Quitting Entrepreneurship, Getting A Job

Quitting Entrepreneurship, Getting A Job

Open up Indie Hackers or self-funded Twitter and you'll find a stream of folks excited to quit their job to work on the app they've built that's now reached $10k MRR.

And it is a significant achievement! It is a milestone to take something from zero to one and quit a job they don't feel as passionate about as their product. It should be celebrated.

But no-one talks about making a move in the other direction: from entrepreneur to job (outside of a post-acquisition obligation to stay on). Perhaps it's because from the outside it looks like defeat, someone who was unable to succeed in entrepreneurship forced to get a day job to pay the bills.

I sold my Shopify SaaS app business last year for a life-changing amount. It was the culmination of working on my own things for seven years. After I sold, I took a year and a half to explore what to do next. And also to take a breath after the intensity of my startup.

During that time, opportunities popped up. I developed an idea into a product. As an exited founder, people and money now came to me. I was offered co-founder roles at funded startups. Investors reached out to fund my own thing or wanted me to deploy their capital.

For the good part of a year, I was sure I'd be jumping into one of these entrepreneurial opportunities. That was, until a job offer came that lead to a lot of reflection about who I am, what motivates my work, and what is best for my path.

I turned down all of these entrepreneurial opportunities to take the job. A younger me would be baffled by that decision! It was a tough decision.

This is the seldom-told story of quitting entrepreneurship and taking a job.


When I sold my 7-year-old Shopify app business at the start of last year, I had only the vaguest idea about what I might want to do next. I gave myself space and decided to not commit to any one thing for the first year.

That year turned into a refreshing year and a half of exploration. I am usually laser-focused on one main thing. I swapped the intenseness of building a company with a childlike distracted curiosity.

Many of the mistakes I've made in the past have resulted from searching in too limited a field of opportunities, having a narrow definition of who 'I am' and what defines my professional success, and doubling-down too early on long-shots, where going all-in was the wrong choice.

I instead tried things just because I was curious about them, rusty on, had neglected, or weren't natural for me to do. I dusted off my code editor and built a Shopify app store optimization product. Got involved in Twitter and Facebook groups. Collaborated with people I admire in the community. Helped out app developers. Explored co-founder opportunities. Made some small investments. And spent a lot of time with my new young family.

I could give myself this permission to explore as long as I knew where I wanted to end up. Just flitting from one thing to another would've been too stressful. I established some purposefully broad and vague goals. This gave me a general direction that wouldn't limit me on what to try. Some goals I defined at the start, others came into focus as I explored.

My goals were to:

  1. Be working on something I'm passionate about.
  2. Get to an income, or have a certain path to an income, that covers my personal needs.
  3. Have potential for uncapped financial upside event(s) in the medium term.
  4. Be working on it with peers that I enjoy working with and will learn a lot from.
  5. Not compromise family time.

By the end of the year, I wanted to choose one main opportunity that meets these goals.


Reflecting on the 20 years of my working life, I realized that the trigger to switch to something new has always been an ebbing of passion. It was interesting to consider why passion had ebbed for me each time.

  • I'd hit a ceiling on what I was learning
  • Work became too easy
  • My colleagues weren't doing good work
  • My friends left the company
  • I felt boxed-in, prevented from working on what could move the needle just because it wasn't engineering
  • Compensation fell behind my responsibilities
  • I didn't get to talk to and see how customers used our product
  • I didn't believe in the company's business and how it was doing it

Inverting the things that deflated my passion naturally gave me a picture of what makes me passionate about work.

  • Working on challenging things out of my comfort zone
  • With colleagues better than me that I can learn a lot from, and enjoy working with
  • Able to see the complete picture and then rally people and resources to affect change
  • Equitable compensation
  • Being close to customers
  • At an organization with great products and values that align with mine

I didn't realize it at the time, but nothing here would pigeonhole me into entrepreneurship. A job, volunteering, or collaborations could just as well satisfy my criteria.

Family & Friends

My family and friends are the most important people in my life. They bring me a lot of joy. Spending time with them is non-negotiable. I want to be a good father to my daughters, be there for my partner, and build strong friendships.

When I'm with them, I must be present in mind and body. Really with them, and not with my thoughts somewhere else, fixated on interesting problems or stressed out about work. Because I enjoy my work, and especially when starting a new business, this part is hard for me.

The People I Work With

We spend a lot of time with our business partners, customers, and colleagues. I want to like them as individuals and enjoy working with them. We should also value the same things. I've worked with a handful of people who don't share my values. Even if they're great at what they do, it is just not worth it in the long run. If and when conflict happens, it is irreconcilable.

Interestingly, different platform ecosystems attract different types of customers and partners. My apps were on several platforms: Shopify, BigCommerce, Google Apps, and Wix. You can see that how the platform does business and what's important to it permeates the entire ecosystem.

I most enjoyed being on Shopify and mixing with partners there. I find them enthusiastic, intelligent, serious, and willing to give back to the community.

The Shopify platform has a broad spectrum of merchant customers. I spoke to thousands of them on email and calls for support, customer development interviews, and productized services over the years. I learned a lot about different types of people and their behaviours. I saw the differences between a free user of our SEO app and a $49/month speed user or a $299 service buyer.

I like merchants attracted by products positioned to be a core function of their business, with a price tag that feels a little expensive but with no alternative. These customers are the most rewarding to work with.

One thing I was resolute in after selling my business was that I wouldn't be a solo founder again. The early days where it was just me were some of the hardest. Motivation was never a problem; the avoidable mistakes and missteps I made were. Once I started hiring a team, it was clear that I could've compressed the timeline and sold a couple of years earlier by bringing people on board earlier.

Then there's the difference between working with a hired team and peers. Peers can be a co-founder, colleagues of the same seniority, or investors. The dynamic between you and your hired team and you and your peers is very different.

In my business, I had no peers. I hired a team that was better than me in their areas, competent, and I enjoyed working with. I am very open and enjoy being challenged. Still, I was the founder and CEO. My words carried outsized weight, and I could feel that.

I missed having peers. Having peers with skin-in-the-game is so much more rewarding and fun. I make my best decisions through collaborating with a mix of my team and peers.


I'm fortunate that my partner has the same relationship to money as me. We don't have a laundry list of things that we lust over and want to buy. Birthdays and Christmases aren't an extravaganza of gifts. That being said, we do like nice things. We'll shop essentials from the discount supermarket then go to the Italian deli for cheeses and meats. We're more likely to buy a designer lamp we'll love for 30 years than a cheaper one that'll have to be thrown away after a couple of years. Or at least that's how we justify it.

We're in a privileged position where we don't feel restricted by money. This is as much to do with our spending as it is about our income. When we subsisted on $2k a month, we also didn't feel restricted by money. Not having to worry about money, or feel like we need more, is something that I want to continue.

We have had some lifestyle inflation since those $2k days, with a house and two kids and everything that comes with that, our bar is higher now.

But the bar is a low bar for a job. With my experience, I would be able to earn a salary that would exceed it.

It's a high bar for starting a self-funded business. It would take at least a year to get there from zero, with no guarantee I could reach it in that timeframe. Adding investors could provide a modest income or add a safety net.

A hybrid was the two co-founder opportunities that I was offered. They came with a salary, co-founder responsibility, and commensurate equity.

Another option would be to invest some of my exit funds to acquire a business at this target income level. Again, there's no guarantee that I'd find a suitable business and close the sale in 1.5 years. Although, right after exiting, I put the likelihood of this as higher than finding a job that met my goals.

Whatever I do, taking home just a salary, no matter how large it is, is not enough. It's odd to me to earn the same amount if what I'm working on is doing great or terribly, and if I am a key contributor to strong financial results or not.

As a founder with majority ownership, I can decide how much to reward myself through distributions, sale of equity, and an exit. In a job, these rewards are more structured through bonuses and equity.

I'd already figured out that equitable compensation is vital to me. I needed to pin down what equitable meant.

There are three components to this. Equitable in relation to how much risk everyone has taken. Equitable to the contribution I make. Equitable in relation to other people in the organization.

Starting a company from zero is a massive risk. Most companies fail. Should they succeed, it is most equitable if the co-founders and early employees walk away with the most significant rewards. As a company clears validation hurdles, building a product, acquiring customers, finding product/market fit, and onward, the risk reduces. Compensation should follow risk taken.

Many companies struggle with rewarding individual employees for the contribution they make. I get it; we can only achieve success when every area of the business works together. We can't put an absolute dollar value on how many revenue dollars a support/engineering/product/marketing person directly contributed.

Still, when someone exceeds expectations, the company should reward them. Conversely, when people are underperforming, they should not be compensated at the same level as those doing what's expected of them. Many companies do not act in these cases, preferring uniformity, not to rock the boat. Good leaders adjust compensation to match performance and do not ignore under-performers.

Finally, the company should compensate people equitably in relation to each other. Again, this does not mean uniform or rigid compensation levels. It does mean a structure so that if everyone's compensation details got leaked, every person's compensation could be justified, mainly based on the contribution they're making and how much risk they've taken.


One's self-concept (also called self-construction, self-identity, self-perspective or self-structure) is a collection of beliefs about oneself. Generally, self-concept embodies the answer to the question "Who am I?".

My goals, what makes me passionate in my work, and what I look for from money was all clear at the end of the first year. What was a lot harder was opening my mind up to non-entrepreneurial opportunities. My self-concept was that I am an entrepreneur.

I didn't know it at the time, but I'd reached a state of identity moratorium when considering the opportunities before me.

Identity moratorium is the status that Marcia theorizes lasts the longest in individuals, is the most volatile, and can be best described as "the active exploration of alternatives". Individuals experiencing identity moratorium can be very open-minded and thoughtful but also in crisis over their identity. An example of this would be a college student who lacks conviction in their future after changing majors multiple times but still cannot seem to find their passion. - Wikipedia

Each entrepreneurial opportunity I had in front of me didn't fit quite right with all of my goals. That was confusing, as I could've only dreamed of these entrepreneurial opportunities ten years earlier. They were all undoubtedly exciting and had considerable potential.

The Opportunities

I was, first of all, a coder. As a kid, I enjoyed playing games on my ZX Spectrum. One day the tape loading glitched out, and I could see the game's source code. That started me on the path of software engineering. I founded a web agency, sold it, worked my way up from engineer to development manager and then consultant before starting my Shopify app business. After selling, I was curious to learn if I should get back into engineering.

For the last couple of years of the business, I hadn't written a line of code. My team were much better at that than I was. But after I sold, I wondered if engineering was something I'd enjoy getting back into. I got my skills up to speed and built out a product I'd have loved to have as a Shopify app developer: App Store Analytics.

It was fun to build again. It reached $2.5k MRR pretty quickly and attracted people in the community I've long admired. I could see a path to the magical $10k MRR hurdle.

Reflecting on my goals, though, it met surprisingly few of them. It wasn't particularly challenging; building a business like this feels well within my comfort zone. I was doing it alone. Bootstrapping with limited people and resources felt restrictive. Still, I knew if I stuck it out, I'd be well compensated. I loved speaking with customers and helping them. And, of course, the company and values aligned with mine! App Store Analytics met some of my goals, but not enough.

The market for acquiring Shopify apps is hot. Four opportunities presented themselves. One was an awesome exited founder who I gelled with immediately, where we'd buy and operate an app together. Another one was where two investors approached me separately, looking to get into the Shopify space. They would put up the cash, and I would find and operate apps to buy. The final opportunity was two very credible young founders with a finance background. They had secured funding and were well on the way to copy what's happening in the fulfilled by Amazon space on Shopify.

Each of these had its own merits and drawbacks. Some I'd have to take the lion's share of the risk to search for and close acquisitions. I was already a year in post-exit; the prospect of spending at least another year with no guarantee of success didn't feel like a substantial step forward. Some opportunities would involve working alone, or with peers I didn't feel were on the same wavelength.

On the plus side, I enjoyed my own M&A and was excited to work on the challenge of acquiring companies. It felt out of my comfort zone but still where I'd be able to do an excellent job of it. Compensation was very equitable as equity and debt funding in the current market comes on good terms. I could learn a lot from the people I'd be founding and partnering with. Again, this met some goals but not all of them.

My final entrepreneurial opportunities came in the form of two serious offers to co-found Shopify apps. One was a modest existing business where I'd become an owner, and we'd raise funding to build our app. Another was an exited SaaS founder new in the Shopify space. I found it hard to get passionate about taking another Shopify app from zero to one in both cases. I need this passion in my work.

Then the job came along. When Mike, the co-founder and CEO of Rewind, reached out to talk to me about joining, I was in two minds about whether to take the call or not. I didn't want to waste time and lead him on. I still had this prejudice against taking a job due to my self-concept as an entrepreneur. And yet, I'd long admired their SaaS product, strong Shopify business, and the people I'd met there, so I felt compelled to at least spend 30 minutes on it.

On our call, there were a few things that struck me. Mike was open and transparent to a degree I didn't expect him to be with an outsider. When he asked me what I was looking for, it was with a genuine interest in if it would be good for both of us, not just to see if I could slot into a gap they had. Mike listens intensely and is thoughtful about what he says in a way that's difficult to describe.

We talked about what makes me passionate about my work. I said I didn't know my ideal role or even if I wanted to take a job. Mike said I'm probably like him, a generalist, and that we'd both broadened our experience from our initial specialisms.

All well and good, but I couldn't see how one of the components that makes me passionate about work, being able to execute with a broad view across functional areas, could happen in a job. I'd only been able to achieve that as a founder and CEO. And I doubted Mike was ready to move on.

Sam, the COO, floated the idea of General Manager. Their Shopify business has strong growth, great products, and an experienced team. Armed with VC funding, they're looking to expand on the platform. I would lead this.

Now, this was exciting. I had the same feeling as when I received an offer to buy my business. It felt right but not fully resolved in my head. My mind brimmed with ideas. But I hadn't yet quite fully adjusted my self-concept to accommodate not being an entrepreneur. Was I really going to take a job? Could it be that this, here, is a better fit for me than anything else right now?

On Balance

It was clear to me that to ignore the possibility of taking the right job and blindly pushing back into entrepreneurship would not be a balanced decision. I just needed something to give me that final push over the line.

By this time, I'd chatted with a lot of the Rewind team. Any doubts or concerns about what it'd be like to work with them had been ironed out, and I just became more excited to call them my colleagues—one little wrinkle: money.

If getting rich is your thing, a job is not likely to get you there. A windfall from a job's stock options is nice, but it isn't retire-at-30 money. If you want that kind of money and can tolerate the risk and sacrifice, start a business (however, that in itself is a terrible reason to start a business).

As I wrote earlier, I'm looking for enough money not to feel restricted by it and for the compensation to be equitable.

The offer was for salary, bonus, and stock options. That wasn't because I'm something special- Rewind offers every employee this structure. That tells me that they want everyone to share in the success and that they care about performance.

When I was a founder with majority ownership, I could pay myself whatever I liked. Here I needed to trust the leadership not to play games with bonuses and stock and keep compensation equitable. At a previous company, early employees' options and bonuses through sleight of hand became worthless while an executive cashed in, rolling up to the office in their new Lamborghini.

I talked with current and former Rewind employees who clearly respect and trust the executive team. Their perspectives and the openness, consideration and humility I saw from Mike, James, and Sam, easily engendered my trust in them. The offer looked equitable today, and I trust it to continue to be so as they navigate the next period of rapid change.

It was time for a spreadsheet. Before I sold my business, the spreadsheet told me that I'd make more money in almost all scenarios if I didn't sell for another couple of years. I still sold. But to see those hard numbers stare back at me from the screen solidified my decision and minimized the chance of future regret.

I developed a tool with my psychologist where we go into the future and think about how I'd feel in various scenarios.

I modelled the scenarios here. Of course, the entrepreneurial scenarios varied from making much, much more money than in a job, to losing money. The most usable scenario was to look at the most likely outcome for the job across salary, bonus and equity, and comparing it to my previous experience starting businesses when things went well.

Here I'd still make an order of magnitude more money by choosing entrepreneurship. No matter how it appears, money does have a strong pull on me. It isn't easy when it feels like you're forgoing that kind of money. However, I knew that I needed to soundly assess this with my goals, passion, and money criteria. And evaluate it with how it feels.

The critical question and the heart of the matter is: if I passed up an opportunity to co-found a business that goes on to a massive exit while I'm working at Rewind, how would I feel? I knew I would not regret it.

With all things considered and echoes of my decision to sell my business, I decided to quit entrepreneurship and take a job. I signed as General Manager - Shopify at Rewind. A few weeks in, wearing my corporate hoodie and typing on my company-issued MacBook, working for someone else for the first time in 10 years, I couldn't be happier.

I haven't written this as a sales pitch for Rewind. I hope more than anything that if you're sitting out there wondering what your next move will be that what I've written helps you find what's right for you.

If that turns out to be a job, let's talk. We're hiring for a bunch of roles, including on my Shopify team, plus there's always space for talented people. Email me, I'd love to meet you.

Epilogue: The Entrepreneurial Path

Sorry, the title I chose was clickbait. I don't consider that getting a job is at all quitting entrepreneurship.

Many may not consider me an entrepreneur right now, but I think like one, and I'm still firmly walking my entrepreneurial path.

A job is an education like no other.

The first time I got a job was after I sold my web design agency. I had taught myself web development, design, business, and marketing to start it back then. I learned by making many mistakes, safely living under my parents' roof and eating their food. It did grow into something saleable, but I was woefully aware of how much I didn't know. I had skipped university to start the agency. Going to uni felt like a backwards step, so instead, I took a job for my education.

I find myself in a similar position now. My third tech business was much more successful than the others. I feel solid in many areas and confident I could do something similar again. But what does a well-run, venture-funded company of over 100 employees, whose values align with mine, look like from the inside? There's a lot to learn here now and to learn as we continue our strong growth. The people I've met at all levels and in different areas are impressive. There is no better education than this to arm me when I build a similar company in future.

With the right boss, you can act like an entrepreneur in any job.

One of my first jobs was in business development for an interior landscaping company. They sold office plants on contract and did large installations. Think palm trees in the atria of multinational corporations.

My role was to find these jobs and pass on warm leads to the team. My entrepreneurial mindset heavily influenced how I did the job. My boss expected that I'd hammer the phones, and that was pretty much it.

Instead, I built a CRM (before I knew that's what it was called) in MS Access that all key account managers and I could access. The CRM meant we had a clear view of the pipeline and worked more efficiently.

Our leads came primarily through architects. The challenge here was twofold: getting them to specify interior landscaping as part of their projects and putting our company top-of-mind.

I pitched the idea of an interactive CD to my boss. I knew I could build it myself since I knew web development and a little design. She loved it, and her boss did too. The CD generated a lot of new business, and a nice bonus followed.

Both of these initiatives were not expected from me in the role. My colleague with the same job just banged the phones, which was also okay. My boss was forward-thinking enough and gave me autonomy and purchase to execute these ideas. With the right management and role, I thrive when given a mission that my entrepreneurial mind can execute.

Speaking with Mike and Sam, I can see that this behaviour is encouraged and nurtured at Rewind. The remit of my role is broad across all functional areas.

At Rewind, I'm in, yes, a job, but one I'm passionate about and that allows me to act like an entrepreneur. When I move on from the company, perhaps starting something again, I'll be well-equipped to make an even greater success of it because of my experience here.