Win Even if You Lose

People love to give advice after they've made it big, telling you to "stay motivated."

But how about someone who keeps going after falling on their face day after day for years?

That’s my story. Need proof? Here are 30+ ideas that didn’t work out:

Despite these failures, I continue to keep going, and still have fun along the way.

The Mindset

It’s scary to start something. What will people think? What if I waste my time, money and energy?

With Imeldá, I can’t even say with confidence I’ve found PMF (product market fit).

I used to be the opposite of resilient. For most of my life, I found refuge in my safe little bubble of the filmmaking world.

But after leaving it all behind and moving into tech, the itch to create something could not go away.

I tried very hard to focus on my day job (for a total of 3 weeks) - but visions of side quests kept coming. Entrepreneurship was the most challenging, fun, and philosophically aligned concept that I’ve ever been exposed to. I was hooked.

So I dove deep into the business books, listened to the podcasts, created business plans. Tried a bunch of things. But nothing worked. And to this day, nothing technically has.

Failure Stacking

If you learn from your failures, every failure is a lesson brings you closer to your goal, empowers you with more skills. This compounds over time.

On this journey, I have felt lost, frustrated, angry, and sad more times than I can count. I have “wasted” tens of thousands of dollars and hours hiring people, building prototypes, running ads, and buying courses. You name it.

But to focus solely focus on the results is missing the point. Throughout this process, I’ve acquired skills, frameworks, and scar tissue to understand how business works in a much deeper way.

Examples of learnings from each project:

• Starting a Micro PE firm: the abstract art of valuations, multiples, and how to study balance sheets.

• Supplement Companies: branding, e-commerce and FB ads.

• Design System Agency: Lead gen, sales, and operations.

• Productivity App: Software is not my circle of competence at all.

The Most Underrated Fuel

The most underrated way to keep the momentum going is to have a supportive partner. It could be a friend, family member, or your spouse.

This person is someone who is supportive, but constructive. If you even have one person like that in your life - count yourself lucky.

The greatest victim in this whole journey, is not my ego, or my bank account. It’s my wife. She has patiently listened to me pitch a new idea every month. Giving me feedback when I need to, and sharpening my thinking. Not all heroes wear capes.

Do it

Experience is king when you are starting out.

If you have a project that you have been procrastinating on, I hope you can find sometime to start.

What does it look like in reality if you have a day job? For me, it means waking up at 6-7am, hitting the gym, and doing 2 hours of deep focus work before the day starts. This is more doable than you think.

It could be as simple as opening up your notes app, and writing an idea down.

Reid Hoffman, co-founder of LinkedIn, said: "If you are not embarrassed by the first version of your product, you've launched too late."

Everything is a trade-off, and there is never the “right” path. The entrepreneurial journey is as much of a spiritual one around self-development, as it is a professional one. It is not better than any other journey.

I’ll end this newsletter with one of my favorite poems by Shel Silverstein.

Woulda-Coulda-Shoulda
All the Woulda-Coulda-Shouldas
Layin' in the sun,
Talkin' 'bout the things
They woulda coulda shoulda done...
But those Woulda-Coulda-Shouldas
All ran away and hid
From one little Did.

If you liked this, I would appreciate you sharing it with someone who might find this helpful 🙏

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