Reaching For Impact

When I joined Microsoft in 2000, it wasn’t for the money, or for the job. I negotiated a starting salary of $57,600 (if you’re a geek with gray hairs, you might recognize the significance of that number), and started as a technical writer in Exchange. The reason why I joined was simple, though: there was (and remains) almost no other place in the world where you could have the impact that you could at Microsoft. Anything you do there has the potential to touch the daily lives of millions or even billions of people.

In Office, I worked on stuff that over a billion people used. I mean, who does that? The work got more interesting as I gained experience and I got to do stuff with a larger impact. So I barely even paid attention to the money, until the point where I noticed that my pay wasn’t too far off from what new college hires were getting. This seemed incongruous so I started looking around.

I stumbled into an opportunity with Microsoft Research and was again lured in by interesting work, even though it meant less money than I was already being paid (the work was in Beijing, so Microsoft switched me to the lower China salary scale). What’s more interesting than working on stuff that a billion people use? Helping to advance the field of computer science, which touches the life of nearly everyone on the planet. I had enough to live so until my lungs started bleeding from the polluted air, I didn’t really worry about the money.

I left, went for an MBA, and learned that most jobs are far less interesting and have far less impact than anything I have ever done professionally. I also learned how lopsided the economics of a successful startup can be in favor of the founders. So, with my co-founders Steve and Pinguino, I started my first company, Cuddli. We were too early with the idea, and we built way too much software, but damnit, we were right (multiple successful dating apps are finally starting to copy our features). Dating apps have a financial incentive to be bad at their jobs because they charge users for their services, so instead, we thought we’d make money by connecting people to one another, but also to date experiences which would be complementary. We could make money without introducing friction and charging to remove it, which is what nearly every other dating app in the world does. The opportunity to help millions of people fall in love was interesting work. Unfortunately we failed to do that and ended up in a niche market, where we’ve struggled to find a sustainable business model. My life’s savings drained away.

Given that Cuddli wasn’t going to be big, my amazing co-founder Pinguino stepped up as CEO. I stepped back to a chairman role (no longer responsible for day-to-day operations) and founded PCPursuit. Early on, it was promising. We figured out what is, to just about everyone I have talked to in the information security industry, one of the most innovative solutions to easily implementing multi-factor authentication in a Windows environment. Mach37, the top information security accelerator in the country, accepted us with $50,000 in funding. Unfortunately, the farther we got into this, the more we learned. Eventually we figured out it will take about a year and a million dollars to build an MVP (because infosec is hard, and hard problems are actually complicated to solve, and no we can’t just do a Kickstarter). The investor community has no appetite for funding projects like this (for the most part they want to fund stuff that is already built, growing, and profitable) so we hit a wall. Eventually we pivoted into doing some boutique consulting for the legal industry. It’s revenue, but these aren’t big problems and they don’t impact a lot of people. Neither my co-founder or I can see spending the next 7 to 10 years of our lives on this.

I’m working on a side project in the travel industry called AwardCat that I’ll be launching soon. It’s not ready even to attract angel funding (I kicked the tires and got a soft pass) but I’m inclined to run it as a lifestyle business anyway, with no outside funding and operating as an LLC. I’m not sure I want to live on a fundraising treadmill, and I am not actually good at fundraising anyway. That’s a project I can work on part time, and just grow by reinvesting in the business. It’ll generate revenue right away.

So, I’m teaching a class this quarter at The Evergreen State College on startups and entrepreneurship (I have learned a lot about what not to do if nothing else). We’re working on a project at PCPursuit, which will bring in some cash, but isn’t full time. Cuddli is in the capable hands of my co-founders, and Pinguino’s leadership has been far better than mine.

I’m pretty much out of runway. And I’m simply not working on the kinds of large, important problems I like to work on.

There is a very big problem I want to solve: SS7 is broken and this has a direct and immediate impact on everyone in the world who uses a phone. It is an urgent and pressing problem. This isn’t the kind of thing that (probably) gets fixed in a startup, and I think it’s also not the kind of thing that gets fixed by phone companies. It’s the kind of thing that gets fixed by companies that make phones. So, if you’re at Google or Apple and are interested in discussing these problems and how we might be able to work together, my DMs are open.