Why I don't have a plan B

A friend of mine was trying to decide whether to start a company himself, and he reached out to me. There was one question he phrased ten different ways: what's your plan B?

I told him there isn't one. Starting up is a calculated, concrete sequence of steps with a range of possible outcomes. Apply the lower bound and the upper bound, and luckily every outcome leaves me better off.

Where the confidence comes from

Okta spoiled me for the identity domain. I could see enterprise companies struggling with the same problems and somehow managing to duct-tape things together. I've always been a generalist, so I can do pretty much everything (except great UI), but Okta helped me realize that identity is the domain I want to focus on.

Interviews as client calls

Fast forward: I interviewed with quite a few companies, almost all big names, all with IAM roles that had been open for a while. I was lucky enough to land some great offers.

There was one common theme across the interview panels. Most of the people on them didn't have much depth in identity: its challenges, opportunities and trade-offs. That can make a job less fun when management doesn't take security as seriously as you do. They wanted it for compliance, because an enterprise customer was asking for it, or because they were preparing to go public.

Walking away from that kind of money and a predictable path was challenging, for sure. But the idea of adding more duct tape didn't help my motivation either.

Somewhere after the first few interviews (and offers), I realized I was treating them as client calls: gathering requirements and pain points that further justified my conviction.

It's worth calling out that there were also some great people and opportunities that felt like a match made in heaven. Unfortunately, their compensation ranges were too low for me to make it work. I did promise myself I'd go back to them when I'm no longer working for money 😀

The common problem

Luckily, they all had one more thing in common, and it inspired me even more to work on this problem: every one of them struggled to manage both customer identity and enterprise identity.

Everyone buys an off-the-shelf solution for enterprise identity, meaning their employees. For customer identity they start with something home-grown, to save money and keep flexibility, until their customers turn out to be other enterprise companies.