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The 2026 Bootstrapped Report

The data on how businesses grow from $0 to $250k

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Deep Dive

What I learned from 56 $250k+ businesses

Some of the key takeaways from the 2025 Bootstrapped Report
January 21, 2025
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A YouTube-style thumbnail featuring two men side by side. On the left, a man with red hair and glasses wearing a green sweatshirt gestures with his hand as if making a point. On the right, a man wearing a white polo shirt with the Smart Biz iT logo smiles at the camera. Between them is a white speech bubble styled like a social media post, attributed to Matthew Gira with a verified checkmark, reading "The three things I would try..."

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.
June 16, 2026
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A YouTube thumbnail showing two men side by side against a bookshelf background. On the left, a red-haired man in a light gray zip-up is mid-sentence with his arms crossed. In the center, a white speech bubble reads "Lost $250k Built $250k+" in bold black text. On the right, an older man in a dark suit and red striped tie is smiling at the camera.
Deep Dive

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.
June 9, 2026
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A YouTube thumbnail featuring Matthew Gira, a man with glasses and short reddish-brown hair wearing a sage green button-up shirt over a white t-shirt, seated in a warmly lit room with bookshelves and lamps in the background. A white card overlay on the left reads: "Matthew Gira" with a blue verified checkmark, followed by bold text: "12 founders. 1 day. A roadmap to $250k."

The first Quarter Revenue Retreat Recap

I should have done this retreat sooner
June 2, 2026
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Video thumbnail showing Matt Gira with text overlay reading '2025: Tried it all' and '2026: Back to basics

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.
January 20, 2026
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Phil Hayes-St Clair smiling at camera in blue sweater, sitting in modern office with white text bubble displaying "My partnership framework changed everything" next to his name and verification checkmark on white rounded rectangle background
Deep Dive

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.
November 13, 2025
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YouTube thumbnail featuring Jessica Lackey smiling in a black leather jacket on the right side, with a white text bubble on the left displaying her profile photo, verified name, and the quote "I ignored McKinsey & Nike" against a green background with compass and coin illustrations.
Deep Dive

She ditched her elite networks to build a $250k biz

Why the local business community mattered more than her corporate rolodex
October 16, 2025
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Deep Dive

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.
April 15, 2025
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Deep Dive

Data built a $250k Ice Cream Shop

How a data scientist built a $250k ice cream shop before serving a single scoop.
April 1, 2025
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Deep Dive

Four Crashes Couldn't Kill This Business

How Geniuslink solved geofragmentation, survived four "revenue-cut-in-half-overnight" catastrophes, and emerged as the leading smart link platform for creators.
February 27, 2025
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Deep Dive

Making Candles Instagram Worthy Made Her $250K

Sara Jennetten built Blank Mason into a $250K candle-making experience by designing every detail to be Instagram-worthy from day one.
February 4, 2025
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Deep Dive

What I learned from 56 $250k+ businesses

Some of the key takeaways from the 2025 Bootstrapped Report
January 21, 2025
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Deep Dive

They turned one viral video into a $200K biz

Chris & Sara turned one viral van tour into a $250K business that lets them travel the world while doing work they love.
January 7, 2025
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Software

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
February 28, 2024
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Software

Save thousands on software tools with Secret

Save thousands of dollars on software you're already using.
September 30, 2023
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Software

My favorite online community platform

Community businesses are becoming a hot trend. Here is Matt's favorite online community platform.
August 6, 2023
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