Chris - there’s a lot of great precedent for this exact move, not the least of which is perhaps the OGs themselves 37Signals - also Amy Hoy, Metalab, and many, many more.
Amy wrote about this masterfully/hilariously in a response to a post some agency made about their own failure to successfully transition to products.
Amy’s post is great and there’s a lot you can learn from her points in there. There’s also a lot you can learn from the cringe-worthy fail-post she’s responding to in terms of the wrong mindset and approach to have.
Some added thoughts:
The Long, Slow, SaaS Ramp of Death is a real thing. My friends and I have coined the “1000 day rule”, basically, don’t be surprised if your product doesn’t go $25k/mo recurring in month 1. Shit takes time. 3 years for a SaaS to start covering your (SMALL team’s) market salaries seems to be a common theme
Dogfood with caution
"Build a product you want to use" is fantastic advice. But there’s a catch. If you’re coming from the world of software consulting, it turns out that that’s a tricky market to develop for - it’s extremely well served.
There’s an ocean of project management, bug tracking, time tracking, client-support, etc… products available for the agencies of the world. Don’t be afraid to swim into blue ocean to build apps for more under-served markets filled with non-developers who are hungry for delicious SaaS products.
That’s exactly what we did (we make a mobile photo app for street marketing teams. Link in the profile.)
Pick up the phone.
Sell on the phone. Make cold calls.
It’s ridiculous how few bootstrapped B2B software folks do this. It’s effective, and will teach you more about your customers, their pain points, and how to sell your product than any amount of copywriting and a/b testing will, especially in the beginning.
Share your story
Document your journey and share it with the world in a blog or podcast. It’s a great platform to have, and will help others find and relate to you.
Content marketing can be like cheat codes for bootstrappers. Get it in.