Pivots, perseverance and insights

The most precious asset any entrepreneur has is time.

Because time is constantly slipping away, one of the most basic entrepreneurial dilemmas is knowing when to pivot and when to persevere. When to take flight and when to keep fighting.

Like an oil prospector in search of his first strike, an entrepreneur traverses the dangerous terrain of rapidly shifting markets to find elusive black gold. You never know whether you’re meters away from hitting the lucrative depths of product-market fit or whether you should pack up your rig and find another spot to set up camp.

Great companies, however, aren’t built on pivots or perseverance, but on insights. Mark Zuckerberg’s decision to build Facebook wasn’t based on a conscious decision to pivot or persevere but instead on a core insight into a human behavior that could be ported to the Internet. Similarly, an oil prospector chooses when to keep drilling and when to give up based upon the insights and clues he collects along the way: that rock formation looks suspect, these deposits look promising, that river seems to have moved.

For entrepeneurs, there is more than one way to identify a promising spot to drill so you can start sifting through the mud to unearth these gems of insightfulness. And no one heuristic is necessarily better than another in the way that no one philosophical theory is demonstrably better than another—because they’re just models of thinking.

One way to start drilling is to identify an acute and widespread pain point, one that you’ve experienced personally or have seen others struggle with, and try to solve it. Think of Instagram making photos on your phone not look like shit. Another is to look for a large, validated market and find a better way to serve it. Think of how Amazon plans to restructure the logistics industry with their delivery drones. Yet another is to target a large incumbent business and use new technology to dislodge their hold on the market. Think of how Netflix murdered Blockbuster (RIP).

Even when you use one of these frameworks as a starting point, it remains incredibly hard to build something people actually want. The soul-crushing aspect of entrepreneurship is that you may never find black gold at all. And since our time is finite, you can only place a finite number of bets. The good news is that as you pivot and persevere in your entrepreneurial drilling, the insights you collect along the way go into an insight bank you can draw from to make smarter subsequent bets, increasing your odds of eventually uncovering something worthwhile.

These insights are what you need to be chasing after; they are the only currency that matters because they are the guideposts that can lead you to a gusher. Since you don’t know in advance where your big strike will occur, and you can’t counterfactually know where you might have striked had you persevered instead of pivoted, you have to approach your entrepreneurial drilling more holistically so you don’t go completely crazy. The question you have to ask is:
What framework helps you uncover insights faster?

Full disclosure: I am solidly in the camp of entrepreneurs who hasn’t hit it big, so this just my current perspective and philosophy, having drilled and had moderate but not breakout success and observed those who have succeeded.

You can’t fake being passionate about the space. If you think about the areas of your life where you have the most insight, it’s likely to be the areas you are most passionate about. For example, other than startups, I am passionate about politics and economics, so I have insights about these topics all the time simply because they have mindshare in my brain. If you ask me about quantum mechanics or Miley Cyrus, I come up dry. When marking off some territory on the map that you’d like to explore, it makes sense to identify spots where your passion, past experience and domain expertise would give you a relative edge against all other drillers. It’s no coincidence that Kevin Systrom, founder of Instagram, was an avid photographer or that Woz was tinkering with gadgets long before he ever built the Apple I.

Being around the right people is not a cliche. The problem with being a lone wolf is that you can’t get much done and it’s extremely easy to lose the perspective you need to pick up on the right signals. Both problems make it extremely difficult to uncover great insights. Having bad people around you is even worse, because you work on the wrong things and stumble across faux-insights you only later discover are worthless, after tons of mindless digging. Having at least one partner that is more talented than you and has a complimentary skill set is tablestakes for getting the right things done, banking valuable insights and making the bets that can pay off. And having passion for the space you are attacking will help you attract the right partners, who will likely share it.

Adapting without being reactionary is an art form. As part of a team of two or more people, you have to continually get better at adapting to the terrain around you without being reactionary. Big insights usually take a ton of observation. They aren’t the kind of thing that you can distill in an hour or day and usually take weeks or sometimes months. Jack Dorsey takes the bus to and from work every day so he can observe commuters and silently perform market research. “I saw the rise of Instagram here. I saw the rise of Vine and Snapchat, and how many more people were using Facebook versus Twitter, and it’s amazing”. Hustle and speed are important, but don’t rush the insights—let them come organically. It’s also extremely easy to get into this grass-is-greener situation where the untouched land over the hill looks much better than the space you’re currently exploring, but it’s a mirage. If you bounce from idea to idea you aren’t drilling at all—you are just bouncing. Bouncing doesn’t lead to insights, only drilling does.

As you progress on your journey, the land around you will be littered with failed prospectors lying in ditches who blew their last bitcoins on booze and prostitutes. Your job is to hang on long enough and drill smart enough to hit your gusher. The struggle between pivoting and persevering applies to many facets of life: your job, your relationships, where you decide to live. The key is uncover the insights that let you know when to pivot and when to persevere.