Deep Dive
What I learned from 56 $250k+ businesses
Some of the key takeaways from the 2025 Bootstrapped Report
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How Erin Rollenhagen built a million dollar software business in a recession
She built a thriving software agency in Iowa. From naive beginnings to a 20+ employee company, learn the strategy that fueled People-Friendly Tech's success for the last 17 years.
How Neil Yeoh bootstrapped a climate business to $1 million
How OnePointFive is on a mission to train up 100,000 climate experts and build an eight-figure business while they're at it.
She left VC-backed startups to build a $500k company
Asia Orangio and DemandMaven have built a $500k/year company by helping companies with growth operations.
How Terry Rice built a six figure business by teaching
For Terry Rice, getting fired from Facebook was one of the best things that happened to him. Within 18 months of being fired from Facebook, Terry Rice developed a consistent six-figure business as a teacher.
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.
One bootstrapped biz is solving the nursing crisis
From $40K credit card debt to $4M annual revenue: How one teacher built a bootstrapped business that's solving America's nursing crisis one student at a time.
How a $5,000 Lean Startup Experiment Became Michigan’s Innovation Hub
Launched above a Detroit bail bonds office with borrowed money and Ikea furniture, Bamboo has grown into a community that’s reshaping Michigan’s startup ecosystem.
From Classroom to $25M Software Agency
What happens when a professor trades lesson plans for business plans?
A Baby's Sleep Problem Led to a $3.5M Business
Liz Hilton couldn't sell her baby sleep product through retail or Amazon - until one TikTok video changed everything.
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.
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.