Deep Dive
What I learned from 56 $250k+ businesses
Some of the key takeaways from the 2025 Bootstrapped Report
Read More
How I'd Get Smart Biz iT to $250k
A breakdown of how Smart Biz iT could reach $250k in annual revenue by narrowing to the right customer, building a partner referral network, and running three targeted experiments.
How Losing $250,000 Led to a $250k Business
Jay Helton and David Osthus lost $250,000 before making a dollar, launched into a pandemic, and still built a $250k business by stacking three simple revenue strategies on top of one another.
Why I'm Posting Less Content in 2026
I'm shifting The Quarter's focus in 2026 after a year of big decisions and mixed results.
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
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.
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.
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.