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.
8-Minute Proposals Built a $250K Email Business
How Allea Grummert turned her passion for email marketing into a $250,000 agency by mastering one perfect productized service.
100 Videos Led to Being Acquired by Fiverr
When no YouTuber would promote his dropshipping tool, Lior Pozin made 100 videos himself - a decision that led Fiverr to acquire AutoDS 8 years later.
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.
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.