I Needed Every Single Failure.

I Needed Every Single Failure

Read time: 5 minutes

Hey, welcome back.

Last week, I talked about the ups and downs of my fitness journey, and how it's making me a better dad in the process. You can read that (and all past issues, here)

Today I want to talk about losing. And why most of the losses I've taken turned out to be the most useful things that ever happened to me.

A Tweet That Said It Better Than I Could

I saw this from @thedulab recently:

"If a loss makes you believe in yourself more, it was never a loss. Get rejected by someone. Roundtrip a position. Blow an opportunity. But did it expand your awareness of what was possible? Failing forward normalizes excellence. Use the L's to show yourself what you're capable of."

Use the L's. I love that.

Because when I look back at everything I've built, every single good thing I have traces back to something that felt like it was falling apart at the time.

My First Startup Failed

Grabble was a fashion discovery app. We raised money. We got press. We had users. And then it didn't work. The business model didn't hold up and the company died.

At the time it felt like the end. I'd put years of my life into it. I'd told everyone I knew about it. My identity was wrapped up in being a founder of this thing, and when the thing stopped existing, I didn't really know who I was anymore.

What I didn't realise at the time was how much I was learning. How to build a product. How to raise money. How to hire. How to manage a team. How to deal with things going wrong. All of that knowledge just sat there, waiting for the next thing. I couldn't see it because I was too busy grieving the loss.

Then I Fell Apart

After Grabble, I burned out completely. Six months of insomnia. Less than an hour of sleep most nights. Crippling anxiety. Depression. I was sweating through my shirt sitting at my desk doing nothing. My body was sending me every possible alarm signal and I just kept ignoring them because I thought pushing through was what entrepreneurs do.

I tried therapy. Sleep apps. Meditation. Alcohol. I even got prescribed sleeping pills that I never took because I knew they weren't going to fix the actual problem.

That breakdown was the lowest point of my life. And it led me directly to a dietitian's office where a woman I'd never met before diagnosed me in about sixty seconds. She told me my brain was starving. She recommended DHA omega-3s, B vitamins, and blueberry extract. Within two weeks, the tension dropped and I was sleeping through the night.

Without that breakdown, I never meet that dietitian. Without that dietitian, I never discover brain nutrition. Without brain nutrition, Heights doesn't exist. Joel and I don't start a newsletter. We don't spend 18 months developing a product. We don't build a company that's now been ordered over a million times.

Every single piece of that story required the failure that came before it.

Being An Outsider Was Supposed To Be A Weakness

When Joel and I decided to start a supplement company, we knew absolutely nothing about the industry. We were tech founders. We didn't know how to source ingredients or manufacture capsules or navigate food safety regulations.

Every person we spoke to in the supplement world made us feel like we didn't belong there. And they were right, in a way. We didn't know the rules. We didn't know the shortcuts. We didn't know how things had always been done.

That turned out to be the whole advantage. Because the way things had always been done in supplements was terrible. Cheap ingredients, misleading labels, products sitting on shelves for years, losing potency. We came in with no assumptions about how it was supposed to work and built it the way we thought it should work. Science first. Sustainable sourcing. Blood-tested for efficacy. Clinical trials.

Being the outsiders who didn't know what they were doing forced us to ask questions that people inside the industry had stopped asking a long time ago.

What Failure Actually Does

I've built five startups now. One clear win, one clear fail, and three still going. Every lesson I use daily at Heights came from something that went wrong somewhere else.

The way I hire now is shaped by hiring mistakes I made at Grabble. The way I manage my energy is shaped by a breakdown that nearly destroyed me. The way I build products is shaped by years of watching things not work and slowly figuring out why.

None of those lessons were available to me in a book or a podcast or a course. They only became mine because I went through them. Because I took the loss and kept going long enough to see what it taught me.

That's what the tweet means when it says failing forward normalises excellence. When you've failed enough times, the fear of failure loses its grip on you. You've already survived it. You know what it feels like. And you know that you came out the other side with something useful every single time.

What I'd Say To You

If you're in the middle of a loss right now, whether that's a business that isn't working, a deal that fell through, a relationship that ended, a health scare, or just a stretch where nothing seems to be going your way, I'd ask you one question.

Is this expanding your awareness of what's possible?

Because if it is, even slightly, even painfully, then it's doing its job. You're collecting information that your future self is going to need. You just can't see the full picture yet.

The founders I admire most all have a long list of things that went wrong before anything went right. The failures weren't detours. They were the training ground.

Use the L's. Every single one of them is teaching you something about what you're capable of.

To failing forward,

Dan

P.S. If you've had a failure recently that you're still carrying around, try writing down three things it taught you. Not three silver linings. Three actual lessons that changed how you do things. You'll be surprised how much you've already taken from it.

Humankind - Rutger Bregman

Not yet finished but loving this optimistic view on humanity

Read Here

Smartless

Tom Hanks

Listen Here

Send Help

Rachel McAdams in a superb comedy horror. Loved.

Watch Here

A 2020 study published in Emotion found that people who learned to accept their “non-ideal emotional states”, including low motivation, low energy, and neutral days, experienced significantly higher overall well-being and lower stress.

The key insight: self-acceptance amplifies emotional resilience, while self-judgment weakens it.

📌 Quick Takeaway →

Your average days aren’t failures; they’re emotional training grounds.
When you stop punishing yourself for being human, everything in your life compounds faster.

→ Link to study

In my goal to help more entrepreneurs/people who are looking to level up their careers, I've just started taking 1-1 consulting calls (only 1 a week)

Why book a call? Some of my expertise/success:

I've built 6 startups. 3 fails, 1 win, and 2 still going.
E-Commerce: Heights - with revenue over $40M a year.
Community: Foundrs, one of the UK's top founder communities
Podcasting: Leaders Media - Bootstrapped to #1 in business and 10M downloads
Health/Mental Health: Overcame depression, insomnia, burnout and anxiety in pursuit of success
Angel Investing: I've invested in over 100 companies
Personal Brand: Over 400,000 followers across social
Hear me on Diary of A CEO with Steven Bartlett

So if you're interested in booking a session with me to talk all things business or building a personal brand, book for 30-minutes or 45-minutes. (limited spots).

Book a Call with Dan