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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.
Helpful Content from Others:Sam Parr & his magazine articleSam 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 BookIf 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:
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 :) |
How revenue-first businesses go from $0 to $250k in annual revenue.
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...
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...
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...