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- Fall Hard, Rise Smart. How Founders Bounced Back From Brutal Setbacks.
Fall Hard, Rise Smart. How Founders Bounced Back From Brutal Setbacks.
Inside the real moments founders almost gave up - and the exact moves that got them back on track.
The Startup Leap
June 15, 2025
Hey Startup Leapers 👋
Before we dive into this week’s theme, a quick pause to recognise Father’s Day.
Whether you're a founder-dad balancing investor calls with nursery runs, or someone navigating early-stage life with fatherhood on the horizon - we’re raising a glass (or coffee) to you today!
We’ve also got a couple of brilliant updates from your hosts:
🗣️ Maria took the stage (and smashed it!) at SuperVenture 2025 on the Micro VC Panel, sharing sharp insights on backing operator-led startups early. Catch her reflections here.
💼 Massive congratulations to Yvonne who has been appointed to the Advisory Board for JPMorganChase's Fintech Forward Programme.
This is a major initiative supporting early-stage fintechs working to build a more inclusive and resilient UK financial ecosystem.
Now, onto this week’s focus: Resilience.
Every founder talks about it.
Few break down what it really looks like in practice.
So this week, we’re spotlighting three founders who faced real setbacks - and we’re unpacking how they responded.
Let’s get into it 👇
🎧 Sait Cham - The Startup Almost Collapsed. He Stayed.
Before founding Hutch and Pimento, Sait was working at an early-stage company - and it hit crisis mode.
The startup had run out of money.
Payday was the next day.
People turned to Sait asking, “Are we getting paid?”
He didn’t know what to say.
He wasn’t even a founder yet. But the pressure was real.
Here’s what he did:
🔥 Takeaway: You don’t need to be a founder to build founder resilience. Crisis teaches.
Try this → In your current role, ask: “If this was my company, what would I do differently?” Then do 10% of that today.
🎧Eshita Kabra-Davies - Solo Founder, No Tech Team, Pre-COVID Fashion
Eshita founded ByRotation as a side hustle - mapping the market on a honeymoon spreadsheet.
Five months in, she quit her finance job. Then COVID hit.
Fashion rental? In a global lockdown?
But here’s what she did:
Doubled down on community - launching the #RepeatRotator campaign.
Turned a marketplace into a social network.
Focused on trust, sustainability, and high retention.
Today, ByRotation is the world’s largest shared wardrobe - grown on just $3M.
🔥 Takeaway: Product-market fit isn’t always tech.
Sometimes it’s culture.
Try this → Turn your “blocked” channel into a community loop.
Ask: What non-product habit could keep users engaged?
🎧 Timbo Drayson - Left Google, Faced Doubt, Built Anyway
Timbo had a dream job at Google - launching Maps across Europe, the Middle East, and Africa.
He was about to move to San Francisco to lead Chromecast.
Instead, he took a sabbatical, travelled in Africa, and got obsessed with one stat: 4 billion people without formal addresses.
But the leap wasn’t easy.
He gave up a stable job and salary.
Friends thought he was crazy - leave Google for what?
And building OkHi? Harder than expected.
He faced visa issues, regulatory hurdles, even self-doubt.
Still, he built.
OkHi now powers smart addressing across emerging markets.
🔥 Takeaway: Obsession is a compass.
If a problem keeps you up at night - follow it.
Try this → Ask yourself: what problem do I keep noticing, even when I try to ignore it?
That’s your starting point.
Resilience isn’t flashy.
It’s often quiet, slow, and uncomfortable.
But it’s what keeps you moving when momentum fades.
Until Next Time!
📚 Interesting Reads & Resources
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