Failure is the best story

This is how you’ll build a great 2024
Jan. 9, 2024
Otto Pohl

I took a trip to France with my family this fall during a long school holiday in Germany. The story we had the most fun telling? The time we got to the Angoulême train station with just minutes to spare, only to find the car return office closed and the lot for after-hours drop-offs full. Madness ensued as we desperately tried to reach a rental representative on the phone while a policemen threatened to impound our illegally parked car, and our TGV to Paris was pulling into the station…

Would you rather hear that story, or the one about the lovely Michelin-star meal capping a sunny day in Provence?

Laughter might be the best medicine, but failure is the best story. Things going according to plan? Boring. But that time my mother asked me and my college buddies to be the servers at my dad’s 60th birthday party and we all got drunk on the leftover welcome-toast champagne and I fell down the basement stairs and my friends let the water run until the well ran dry and my mom had to ask the guests not to flush? The disasters are the only reason we still remember and laugh about that party, decades later.

We spend a lot of time white-washing our career paths, and certainly as entrepreneurs we reflexively announce that everything is great and only getting better.

At the beginning of this new year, at a time when we’re making plans about how we’re going to make this year better than the last, take the time to think through the failures you’ve endured and how you can use them to make your conversations more interesting, your investors more attentive, and your sales calls more effective.

Like success, of course, entrepreneurial failures need to be deployed strategically. Done right, failures can project humility, an openness to learning, of motivations gained and important lessons internalized.

In your quiet moments you might admit to yourself the persistent weaknesses that you have. I spent many years cataloguing my weaknesses with redoubled determination to reduce or eliminate them; I have since learned it’s much more effective to double down on my strengths and simply avoid doing things I’m not good at. However, unless you can find an appropriate moral that makes their telling worthwhile, those potentially lifelong shortcomings are best left to conversations with your career coach.

I’m talking about using failures to improve your external story, not your internal learnings.

When it comes to startup storytelling, use failures that plausibly highlight the great other stuff you have going on. Let failure yin magnify success yang.

Some ideas:

To investors: You’ve tried and failed at certain initiatives, and that gives you strength and conviction for your new path. It highlights the speed with which you move, and the learnings you extract. A client of mine offered mortgages to international clients and failed marketing to many countries before realizing that mortgages to Chinese buyers were a huge and lucrative market. In the telling, the learnings from the failures made the success resonate.

To employees: Give them the courage to fail and they will be innovative. Why is government so lethargic? Because everyone spends their time on CYA. Meanwhile, Google celebrates failures with applause and time off, and even old-economy stalwart P&G has a Heroic Failure Award. Eliminate the stigma of failure and your employees will be bolder.

To customers: Disarm them. I had a client that worked on many different configurations of silicon anode for lithium batteries before finding the best way to minimize silicon swelling during the charge cycle. Describing the solution straight away wasn’t nearly as powerful as taking potential industry partners on a journey through several failed attempts first.

To your keynote audience: Get on their side. Tell them the number of rejections you received before getting your first investment. Or the first two (or ten) ideas you pursued until you pivoted to something that worked. A news industry company I was working with tried every idea they could think of until short-form Instagram stories proved to be a hit. The journey was far more entertaining than the destination. For all of these, it’s the contrast between the failures and the successful happy ending that gives the story its punch.

Take the 30 seconds to watch this inspirational ad by Michael Jordan about his on-court shortcomings. It works because it makes his successes more vivid. Failures? Bring ‘em on! That’s how you’ll build a successful 2024:

What failure can you weaponize in the quest for the most engaging, powerful story?

Otto Pohl is a communications consultant who helps startups tell their story better. He works with deep tech, health tech, and climate tech leaders looking to create profound impact with customers, partners, and investors. He has taught entrepreneurial storytelling at USC Annenberg and at accelerators across the country. Learn more at