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
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.
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 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.