First time founder mistakes? Happy to have made them all.
By: Jesse Link
Tags: Life Lessons, Entrepreneurship, Founder Advice, Founder Stories

There’s never a right time to take a leap into start-up life, they say. You will make all the same mistakes first time founders make, they say.

I knew I would make some, but all? Couldn’t. Wouldn’t. Timing to leave my 6+ year stint on wall street was perfect. Great advisors were in place. A clear goal, vision, alignment with my co-founders. Name a book about start-ups, I’d read it. Name a podcast on founder stories and their struggles, already heard it (twice). I knew it wasn’t going to be easy, I wasn’t letting myself be that naïve, I was just confident I would see those telltale lights of an impending mistake flashing.

Six-months into being full time on my venture, Rella, one thing was resoundingly clear, my ‘contact prescription’ needed some serious adjusting. I did not see those ‘telltale’ signs of a mistake. How do I know this? Well, quite simply, we already made all of them. And boy am I glad that we did.

Let’s quickly relive these shall we…

Early over-build (aka going too fast w/o the right validation) ✓

Over-spend on contract work and consultants ✓

Running tests without solid OKR’s ✓

Spending too much time and energy on things that can only occur in the future ✓

Being too in the weeds and details to tell the crisp & concise problem / solution story ✓

Not getting in front of more and more users, early and often (aka waiting for the perfect MVP) ✓

Toxic co-founder dynamics (vision and culture differences, have since split from one) ✓

There are more, but for your sake and mine, you get the drift. We hit most of the big ones.

Yet, we are still standing. And if anything, am way more confident in our future then I’ve ever been before.

Why? Quite simply, resilience.

Willingness to embrace these missteps for what they are and learn. Super simple to say, insert raw emotions, much harder to practice. And we now have proof that we can.

I reached out far ‘n wide across founder, investor, advisor communities to enlist feedback and seek advice on how to handle. We spoke with over 25 individuals about our missteps and struggles. Those books, those podcasts were great stories about those founders struggles. These were uniquely ours.

These mistakes, especially dealing with the decision to and aftermath of a co-founder split, forced serious grounding. It forced moments of introspectiveness which were frequently lost in the race to get…somewhere. It forced open and deep discussions about our core vision, mission and values. What we believed to be on the same page about is now quite literally solidified on a page.

We feel ‘battle tested’. Our weaknesses exploited. Our strengths emboldened. My bond and trust in my other co-founder (who does happen to be my twin sister) is stronger than ever.

I’ve learned more about myself in the last six-months than I did in the last 5 years. Grasped mistakes and turned into growth. Let cooler, rational heads prevail when emotion pulled the other way. Many a sleepless night, iPhone note section filled to the brim, 3–4 months behind where we wanted to be and a great friendship potentially lost. Those are the scars of our first six months.

Certainly can’t call that perfect. Nor, looking back, would I ever have wanted it to be.

I wouldn’t trade those scars. Those scars have made me a better founder, a better CEO, a better brother, a better person. Those scars remind me that the past is real and that as long as you are resilient, the future is bright and endless. I am more excited, determined and confident than I have ever been. Many many more mistakes will plague us, but we will handle each as we have before.

I now join the chorus, “you will make all the same mistakes”. But will add “embrace the hell out of them”.

(and yes I did just quote papa roach)