Become a fitter founder in 7 days.
Most founders overthink their health. Ice baths, coffee timing, staring at the sun. Meanwhile they skip the thing that actually moves the needle: a short workout, every day.
You can't declare yourself a fit person. You build the identity two ways: the daily habits of a fit person, and a community that holds you to them. This challenge gives you both.
One day at a time: a founder story, a business challenge, and a workout. Most need no equipment.
One email a day for 7 days, then my Thursday newsletter. Unsubscribe from either any time.
Day 1: from failing milkshake salesman to billionaire
He was 52 and stuck. One bold move changed everything.
One of the worst sentences in the English language: “in another life.” The admission that you gave up on a meaningful life without ever trying.
Ray Kroc was a 52-year-old milkshake machine salesman dealing with diabetes and arthritis. Not exactly something that impresses the in-laws at Thanksgiving. He could have called himself too old and quietly quit.
Instead he found the McDonald brothers' restaurant in San Bernardino and built it into the $200B+ empire it is today.
Today's lesson: It's never too late to change your life and build founder fitness.
Founder challenge: make one cold call
Make ONE call (yes, on a phone) to the major customer, supplier or recruit you've been putting off for months.
Fitness challenge: the 100s workout
At home:
- 100 air squats
- 100 sit-ups
- 100 push-ups
Any order. Do all the squats first, or mix it up (20 squats, 15 sit-ups, 10 push-ups) until every rep is done.
Day 2: the foster kid with the egg empire
From foster care to $10M+ revenue. One gritty step at a time.
Sarah bounced around foster homes in Boston. While she worked at a diner, a wealthy childless couple who were regulars decided to pay her way through college.
She finished a business degree wanting to buy a business, with zero clue how. So she turned the college library into an office, filled it with interns, and cold emailed her way into a meeting with the owner of eggcartons.com.
With little savings, she got the banks and the seller to finance the deal with almost nothing down. The business passed $10M a year in revenue in 2024.
Today's lesson: There is unlimited upside for those who refuse to accept the cards they were dealt.
Founder challenge: find your energy drainers and gainers
Draw a T-chart. Left column: tasks that drain you. Right column: tasks that fill you up. Then kill one drainer this week:
- Delegate it to a team member
- Hire for it
- Eliminate it if it isn't critical
Fitness challenge: EMOM burpees
Every minute on the minute, do 5 burpees, then rest until the clock turns over. Keep going until you can't. Beginners start with 3. Advanced, go 10 to 15.
Day 3: the $30B dealer selling shoes like stolen stereos
Phil Knight sold from his trunk. The obstacles became the path.
Social media makes us forget it, but building a company is hand-to-hand combat, especially early. Even for the founder of Nike.
Phil Knight sold shoes from the trunk of his car at track meets. Then it got worse: sketchy credit lines that risked bankruptcy every payroll, a key supplier that tried to cut him out, and a years-long fight with U.S. Customs that nearly sank the company.
He stayed founder and CEO for 40 years. Marcus Aurelius had it right: the obstacle is the way.
Today's lesson: Becoming a fitter founder isn't linear. Expect obstacles, control what you can each day, and let it compound.
Founder challenge: build one SOP
Find the lowest-leverage task that steals the most time, like monthly admin or bookkeeping. If AI can't automate it, record a screen-share walk-through in Loom. It drafts the step-by-step SOP for you.
Fitness challenge: super legs
5 rounds, at home:
- 20 air squats (add dumbbells for spice)
- 20 alternating lunges
- 20 alternating jumping lunges
- 10 jumping squats
Apologies in advance to your legs.
Day 4: living in a shack in China on $1 a day to $2B a year
Nick Mowbray bet on tiny tests, not luck. Fire bullets before cannonballs.
Nick Mowbray went to China with no money, no plan and no language. He slept in a bush outside the airport, built his own factory when no manufacturer would work with him, and lived on about $1 a day for years.
When lawsuits hit or purchase orders died, he found new products and new markets. He made small batches of toys, tested them at trade shows, killed the flops fast and poured money into the winners. ZURU is now one of the most profitable toy companies on earth.
The point isn't to move to China. It's to fear not trying more than you fear failing.
Today's lesson: Don't fear failure. Fear not acting.
Founder challenge: ship your KPI scoreboard
Pick 10 weekly KPIs and review them every Friday. A simple start:
- Qualified leads
- Calls or demos
- Proposals sent
- Pipeline created ($)
- Closed-won ($)
- Cash in bank (weeks of runway)
- Gross margin %
- Days to first value
- Founder deep-work hours
- Workouts completed
Block 30 minutes every Friday. Update the numbers. Write one sentence on what changes next week.
Fitness challenge: 20-minute hill climb
Max the incline on a treadmill and run or walk for 20 minutes, as fast as you safely can. If you're dripping sweat and checking the clock every 30 seconds, you're doing it right.
Day 5: the fax machine sales rep who rewrote underwear
Sara Blakely turned every no into a smaller ask. Tiny wins stacked into SPANX.
Before SPANX, Sara sold fax machines door to door in the Florida heat, six days a week, to receptionists trained to say no. It taught her clear messaging and how to take rejection.
She cut the feet off her pantyhose before a party and the idea stuck. With $5,000 and no fashion background she called factories until one owner said yes, then talked her way into ten minutes with a Neiman Marcus buyer and closed her first order in the meeting.
The Oprah moment that made SPANX famous came after five hard years.
Today's lesson: Create your own luck. When someone says it isn't possible, ask “why not?” and then ask for something smaller.
Founder challenge: film your elevator pitch
Most of your network has no idea what you do. Film a selfie video on your phone: what you do, and your single biggest ask (a hire, referrals, product testers). Post it and see what comes back.
Fitness challenge: the blackjack workout
For time, zero equipment:
- 20 push-ups, 1 sit-up
- 19 push-ups, 2 sit-ups
- 18 push-ups, 3 sit-ups
- Continue down to 1 push-up, 20 sit-ups
Day 6: 100+ rejections to a $42B platform
Melanie Perkins started with a tiny wedge. Persistence beat pedigree.
Before Canva was worth over $40B, Melanie Perkins and her team were turned down by more than 100 investors.
Instead of taking on Adobe, she started narrow: Fusion Books, a yearbook design tool that proved non-designers would create when given smart defaults. After each rejection they didn't add features. They removed steps, which made the product faster and the pitch tighter.
Seneca wrote that difficulties strengthen the mind, as labour does the body. Those rejections built the company.
Today's lesson: Constraints produce clarity. No pile of investor cash forces you to build something profitable from day one.
Founder challenge: win back a customer who ghosted you
Send this to at least 10 lost leads today:
“Hey [name], I didn't hear back on my last email. Are you still planning on [the problem you solve] this year?”
Mine reads: “Are you still planning on selling your business this year?”
Fitness challenge: the card workout
Grab a deck of cards:
- Diamonds: push-ups
- Spades: squats
- Hearts: burpees
- Clubs: sit-ups
Number cards are face value. Face cards are 10. Aces are 15. Jokers are a 1-minute plank. Clear the deck as fast as you can.
Day 7: growing up on food stamps to a $19B app
Jan Koum was rejected by Facebook. Facebook later paid $19B for his company.
Jan Koum grew up in Ukraine in a house without running water. In the U.S. he swept grocery store floors, relied on food stamps, and taught himself to code from second-hand books. Facebook turned him down for a job.
He didn't reinvent social networking. He built dead-simple, fast, private texting that worked on any phone and any network, and kept removing steps, settings and screens. Founders answered support emails. Outages were treated as existential.
WhatsApp spread worldwide, and Facebook fixed its hiring mistake with a $19B term sheet.
Today's lesson: You're probably overthinking it. Make your business so simple a stranger gets it in two minutes. (Not your mom. She'll say it's great anyway.)
Founder challenge: fire yourself from a job
For the next week, log what you work on and for how long, every day. Then pull out your T-chart from Day 2 and kill as many drainers as you can:
- Delegate it
- Automate it with AI or software
- Hire for it
If none of those work, you're either a control freak or you need to learn to love that task.
Fitness challenge: outdoor finisher
For time:
- Run 800m
- 60 air squats
- 40 push-ups
- 20 burpees
- Run 800m
Aim to run the second 800m faster than the first.
You made it. Pick one habit to keep daily next week: a 20-minute walk, one cold call, or one customer message. Momentum beats motivation.