Week 7: Experiment over, I'm all in

I've got big news: I set out on this journey to launch 4 startups in 4 quarters with the hope that I could find at least one good business to run. I'm 7 weeks into my first quarter, and as the election pundits say: I've seen enough.

I'm going all-in on ShadowTraffic for the rest of the year.

Launching three more products would have been fun, but the traction I've seen has been beyond anything I could have hoped for. I can't say with certainty that it will succeed, but I'd be a fool not to put my full attention on an idea that's clearly working.

I'll continue to write updates here. I have no plans to raise money, so you'll keep getting a transparent view of what it's like to bootstrap a company from day 1.

What is the lesson here? Was 4 startups in 4 quarters a mistake? Should I have tried something more modest instead?

I think that'd be the wrong conclusion—I'll explain.

Framing is everything

When I set out on this journey, a friend asked me what my motivation was to publicly declare 4 startups in a year. Was it to grab attention? To build a safety net for failure?

Both of those are somewhat true, but the real reason is that it forced me to behave in a certain way. I made a public statement, and I wanted to deliver. That commitment changed me in three ways.

#1: Prioritized finding customers

It sounds like finding customers would be the obvious priority when you're starting a company, but there are a lot of things conspiring to take you away from that: raising money, getting a website, building a team, getting accounting, working on the tech.

When I signed up for the goal to ship in 90 days, it forced me to set almost all of that aside. All I wanted to know, as soon as possible, was: is this a dead idea? If it is, I need to either reframe it to solve a different problem or move on to my next idea.

For weeks, my only priority was talking to people about their problems. Because I pursued those conversations so aggressively, I was able to hone my problem statement and product roadmap, which in turn made it more likely that people would want to talk to me, and so on. It had momentum.

#2: A sense of urgency

To state the obvious, 90 days is extremely short in the business world. I knew that if I worked like I did at a salaried, stable job, I wasn’t going to have a chance to make the deadline.

By holding myself to a 90-day commitment, I changed how I assess risk. I much more frequently ask myself:

• Do I really need to be doing this?

• Does this need to happen now?

• Could I achieve the same thing in a more practical way?

Every week, I start by asking myself, what’s the goal here? How is this arc of work going to lead to me shipping on time? Every day, I set little milestones that make progress on that arc.

The result? 7 weeks of the highest output of my life, in only 40-45 hours/week.

#3: A sense of detachment

When you raise money at the start of a company, there’s pressure is to deliver on that idea. But the problem is that you don’t yet know if it’s a good idea, so you’re incentivized to make it work on behalf of your investors.

Committing to 4 startups in 4 quarters gave me the levity to let bad ideas go. Solving the problem of simulation data might have been a complete and total flop. And while that would have bruised my ego a little, it would have been fine. I was only ever one quarter away from trying something new.

While I tried my best to make ShadowTraffic a success, I kept telling myself, “I’m an entrepreneur. I try many ideas. My identity isn’t tied to a particular one. If this one doesn’t work—fine—I’ll go on to the next”.

Listen to your customers

Jeff Bezos, as usual, has an apt quote for what I did this week:

“I constantly remind our employees to be afraid, to wake up every morning terrified. Our customers have made our business what it is, and we consider them to be loyal to us – right up until the second that someone else offers them a better service.”

I spent the entire week working on what my early users wanted. Fixed bugs, improved documentation, discussion and input on the long-term roadmap.

Next week, I’ll talk more about the balancing act I’m learning between working on short and long-term goals.

The more users I get, the harder it becomes.