
This Substack is a build-in-public operating log for people curious about buying and building real businesses in an AI-shifting world.
| Platform | Pricing | Only free issues | Publishes | Weekly | |
|---|---|---|---|---|---|
| Issues | 16 | Founded | 7 months ago | Last Issue | 13 days ago |
| Active | |||||

I built a career on being good at getting things done myself. Fast, thorough, no hand-holding required. That’s the whole value prop of being a solopreneur — you don’t wait on anyone.
Then I ended up buying a business with ten people, and I...
When Katie and I bought What’s Up Dog ten months ago, the space was … rough. Not charmingly rough around the edges. Bad. Burned out lightbulbs. Doors barely on their hinges. A half wall that was essentially falling down. Storage that looked...
I recently finished reading Unreasonable Hospitality by Will Guidara, the former owner of Eleven Madison Park, and one line really opened my eyes:
“Luxury means giving more. Hospitality means being more thoughtful.”
Thanks for reading Sit...
We heard it from advisors. We heard it from other daycare operators. We knew it intuitively. In-person events are one of the highest-leverage things a small service business can do.
It makes sense. You’re not selling a product someone can...
A few weeks ago, one of our regulars mentioned something offhand that I keep coming back to.
She works part-time at another doggy daycare and she’d noticed that her dog is dramatically different at What’s Up Dog than he is at her own workp...
Subscribers, engagement, traffic and sponsorship for Sit. Stay. Build..
| Subscribers | Engagement | 67 | Monthly Web Visits | ||
|---|---|---|---|---|---|
| Accepts Sponsors | Estimated Cost per Ad | ||||
The writers behind this newsletter.
Founder, operator, and creative strategist. I bought a doggy daycare business to diversify my income and build something AI-resilient. Writing through what it actually looks like to buy, operate, and build real businesses.
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