Code with Jason: People Buy From People
I went on Code with Jason for the second time. Jason and I got into the Fireside acquisition, how to actually find and finance a business to buy, why support is a product, and where I think developer tools are headed in the AI era.
Some of the highlights:
Why I Bought Fireside. Complete happenstance. I was already paying Garrett Dimon to push Flipper forward, and Garrett had worked on Fireside for Dan Benjamin back in the day. Dan had lost interest and was trying to sell, but it was too big for the small players and too small for the big ones. The math was simple: if I bought it, the profit could pay for Garrett to work on both Fireside and Flipper instead of it coming out of my pocket every month. I'm a long-term person, podcasts aren't slowing down, and it lined up with the analytics and content hosting I'd done before with Gauges and Harmony. So we did it.
Finding Deals. The marketplaces (Quiet Light, FE International, acquisition.com) are mostly where people list a dying SaaS expecting four to eight times multiples. That's not reality. A declining SaaS is more like 1.5 to 2.25x. The deals that actually work come through your network, someone who knows someone quietly looking to sell. Stick to what you know. And since the paperwork is identical whether the thing makes fifty thousand or five million, you might as well take the bigger swing.
Financing It. You don't need a pile of cash. My house was paid off, so I borrowed against the equity. Banks know houses cold, so they'll lend up to 80% the next day, no questions asked. Farmland is more like 50%. SBA loans were running 10 to 12% at the time versus 5 to 6% for a bank loan, so the margin matters. I took a 15-year term for the low payment even though I plan to pay it off in five to eight. It forces the business to clear at least that much profit, and then it just quietly pays for itself.
People Buy From People. Right now Fireside's edge is simple: Garrett and I do the support and build the product. If you send me the right request and I can knock it out fast, I'll ship it before I even reply. Most customers aren't technical (lots of Linux shows and religious orgs), and they value a real person who'll hop on a Zoom and fix their DNS.
Marketing to the People You Already Have. Churn is around 2% and most of the focus has been telling existing customers we're listening and shipping. Churn is a trailing indicator. By the time someone leaves, it's too late to do anything about it. So we get ahead of it. The more aggressive growth (conferences, underserved niches) is the next wave.
Onboarding and Retention Are the Same Coin. Frictionless onboarding helps the self-serve people and the hand-held people at the same time. Every time you onboard someone manually, automate a little more of it so the next one is easier. I just rebuilt Flipper's migration to be one click from the UI, the CLI, or the console. So slippery you slide right down the waterfall, and then you're pulling out your credit card wondering what just happened.
A Scrappy, Opinionated APM. I'm building a lightweight APM (I called it Caboose on the show, it's Flare now). The trick is that being opinionated makes it cheap. The expensive tools store everything so you can ask any question later. I'd rather pre-compute the answers to the questions you actually ask: count, sum, and error count per endpoint and job, the network breakdown (db, view, cache), and a handful of samples of slow requests. That solves 80 to 90% of performance problems for ten to fifty bucks a month instead of New Relic pricing that explodes the moment you add a teammate. This comes straight from my GitHub years doing analytics, statsd dashboards, and the Datadog migration.
Ops Without a UI. Honestly you barely need a dashboard. You want an API, a CLI, and skills or MCP so Claude can speak your language and pull the data. I did this with Flipper: dumped the gate data and 30 days of telemetry, asked Claude which flags I could delete, and cleared out about 15 stale flags and 600 lines of code in one pass. That's the moment I knew I wanted the same thing for the APM. Knowing what's happening in production and shipping safely matters more every month as people read less of the code themselves. GitHub Scientist style stuff, running two code paths and comparing them, is next on my radar.
We also got into Riverside versus Descript, why trying to do recording, editing, and hosting all at once turns into the PDA of old, being friends with your competitors, and my current obsession with Railway.
Code with Jason