What’s the best mistake you’ve ever made?

I asked 100 CEOs this question, and here are key takeaways from top 6 answers:

Want people to talk about your brand? Do something absurd.
Scale only if your culture can survive it.
Kill your assumptions before they kill your business.
Forget trends: build a brand that looks like you.
When the world flips, pivot fast and go all in.
Results matter, but power comes from people who vouch for you.

Intrigued? Keep reading...

Steven Bartlett, Founder of FlightStory, Thirdweb, The Diary Of A CEO & Investor in more than 60 companies.

"When I was 21, before we even had desks, I blew £13,000 installing a huge blue slide and ball pit in our office. Objectively, it was financially reckless - the exact thing an accountant would warn a start-up against. Yet that absurd slide - rare in offices back in 2014 - became our greatest marketing asset. Journalists and TV crews cared less about our work and more about getting a photo of me lying in the ball pit.

The slide’s absurdity communicated clearly: “These kids are different, disruptive, unconventional,” perfectly mirroring our company’s identity. It made people believe in us.

This taught me something crucial: the most irrational and impractical things often become your strongest storytelling assets. People vividly remember absurdity because it activates emotional centres in the brain, such as the amygdala, enhancing long-term memory. Surprising experiences leave deeper traces, making your authenticity, confidence, and distinctiveness undeniable. If you’re willing to put your money where your mouth is and waste £13,000 on something absurd, your ideology must be genuine - your walk matches your talk. This absurdity also fuels word-of-mouth and social media far more powerfully.

Great brands intentionally design absurdity, personality, and surprise into their customer experience for exactly this reason."

Nadine Merabi, Founder and Creative Director of her self-titled globally recognised luxury fashion brand.

"Our “best” mistake was growing 800% in 12 months in 2022.

We scaled from 30 to 100 people. On paper, it looked like a dream. Behind the scenes, it was stressful as hell. Orders were delayed, (...) customer service was overwhelmed, the website oversold stock and we lacked strong leadership.

I panicked and hired fast. I brought in the wrong people, which damaged our culture and stressed the team (...) Despite the revenue, I hated it. It took a full year to recover from it.

We had to restructure the business from the ground up. The lesson? Grow within your means, hire slowly and protect your culture. Every team member needs to be the right fit - not just on paper, but in values and energy.

Sometimes you need to say no. Pause and consider all of the consequences. Stick to your strategy and protect your brand at all costs."

Timo Boltd, Founder and CEO of Gousto, a UK-based home meal delivery service.

"I launched Gousto in 2012, and I was convinced we needed a physical store.

I started pitching the idea to landlords. But after the financial crisis, landlords were not willing to take a risk on my small start-up.

With every "no," the doubts started creeping in. I remember lying awake at night, genuinely questioning whether I’d misread the market and wasted the little time and energy we had.

The mistake wasn’t the rejections; the mistake was my thinking.

I was so fixed on the idea of a store that I didn’t stop to ask the right questions: What do customers actually want? How do they want to engage? What’s the fastest way to prove this model works?

It took rejections to shake me out of my own assumptions. Once I did, I realised we didn’t need a store, we needed to be online. I had to admit I’d gotten it wrong. That shift became one of the most defining moves in Gousto’s journey.

It’s not about avoiding those early mistakes in your business, it’s about how quickly you’re willing to challenge your own logic, change your mind, and move on."

Amelia Christie Miller, Founder of Bold Bean Co, revolutionising the way people cook and think through sustainable, chef-quality products.

"My best mistake was the first direction I took Bold Bean Co. (...) I brought a lot of naive assumptions into the brand creation process. Just because you’re a consumer doesn’t mean you know how to build a brand.

At first, I tried to make the brand “trendy”, all lowercase copy and minimal design that mimicked other successful startups. I was chasing the Gen Z audience, convinced they were the future. After hearing Kendrick Lamar’s HUMBLE. at a gig and seeing how obsessed the was, I (cringingly) named the company Humble Foods, which is still our legal name today.

Like the song, the idea was to be ironically PROUD, not humble, flipping the perception of beans on its head. The initial packaging designs were slick and cool, rather than being joyful and exciting.

Feedback from friends and mentors was lukewarm and confused. The irony didn’t land and people couldn’t picture me, a slightly scruffy, wildly enthusiastic bean-lover, behind such a polished brand. I was so convinced this was the way to target the Gen Z consumer that I felt it would be better to step back and be a silent founder in the brand story in order to deliver on this strategy.

As a founder, in the early days, YOU need to represent the brand because the brand is you. When I finally embraced my authentic self and projected THAT onto the brand; a sometimes scruffy, sometimes sensitive woman with wild enthusiasm for beans - the marketing started landing.

Investors got it. And the PR? We ended up on ITV’s This Morning, in The Sunday Times Magazine and You Magazine. Not because we followed a trend - but because we told the truth.

Authenticity is a cheap way to build trust. And it works."

David Abrahamovitch, CEO and Founder of Grind coffee, known for its cafés, sustainable coffee pods, and DTC subscriptions.

"Our best mistake? Launching our coffee pods, just weeks before the first lockdown.

We had quietly launched our DTC business a few months earlier, but when lockdown shuttered our cafés, it became a way for regulars to support us - then it exploded. Orders poured in from across the UK. We’d sold way more than we had in stock, and our team was living in the warehouse, trying to keep up. Baristas who were making coffee in our cafes two weeks earlier were now being retrained to do fulfilment in our warehouse.

Saving the business meant making this work - fast. We were about to spend £1.5m fitting out a new Waterloo site. Instead, we redirected it all into DTC, and we haven’t looked back since.

We rethought everything. We outsourced fulfilment, built a proper tech stack and hired a DTC team while also keeping our cafe teams ready for reopening. I’d spent a decade building the high street business, but overnight I had to learn a new one. Apart from the brand and the coffee, nothing was the same.

It was stressful, messy, and required making decisions with 80% confidence, but it was also fun. That mistake turned Grind from a cool café brand into something much bigger.

I don’t regret any of it. Going from a mature café business back to start-up trenches taught us adaptability and built the version of Grind we have today. Still, I was relieved when I finally had my first flat white back at Shoreditch Grind."

Thai Randolph, Co-founder, an award-winning media executive, entrepreneur, and former CEO of HARTBEAT.

"The best mistake I ever made? I thought the results would be enough.

I grew up on a farm in Holly Hill, South Carolina. No family office, no Ivy League background. So much of my approach to my career was shaped by those early days - watching people in my family and community work hard to (quite literally) enjoy the fruits of their labor. That work ethic became my compass: first one in, last one out. I was determined to outwork everyone, and it paid off. That mindset drove me to build teams, scale companies, raise capital, and drive profitability.

But the farther I got, the more I realized: performance doesn’t always equal power. More than once, I’ve found myself in rooms where the work was welcomed, but my worth wasn’t championed.

That’s when it hit me: It’s not just about how hard you work, it’s about who’s willing to vouch for the work that you do. Less than 2% of venture funding goes to women. Less than 0.5% to Black women. Only two Black women lead Fortune 500 companies today. That’s not a pipeline problem - it’s a power structure.

We’re not short on credentials or capability. What we’re often missing is what I call the “Goodfella endorsement” – a corner office cosign. Not just a mentor, but a sponsor. The one who says, “She’s with me. She’s one of us.” Essentially…a Goodfella. Of course, I deliver - I’m passionate and purposeful about what I do. But I no longer rely on results alone.

I prioritize relationships, mentor others to do the same, and most importantly, I sponsor as many worthy individuals as I can. The best mistake I ever made was thinking I could do it all by myself. I can’t. None of us can."