Deep Dive
What I learned from 56 $250k+ businesses
Some of the key takeaways from the 2025 Bootstrapped Report
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From The Quarter to Bookmark
Introducing Bookmark, a newsletter built for small business owners ready to grow online, with the news, tools, and ideas that actually apply to them.
He Built One Business on the Fly, The Next on Purpose
Shaun Lee built one business that grew fast and nearly ran his life, then built a second one on purpose so it never could.
How I'd Get Smart Biz iT to $250k
A breakdown of how Smart Biz iT could reach $250k in annual revenue by narrowing to the right customer, building a partner referral network, and running three targeted experiments.
How Losing $250,000 Led to a $250k Business
Jay Helton and David Osthus lost $250,000 before making a dollar, launched into a pandemic, and still built a $250k business by stacking three simple revenue strategies on top of one another.
Why I'm Posting Less Content in 2026
I'm shifting The Quarter's focus in 2026 after a year of big decisions and mixed results.
They Made $1 Million+ Going Against Google
Two bootstrapped founders proved that sometimes the best way to compete with a tech giant is to be everything they're not - simple, privacy-focused, and not free.
The Email Strategy Behind Her Template Business
Sam Vander Wielen turned a surprising conference moment into an $8M legal template business when entrepreneurs sought her legal advice instead of her health coaching.
Data built a $250k Ice Cream Shop
How a data scientist built a $250k ice cream shop before serving a single scoop.
Four Crashes Couldn't Kill This Business
How Geniuslink solved geofragmentation, survived four "revenue-cut-in-half-overnight" catastrophes, and emerged as the leading smart link platform for creators.
Making Candles Instagram Worthy Made Her $250K
Sara Jennetten built Blank Mason into a $250K candle-making experience by designing every detail to be Instagram-worthy from day one.
The metrics of a successful online community
If you’re building your own online community, it’s really tricky to figure out what metrics to use for success. Thankfully, Circle provides some answers with their 2024 Community Benchmark Report
Save thousands on software tools with Secret
Save thousands of dollars on software you're already using.
My favorite online community platform
Community businesses are becoming a hot trend. Here is Matt's favorite online community platform.