Deep Dive
What I learned from 56 $250k+ businesses
Some of the key takeaways from the 2025 Bootstrapped Report
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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.
Two Failed Ventures Led to $250k in 11 Months
After two failed ventures taught him hard lessons about entrepreneurship, Phil Hayes-St Clair built The Partnership Lab to $250k in annual revenue in 11 months by teaching founders how to close six-figure partnerships.
She ditched her elite networks to build a $250k biz
Why the local business community mattered more than her corporate rolodex
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.
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.