Deep Dive
What I learned from 56 $250k+ businesses
Some of the key takeaways from the 2025 Bootstrapped Report
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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
My Best Video Isn't the One with 120k Views
A look back at my 2024 creator journey: tracking weekly metrics, focusing on deep dives, and redefining success—less about viral hits, more about building a solid foundation for 2025.
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.
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.