This Could be Our Last Shot

What if this very moment is our last - and best - shot at success?

It's kind of hard to think about, actually. We tend to think about our careers as a whole in a progressive way, where we start at the bottom and climb our way to the top. But our startups are more like a job where we can be the mailroom clerk one year, the CEO the next year, and the doorman the next year.

It puts us in a tough spot because we're constantly wondering whether this is our moment. For those of us that haven't been around long enough, it's worse, because we may not realize yet that those peaks and valleys even exist — all we've seen is the come up.

Striking Lightning

Most startup Founders get one glimpse of "striking lightning" when all of the pieces of momentum seem to be stacked in their favor. At the time, it feels like our ship has finally come in and things are finally going to be going "up and to the right" from here out.

But that's the problem with lightning — it strikes big, but then it goes away. How many startups can we recall that sounded awesome for a second and no one has heard from them since? Most, actually.

We have to realize that this very moment may be the actual peak of our performance, and as such, we may never get another shot like this again. So when things are hot, we have a limited window to execute. It's just really hard to tell how short that window really is, so all we can do is assume it's about to close and go guns blazing while we have the chance.

Taking Money off the Table

Whether we're looking to sell the company or maybe take a little secondary money off the table during a successful fundraise, we always have to wonder whether this might be the last time we'll get this opportunity.

Our minds all oscillate between covering some of our downside with some cash in the bank and kicking our future selves for selling out too early. What we assume, though, is that the opportunity to cash out is constant, and we're just choosing when to do it.

The reality is there are very few opportunities to get liquid, and this in fact may be the last one we ever get. We need to think about protecting our downside first, and then optimizing for upside. We can't pay bills with future upside.

Our Last Shot at Risk

We also get hung up on whether we'll be able to take this much risk again. When we're younger, we obviously have more tolerance (and less consequence), not to mention we just have more time to fix whatever mess we get ourselves in!

But as the decades pass, and we get into mortgages, families, and (gasp!) retirement, our risk profile drops precipitously. We start thinking in terms of "I don't think I'm ready to roll the dice like this again."

It's a scary feeling, but it's real. While on the one hand, it makes us a bit more risk-averse, it also helps strengthen our commitment to an outcome. It's a lot harder to consider failure when we know we don't have an alternative.

Yet all of these issues are the same — they have us wondering whether this is our best year or just one of many. The only answer is to treat every opportunity like it's our best year, and deal with whatever "costs" may come from being that bold that early. Our biggest cost will always be doing nothing at all.

In Case You Missed It

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Being Leveraged Means Having Zero Choices (podcast) Early on, Founders tend to believe that choosing an investor is an option. It's possible, but unless we're in the top 5 percent of those that have been on this route more than once, we don't get the luxury of choice here.

How I Harness My Insane Startup Anxiety. There are two types of Founders: those that admit they are wracked with anxiety, and those that are lying about it. We’re all going to deal with it for the rest of our lives — so why not use it as a superpower, instead of reacting like it’s kryptonite?