Most startups don’t fail with a bang, they fail with the quiet optimism of a single desperate decision.

Looking back, you can always go back to when it all started to go wrong. But as that happens, it’s much harder to really feel the weight of every day-to-day decision. It is only with experience that you begin to get a sense of when the choice you are about to make could possibly ruin the business.

But this is where the myth of failure falls apart. In many cases, even experienced founders will choose the option to fail anyway. Because this option is mandatory. And failure is not an option at all.

I’ve been thinking about failure a lot lately. In today’s economic climate, most of my entries as active entrepreneurs are about avoiding failure rather than pursuing success.

It shouldn’t be like that. Most entrepreneurs do what they do because they love what they do. And if you really love what you do, failure isn’t failure until you give up. So to debunk the myth of failure, you must first understand love.

Learn more about The Mandalorian’s love

Last week, I had the opportunity to participate in a Q&A session with Giancarlo Esposito at a convention. My kids love The Mandalorian as much as I do, so this was a session we could all agree on. He was asked the standard fandom stuff, including what he owes to his longevity as a successful actor. And just when I was starting to ignore his response (I was waiting for the Season 3 clues like everyone else), he started talking about love.

What? Listen, I can recognize when a speaker is about to give a standardized answer. But I will tell you this. Whenever someone starts talking about love, I start paying attention. Although it may not be a driving force you suspect of me, I personally believe that love is the answer to 90% of the world’s problems (and therefore 90% of mine).

Now I’m paraphrasing what he said, because I wasn’t recording the session and only half listening when he started, but he went from his success being directly tied to his love of the game to talk about the environment – and he said if you love the Earth, you’ll find a way to fix it. And he talked about politics and said if you love your country, Republican or Democrat, you’ll find a way to bridge any gap.

When he finished, the crowd went crazy. More than crazy fandom.

I thought about his answer for a while (the next question was about Breaking Bad and I haven’t found the time to watch it yet). And since I was already thinking about failure, the answer hit me.

If you’re doing something you love, there’s no failure, only setbacks.

I know it’s true because I’ve been through it.

The decision to fail with hindsight

I’m not here to tell entrepreneurs how much risk they should be able to tolerate. You only have to look at crypto and NFTs to see how blind belief can ruin someone.

In fact, I’m probably the coldest entrepreneur I know. I have never encountered a risk that I did not want to mitigate. I will put backup plans on my backup plans. But I’ve also come to realize that over-planning and over-cautiousness can doom a startup just as quickly as a hasty decision. It just takes a lot longer and it’s more painful.

I ran my first one-off startup, Intrepid Media, for 12 years before giving it up. It was the first social network for writers, and one of the first social networks before social networks were even a thing. We had an incredible arc, rapid growth with super highs, and a durability plateau that was both comforting in its stability and frustrating in its stillness.

As social media began to proliferate and become less about content and more about ads, I made the decision to stick to my bet on the value of good content winning this battle. I did it because I loved what Intrepid Media was – great content from great writers backed by grateful readers.

It was kind of like Medium long before Medium, and obviously I lost that battle and Facebook and Twitter won. But while the battle itself was swift, it took years for the damage to eventually stagnate Intrepid Media into a startup with a bright present but no future.

In 2011, 12 years after starting, I finally gave up. But not without a plan.

When failure is just a setback

A year earlier, in 2010, I had founded ExitEvent solo. His clients were entrepreneurs whom I would connect with resources – investors, support organizations, service providers, etc. – both locally and digitally, via the website.

It worked, but it needed a catalyst for growth. Yes, entrepreneurs needed resources, connections, and investments, but what most of them really needed was information.

I had an engine for that. An engine I knew worked very well for 12 years. I found my catalyst in the code I had built for Intrepid Media, the code that managed and promoted valuable content. I lifted this code, repurposed it for contractors instead of writers, and literally pushed it into the ExitEvent architecture.

Then I closed Intrepid Media. And I sold ExitEvent three years later.

It was the love of creating value from content that led to this pivot. Intrepid Media’s failure was just a setback, and in that it became the fuel to keep doing what I loved to do until I found a way to make it successful.

I’m recycling that same love, if you will, and a lot of the same ideas for Teaching Startup, my latest solo-founded startup. And this time I know I won’t fail until I stop.

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