Strategy Turns

Real rockets don’t go straight up. They go up, and then they turn.

Rockets do this to transition from “mostly going up” to “mostly going sideways” in order to achieve orbit. This is known as a gravity turn (technically, they pitchover, but that’s a less catchy title).

I see a lot of “turns” in life - when something makes sense to do at first, but becomes a bad idea once you’re established, and you notice the “pros” do something else instead.

This was inspired by listening to a recent Creator Lab podcast with Tim Urban. In his words:

“Early on, it was all about ‘How do we get these posts to be read by the most people’… I was trying to do enticing headlines and feature drawings… I think early on, I definitely think you want to think about SEO and keywords and headlines, and all of that.”

And the turn:

“As the blog started to get more attention and there were more people signing up, it doesn’t matter what the headline is for the newsletter… So it’s become less about “how do we get this to go viral on social media”, and more about “the newsletter is going to automatically bring a certain minimum people”.

You can listen to the podcast for the rest. But essentially one of the most successful bloggers in the world is telling us that you should use clickbait and SEO when you are just starting out, even though he doesn’t do it. Tim’s first post was 7 Ways to Be Insufferable on Facebook, written for a Facebook audience). But once you achieve some form of “escape velocity”, you earn the right to title your posts authentically to your artistic sensibilities (like ”The Fermi Paradox”).

I’ve taken to calling these Strategy Turns.

Examples of Strategy Turns

You see them everywhere once you know how to look:

• Founders: “First time founders are obsessed with product. Second time founders are obsessed with distribution.” - Justin Kan
• VC Startups: many VC funded startups have the explicit strategy of going for growth first by not charging anything. The Monetization Strategy Turn can be brutal, and most startups would be better off trying to figure out positive unit economics before scaling, but it can be the right call if there is a land grab to be had.
• Project choice: “The danger of pursuing many good projects is not having the time to pursue many great projects. A rule of thumb: Move slowly when choosing what to focus on. But move very quickly once you’ve decided.” - Julian Shapiro
• Technology Adoption: Otherwise known as Crossing the Chasm. You start out motivated by pure technical excellence, which attracts enthusiasts and early adopters. But when you try to go for the mass majority you will hit a wall — unless you can execute a strategy turn. This often means investing in less technical factors like documentation, third party ecosystem, and lighthouse users. Cheng Lou of the React and Reason teams famously called this the Metalanguage around your code.
• Developers: most developers hit a point where the impact they can have is rate-limited by other developers and nondevelopers. This can result in a career change to engineering management or architect role. This can even get to the point where you are making a mistake if you are coding at all.
• Blogging: There is a tradeoff between blogging on your own site (more ownership and email list building) vs blogging on a community site like Medium, Dev.to, or Hashnode (more discoverability and social features) vs microblogging on social media like Twitter, LinkedIn or Facebook (even more discoverability and social). I think you should start blogging on a community site, and then do a strategy turn to your own. I’ve written before about how you can use Dev.to as a Headless CMS (this is what I am doing to write this very blogpost), but when in doubt, do not let get coding get in the way of your blogging.
• Audiences: Newer creators get the Audience First and Build in Public religion and think it’s the holy grail to business success — because they are new at building audiences. Experts — who can build audience in the middle of a desert — understand that product first and building in private has benefits. Better to be rich and anonymous, than rich and trapped by your business. Paul Jarvis deleted his newsletter, social media, and website. I used to admire people with big Twitter followings, now I understand why CEOs hire people with big Twitter followings and choose to keep a low profile themselves.
• Investing: It’s a good idea for most people to create a diversified portfolio of small bets and to stay invested in the market, but at the elite levels you see Chris Sacca going all-in on Twitter and Warren Buffett sitting on $137 billion in cash (so he has capital to make concentrated bets in bad times) — even as he tells most Americans to invest in index funds.
• Learning is basically the same as Investing. Start as an explorer going wide, then go deep when you strike gold. More in my post on Learning Gears. Also known as the Explore/Exploit transition, and modeled by Simulated Annealing
• Regulation: As a startup founder, you want no regulation to minimize the cost of business and to enable more experimentation. But once you are established, you want your industry to be as regulated as possible to make it harder for newer startups to come up the way you did and to draw clear lines on complying with the letter of the law instead of the endless task of making tradeoffs on behalf of all stakeholders. You want this so much that you will publicly call for governments to regulate you, and of course you will gladly make yourself available for consultation out of the kindness of your hearts.
• Tech Infrastructure: It makes sense at the early stages to outsource as much of your IT as possible, but as you scale up, the high margins of your dependencies start coming into question. Eventually it’s not even out of the question to build your own datacenter and move off public clouds if it will save a few billion dollars.

Sidenote: These kinds of turns are also a common fantasy trope, from Discworld to Star Wars (I tried but cannot find a source for this idea - the closest is the Too Awesome To Use trope). Magic users start out using magic for everything, but the wizened masters of the craft spend more time thinking about when not to use it.

“You haven’t mastered a tool until you understand when it should not be used.” - Kelsey Hightower

Learning from Strategy Turns

My takeaways from observing strategy turns are simple:

• Mind the difference between “noob game” and “pro game”: You instinctively only want to hear from famous people in your industry who have “made it”, but understand that you shouldn’t use a playbook that you haven’t earned yet, even though it might work well for others.
• Today’s success stories are based on yesterday’s rules: The rules of the game are constantly shifting — what worked for successful people starting out may not work for you. Yet we tend to only pay attention to advice from people who are already successful today. Tim Urban is pretty honest about this in his podcast interview:

  “It is a different world. 2013 happened to be a good time to start a blog. Totally luck of the draw for me, but it was a time when Facebook especially was a crazy engine for growth of something new like this.” He goes on to describe how you could get a blogpost in front of 500,000 people for $500 in the early days of Facebook.

  Learning from successful people is good, but you should balance that by swapping notes with peers actively exploring new directions today to ensure you don’t try to replicate strategies that no longer work. (I run a mastermind for this purpose)
• Mind the Metagame: Just when you have achieved some success with one playbook, you should be looking ahead to how that playbook should change. Sometimes the “turn” is such a strong turn that you fully invert. This isn’t an easy call — sometimes you haven’t exhausted your playbook yet, and you shouldn’t try to fix what isn’t broken.

What’s the Third Level?

Fans of both poker and Christopher Nolan movies know that there should be a third level after a “turn”. Thesis and antithesis are always followed by synthesis.

Strategy is probably no different. What comes after Strategy Turns?

Note: I have figured this out and will talk about it in an upcoming post on Strategy Moonshots.