Why This Founder Said NO to Easy VC Money Matt Gira July 24th, 2025 This week's deep dive is a fun one for me. This company was being built while I worked with this guy on a daily basis. We were working on my last startup together and on the side, he worked on this venture. Ironically, his venture was the successful one. This deep dive is jampacked. Reply and let me know what you think :) In 2020, raising money was easier than ever before, and yet, Bryce Kaiser and his wife Lauren did...
9 days ago • 2 min read
She Got Paid for Her MBA Instead Matt Gira July 1st, 2025 This deep dive was an adventure to create. I was prepped to record and then a bunch of Stuart Little's decided to take over my recording studio at home. So, you all get to see what my childhood bedroom was like in this one. No, my high school trophies are not still in my bedroom. Sorry for disappointing. Enjoy this week's deep dive with Layla Pomper! Let me know what was most helpful. "By saying it's my MBA business, I basically gave...
about 1 month ago • 2 min read
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!...
2 months ago • 2 min read
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...
2 months ago • 2 min read
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...
3 months ago • 2 min read
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:...
4 months ago • 2 min read
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...
4 months ago • 2 min read
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...
5 months ago • 1 min read
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...
5 months ago • 2 min read
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...
6 months ago • 2 min read