Preparing For Luck: The Entrepreneur’s Journey

My first successful business was SuperAwesome. (I’m not bragging, that’s the name.) It took quite a while to build and to be understood; we were a little ahead of our time, so the first five years were a bit of a struggle. Then we were acquired by Epic Games, starting the inevitable discussion as to which one of us had the best name.

SuperAwesome was founded on a vision. We wanted to make the internet safer for kids. Many of the difficulties we faced involved compliance with different privacy regulations around the world. It’s not a very sexy subject and we struggled to get people interested in it, even while we were building a lot of tech to help people deal with it.

For a long time, we could get people to admit that it was important — who doesn’t say “yes” to “is child safety online important?” But we couldn’t get anyone to actually care enough to do something about it.

What changed?

Edward Snowden and Cambridge Analytica: privacy in the news

Two events shifted the Overton window on digital privacy: Edward Snowden’s revelations, and the Cambridge Analytica exposé. When those scandals broke, at approximately the same time, we found everything became much easier. There was a massive mindset shift: suddenly, everyone you talked to wanted to take privacy seriously. It wasn’t just companies, or tech people; it was everyone.

Once that shift happened and people were talking about privacy, they understood our argument much better. While people often didn’t feel competent taking on the whole realm of digital privacy, which remains complex, they’d become far more aware of the dangers, including to children and young people.

Now, instead of indifference, we were met with the attitude of: “There seems to be a lot of bad stuff going on in relation to privacy. It’s complicated and we don’t know what to do about it, but let’s at least make sure the kids are safe. That, at least, we can do now.”

Because the conversation had pivoted and background attitudes had changed, we went through a real acceleration phase, where it was far easier to get people to focus on (kids’) privacy. As more details of the key scandals emerged, more companies decided they wanted to be at the forefront of keeping kids safe online. In particular, businesses whose key customers were kids (for example, games companies) were much more receptive to talks about tech solutions to privacy issues. We had spent the previous five years building and advocating for those solutions, so we were both lucky and prepared.

The luck-survival nexus

The story above underlines an underappreciated element of business success: luck. In 2012, we had a good product, a good idea, and a good mission and no-one was all that interested. Even when we got the chance to talk to people and we used the right messaging, they still weren’t very responsive. Then something in the wider world changed and suddenly, what we’d been saying all along resonated. We didn’t cause that change; it’s a conversation people were already having. But we were there when it happened, and we were ready.

It’s also easy to underestimate the impact of your own actions. Failing to prepare means you’re not in a position to capitalize on good fortune when the time comes.

The actor Peter Dinklage, who played Tyrion in Game of Thrones talked about this in a 2013 interview. He told an interviewer that, while he realized he had landed a great role, he didn’t like being told he was “lucky” to do so.

“Living in Brooklyn in an apartment without any heat and paying for dinner at the bodega with dimes — I don’t think I felt myself lucky back then,” Dinklage explained. ‘“Doing plays for 50 bucks and trying to be true to myself as an artist and turning down commercials where they wanted a leprechaun… So I won’t say I’m lucky. I’m fortunate enough to find or attract very talented people.”

I never had to go through that, but the companies I’ve founded — Mindstone is number six — often went through a similar process. You have to be in the right place for luck to happen to you, in order for you and the right people to find each other. And, of course, you have to have the goods too.

If we’d packed up SuperAwesome’s offices in 2017, before the Cambridge Analytica debacle, we wouldn’t have been around with solutions when people suddenly realized how serious a problem digital privacy was. If Peter Dinklage had gotten tired of Brooklynn earlier, someone else would have played Tyrion Lannister. In both cases, survival and preparation were as important as luck. But more importantly, they were controllable.

Skate to where (you hope) the puck will be

Putting yourself in the right position to be lucky isn’t so much about serendipity as it is about consistent, directed effort. Not over-emphasising luck means we respect our own hard work and agency, and enables us to prepare to take advantage of opportunities.

But it also doesn’t make sense to ignore the role luck plays. It worked for us that we were in the right place to take advantage of fortune when it arose, and around long enough to still be alive (as a company) when it did. In our case, that took about five years. I think it’s important that entrepreneurs are prepared for that sort of timeframe.