Hi friend! This week's deep dive is from June, but there are some updates! If you don't know Nathan Barry and Kit, check out this week's deep dive. Nathan has a fantastic story and is leading the way in building a scalable software company entirely bootstrapped. Now, on to this week's deep dive. Here's this week's deep dive:Today, Nathan Barry is the CEO and founder of Kit. Kit helps creators who mean business and is primarily an email newsletter tool for creators. Today, Kit makes over $40 million in annual revenue, has over 80 full time employees around the world, and is completely bootstrapped. There’s a lot of cool stories about how Kit became what it is today, but the story I want to focus on is Nathan’s journey from full time employee to creator. This is a journey that Nathan was pretty public about on his blog and I spent about 20 hours going through all of it so you can potentially implement some of the strategies Nathan used to create his $256,000 business.
Helpful Content from Others:Indie Hackers Product PageExcited that Indie Hackers is on their way to building their own version of Product Hunt. Such a smart move and excited to see how this will help other bootstrapped founders launch. Your best posts aren't always perfectMatt Ragland's post on Linkedin this past week was so true. He mentioned that his best-performing video content was far from perfect, yet it's a huge favorite for everyone. If you're debating whether or not to post something online, do it and see what happens :) 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 bootstrapped businsses go from $0 to $250k in annual revenue.
How a $5,000 Lean Startup Experiment Became Michigan’s Innovation Hub Matt Gira September 16th, 2025 This deep dive is one of the most unique ones I'll ever draft. That's because I'm announcing that I'm joining this business... But this isn't me stepping back from The Quarter. If anything, it's going to make The Quarter better. I'll be meeting more founders who've bootstrapped from $0 to $250k in annual revenue, and I think there are going to be great opportunities to do things in real life...
From Classroom to $25M Software Agency Matt Gira August 19th, 2025 One of the most strategic founders I’ve ever met almost flew under my radar. I always thought Atomic Object was a solid software agency and Carl Erickson a kind leader. But when I worked closely with him in 2019, I realized just how sharp and intentional he really is about building both a company and a culture. Atomic turned out to be far more impressive than I ever imagined. Not just in the work they do, but in how they’ve...
A Baby's Sleep Problem Led to a $3.5M Business Matt Gira August 7th, 2025 This week's deep dive is a fun one. Who said you can't bootstrap a physical goods company?? Also fun because I've known Liz for such a long time and saw this all happen live. It was so cool talking with Liz about the journey and seeing her manufacturing space in Holland, Michigan of all places. Check out this week's deep dive 👇 "Liz, you are gonna sell a million of these." That was Liz Hilton's husband's reaction when...