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.
How she makes $20k/month from 572 email subscribers
From corporate ghostwriter to $250k/year business owner: How Kendall Cherry found success by going smaller, not bigger - and why she thinks referrals are holding entrepreneurs back.
Why this founder shut down his $250k juice biz
How Jermale Eddie built - and mindfully closed - a thriving juice bar
From Upwork to a $1M Analytics Agency
MaryBeth Maskovas turned a $3,000/month Upwork gig into a $1M analytics agency. Learn the key strategies driving its growth, from repeat clients to strategic partnerships.
How an Actor Built a $700K Speaking Business
Discover how actor Eduardo Placer built Fearless Communicators, a $700K public speaking business. Learn how networking and events drove his remarkable growth.
How she built a $100 million biz with webinars
Uncover Amy Porterfield's journey from corporate worker to $100M online marketer. See how she leveraged Facebook, webinars, and email to build her course empire - starting with just a $267 launch.
How Two MBAs used their alumni networks to create a $1 million company
It takes a few swings to craft the perfect product. Follow Ben and Fred's journey from Yale MBAs to $1M furniture brand founders. See how Hugo & Hoby pivoted from B2C struggles to B2B success, leveraging alumni networks and craftsmanship.
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.