Deep Dive
What I learned from 56 $250k+ businesses
Some of the key takeaways from the 2025 Bootstrapped Report
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Why This Founder Said NO to Easy VC Money
When everyone was raising "free money" during the 2020 COVID boom, this founder did the opposite
She Got Paid for Her MBA Instead
Instead of paying for an MBA, Layla Pomper treated her business as her education and got paid $250,000 to learn while building ProcessDriven from an overqualified virtual assistant into a YouTube-powered operations consulting company.
Sleeping in Boats Led to This $300k Studio
How Kylen Blom turned a college pitch competition into sleeping in boats around the Great Lakes and eventually building a $300k creative studio in Holland, MI.
NASA Writer to $1M Founder
From NASA writer to $1M web agency founder through mindset shifts and putting service before sales.
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.
How Tally Reached 11K Users in One Year
Discover the strategies that propelled Tally Forms from startup to 11,000 users in just 12 months.
How he made $256k with books while learning to write
Discover how Nathan Barry, CEO of ConvertKit, used consistent writing, community engagement, and platform leverage to build a $256K business from scratch.
Taking risk in your career with Jorge Torres
Are you taking enough risk in your career? If not, what does your world need to look like so you can take some risk in your career?
Why a company should consider using Notion with Cat Mulvihill
Notion is a popular tool for many individuals, but using Notion as an organization is a different experience.
Why you should build custom internal software with Mark Johnson
Building internal software is like...cooking?
The future of women’s sports with Fielding Kidd Jamieson
The biggest, the best investment, the biggest growth opportunity right now is women's sports.
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.