and The Sleep Revolution. In 2016 she left HuffPost to start Thrive Global, a company built on the lesson. She has called the collapse the best thing that ever happened to her.
Why did Rand Fishkin step down as CEO of Moz?
Moz, 2014
The situation: You turned an SEO consultancy into a software company with tens of millions in revenue and venture money behind it. You're working 70 to 80 hours a week and you're deeply depressed. You're still the CEO.
What they did: Rand Fishkin stepped down in January 2014, promoted his long-time COO Sarah Bird to CEO, and stayed on as an individual contributor. He left in 2018 to co-found SparkToro. No neat ending, though: he has written that he often regretted stepping down.
What did Elon Musk say about burnout in his 2018 interview?
Tesla, 2018
The situation: It's the hardest year of your career. Production is behind, you're working up to 120 hours a week, you spent your birthday in the factory and you need sleeping pills to sleep. A major newspaper asks for an interview.
What they did: Elon Musk told the New York Times it had been the most painful year of his career and that anyone who could do the job better could have the reins. Tesla shares fell nearly 9% the next day. He didn't step back, and stayed on as CEO.
What happened to Gumroad after the layoffs?
Gumroad, 2015
The situation: Growth has stalled, the next funding round isn't coming, and you've laid off three quarters of your team, many of them friends. A tech site has written about it. Your billion-dollar startup is now a public failure.
What they did: Sahil Lavingia moved to Provo, Utah, learned to paint and wrote fiction, while answering support emails and fixing bugs himself to keep Gumroad alive. In 2017 an investor offered to sell its stake back for $1. Gumroad survived as a profitable business without venture money.
Source: Marker, Indie Hackers
Why did Jerry Colonna leave venture capital?
Flatiron Partners, 2002
The situation: You co-founded one of New York's best-known venture firms. After the dot-com crash it winds down, and you land a senior job investing a huge fund at a big bank. You're successful, and you've started to hate the work. A deep depression sets in.
What they did: Jerry Colonna walked away from venture capital and became a coach to founders and CEOs, later co-founding the coaching firm Reboot. One of the founders he talked with about depression on his podcast was Rand Fishkin.
Source: TechCrunch, Reboot
Why did Bumble give all its staff a week off?
Bumble, 2021
The situation: Months ago you became the youngest woman to take a US company public. Users have surged and your 700 staff have had the busiest year of their lives. You can see they're burnt out.
What they did: Whitney Wolfe Herd gave the whole company a paid, fully offline week in June 2021. A few support staff stayed on to cover users and took their week later.
Source: BBC, CNN via ABC7