The Quarter

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

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

    07/29/2025

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

    Download the Bootstrapped Report: 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

    13 min
  2. Why This Founder Rejected VCs

    07/24/2025

    Why This Founder Rejected VCs

    Download the Bootstrapped Report: https://www.jointhequarter.com/bootstrappedLearn more about Centered: https://centered.teamFull Deep Dive: 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.

    17 min
  3. She Got Paid for Her MBA Instead

    07/01/2025

    She Got Paid for Her MBA Instead

    Download the Bootstrapped Report: https://www.jointhequarter.com/bootstrappedRead the full deep dive: https://www.jointhequarter.com/blog/processdrivenCheck 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.

    19 min
  4. Sleeping in Boats Led to This $300k Studio

    06/03/2025

    Sleeping in Boats Led to This $300k Studio

    Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedSilkscreen Marketing: https://silkscreenmarketing.comFull Deep Dive: https://www.joinstation.co/blog/silkscreenmarketingPhoto 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.

    20 min
  5. NASA Writer to $1M Founder

    05/20/2025

    NASA Writer to $1M Founder

    Download the free Bootstrapped Report: https://www.joinstation.co/bootstrappedRead the full deep dive: www.joinstation.co/blog/brandibernoskieLearn 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.

    16 min
  6. They Made $1 Million Going Against Google

    05/06/2025

    They Made $1 Million Going Against Google

    Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedPlausible Analytics: https://plausible.ioPlausible's Live Public Stats: https://plausible.io/plausible.ioFull Deep Dive: www.joinstation.co/blog/plausible 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 fast forward to today, and there's a good chance you might use a company called Plausible Analytics, which now makes over $1 million in annual revenue by being everything Google Analytics isn't. Plausible is simple to use, doesn't track individual users, and isn't free… You might think charging for something Google gives away for "free" is business suicide, especially for a bootstrapped two-person team. But Plausible's story shows that sometimes being the paid underdog with a clear "we're not Google" positioning is exactly what people want. Now, how Plausible has grown this has been a little unique compared to the dozens of bootstrapped companies I’ve studied in The Bootstrapped Report because it’s maybe the most straight forward growth strategy I’ve seen.  With online privacy being a key concern for many right now, let's dive into how Plausible Analytics has bootstrapped their way to over $1 million in annual revenue by being the privacy-focused alternative to Google Analytics.

    16 min
  7. The Email Strategy Behind Her Template Business

    04/15/2025

    The Email Strategy Behind Her Template Business

    Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedCheck out Sam's book: https://www.samvanderwielen.com/book/Try Kit for free: https://partners.kit.com/matthewgira (this link is an affiliate link, so I do get some credit/rewards if you sign up to Kit!)The full deep dive: www.joinstation.co/blog/samvanderwielen Sometimes the thing people want from you isn't what you're trying to sell. That's exactly what happened to Sam Vander Wielen. After spending 4 years as a corporate lawyer, she decided to become a health coach in 2016. But when she showed up at a creator conference called "The Good Fest" to find clients for her health coaching business, something unexpected happened. A lot of people wanted to meet with Sam, so much so that there was a line to meet her, but it wasn’t about her health coaching business. They wanted to meet her to talk about how to protect their online business legally. Mind you - Sam barely had an audience at the time. She had around 600 Instagram followers and that was it. Fast forward to today, and she's built a business that has made over $8 million in the last 8 years with the same core products she started with.

    16 min
  8. Data built a $250k Ice Cream Shop

    04/01/2025

    Data built a $250k Ice Cream Shop

    Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedFull deep dive: https://www.joinstation.co/blog/elenasonorangeElena's on Orange: https://www.elenasonorange.comElena's on Orange Instagram: https://www.instagram.com/elenasonorange/Blank Mason Deep Dive: https://www.joinstation.co/blog/blankmason What happens when a Head of Data Science from Airbnb opens an ice cream shop? You get a store with 1,000 potential customers before making a single scoop, flavors tested through Instagram with 10,000 views per post, and a neighborhood hub that became the go-to spot for a 9,000 person community. Elena Grewal opened Elena's on Orange in November 2022, bringing her data scientist mindset to the world of ice cream. Within just seven months, this small neighborhood shop hit $250,000 in annual revenue – all because Elena understood exactly which metrics actually matter.

    18 min
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About

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

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  • Creator
    Matthew Gira
  • Years Active
    2K
  • Episodes
    27
  • Rating
    Explicit
  • Copyright
    © TM 2025 Station
  • Show Website
    The Quarter