Pivoting Ain't Easy

I had wanted to write a book for years before I finally did it. I buckled down, writing at nights and on weekends for eight months, and eventually self-published on Amazon in late 2015. It was a great moment of personal satisfaction to check off a bucket list item. But in fairness, it was a commercial failure. My most recent royalty check from Amazon in the amount of $2.47 (which does not buy you a cup of Starbucks coffee but does buy you a pound of zinc oxide) sums it up pretty well.

 Literature is DEAD, people!

Literature is DEAD, people!

So as disappointing as it was to write a book that almost no one read, there was a merciful finality to it. After a few months of trying to promote it, I accepted that the book wasn’t going anywhere and moved on. Startups aren’t like that though — for better and worse.

As creative endeavors go, the blessing and curse of a startup is the ability to pivot when things aren’t working. It sucks if your audience doesn’t like your book, or movie, or painting, but that’s pretty much the end. When your company hits a wall though, you can iterate — and thank God for that. But iteration can take a whole different toll on your psyche. Investing time, money and energy into a strategy, only to have the market not respond is like taking a punch. You might not get knocked out, but the effect of multiple blows can take a toll on your confidence and enthusiasm. I haven’t sampled all the joys of what Ben Horowitz calls “the struggle” yet, but the scar tissue is building.

Over the last year and half building my company UserMuse, I have often been the happiest and most creative I’ve ever been. But in that same period, I’ve also experienced some equally poignant bouts of depression. To some of you reading this, that won’t sound unusual at all. This shit is hard. It can get to you.

  I can’t focus on the product because I need to find a developer again? Super-duper.

I can’t focus on the product because I need to find a developer again? Super-duper.

Even before we launched, there were a few discouraging setbacks, and some of the most challenging ones centered around people. Finding a co-founder, enduring multiple development setbacks and people losing interest and leaving were draining experiences. Those curveballs aren’t fun, but they happen. At least with the people on your team you can talk to them directly — the market is less forthcoming.

Both strategically and tactically, building a company from scratch is a never-ending cycle of thinking, experimenting, analyzing, and experimenting some more. Some of those experiments are small-ish, like a new Facebook advertising tactic to get people to sign up for the service. Others are much bigger calls, like when I decided to pull the expert networking component of our service front-and-center (UserMuse connects people who design/build enterprise software with potential users to help the former validate what problems they ought to focus on solving for the market). Product strategy, UX, marketing, user metrics, hiring, content, funding…unless I’m very engaged in something else, I’m thinking about some part of the business almost every minute of the day. Sometimes, that becomes a problem.

 Typical end to a brainstorming session.

Typical end to a brainstorming session.

Creativity is about thinking — connecting many different dots into new ideas with new meanings. Creative people in general think more, and they also think about their thoughts. The more of this you do, the more likely you are to fixate on your mistakes and missed opportunities in a way that leads to depression. When you’re considering a strategy, you visualize a cause-and-effect chain that could lead to the outcome you want. When you spiral on your mistakes, you instead envision how your decisions might eventually lead to failure. As the feedback loop of negativity gathers strength and sucks in more of your energy, it ruins your productivity. (It’s true that there’s a correlation between creativity and depression, but depression in no way enhances creativity. It shuts it down.)

  They’re gonna love it! I hope.

They’re gonna love it! I hope.

One of the most natural questions as a founder, especially if you’re a first-time is to wonder if you’re f---ing everything up. There’s a reason why Andy Grove told us that only the paranoid survive; introspection is a critical piece of the manager’s toolkit and fuels the motivation for self-improvement as well as keeping an eye out for opportunities and threats. But being paranoid is rarely described as “fun.” the more time you spend in your own head wrestling with your thoughts and wondering if you’ve already made the critical mistake that could lead to your doom, the greater the odds of stumbling into a depression loop. It’s a probability thing.

In my humble opinion, pivoting and iterating without getting sucked into depression for too long requires you to know thy self. Some people are more prone to depression than others, but few if any are immune to the pressure and stress. There is an absolute ocean of founder advice out there for you to read. Much of it is great, but a lot of it also won’t apply to you. Learning from experts and finding ways to get better is important, but it’s even more important to understand what you can be excellent at, and find ways to leverage your strengths to the benefit of the business.

  Just because a billionaire did it, that doesn’t mean it will work for you.

Just because a billionaire did it, that doesn’t mean it will work for you.

Jack Burry, an eccentric hedge fund manager with Asperger’s who was portrayed in The Big Short, has a really interesting take on this that has stuck with me since I read it in Michael Lewis’s book. I've quoted it in another post before on this blog, so skip right ahead if this is old news to you.

At one point I recognized that Warren Buffett, though he had every advantage in learning from [legendary investor] Ben Graham, did not copy Ben Graham, but rather set out on his own path, and ran money his way, by his own rules…I also immediately internalized the idea that no school could teach someone how to be a great investor. If it were true, it’d be the most popular school in the world with an impossibly high tuition. So it must not be true.

That is not only wonderful thinking, it’s wonderful for thinking — and it’s a good thing to keep in mind if your business is at a pivot juncture. Trying to fix a strategy will likely be even more stressful if you’re fighting your personality. If you’re methodical and averse to spur-of-the-moment decisions, then “move fast and break things” is not a philosophy that you should necessarily try to live by. Just because it works for Mark Zuckerberg doesn’t mean it’s how you’ll be a successful manager. You’re probably better off finding a way to make that work for you than trying to be a facsimile of someone else. Gary Vaynerchuk calls this “being true to your DNA”, which is as good a way to look at it as any. If you’re trying to ape a style that doesn’t fit you, you’ll really be at sea when things go wrong.

The same principle holds for marketing, by the way. I think of marketing as an extension of a company’s personality, and when a company is brand-new, it’s easier to blend the company’s public-facing personality with your own. I wish I was the type of effortlessly outgoing person who had a knack for pulling off cool publicity stunts like Ryan Holiday or someone like that. But I’m not. I wouldn’t mind getting better at that, but creating written content is a natural strength for me. I do better capturing my thoughts in writing, so I’ve tried to find ways to turn my bookishness into a marketing tactic like publishing our research via popular blogs to get attention. That’s lets me be creative in a way that’s natural for me. I’m looking for ways to extend that skill into as many related areas as I can (writing for other people’s blogs, writing more provocative content, creating more visual artifacts, etc.)

As a founder, you have a rare the opportunity to blend your personality into the fabric of the company you’re building. I’m determined to take advantage of it. How could I enjoy the journey otherwise?