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The Quarter

Podcast by Matthew Gira

English

Business

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About The Quarter

The stories of how bootstrapped businesses go from $0 to $250k in annual revenue

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27 episodes

episode I've seen 1000+ student startups. Here's what works. artwork

I've seen 1000+ student startups. Here's what works.

Download the Bootstrapped Report: https://www.jointhequarter.com/bootstrapped [https://www.jointhequarter.com/bootstrapped] We're heading into the start of the academic year where many students want to start their own business while taking classes. Building a startup within a university is actually a great time to do it – you have stability from classes and lifestyle, plus lots of people to bounce ideas off of quickly. But your time as a student entrepreneur is extremely limited, especially if you're an MBA student with two years max. Two years might feel like forever right now, but that's nothing in the grand scheme of building a business. How do I know this? My full-time job is leading student entrepreneurship at Yale, and as a creator, I've developed The Bootstrapped Report where I've analyzed 50+ bootstrapped businesses that have grown past $250,000 in annual revenue. It takes on average two and a half years to reach that mark. In this video, I'll cover: - The biggest traps for student entrepreneurs - How to overcome the most common challenges - How to make the most of university resources that you only have access to as a student founder

29 Jul 2025 - 12 min
episode Why This Founder Rejected VCs artwork

Why This Founder Rejected VCs

Download the Bootstrapped Report: https://www.jointhequarter.com/bootstrapped [https://www.jointhequarter.com/bootstrapped] Learn more about Centered: https://centered.team [https://centered.team] Full Deep Dive: https://www.jointhequarter.com/blog/hoomhouse [https://www.jointhequarter.com/blog/hoomhouse] In 2020, raising money was easier than ever before, and yet, Bryce Kaiser and his wife Lauren did something that was a bit crazy. They said no to all of it. While everyone was raising money because it was "free money" during the COVID boom, the HoomHouse founders deliberately chose to stay bootstrapped. Then on top of that, they walked away from maybe the hottest market in the entire world at the time: telehealth. And instead they just doubled down on one simple growth strategy. Three years later it all worked out. They sold the company on their own terms. In this deep dive I break down with Bryce, his simple approach to building a marketplace business, why saying no to VCs was actually the smartest move they ever made, and the surprisingly simple approach that made their exit possible.

24 Jul 2025 - 16 min
episode She Got Paid for Her MBA Instead artwork

She Got Paid for Her MBA Instead

Download the Bootstrapped Report: https://www.jointhequarter.com/bootstrapped Read the full deep dive: https://www.jointhequarter.com/blog/processdriven Check out ProcessDriven: https://processdriven.co By saying it's my MBA business, I basically gave myself permission for the first three years to just focus on learning and getting paid anything to learn is great when you compare it to an MBA where you're paying to learn." That's Layla Pomper the founder of ProcessDriven, a company that helps small teams clean up their operations so they can turn their messy chaos into control. Layla has bootstrapped ProcessDriven to over $250,000 in annual revenue and over 100,000 subscribers on YouTube. But here's the thing - ProcessDriven was never supposed to be like this. It was supposed to be just a business that she would run for maybe two or three years. Well, seven years later, and Layla still hasn't applied for a new job. In this deep dive, we'll explore the mindset that helped Layla grow ProcessDriven initially, the three different chapters or pivots of ProcessDriven, and how Layla has used YouTube to grow ProcessDriven to where it is today.

1 Jul 2025 - 19 min
episode Sleeping in Boats Led to This $300k Studio artwork

Sleeping in Boats Led to This $300k Studio

Download the Bootstrapped Report: https://www.joinstation.co/bootstrapped [https://www.joinstation.co/bootstrapped] Silkscreen Marketing: https://silkscreenmarketing.com [https://silkscreenmarketing.com] Full Deep Dive: https://www.joinstation.co/blog/silkscreenmarketing [https://www.joinstation.co/blog/silkscreenmarketing] Photo Credit: https://www.hollandsentinel.com/story/news/2011/12/25/mygreatlakeonline-allows-fans-to-show/45298490007/ When I started my entrepreneurial journey, Kylen Blom was one of the founders I immediately looked up to. He had legendary stories like sleeping in boats to sell his t-shirts, and he was already running his business full-time right after college while I was just getting started. That felt like the dream. Today, Kylen is a good friend and someone I still admire. He's the founder of Silkscreen Marketing, an art-focused production studio in Holland, MI. He's built an incredible studio that takes swag items that usually come out generic and boring and makes them genuinely creative and memorable. In this deep dive, we'll explore how a college pitch competition led to sleeping in boats around the Great Lakes, how a small local team competes with giant competitors, and how Kylen and his team think about growth in a different way than most.

3 Jun 2025 - 20 min
episode NASA Writer to $1M Founder artwork

NASA Writer to $1M Founder

Download the free Bootstrapped Report: https://www.joinstation.co/bootstrapped Read the full deep dive: www.joinstation.co/blog/brandibernoskie Learn more about Brandi: https://brandibernoskie.com 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 into what is now a $1M website agency, Alchemy & Aim. In this deep dive, we’ll explore the mindset shifts Brandi made to go from side hustler to $1 million business owner, how her focus on service helped her stand out, and why her approach directly challenges one of the other founders I’ve featured here on The Quarter.  And after studying dozens of bootstrapped businesses in The Bootstrapped Report, Brandi’s story stands out as one of the clearest examples of how to grow a healthy, sustainable company.

20 May 2025 - 15 min
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