Why Celebrating Missed Opportunities Is So Important

After weeks of speculation, Uber IPO’d last month at a valuation of $82 billion, i.e. $82,000,000,000. Wouldn’t it be nice to have picked up some stock options back in the day, when Uber was still in the pitch deck phase? Even a tiny slice of the Uber pie would be worth a fortune today.  

So, I had the chance … and turned it down.  

In 2013, when Uber was still known as UberCab and focused on luxury vehicles, I met up with one of the company’s first employees. At the time, apart from running Hootsuite, I was still an active partner in a web development agency I had founded called Invoke. Uber was looking to contract out its mobile app development, and they thought my agency would be a great fit.

One catch though: Uber’s budget was tight. They couldn’t pay us for the work, but they were able to offer us equity in the company. But … after some deliberation, the decision was made to turn down Uber’s offer. We needed cash flow at the time and couldn’t really afford to work for free.  

Go ahead. Do the math. Even a .1% stake in Uber would translate to $82 million at today’s valuation. Safe to say we made the wrong call, big time.

Enter the anti-portfolio

But, it happens. In fact, investors even have a word for all those golden opportunities they let slip away: their anti-portfolio. Think of an anti-portfolio as the evil twin of an actual portfolio. It’s all the dream companies you could have invested in but didn’t. Big investment firms like Bessemer even showcase their anti-portfolios online. Turns out Bessemer passed up on chances to get in early on Airbnb, Apple, Facebook, Google and Tesla. Wow … now I don’t feel quite so bad.

But all of this got me thinking, not just about missed opportunities in business but in all areas of life. After all, we all have our own anti-portfolio stories: the decisions we didn’t make; the opportunities we failed to seize; the people we let slip away. The reality is that, just like back in the day at my development agency, time and resources are always limited. You can’t do everything — you can’t race down every possible path and pursue every option. You make the best decision you can with the information you have available. And you hope for the best.    

Often things work out. Often they don’t. This may not sound especially profound, but I think that the real lesson here is this: at the end of the day, it’s far better to have an anti-portfolio in life than not to have one. That might sound counterintuitive. Let me explain.

The redemptive value of life’s missed chances

It’s hard to live a complete and fulfilling life — hard to succeed in business or in any pursuit — without stumbling along the way. In fact, I’d say that a catalogue of missteps and wrong decisions isn’t just inevitable; it’s actually essential for success.

All decisions, and any real growth or progress, involve risk. The worst-case scenario is to be paralyzed into inaction: to be so afraid of making the wrong decision that you make no decision at all. Gretzky said it best: “You miss 100% of the shots you don’t take.” And I think in life a lot of people just never take that shot. They stick with what they know. They stick with the tried and true. In other words, they’re so terrified of having an anti-portfolio, that they never have a portfolio at all.

I take solace in the fact that, back in the day, we made the tough calls all the time — even if they sometimes turned about to be the wrong ones. We said no to Uber. But we said yes to plenty of other opportunities.

One of those was Hootsuite. Just a few years earlier, I had split Hootsuite off from my agency as its own business — taking along seven employees on a zero-revenue project. It was a massive risk, but social media was just emerging as a business tool and companies were looking for a platform to manage all their efforts from one place. This year, Hootsuite turned 10 years old and now has 18 million users, including 800 of the Fortune 1000 companies. So, yup: It definitely pays to take those shots, misses and all.    

But that’s just part of it. Just as important as having an anti-portfolio story is learning from it. I don’t mean stewing in regret or disappointment. I mean extracting the value you can from the experience and helping that inform how you move forward and do things differently in the future. For me, the Uber experience confirmed that I should put more trust in my own intuition — that mysterious internal algorithm that seems to sense the right answer before we even ask the question.

Case in point: My very first email to my business partner after hearing Uber’s pitch back then was, “This is gonna blow up. Let’s get after it.” The iPhone was only a few years old and mobile technology was just becoming ubiquitous. At the same time, hailing a ride was a practically universal inconvenience that everyone hated — all that time spent waiting in the street, waving your hand, etc. Here was a massive, global pain point begging for a solution. Uber didn’t have all the kinks worked out back then, but they were poised to catch a huge wave, well before anyone else. It was brilliant.

Alas, we passed anyway.

Do the anti-portfolios in life hurt? Yes, of course. But every business worth building will be marked by setbacks as well as successes. Disappointment is part of what we signed up for as entrepreneurs ... really, as humans. That effortless rise to success, fulfillment and lasting prosperity? I can’t say I know many people whose lives or companies fit that description. We all shoot wide of the mark. What matters is lifting the stick and taking another shot — and ideally a better one.

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