Transition From Corporate Job to Startup

Episode 3

Making the transition from a corporate job to starting your own company can be really difficult. We'll share some thoughts of how we made the transition and talk about going from a nights and weekends business to full-time on your business.

Thanks for listening to this episode of The Stretch Goals Podcast! We'd love to hear your thoughts on this episode and answer any questions.

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Robert: In this episode we’re going to talk about how to transition out of the corporate world, and into your startup. This is the Stretch Goals podcast, where each week we’ll share insights and lessons learned based on our experiences as entrepreneurs. We’ll challenge you to create ambitious goals as you start and grow your business. I’m your host, Robert Dickerson.

Scott: I’m Scott Davis.

Robert: Making the transition can be really difficult, Scott I thought this would be a great area for us to talk about since we both transitioned our businesses starting kind of from a night and weekend type business, to a part time, and then finally making the leap into a business that can support us full time. There’s a lot of risk in this eye, I’m very risk averse, and so I tried to take the most stable approach to kind of transition into a business where I still had a solid revenue stream.

Scott: Yeah, I’m risk averse as well, except that I’m risk averse, and then I like to jump in the deep end.

Robert: Well I think you have to at some point, right?

Scott: Yeah.

Robert: Because I’ve found that if you have that rope, the lifesaver, whatever, from a full time job, sometimes that can hinder your ability to jump full time into your startup.

Scott: Yeah, there’s that … It’s like an imply … Not an implied, but there’s just this thing holding you back. I agree. For me, when I was transitioning over from this corporate world to startup space, it was very much like you just said. I had sort of a proof of concept that I wanted to see if it was viable. As a technology entrepreneur I was able to build that myself in my spare time, you know, just an hour here, an hour there, I didn’t want to waste a lot of time, I didn’t know if it was a worthwhile idea, I didn’t know if there was a customer base behind it or not. I would use my spare time to sort of chip away, and create this product. Then once I did, and I launched it, and started getting more traction, then what happened was now I’m spending more of my spare time trying to create this product, and evolve it, and try to get more customers.

One of the hardest things, I think, was just trying to grow the business while having a full time job. Support calls, or customers wanting to call you, and then you’ve got this conflict of interest, taking a phone call while you’re at your nine to five, and how to navigate around that. What’s ethical, what’s not, but at the same time, your eyes are on that long term target of getting out of the nine to five. Is that the same for you?

Robert: Yeah, I’ve had the same kind of problems. Let’s talk about the first phase. The first phase is really starting with a nights and weekends type business, and you brought this up that it’s really to build your product, and to validate your idea. That’s what I’ve done with MapOut, was I started … It’s actually taken me about six to eight months to develop doing this model of nights and weekends. We can get a little bit more into outsourcing, that was one area that we talked about, is bringing other people in to help you, because nights and weekends you only have so many hours in the day. We both have kids, and want to spend time with our families, so I don’t have as much time as I use to, to just sit down, and come home from work, and invest building a product. I think that’s an area we can talk about too, is how to find people to help you and outsource different components.

I think in the nights and weekends phase of the business, it’s really about taking your passion, and staring to build a products, and to acquire those first couple customers. The nights and weekends can be product development, but it can also be networking, attending networking events, and trying to grow that customer base. In this phase you really need to contribute all the capital to the business, and any revenues you start generating, really, cycle back into the business so you can start growing it.

Scott: Yeah, so I think one thing that really helps when you’re in the corporate world, and you’re trying to transition over, is that you have this income already established. There’s less risk for you, as an entrepreneur. You’ve got the bills paid, you’ve got a comfortable level of living, and so when you’re spending this free time building those products, trying to acquire customers, you’re not at a dire need for cash, you’re not at a point where your spouse is on your back because you’re not paying your bills, you know. You’ve got a comfort level, so there’s this security blanket. That’s where a lot of people get stuck, in my opinion, honestly, is they had this security blanket, and they don’t know how to get out of that mindset of benefits, and the steady income, and this just notion that every day you’re going to the office, and you have this job, and it’s not really going away as long as you just do your work. It’s completely different mentality once you transition to something that you’re doing full time, or even part time, splitting it with some other revenue source.

That security blanket either hinders a lot of people because of that sense of security, or other people, like myself and you, we use it as an asset. We said, “Look, this is money that can funnel into my business, that’s paying my bills, it’s giving me flexibility to work on this thing I’m passionate about.” It really helped me grow my business the way I did, because I didn’t have anything to lose in my business, because it wasn’t my sole source of income. I just tried everything I could, and it didn’t really matter. The security blanket for me was actually an asset.

Robert: I would agree. What I did with MapOut was basically I used the income I was earning from my jobs, from my consulting gigs, and funneled that back into product development, so I hired a small team of contractors to help me develop the product. I didn’t spend a lot of time developing it, I was more architecting it on the nights and weekends, talking to customers. It was growing alongside, and I did use the income from my full time job as a security blanket. That really helped me grow the business. Then it became sort of a liability to have all this work, because I’d have a full time job with MapOut growing, and it’s how do you transition. How you make that transition, right? Because you’ve got all this consulting work, you got all this full time work, and now it’s hard to break away time to go talk to customers during the day, and make those sales calls during the day.

Scott: Sure, and not only that, you said liability. I mean it’s … You have a lack of interest, presumably, in your full time job, that’s what’s motivating you to go down this path of your own business, your own product, whatever, and then you sort of become disconnected from what you were already working. It’s this tough thing where maybe you were like an A+ student at your nine to five, and now you’re probably like a B- or a C.

Robert: Sometimes that’s good enough though, to continue on.

Scott: Yeah, that’s true, that’s true.

Robert: I’m not advocating stopping working at your full time job, but you know, you’re not contributing to your fullest extent. Sometimes you have to kind of make that … Weigh those trade offs there.

Scott: In other words we’re not condoning lame duck syndrome here, on the podcast.

Robert: Yeah, get your work done. They’re paying you to do that.

The next phase is transitioning from a corporate gig, a full time corporate gig, into part time work, or either consulting work. I actually did this over a period of time, and I started out, basically, taking Fridays off, every Friday off, every other Friday off, and using that time to invest in my business. I found that was really helpful, because I could use that time to make sales calls, to really devote the business. What I would do is I would map out what I needed to do for that day, so I could really get it done, because I found when you’re running your own business, a lot of times, you’ll sit down, and you’ll have so much to work on that kind of … That can be paralyzing, because you don’t know exactly where to start, whereas a corporate gig, your boss tells you what to do, you have milestones, you have other people working with you, and so it can be easier to get in the groove. Whereas in a startup you’re making those decisions, you’re deciding what’s the most important thing.

After I took every Friday off, the next thing I did was actually did was go into a part time role with the company. I cut my hours down to about 30 hours a week. Then I eve had more time, about a day and a half each week, to invest in the company. After that I cut my time even more down, to two days a week. If you have the flexibility to do that, that’s great. Some people in their corporate job don’t have that flexibility. Luckily, I did, but it was a great way to slowly transition into the business while still bringing in income from a corporate job.

Scott: You know, in your situation you said you had that flexibility, but whether you had the flexibility or not, how did you negotiate that discussion with your boss, your superior, and say, “Hey, I want to take every Friday off, or every other Friday.” Then next thing you know you’re asking for, “I want to go down to a 30 hour week.” How do you do that without raising flags?

Robert: Well I think in my situation, talking to the CEO, he knew that I was interested in starting my own business. It was actually a really unique situation, and I don’t think many CEOs would do this. A lot of companies want you to work only on their products, only their things, and so they’re not willing to negotiate. Also, within the corporate world, I also had a lot of pull. I worked myself up to a program manager, so I was running my own projects, I was running my own teams within the company. I had more flexibility, and I could continue to move the projects along, continue to bring revenue in with the for business. That was one of the main reasons why I was able to transition, is because I had that asset in the company, and they wanted me to continue to grow that asset. I was able to by working fewer hours.

Scott: Yeah, I was in the same position. Once you have a well oiled machine, you got to sit sit around twiddling your thumbs, and for me, I told our CIO at the time, I said, “Look, I’m not looking to leave, but I got to do something with my time. If it’s all right with you I’m going to duck out for lunch for a couple hours, and work, on something.” It worked out well. What tips or suggestions do you have in terms of broaching that conversation. Maybe you don’t have a close relationship, or maybe you’re not a stellar employee. Do you have any insight or thoughts on how somebody could go about looking for that type of flexibility?

Robert: I think you need to figure out what value you’re going to bring to the company, and approach it that way as to not necessarily we’re just going to stop working at the company, but what value do you bring, and how can you take your current job, and make it valuable to the company maybe with fewer hours.

Scott: I don’t know, I’ve always been in these unique situations where I knew my bosses pretty well. In my last situation, or career, in the corporate world, I was not, by any means, a favorite, or knew anybody. I worked my way up to the product manager of a product, and I had it just well oiled. I probably worked, in all honestly, actual work, maybe four to six hours a week. The rest of the time was just researching, and reading about things that I could do to make the product better, but in all honesty I wasn’t getting paid to do that. I was getting paid to actually work on these other things that only took me a very limited amount of time. I basically just said to them, and I had flexibility in terms of my employment that basically said I could work on other things as long as it wasn’t impact my work. I told them in full disclosure, “I’m going to be working on some other stuff,” and they said, “That’s great.” It was an awkward conversation, but it was a conversation I needed to have for my own mindset. The reality is if they had said no, I couldn’t do that, I probably would have quit. At least that’s me and my position.

Robert: I think it’s important. I’ve always found that it’s important to be open with people. Usually if you’re open with people, and you tell them what your intentions are, and they know that you’re interested and engaged, and also if you can find ways to, within your startup, your learning things that you can contribute back into your corporate job, that’s always a benefit to them, because you’re learning on your own time. You’re investing skills in your own time. If there’s a synergy there that you can bring back into their business, most people are open to that. I think like you said, being open and transparent about what you’re trying to do, what your goals are, most people are receptive to that. If they’re not, then you really have to think about is this the job that I want while I’m trying to grow my business.

Scott: Yeah, absolutely. You know, my first business that I sold, it actually worked just like that. They didn’t have a mobile application for anything that they were doing in the telecom space. I said, you’ve got this Mac over here from a designer who is no longer employed. It’s been sitting here for 6 months, do you mind if I take it, and learn how to develop apps on it? They’re like, “Yeah, sure. Whatever.” I did, and I started buildings apps, and I got in the newspaper, I got in the news, I started getting all these customers, and they knew that. While it was a conflict of interest, they also knew that I was now developing a skillset that I could bring back into the company. I later ended up developing seven apps for them, for enterprise use, and for some of their customers. I brought, like you said, I brought the skillset, and the knowledge, back into the company. It became an asset to them as well as myself.

Robert: Well you took that initiative too, to kind of define your own way. I think that’s really important when you’re working in a corporate job, that you make the most of the job. Don’t wait for someone else to tell you what to do. You need to identify opportunities, and identify opportunities where you can contribute to the bottom line of the business, not just get work done. You don’t want to be a cog in a system. You want to figure out what skills can I find that I can develop products that will generate revenue for the company. I’ve found when you can start generating revenue, then your value goes up tremendously, because you’re not just a cog in the machine working, you’re innovating, you’re moving the company forward, and that gets you noticed.

Scott: Absolutely, and you got to think about how many great ideas in the world have come, that very same way. There was probably some guy who was making hot dogs, and just eating them with a fork, and some guy was like, “Hey, do you mind if I just put a piece of bread around this thing?” Then we got a hot dog bun out of it. Obviously I don’t know if that actually happened, but my point is those types of things happen every day, right? Somebody says, “Why don’t we just try it like this?” Some manager probably was like, “No, we don’t have the time,” but somebody then took the initiative, tried something new, and it turned into a new product, a new idea. That’s just being human.

Robert: Another thing that I’ve done too within the corporate world is find those leaders that are innovated, that are already pushing the company along.

Scott: Yeah.

Robert: Go work under them, because they have a much greater understanding of what it takes to push the company forward. They’re more flexible in terms of letting you try new things, and I think they’re more open to this working side business, because they know how that can develop ideas, and skills, that you can then apply to the business.

Scott: Yeah, I think as long as you let them know that you’re still loyal to them, you’re still doing the best you can for that business, and like you said, just be open, and say, “Look, this is something I want to explore.” I think everything will be fine as long as you’re open and honest.

Robert: I agree. After you’ve kind of transitioned into maybe a part time role, or you’re doing consulting work, now you’re ready to make the full time leap. Now I think it’s important before you make the full time leap that you’ve really validated that your product solves a pain for a customer set, maybe you have a couple of first early customers, and you really see a path forward to generate revenue for the business, and some type of salary for yourself. I know we’ve talked about this, is that you have to think about that when you’re starting business … When you’re starting this business out that a lot of the revenue is going to be contributed back into the company. You’re not going to be taking out a lot for yourself. I think that’s an important thing to think about when you make the leap, that you might have to be taking less money than you were working in a corporate job.

Scott: Sure, at least for a period of time.

Robert: Yeah.

Scott: As you get things stable.

Robert: Make sure you’re saving, or you have some sort of way to make that transition, because it’s sometimes not an immediate thing. It takes more time to make the leap.

Scott: Yeah, but let’s be honest, right? You and I, we’re conservative in terms of managing our money, at least I am most of the time.

Robert: Except when it comes to new iPhones.

Scott: Not when it comes to new gadgets, man, yeah. Let’s be honest, not everybody is that way. Let’s flip a coin, and say it’s 50% of the people are that way, and 50% aren’t. That means there’s a lot of people out there listening to this right now, who don’t want to wait until they have six month’s salary, or whatever the case may be. They don’t have a net to save them, right? They’re just … They’re like, “You know what? I’m just going to leap into this thing. I’ve got like $800 in my bank account.” What do they do?

Robert: Personally I wouldn’t do it, but I think that you have to decide that for yourself as to what’s the opportunity moving forward. There have been a lot of successful businesses that have started that way that have scraped by. You could look at raising money from friends and family to help support you.

Scott: Crowdfunding.

Robert: You know, for me personally, I have two kids, and a family, and so I can’t afford to take that route. I have to be really …

Scott: It’s a life stage thing.

Robert: It is.

Scott: If I’m in my early 20s …

Robert: If I had just come out of college, then you know, yeah, I could live on Ramen noodles. You could take more risk at that stage.

Scott: Right, no, it’s absolutely the case. I think, honestly, you’re life stage puts you in these buckets of how conservative you are with your money, or how much risk you want to take, at least as a normal person. You know as well as I do there’s people out there who are just … They’re selling all their furniture, and packing up, and living in their car, and they’re grinding, man, to try to grow a business. That’s not me, but more power to them. If you’re listening to this, and you’re thinking, “Man, this podcast is talking about just being conservative.” It’s not the case, I mean we’re trying to touch on all these topics, but that’s a real world scenario. People are out there, people are taking these risks, and dropping everything, the concepts still apply though. You got to have a stable product, you want to be able to support yourself, because long term, you can’t live in your car forever. You got to keep building this thing.

Robert: I think the other thing to think about as well is when you’re thinking about risk, and you can always go back and find another job, right?

Scott: Oh yeah.

Robert: If you take the leap, and you try it out, and you’re not successful, you can go find a job.

Scott: Yeah, and if you don’t burn your bridges …

Robert: Yes.

Scott: … you’ll probably still have good rapport at your other company. What about … Let’s pause on that for a second. What about the concept of just taking a leave of absence? Is that viable? Robert: I think it is, if your job can support that, you could ask for a leave of absence so you could try it out for a couple months, see what happens. Just take it without pay.

Scott: Yeah, I never thought about that when I was in that position, but that’s something maybe more structured corporate environments might allow for, what they call a sabbatical, or something like that.

Robert: Sure. That may be a good way to dip your toe in the water, and try it out, see how it works, and then make the transition.

Scott: Absolutely.

Robert: I think this whole topic really, it’s hard, it’s not easy. It really is personal as to what your risk tolerance is, your situation in life, the type of business you’re trying to grow. A lot of this you have to think about for yourself, what makes sense.

Scott: I mean, we always calla it make the leap, or cut the cord, or whatever, but probably 75% of the time it’s a gradual transition. There’s not this direct, “Hey I’m just going to jump in.” I’ve talked to probably ten different people over the last month or two, who they’re now in their own startup, and talking to them, it’s been a two year transition for them. Going from whatever environment they were in, but the thing is, you can see the difference in their happiness level now, personally, they’re much happier, because they’re not thinking about, “When am I going to quit my full time job and go into my business?” That weighs on you, that’s a stress that you don’t need. Then you get a whole new set of stresses when you are just working for yourself. I remember having those nights where all I could think about was, “Man I just want to do my thing full time.” Did you have that same sleepless nights syndrome?

Robert: Yes, for a long time, for months. It built up to the point where I was working for so many other different companies, doing consulting work, doing the corporate job, that I didn’t have any time to really focus on my business, and I knew I could be successful with it, but I had to carve out that time, I had to get rid of other things, so that I could have that flexibility. Yeah, so it weighed on me for months as to how do I do this. I guess for me, making a leap is really, for me, I think about it as cutting the cord. I’m going to focus full time on my businesses, and that’s it. I’m not going to work other corporate jobs. For me, it really was like a mental jump, a mental, “I’m going to resign from these jobs, and I’m going to really focus on it.”

Scott: You felt lighter.

Robert: Yeah.

Scott: You felt lighter afterwards didn’t you?

Robert: I did, and I felt a lot more focused. I can get down to work now, I can start working on these things that I had in my backlog for so long.

Scott: Yeah, it’s kind of like that bad girlfriend you just dragged along for six months because you didn’t feel like breaking up with her. It’s the same type of thing.

Robert: Pretty much. Well a lot of times too is you’ve kind of checked out from some of these other gigs. You’re putting in the time, you’re doing the work, but you’re not really thinking forwardly of how am I going to grow this product? How am I going to build this business? You’re really focused on your own stuff. At some point it doesn’t really do any good for you to continue in that role.

Scott: Right, yeah. One area that you had brought up was outsourcing when needed to develop the product. I want to talk a little bit about that, because I think it implies, really, to all three of the different stages, especially when you’re getting started, because you might not have a whole lot of time to grow a product.

Robert: Yeah, it’s hard for some people to do. It was hard for me, and actually, I wish I had done more of this the first time. Basically the idea, when we say outsource, and we don’t necessarily mean send your product to China. We just mean use people who have got time to get things done for you, because especially if you’ve got a full time job, you don’t have as much time. Pay somebody $10-$15 an hour to get some things done for you, so that you can grow your product while you’re trying to do this transition dance. I never did that, instead I would stay up until three in the morning working on my products, that’s fine. That’ doesn’t work for everybody, and it doesn’t work at all life stages. I couldn’t do that now with kids, but I could when I was in my 20s, right?

Scott: Yeah, if you’ve got something that can be done by somebody else, pay them to do it. It’s going to save you stress, it’s going to save you time, yeah it costs a little bit of money, but presumably you’re making a little bit of revenue anyway, and you’re growing your product. I think that helps you get to where you need to be to cut the cord quicker.

Robert: Yeah when I was growing Geowake I, basically what you said, I worked til three am in the morning, you’d spend a lot of nights and weekends building the product. From MapOut, now that I have two kids, I don’t have that flexibility to stay up all night. Don’t have a lot of time on the weekend, so I did hire a team of developers to help me build a product. It was one of the best things that I did, because I hired people that really knew, had great skill sets in the areas that they were building the product. They actually did a better job than I would have, a quicker job, and a better job, because they were able to really focus down on those specific areas. I architected, and pulled together how I wanted it built, and then they really focused on it.

Scott: Yeah, and there’s so many resources out there to go out and find that talent, and we’re not necessarily talking about full time talent, you know? In some cases we are and in some cases we aren’t, but they’ve got virtual office assistants who can process spreadsheets for you if you need to do that kind of thing. You’ve got those sites out there to hire a developer to build your website. There’s so many resources out there that can allow you to do these things, save yourself some time, take a little stress off, focus on the vision of the company, and keep growing.

Robert: Yeah, think about working friends and colleagues, and people that you know as well, because they might be willing to contribute to the business.

Robert: That’s true. Maybe as a partner.

Scott: A partner or at a reduced rate, you know? There’s always benefits to working with somebody you know. Except like you, I don’t like working with you, but … I’m just kidding. You know what’s funny is that we’ve never actually We’ve tried to work together. Yeah, we’ve never actually worked together on a project, you know? We basically do the same stuff.

Robert: One of these days it will come together.

Scott: Your hourly rate is too high for me, I can’t afford you. You don’t want to pay me. I’ve got cash flow issues man.

Robert: Let’s wrap up this episode. We talked about in this episode really how to make the transition from the corporate world into your startup. We talked about really three areas starting with a nights and weekends type business to get you going, then transitioning to more of a part time consulting work, and finally making the leap, and really think about the different … The stages that you’re in, what your risk tolerance is, what type of business you’re going to go into. I think that’s something to really think about as you try to make this transition.

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Each week we'll share insights and lessons learned to help you create ambitious goals for your business.

Robert Dickerson


Robert Dickerson is the Founder and CEO of Mapout a mobile learning platform that uses video courses to educate customers and train employees. He helps companies develop and launch their products.

Scott Davis


Scott Davis is the Founder and CEO of MobX, a mobile development software agency. He has 20 years of experience developing software for Government, Finance, Sports and the Telecommunications industry.