We Build Cathedrals Without Nets

My journey started decades ago, as many things do, with a scheduling problem.

I was a kid working at Merrill Corporation, which printed quarterly reports, M&A documents, the kind of paperwork people trade stocks on illegally. I built an internal system to handle print estimating and production scheduling. I called it MPRESS, the Merrill Print Estimating Scheduling System. Clever name for a clever system. It used early AI, expert systems, to augment work people did manually, and it worked. If that sounds familiar, it's not a coincidence. I was hooked on the idea of machines helping people think, something I've never quite recovered from or, frankly, want to.

The web was just being invented. Merrill wouldn't let anyone near it, reasonably enough given what they were printing, so I went home and built something myself. My then-wife was pregnant, and I realized that scheduling milestones for a pregnancy weren't so different from scheduling a print run. "Take this filing to the SEC" and "the fetus is developing arms" are both just benchmarks on a timeline. Back then the web was wall-to-wall static HTML pages, brochures that happened to live online. I got CGI space from a Minneapolis ISP called Winternet and built the Interactive Pregnancy Calendar, a novelty at a time when interactivity itself was new.

One day at work my phone was full of voicemails. Your pregnancy calendar is on CNN. It's on Headline News. My friend who owned Winternet called: your site is burning up all our bandwidth, but I love it. We had an internal counter running, back when websites measured "hits," the number of internal files served, rather than people. The numbers were so out of control I switched to counting visitors instead, a then-novel idea somebody else took up and sold for a fortune later. I'd hit refresh and watch the number jump. Hit refresh again, jump. I was showing someone and kept pressing it just to see their face. My first startup, born from my first pivot, had just gone supernova. Viral, we call it today.

Company two was supposed to be a legal expert system. More AI, more expert logic, more ambition. What it actually became was a label printer. When you file legal documents you have to mail them. Mailing requires addressing envelopes. Addressing envelopes requires labels. Avery Dennison, the label people, looked at my AI legal system and saw something they could use. They bought it. This is completely normal, by the way. Slack started as a gaming company. Cursor began as an email plugin. Pivot is just a polite word for "we found something people would actually pay for." An aside: Avery's print-from-the-web software, the thing I sold way back when, is still alive today, in an iteration older than most people in the AI space.

Avery put me in their new business group, which is corporate for "go invent things; throw stuff at the wall and see what sticks." I pushed out a visitor management system, GE bought it, and relocated me from sunny California to sunny Florida. We drove the whole way, starting in Orange County with its HOA homes and ending a week later in Boca with its HOA homes, an ocean on the other side. Different coast, same sunshine. The physical journey mirrored the business journey I've become accustomed to.

At Avery, a consultant introduced me to value innovation, a concept from a couple of articles that would become, a few years later, the book Blue Ocean Strategy. I started building software around it and caught the attention of the authors themselves, Chan Kim and Renee Mauborgne. We started working together in the US, which is when 2008 arrived and broke everything.

I launched Legalprise, which started, naturally, as another legal expert system, this one to help consumer lawyers navigate the housing collapse. It turned into something else entirely: a housing data company. My numbers were showing up in newspapers. I worked with Congress, Treasury, the Federal Reserve. I had a front-row seat to one of the great economic catastrophes of modern times, briefing the people trying to stop it. I made almost no money but it was the wildest ride of my life.

Eventually Chan and Renee invited me to join them at INSEAD in Fontainebleau, France, to keep pushing the strategy software forward. The intellectual work was some of the best of my life. The software and writing were fantastic. The French food and wine were better.

Builders can't stop building. I suppose you can say we're the C in OCD. Anyway, I brought the evolved version of my software home to the US. VSTRAT.ai is my fifth swing, an AI strategy platform that helps companies do what good strategists have always done, just faster and better. If that sounds similar to the earlier systems, it's not a coincidence. A friend recently suggested I take the part where users prepare for a board meeting by sparring with synthetic board members and turn it into a dating prep app, another off-the-wall pivot. For now, I'm marching forward.

Here's what five companies teaches you: we build because we can't not. Much like medieval craftsmen spent their lives raising cathedrals they'd never live to see finished, sleeping in hovels while the spires went up, we build for the love of building. The money is nice when it shows up. It's rarely why we started.

The field is also full of sharks. I say this not to complain but to prepare you, because if you're a founder you've met them or you will. The person who wants half your company for the privilege of their involvement. The one demanding 15% of gross revenue in exchange for, well, that was never entirely clear. Another who wanted 20% equity while keeping their full-time job elsewhere. The one who called with demands while I was lying in a hospital bed. (I have MS. It's under control now. At the time it was not, and yet there he was.) You learn to spot them. You learn to say no. That's practically part of the job description too, right alongside the building.

You keep going anyway, for the same reason those ancient cathedral builders worked without nets. The cathedrals get built. The companies get launched, and sold, and launched again. The sharks often bite but occasionally get outsmarted, or at least ignored.

Which brings me to why I’m here. I want to hear from founders: all of you. The person running a scrappy Etsy shop hiring their first employee, the serial entrepreneur on swing number seven, the accidental builder who woke up to a phone melting down with voicemails.

If you’re building something because you can’t not, let’s talk. I want to tell your story. Skip the pitch deck (nobody reads them anyway) and talk to me.