Startups For the Rest of Us
Episode 815 | Unexpected Skills Your Day Job Can Teach You About Entrepreneurship (Rob Solo)
13 Jan 2026
Chapter 1: What is the main topic discussed in this episode?
Welcome back to Startup for the Rest of Us. I'm your host, Rob Walling, and in this episode, I'm going to talk about the unexpected skills your day job can teach you about entrepreneurship.
Chapter 2: How can a day job prepare you for entrepreneurship?
And I don't just mean if you are working for a tech company or if you are a software engineer at a large firm. I'm going to walk back through my history of jobs from when I was a teenager and I was a courier, driving a vehicle all around the Bay Area, delivering things, picking them up, and things I learned during that time, as well as being a construction worker, being a developer.
Chapter 3: What skills can you learn from unclear instructions?
being a manager of developers. And I'm just going to talk about all the things that I learned during those times, as well as a mindset that I had during this time that I think helped me learn more than if I had just shown up every day, clocked in and clocked out. Before I dive into that, applications for this round of MicroConf mastermind matching close in just two days.
Chapter 4: Why is respecting others' time important in business?
Building a SaaS alone is lonely and it can be hard. If you want to surround yourself with a small group of folks who are on this journey with you, you should join a mastermind.
Chapter 5: How does self-education impact your entrepreneurial journey?
Luke, a founder who recently went through the program said, quote, there is something about being in the trenches together with like-minded good people willing to offer up their experiences that's nearly impossible to find anywhere else.
To date, we've facilitated well over a thousand mastermind matches, bringing together founders from more than 50 countries and 20 time zones based on things like ARR, team size, experience level, and geography.
Chapter 6: What does embracing hard work teach you as a founder?
Applications close on January 16th. For all the details and to apply today, and you're going to want to do it soon, don't be the person who emails us five hours or five days after it closes and said, I really want to be matched. You're going to miss it.
Chapter 7: Why is experience more valuable than credentials?
We only do it two, sometimes three times a year. So you're going to want to head to microconf.com slash masterminds. That's microconf.com slash masterminds.
Chapter 8: When should you cut corners in your projects?
So the topic for today, looking at unexpected skills or day job can teach you about entrepreneurship, came up because periodically I get emails or questions about things that folks can learn about being an entrepreneur or a founder, even when they haven't gotten started right before they have the ability to build or launch or do any of the other things.
I believe you can learn from so many life experiences, including traveling the world, living in a different country than where you grew up, being in relationships, whether that's being married or having kids. There's things you can learn from everyday life, but I think...
that a lot of folks wanting to be entrepreneurs are so anxious or so motivated or so in a hurry to get away from their day job or to never have a day job that I actually think they might do themselves a disservice by not taking advantage of what a day job can teach you. A day job can offer you a steady paycheck and it can offer you health insurance if you're in the U.S., it's a big deal.
It can offer you a lot of things, but something that I think a lot of entrepreneurs aspiring entrepreneurs and founders overlook is how much I believe you can learn from a day job. In fact, I think I would be less successful or it would have taken me a lot longer to achieve the success I've achieved if I had not worked several of the day jobs that I'm about to talk about in this episode.
And my hope in telling my own story is that you can see some of the things that I learned from unexpected places. Like how could I possibly learn how to be a better entrepreneur from driving a car around the Bay Area and picking up and delivering packages? We're going to find out in this episode.
Really, the conceit of this episode is almost any full-time job can teach you skills that make you a better entrepreneur if you're paying attention. And I had a string of pretty normal jobs. As I said in the intro, what a courier, an electrician, and developer, and then managing developers. And at the time, none of them felt like entrepreneur training.
But in retrospect, I can definitely trace a straight line from things I learned as an employee to things that later helped me as a founder. So hopefully hearing this can make you look intentionally at the things you do day to day in your day job that you might be able to learn and use to your advantage. But I do think you need to be pretty deliberate about doing so.
Or I should say, I think the more deliberate you are and the more you seek it out, the more you'll get. So I have 11 lessons that I learned throughout my entrepreneurial journey. And I'm going to kick it off with the first one. And it was as a teenager, as I was a career in the Bay Area, I had to learn how to figure things out when instructions were unclear or when there were no instructions.
So this was pre-cell phones, it was pre-GPS, and oftentimes I was given vague instructions. and expected to deliver or pick something up. There were locked doors. There were buildings that were in the wrong places. There were construction sites that didn't match up with the directions. There were no addresses. You know, I just had to figure things out.
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