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The Quarter

How bootstrapped businsses go from $0 to $250k in annual revenue.

A promotional graphic showing a person wearing glasses and a green hoodie with a social media-style card displaying 'Matthew Gira' with a verified checkmark and the text 'It takes longer than you think
Featured Post

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...

Kylen Blom sitting on a couch in his bright, art-filled studio space, wearing a dark button-up shirt and baseball cap, gesturing while speaking during an interview

Sleeping in Boats Led to This $300k Studio Matt Gira June 3rd, 2025 Quick idea I'm testing: What if I did a monthly report on bootstrapped companies? Different focus each month. Examples could be data on how founders spend their time, growth channel deep dives, the most popular tools among bootstrapped companies. Similar vibe to The Bootstrapped Report 2025. Would you pay $20/month for something like that? Would you pay $20/month for more reports on boostrapped businesses? YES. I'd buy this!...

Brandi Bernoskie, founder of Alchemy & Aim, with NASA logo representing her journey from NASA writer to million-dollar business owner.

NASA Writer to $1M Founder Matt Gira May 20th, 2025 Hello! The newsletter has an updated look :) Reply to this email and let me know what you think? Brandi Bernoskie didn’t set out to build a million-dollar business. In 2011, she was writing content for NASA and running a small blog on the side, mostly for herself. As she taught herself to code websites and friends started asking for help, a small side project grew into something more. A couple of key mindset shifts turned that side hustle...

Marko Saric, the co-founder of Plausible Analytics, smiling in front of the Plausible dashboard with the word 'GOOGLE' crossed out - embodying their core positioning as the anti-Google Analytics alternative

Hi friend! Welcome to The Quarter! Yep, the new name for this newsletter. Thanks, all for your help on this! And yes, I'm working on these deep dives as official podcasts. More on that soon :) What hurdle are you trying to overcome with your business? I'm happy to help! Here's this week's deep dive: In 2018, when Uku Täht was asked to set up Google Analytics for his company, he asked a key question: "Can we just use something other than Google Analytics?" At the time, the answer was no. But...

Sam Vander Wielen smiling in a white blazer with '$8 MILLION' text overlay, sitting in a bright room with plants in the background

Hi friend! This week's deep dive is one I'm excited to share since I've known Sam since the beginning of my creator journey. Heck, I didn't even really know what being a creator meant when I met Sam the first time. Sam has built an incredible business and I'm excited to be part of her book launch crew which released today! You can check it out here. Check out Sam's full story below. What hurdle are you trying to overcome with your business? I'm happy to help! Here's this week's deep dive:...

Thumbnail image: An ice cream shop sign for "Elena's" with the text "EST 2022" and "ON ORANGE" visible. Someone is holding what appears to be an ice cream cone in the foreground. Large yellow "$250,000" text overlay with an arrow pointing to the sign and

Hi friend! It's been a minute. I went to SXSW a few weeks ago and that took more out of me than I was expecting. A lot of fun and got a lot out of it, but whew, that was overwhelming. Some of the learnings below. Also - what would you name this newsletter? Open to ideas! What would you name this newsletter? Revenue Roadmap Roadmap to Revenue Zero to 250 It's a brand new deep dive in this week's newsletter! Let me know what you think via the poll at the bottom! What hurdle are you trying to...

Thumbnail featuring Allea Grummert smiling in a yellow cardigan, holding a coffee mug next to a desk with a laptop. The image includes a profile bubble with her photo and name, along with text reading '$5K investment to $250K biz' highlighting her busines

Hi friend! I published the condensed, narrative version of this deep dive with Allea Grummert (founder of Duett) a few months ago, but here's something different—the full interview. Which format do you prefer: the complete conversation with all its natural flow and additional details, or the more structured version where I highlight key insights and guide you through her story? Which version do you prefer? Condensed, structured version Full interview What hurdle are you trying to overcome...

Jesse Lakes, co-founder of Geniuslink, pointing at business analytics on a laptop screen with a caption stating 'But still making $2 million/year

Hi friend! I'll be at SXSW next week! Let me know if you'll be there. I'd love to see you in-person! This week's deep dive is a story I've shared a little bit a couple of years ago, but never as a full deep dive. Excited to share this one as I met these founders pretty early on in my creator journey and they've been a huge resource for me. 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...

Thumbnail image featuring Sara Jennetten, founder of Blank Mason, in her store with text overlay reading '4,500 Followers = $250K', highlighting her business success despite modest social following

Hi friend! Thanks for all of the feedback on the Bootstrapped Report. Glad to hear that it's been helpful to many of you! We'll keep building on it as we go here. If you missed it, here's the Bootstrapped Report! If you're interested in building a business from other's content, this week's deep dive should be fascinating to you. 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: These...

Two men sitting on white stools in an industrial warehouse space with exposed brick walls and beams. They're both wearing casual business attire - one in a checkered shirt and khakis, the other in a white button-down and jeans, both wearing brown boots. A

Hi friend! This week, I'm finishing up something I've been working on for MONTHS. So excited to finally share it out next week right here in the newsletter. If you're enjoying the deep dives, this is a supercharged deep dive. If you want a little sneak peek of what it is, check this out. No need to sign up for it. It'll be in your inbox on Tuesday morning! In the meantime, here's a previous deep dive on two people I've gotten to work with since the start of their company. What's one hurdle...