Hiya, I’m Patrick McKenzie. I grew up in the US and moved to Japan right after college. I worked for Japanese companies for six years. Concurrently with doing so, I founded a small software company and it took over my life. I eventually went full-time on that, ran a succession of small software companies, and after about ten years took at job working at Stripe. After six years of working there full-time I transitioned to being an advisor. I am currently on semi-sabbatical.
I had a friend growing up from Puerto Rico. He didn’t love the hard “k” in Patrick, I didn’t love getting called “pato” followed by uproarious laughter, so we split the difference and settled on Patio. I used my favorite number to disambiguate from the other Patios when signing up for CompuServe back in, hmm, 1996.
Enough of my professional life has happened online (particularly on Hacker News, though I’m patio11 practically everywhere on the Internet) that it stuck.
Bingo Card Creator was the first product of my bootstrapped software company. It makes custom printable bingo cards for teachers. I started this in 2006 and sold it in 2015. It eventually allowed me to quit my day job in 2010, after having been a nights-and-weekends affair while I was a Japanese salaryman. (I do not specifically recommend attempting either being a Japanese salaryman or bootstrapping a software business on the nights and weekends. Or, if you must do that, plan to get yourself to sustainability in under 12 months.)
BCC was something of a testbed for me to get good at the mechanics of running a small Internet business. I developed something of a skillset in Internet marketing with an engineer’s eye for rigor and optimization, and was eventually able to apply that to more worthy businesses.
I fell in love with Twilio at first sight and set out to create a business using its API. That business turned into Appointment Reminder, which makes appointment reminder phone calls, text messages, and emails to the clients of professional services businesses.
I ran AR from 2010 through 2016, when I sold it. Think “comfortably supported a small team” for a sense of scale.
What are your big takeaways from AR? SaaS is the best business model ever for software. HIPAA is a pain in the keister but tractable for a small team. Prefer running a business on behalf of customers you would enjoy serving to one where you don’t particularly care about their success; it will make it easier to spend 5+ years solving the scheduling problems of dentist offices doing something you love. Software businesses gain substantial leverage with code written against sales processes in addition to marketing automation.
I got fairly decent at making software companies money in the course of building my own. It turns out that this skill is valuable at larger software companies, too. I consulted for a few years on meat-and-potatoes marketing/sales for B2B SaaS companies. It was a really fun learning experience; I haven’t done it actively since roughly 2014.
I occasionally created or co-created products as a way to get that quality of advice without paying my full consulting rate. Representative examples:
What are your big takeaways from consulting? Charge more. If your professional skillset adds N% to the enterprise value of a software business, it is worth more on larger software businesses. (It sounds obvious when you put it that way. Hat tip to many conversations with Thomas Ptacek and for Paul Graham’s essay ; Ctrl-F for “Measurement and Leverage”.) Virtually no software business, inclusive of $10 ~ $50 million a year companies run by very smart people, is at the efficient frontier for investment in marketing or sales.
I was the CEO of Starfighter, a company which made games to identify talented programmers. We planned on introducing them to firms wanting to hire developers. The game was the coolest thing I ever built (the final level had you hack a stock exchange to catch an insider trader); the business didn’t quite jell in time. My co-founders Erin and Thomas Ptacek went on to create Latacora, which helps startups get serious about security.
What are your big takeaways from Starfighter? Hiring engineers remains decisively broken. Market microstructure is fun and fascinating.
I worked for six years at Stripe working on growing the GDP of the Internet, mostly through helping startups succeed. I was one of the early team members on Stripe Atlas, which lets founders worldwide start their companies on the U.S.’s legal and financial rails, and is now responsible for tens of percent of all incorporations in Delaware (which, for reasons, is the U.S.’s premier jurisdiction for ambitious new companies).
Much of my work was on the Marketing and Communications teams. I may have, at one point, written more than half of the words on the website. The hopefully longer-lasting contribution was helping to build the culture which went on to write many, many more. Stripe remains, as I once called it, a celebration of the written word incorporated in the state of Delaware.
I left full-time employment in early 2023. I am still currently an advisor there.
My proudest professional accomplishment is definitely a one-of-these-things-is-not-like-the-others: I ended up running the U.S.’s shadow vaccine location information infrastructure for a few months during the rollout in early 2021. The team’s efforts likely saved many thousands of lives. I’m honored to have had the opportunity to give us a shot at pulling it off. I tried to capture the experience in words and think that may be one of the most important things I’ve ever written.
I am thinking of starting my own software business. Any advice? Scads. I’d recommend reading this site and sending me an email (address here) if you have specific questions.
My name is Patrick McKenzie (better known as patio11 on the Internets.)
I also write a Bits about Money, a biweekly newsletter on the intersection of tech and finance.