Episode 815 | Unexpected Skills Your Day Job Can Teach You About Entrepreneurship (Rob Solo)

Rob Walling:
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. 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, 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 a MicroConf mastermind matching close in just two days. 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. Luke, a founder who recently went through the program said, “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. 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. 

We only do it two, sometimes three times a year. So you’re going to want to head to microConf.com/masterminds. That’s microConf.com/masterminds. 

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. 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 US. It’s a big deal. It can offer you a lot of things, but something that I think a lot of 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? 

What are you 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 with 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. I just had to figure things out. And I had to find people when it wasn’t obvious where they were. I had to troubleshoot addresses that were wrong, roads were closed and I had to persevere instead of escalating every problem to my boss or to someone else. 

And this was a really good skill for me to learn because when you’re an entrepreneur, the buck stops with you. And although I could pull the ripcord, I could drive somewhere 45 minutes away, and if I couldn’t find someone, I could feasibly just drive 45 minutes back to the shop and tell people I couldn’t find them, but that’s a huge waste of time. And it kind of shows incompetence. It shows, “Oh, you didn’t try hard enough. Figure this out. ” And I was 16 at the time, 17, 18. I think I did it. I did it in summers and during holiday breaks. And I learned that things are often less clear than you want them to be. You want all the instructions to be perfect and you want people to have thought this through, but realistically, everyone’s in a hurry, someone scribbles something down. Sometimes you can’t even read their handwriting and I would just have to figure it out. 

And that was a really good lesson for me to learn as a teenager. Given that founders operate with incomplete information all the time, and that as a founder, you have to make progress without perfect clarity.That’s a core skill of being an entrepreneur. Both of those lessons were things that were driven home for me, and I think it was very helpful. And the other thing was learning to not throw problems back necessarily to the person who asked. Now, sometimes I did have to go find a payphone and call someone. And that was me pulling a ripcord in essence and being like, “I really can’t figure this out. ” And that was fine too. I had a backstop, but learning to handle things that were unclear set me apart from the other folks who were doing deliveries. It’s like, “Why does Rob always figure this out? I don’t really have many problems with Rob doing the delivery or doing the pickup or whatever.” And I think getting better at that was a skill that I wasn’t taught as a kid and learning that as a teenager I think was really helpful. 

The second lesson I learned still with this first job, and this job was a, when was this? It was in the mid ’90s. The lesson I learned was how to work with busy people higher up in an org chart. So I regularly interfaced with executives, project managers, folks who needed stuff done, plans delivered, permits picked up, whatever. At the time I was pretty young. I was inexperienced in a professional environment and I was very unaware of how you’re supposed to interface with these types of folks. And what I learned was that respect includes respecting someone’s time if they’re busy and they’re doing a lot of things. The higher up someone is in an org, the less bandwidth they have for small decisions and the more work I could take off their plate, the more valuable I became. And this was a super entry level. This was the minimum wage job I talk about making 450 an hour starting. 

And I made a little more than that by the time I left. But seeing executives and project managers who were busy and who were some of them entrepreneurial in their own right and that they would make a percentage of the net profit on their projects. So they were highly motivated to execute really well and highly motivated to get a lot done. It kind of taught me this lesson again of like, don’t escalate stuff unless I really need to. Don’t put it back on them. And it also, I think was a decent model for me as I became an entrepreneur of, oh, I should respect my time too. I should not waste my time or care about little minutia when I really need to be looking at the big picture. The third lesson I learned is that self-education can compound pretty fast. The context for this is I was in the car a lot. 

Long hours alone meant that I could listen to a lot of music, which I did, tons of Beatles. This is where I actually really developed that love I have of The Beatles and Bob Dylan, but it also meant a lot of time for audiobooks. And this is before Audible, that’s how old I am. So it was books on tape and CDs. And you can think of the classics, right? There’s good to great. And there was, I think I listened to Seven Habits of Highly Effective People and I was kind of like, “Eh, this isn’t that great.” I did listen to Think and Grow Rich, didn’t love it. But there were books about management. There were books about entrepreneurship and company building. I had never managed a person before. I didn’t really know how to do it. I even listened to books about kind of self-improvement, social skills, confidence, learning how to be … It’s not even like more charismatic, but just how to operate in the world and have difficult conversations. 

I wasn’t taught any of that growing up. And so this allowed me to start installing mental models before I needed them. And as I faced these situations later, I started realizing, oh, this is the thing that one book talked about. And these days, do I listen to audiobooks way in advance of needing them? No, I don’t. I’m much more a believer in just in time learning. But back then, I was such a sponge. I had so much free time and I didn’t know anything. I just needed to be exposed to a bunch of concepts. And so a lot of the books on tape, most of them were from the library. I didn’t have any money. They were the most popular business books and self-improvement and self-help books. And I really feel like those books helped shape a lot of my thinking. I also listened to a ton of books on personal finance and investing because I knew that that was just an important skill that they don’t teach in school. 

So I think a couple takeaways are you don’t need permission to start training for a future role or to start learning. And if you’re listening to this podcast, you already know that. Kudos to you. If you’re a career or a truck driver with long hours and you’re listening to this show and others like it because you are training your mind to be exposed to other entrepreneurs and to think like an entrepreneur. And I think especially in the early days, that can be really helpful. The other thing I think is if you’re just getting started and you’re just starting to learn, the best time to learn these hard skills is before you’re forced to use them. Lesson number four is that hard work is non-negotiable. So after I was a courier, I was actually an estimator for a while, a few summers and breaks as I was in college. 

And then my first job out of college was as an electrician in the field. So I was doing construction work in the Bay Area, physical labor, hands-on labor, swinging a hammer, so to speak. And that job taught me that manual labor is hard. Even in my 20s, I was sore a lot. I needed a lot of sleep and that work doesn’t care how you feel about it. It’s got to get done. Unless I wanted to quit or get fired, I had to put in the work and it was pretty … It was hard on my body, which in my 20s I could take that. I can’t imagine doing it these days, but I didn’t really have a choice because I needed to pay the bills. And if I didn’t want to work, I could go home and not work. It was just a non-negotiable to exist. 

So I showed up every day and I did things I didn’t want to do. This was much like playing sports, although sports was more of my choice. I didn’t have to run track and play football, but working a job as a construction worker was just something, it was just something that I did. And while I didn’t love it, I didn’t really question it either. I mean, I wanted to do a different job ultimately, but day to day, I was like, no, this is what I have to do. The hard work is non-negotiable. And there were no shortcuts around it, even when the work was unglamorous. And I think that the lessons from both sports and from working as a construction worker paid huge dividends for me years later, because I was able and willing to grind in a way that I don’t know that everyone is. 

And I get emails on this podcast about folks who were like, “Yeah, you know what, I don’t really have that much motivation to do it. ” And it’s like, “Well, I’m not sure that you’re going to be willing to do the grind and to do the hard things.” Or I see folks, the indie hacker types on Twitter where it’s like, “I’m just going to launch 20 projects.” And it’s like, it seems like you’re not really willing to do the hard work because the fun work is launching 20 projects. The fun work is building a bunch of projects. I love building, creating, that’s what we are. We’re makers. The hard work is focusing on one and focusing on it long enough to see it through and to put in the marketing and the sales and doing the stuff you don’t want to do and being willing to grind, much like you hear folks that I interview on this show doing. 

So you think of Kevin, the co-founder of Spectora, you think of Ruben Gomez, you think of Jordan Gall, you think of a lot of folks I interview on the show, especially in the early days, maybe not for your whole life, especially in the early days, they’re just wanting to do what it takes to make it work. Lesson number five is that experience beats credentials. So I had an electrical engineering degree coming out of college and I worked alongside electricians with 10 or 20 years of experience in the field. And it was really obvious that the people doing the work who had been doing it for a decade or two were so much more skilled than I was and they knew so much more about it. This sounds obvious, but what? I was a cocky 22 year old, this was humbling. And I realized that putting in the work matters more than reading about the work. 

So all the audiobooks and the courses, they don’t replace actually getting out there into the field and learning all about what it’s actually like to connect this light switch to that lamp and to connect this big data center, UPS to the incoming power. There’s a lot to it and getting firsthand experience with it, much like firsthand experience with entrepreneurship is invaluable. And so you can’t just stay on the sidelines or go to university or read books and listen to podcasts and expect to have anywhere near the same level of knowledge that you would if you actually did it. And that’s not to discount that knowledge because as I’ve just said, I feel like I prepared myself pretty well by listening to a lot of audiobooks and there were no podcasts at the time, right? So it would’ve been podcasts and audiobooks if it was a few years later. 

But realistically, you do have to get out there and start swinging a hammer at some point in order to learn the lessons. 

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Lesson number six is to let the buck stop with you. So as an electrician, and this was in the late ’90s, I was reading blueprints and I was installing circuits and frankly, it was often confusing. The engineer or the CAD operator who had drawn the blueprints had made a mistake or they were in a hurry or whatever. And it was tempting to ask the foreman about every uncertainty. But what I tried to do instead, coming back to treating executives with respect and treating their time with respect was I would do everything I could to troubleshoot at first, right? Avoid escalating every small issue. Even when something isn’t your fault, as an entrepreneur, it’s still your responsibility. And so this whole mindset of just, if at all possible, the buck stops with me and I just don’t have anyone else to … I can’t find the foreman. 

Foreman left to do something. I have to just figure this out even though it’s kind of over my head. And I think that’s a mindset that has really helped me as an entrepreneur. Lesson number seven is learning when I could and should cut corners and when I shouldn’t. So since I didn’t really love working construction and I had written code when I was a kid, I went to the library and I learned Pearl and I think a little bit of PHP and ASP 1.0 maybe, HTML, a little bit of JavaScript. I just checked out books. And in the early 2000s, I think it was in, what was the year 2000, I stopped working construction and I became a full-time software developer, a junior software developer. And it was amazing. I was working 40 plus hours a week writing production code. We were basically like an agency, a consulting firm, and we were building a lot. 

We were in Sacramento and we were building a lot of apps for. Com. So this was during the last year or two of the. Com boom. And what I learned during this time was that sloppiness always comes back to bite you, but there are times when you can and should cut corners on projects. On the flip side, the other end of the spectrum is you can gold plate software. There’s a spectrum between being sloppy and being overbuilt and the right level of quality depends on the usage and the risk and what it needs to scale to. So you can build something that scales to infinity users and is so incredibly abstracted and maintainable and so compact and performant and all this stuff. And then you have five internal users and you just don’t need to really build that, right? So if you have five internal users versus 10,000 simultaneous public users trying to validate a credit card, learning that spectrum and learning when to cut corners, maybe you’re probably cringing if you’re hearing this, but sometimes you just need to move quickly on some things. 

And I think not thinking in absolutes, which I was apt to do. I think a lot of us in our teen years and early 20s think in these absolutes and there’s no nuance to our thinking. I know I was definitely like that and a little too engineery. This is where I started learning, it’s not just some absolute that someone would say on social media that didn’t exist yet, but people love to talk in absolutes and say all caps, always and never. And it is almost always never the right choice to talk in absolutes. So my takeaways from there were that founders do not have infinite time and knowing which corners to cut, how many corners to cut without hurting the company long term was a skill that I learned in that job. Lesson number eight was learning who I wanted to work with and why. 

So I’m a software developer, I’m an individual contributor. And what I noticed is that as I would meet and work with other engineers, I knew within one project who I wanted to collaborate with. And sometimes it was the strongest developers and sometimes it wasn’t. Sometimes it was the people who were coachable, they were willing to collaborate, they had a desire to improve and we worked well together, even if they weren’t the best engineer on the team. And learning to evaluate other coworkers trained me to evaluate candidates when I started getting involved in the hiring process. And I’m going to talk about that in a second, but being able to be involved in the interview process and hiring for engineers was such a boon for me later on when I started my own companies because it translated directly into hiring people to work for me. So even before I was helping with the hiring and doing interviews and such, I was honing my skills of evaluation, of evaluating other team members, sometimes engineers, sometimes business analysts, whatever role it was, I was learning what makes a person really great to work with and that skillset and kind of that mental model helped me for the rest of my entrepreneurial journey. 

Lesson number nine is that managing and motivating humans for me was a learned skill. I didn’t do it naturally. And this started coming about when I started managing engineers, became a team lead, a tech lead, and started managing. And of course, I then reviewed a lot of the management books I had read years prior to that. And I realized for me at least, managing people is not instinctive that it is a learned skill. And I think if you can’t learn to manage and have hard conversations and to motivate people and to paint a picture of why they should be on your team and what you’re building and get them excited about what you’re doing, I think it can cap your growth as an employee if you’re not going to manage anybody, but it can also negatively impact your journey as a founder because this is a core skillset, is to figure out that vision and why should people be excited to work for you. 

They can go work for anyone and realistically they’ll probably make more money if they don’t work for a bootstrap founder. So how was it that at Drip when we were Bootstrapped, I was able to hire some of the best talent in town without paying them as much as they could get from other employers and keep those folks like none of them left, even though I was not … I mean, I feel like I’m a good leader and I’m a mediocre manager is how I would phrase it. And when I mean a leader, like I can paint the vision, I can paint the picture of where we’re headed and get people really excited about it and get them on board. And then week to week, day to day management is fine. I can do it. It’s just not something I’m super excited about. But learning how to do it well enough, this comes back to the grind. 

If I’m not excited about it, why did I do it? Well, because I had to. A, I wanted to make more money as a manager at these companies. And once I started companies, I had to be good at managing and motivating people. And so even if it wasn’t something I wanted to do day to day, it was what would make me a successful entrepreneur. And that goal I valued far above enjoying every minute of every day as I was building these companies. Lesson number 10 is that learning how to hire and how to fire our founders superpowers. So at almost every org … Yeah, almost every org I was at after I was a developer, I became involved in the hiring process and there were two reasons for that. Number one is I would come in and do really good work and write code that wasn’t buggy and I would manage myself and then I’d slowly start being a tech lead and people looked to me for guidance and I was opinionated about things in a right way without being a jerk. 

And then I would raise my hand and say, “I want to be involved in the hiring process.” And one of the reasons is I wanted to control who I worked with, but another reason is I knew it was a skillset that would help me forever. I didn’t know if I would be an entrepreneur. It was a dream, but I didn’t know if it would ever happen, but I did know that it would help me at my day job. And if I ever did start a company, I had to know how to hire and how to fire people. And something I learned as I went through this is that hiring well is hard. You’re never going to be perfect at it, but it does take reps. And the more reps you put in, usually the better you get at it. And firing is actually really tough. 

It’s tough to make that decision because it’s always muddier than you think it’s going to be. It’s never as clear as you want it to be. And usually it’s the really nice but slightly less than competent person who you’re like, “Well, I keep them around because they’re really nice and they get along with the rest of the team.” And there’s always these edge cases and learning that if I wanted to have a high performing team that I had to hire really well and learn how to do that and how to evaluate people and then I had to be pretty picky about it. And then I had to fire relatively quickly to reduce long-term pain was a great, it was a great skillset to learn. I didn’t learn it in a week. I didn’t learn it in a year. It was probably over the course of four or five years, over two or three different jobs because yeah, I was a job hopper, shocker, right? 

This unemployable. I was actually very nice. I never made people mad. I never got fired. I was left with the job, but I would get bored with things. And I think like a lot of entrepreneurs do, kind of get tired of the BS and be like, “Ugh, it should be different. I’m going to go try to do this other job. I’m going to make more money, but I’m also going to try to go to this job that sounds better.” And then usually it wasn’t better. So my advice here is if you can be involved in hiring at your day job, do it and then watch other folks around you watch how good people evaluate talent. If you have a manager who’s really good at hiring, pick their brain like crazy and try to figure out what’s their mental model? Try to get better at it. 

You can also read books about this these days. There weren’t so many 20 years ago. I mean, there were a few, but there’s a lot more these days that can help you get better. And lesson number 11 is exposure to systems that work really well and being up close and personal with them can teach you a lot. So this one comes from the last salary job I had before starting TinySeed. And this was after we sold Drip, I was a salaried employee and I was exposed to what was just an exceptional hiring funnel. Our acquirer had gone from, they had like hired a hundred people in a year or something like this because they had raised $38 million in venture funding and they had a really solid people ops team. It’s what they called their HR group. They had two recruiters, they had a dial and it was really impressive. 

It was kind of the best execution I’d seen to hire folks. And they happened to be hiring locally, but I think that part’s irrelevant. Realistically, they had a very structured way of finding new candidates with both outreach and inbound. They had consistent evaluation criteria, clear decision making. And to be honest, just seeing how that operated was enlightening for me and that helped me get even better at it, right? And any of these shortcuts and lessons you can learn from other departments at a company you’re working at can later help save you months, if not years. So those are my 11 lessons. And I want to underscore this thought of you should be deliberate about extracting lessons or learning lessons from the place that you work, right? Your job is training you whether you realize it or not. And the difference between learning a little and learning a lot is if you go out and seek it. 

I don’t think a lot of these would have happened by accident. I would have gotten some training about being an engineer or about being an electrician. But when I was working at the construction firm, for example, I would walk into other departments. I knew folks in different roles and I would ask how their job worked, right? So I’d talk to accounts payable about purchase orders and invoices. I didn’t really understand how all that worked. Or I would talk to accounts receivable about collections and what happens when customers don’t pay. Sometimes people were too busy. Other times they were super happy to explain to me. They loved being an expert, right? They liked teaching someone who’s genuinely curious, which was me. And I did the same thing later as a developer at … I worked at a credit card company and we had an onsite call center in Los Angeles. 

And I talked to the woman who ran it and I asked her, how do you handle rude customers? What happens if call volume spikes and the wait is suddenly really long? And what happens if you have downtime or staffing mismatches? None of that was my job. I was just curious about it. And at that time, I was a nerdy developer who loved writing web application code, but learning how finance, operations and support worked gave me a much broader understanding of how businesses in their entirety actually function. And this was before I was an entrepreneur, well before. I was trying to do stuff nights and weekends at the time, but I was trying to do little tiny software projects, just me, no employees, no contractors. But when I did eventually start my own companies, all of this mattered. Everything I’ve talked about in this episode and probably more than I’m missing mattered. 

I felt just a little bit more comfortable, a little less intimidated because I understood the pieces of how a business works. And if you think about all these roles, courier, electrician, developer, development manager, VP of product, I think was my title after selling Drip, managing a team of 20 engineers and product people. In most of these roles, I was not even a manager. In some of these roles, I was a teenager and I was just trying to do good work and learn and looking back, my deliberate curiosity absolutely paid off in spades for me over the next couple decades of building companies. So thanks for hanging around with me today and learning some of the unexpected entrepreneurial skills you can learn if you’re still in a day job. I appreciate you listening this week and every week. If you have any questions, comments or thoughts on this episode, I would love it if you’d at mention me on Twitter. 

I’m @RobWalllling, or you can email questions@startupsfortherestofus.com. This is Rob Walling, signing off from episode 815.