What I learned from 56 $250k+ businesses


Hi friend!

I'm so excited to share what I've been working on for months: The Bootstrapped Report. It's a study of 56 different bootstrapped businesses. You can check out some of my takeaways below and download the full bootstrapped report here.

What's one hurdle you're trying to get over with your business? Happy to try to help if I can!

Now, here's this week's deep dive:


Here's this week's deep dive:

For the past 6 months, I've been creating deep dives on how bootstrapped businesses grow from $0 to $250k. While I started noticing patterns, I wanted data to validate these gut feelings.

So I spent months digging deeper - analyzing my deep dives, listening to podcasts with bootstrapped founders, and studying "build in public" posts. The result? Research on 64 founders (56 businesses) that reveals who they are, what they built, and exactly how they built it.

I've compiled all the findings into the comprehensive download the full bootstrapped report here.


Recommended Tool of the Week:

This email/section contains affiliate links. I earn a commission if you make a purchase at no extra cost to you :)

If you're someone that wants a level up from some of the more basic website builders, I highly recommend Webflow.

I use Webflow for my website and I've been using it the last few years.

You can customize everything you could ever imagine and the library of pre-made website elements keeps getting better and better.

You can try Webflow for free here.


Helpful Content from Others:

Sam Parr & his magazine article

Sam Parr works out of a library and sometimes goes to the magazines to flip to a page he's on to see if people notice. How funny.

Everybody Writes Book

If you're looking to become a better copywriter, check out Everybody Writes by Ann Handley. It's been helpful for me to reference when it comes to crafting LinkedIn posts especially.

Another newsletter you should check out:

Image for The Workin' Process

The Workin' Process

By Layla at ProcessDriven

Subscribe for weekly systems that boost clarity, avoid meetings, and make work feel less chaotic. Trusted by 16K+ small business leaders run smoother, saner teams.

Thanks for reading!

Matt

P.S. Looking for recommendations on software or content? Check out my personal recs here. Some links in this email and in recommendations are affiliate links, so I do get some credit if you sign up for things with these links :)

The Quarter

How revenue-first businesses go from $0 to $250k in annual revenue.

Read more from The Quarter
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

How I'd Get Smart Biz iT to $250k Matt Gira June 16th, 2026 Hi friend! This week's newsletter isn't a company that is at $250k yet. It's all about how I would plan to get to $250k with this company. I went deep into ideal customer personas and adjacent partners if you're looking to nerd out. My friend Shawn Thornton is the founder of Smart Biz iT, where he helps startups and SMBs get audit-ready, pass enterprise security reviews, and scale with compliant IT infrastructure. If you've never...

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

How Losing $250,000 Led to a $250k Business Matt Gira June 9th, 2026 Hi friend, I've seen a lot of founders persevere through a lot, but this week's founder story was a little extra when it comes to product development. If you're not a technical founder but have a technical idea, this is a good deep dive for you :) If I told you just a few key moments built an entire business, would you believe me? Today, Creative Senior Planning is a software that helps manage the entire backend of senior...

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 le

I Should Have Done This Founder Retreat Sooner Matt Gira June 2nd, 2026 Hello! It's been months since I've sent this newsletter. Excited to let you know that we're back on a weekly basis. Sharing insights about how to grow your business from $0 to $250k in annual revenue. If that's no longer you, no worries. Feel free to unsubscribe at the bottom of this email. If it is you, well, there's a lot of updates. Check out all of them below! This idea should have come to me so much sooner. For the...