--- title: What Bootstrapping Actually Looked Like slug: song-of-an-entrepreneurs-soul kind: essay published: '2015-08-31T09:00:00-04:00' revised: '2026-11-02T12:00:00-05:00' topics: - writing - entrepreneurship - sleep-medicine canonical: https://waltspence.com/notes/song-of-an-entrepreneurs-soul reading_minutes: 6 original: https://waltspence.com/notes/song-of-an-entrepreneurs-soul/original --- # What Bootstrapping Actually Looked Like _On hustle culture, the gap between the lifestyle being sold and the life being lived, and what it actually looked like for me._ > Edited 2026-10-31. Original: https://waltspence.com/notes/song-of-an-entrepreneurs-soul/original I want to vent about the entrepreneurship community on the web. I’ve bitten my tongue for too long, watching talking heads glamorize “hustle culture” when there is little to no glamor in it. Many of you will think this sounds bitter. Fair enough. I’d rather share something that means something to me. There are way too many articles selling a lifestyle that doesn’t exist for everyone in this startup community. So here’s my own story. Many people will dismiss it and say I just need to “get out” and get another job. That’s fine. Fall of 2007. I was working as a polysomnographic technician, which paid well enough for the nicest apartment in the nicest part of Richmond, Virginia. I also did web development as a hobby, as I have since ’96 or ’97 (way before it was called “coding”). Since it wasn’t my main job I was a little behind on the latest techniques, but I thought I was very good. Then the economic downturn came, and I was laid off from a job I had no intention of ever leaving. After several failed attempts to join another practice, I decided to use the skills I’d picked up over the years and do what the people I read and listened to kept saying to do. I was going into business for myself. I had $1,500 in the bank and felt confident in my ability to sell and in my skills. I knew I would be ok. I was finally going to stop making money for someone else. After chasing clients and mostly coming up short, I learned what I didn’t know. I was young and comfortable and I hadn’t done any research. Web development in Richmond had grown a lot while I wasn’t looking. There were plenty of freelancers thanks to technical schools and online courses. That was my first clue that I wasn’t the businessman I thought I was. That first attempt was a total failure. I didn’t understand the market and I overestimated my value. I felt crushed. I didn’t have the money to keep the business going, so I started looking for jobs in my field so I could feed myself and pay bills again. I went back to the first clinic where I’d been a technician and realized it was close to going out of business because of poor management and changes in Medicare reimbursement. I saw the signs and jumped at a job at a hospital an hour away, for the stability. For a while I was completely satisfied, but after a few months I saw that even hospitals were feeling the Medicare changes. The politics there were also way too much for me. After too many long days and nights of worrying about the future, I went back to the video that first got me thinking about working for myself: Steve Jobs’ commencement speech at Stanford. Watching it again, I knew it was time to start planning another go. This time I had saved a little more cash and had been educating myself for a while before making the jump. I had gone through everything I could find on small business, startups and management: books, documentaries, TV shows, radio shows, podcasts. I felt ready. I decided to try a different kind of business, so I could keep up with web development and learn more about commerce with a partner I trusted. So I went into business with my brother. We took over a consignment retail store in Waynesboro, VA. We had very little traction, but within the first few months we turned that around. We were breaking sales records by listening to our customers, getting involved in the community, creating an online store and working as hard as we could. That still wasn’t enough for our goals, so we changed the model from full consignment to about 50/50 new and used inventory. That made all the difference, and I learned a lot about markets, supply, and demand. I also learned about sacrifice, and that I still wasn’t as good with money as I hoped. I hadn’t saved enough. We reinvested in the store and didn’t pay anyone, including ourselves, for the first 2–3 months. When my money started running out, we agreed to pay me a little to help with the car payment, but that still wasn’t enough to feed myself. So I worked late nights on the weekend putting out signs for a local real estate company, for months, in all kinds of weather, including over a foot of snow, just to stay afloat. There was no glamor in any of it, whatever some talking heads would have you believe. Sacrifice was a hard lesson, but as important as any business lesson so far. With those lessons, and many late nights learning more web and app development, I started missing my old business and my family home in Richmond. I went home to try again on my own. I wanted to show myself I could do it. This time I did rather well on client work, but money was still tight. I’ve grown tired of chasing clients, so I’m changing direction again, back towards what I actually care about. I believe in good ideas and smart people, so I started recruiting people who wanted the same thing. I have a clear idea of where EnLab is going over the next 5 years. That has led to a team I could only have dreamed of a couple of years ago, and conversations with investors about seed rounds. Even so, I still work part time at night on weekends doing what I used to do. I look forward to seeing what a partly client services, partly app studio model does for the company, the team and the community. Whatever happens to EnLab from here, this has been a long and difficult road. I wouldn’t wish some of the lows on anyone, and the highs sometimes feel few and far between. I have gone months without maintenance on my vehicles, and I haven’t been to a doctor in at least 3 years because I haven’t had health insurance. It’s not glamorous. We don’t all come up with an idea and suddenly have a fancy office in San Francisco or New York. Even so, I think this is the best path. I’ve grown, the business has grown organically, and I wouldn’t trade what I’ve learned. I’m still learning, right now the difference between small business and fundraising for startups (converts, Y Combinator’s simple agreements for future equity, how long a seed round should keep a company running, etc). We all wish we could build a killer app and have that be the end of the story. For most of us it’s slow and hard. If you’re bootstrapping, patience isn’t optional. It’s a long game.