How it felt transitioning from seven years as an entrepreneur to a full-time employee

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“I had a panic attack this morning,” my friend Dennis shared with me.

Dennis hadn’t had a “real job” in twenty years. He’d dabbled in various businesses, but now, shortly after joining our startup, we were entering into an acquisition. That meant both he and I would be taking on full-time jobs on the backend of the deal.

He was nervous—to the point of having a panic attack.

So was I.

In this post I wanted to share what the journey has been like going from entrepreneur to full-time employee. But first, I want to share some of the evolution that led to our acquisition, starting from the beginning.

Starting a Company from Our RV

Since I left my job in 2014 to start traveling with Alyssa, I haven’t held a “real job”.

We’ve worked with a hand full of clients over the years, sometimes for months at a time, but most of our income has come from projects we own. Not only had we skipped the commitment of a full-time job, but most of the decisions we made were geared towards attaining even more freedom.

After our first year on the road, we started a freelance videography business that allowed us to keep traveling. While we loved the people we worked with, we felt that multiple clients were akin to tiny little bosses. After three years in our service business, our side projects like this blog, Alyssa’s book, and our conference made enough that we no longer needed to do both. So we quit taking on client work.

When it came time to decide what we should do next, the primary deciding factor was, “What will give us more freedom?”

With each of the decisions—leaving our jobs to start a client (service-based) business and then moving to a product-based business—we found a little more freedom. With this freedom we kept RVing, spent time in the outdoors, and eventually started traveling internationally.

Then I started a tech company.

At first, the idea behind Campground Booking was that Paul, my cofounder, and I would prioritize our nomadic lives and the business would integrate into the lives we’d created. Our business would fit into our lives and not the other way around. After all, we’d already worked so hard to own our time.

For a while, this was the case.

In the early days of Campground Booking, Alyssa and I still traveled full-time. We drove across the US in our RV. In early 2018 we packed up and campervanned in New Zealand for two months. We continued to do all of the other projects (like this blog) that we’d always done.

Then, in early 2019 Paul and I made a decision to go all-in on Campground Booking. In some ways, the decision was almost made for us. We’d were experiencing growth, which meant more support was needed and more features needed to be added to the platform.

On the personal side, we’d also found out we were pregnant. Alyssa and I decided to rent an apartment for a year to have access to medical care and without traveling full-time, I could really focus on scaling Campground Booking.

This period was a make-or-break for the company. We were starting to make a little bit of money, but not yet enough to cover any kind of salary. We’d either make a real go of it or pivot to try something new.

In this phase, I did a complete 180 on how I’d been running my business. Instead of working from an RV in between hikes and travel, I went into a coworking space every day. Paul quit taking on lucrative side coding projects to further develop our product. Our eventual goal was to bring the company to a point where we could step out and sell it, but there was a lot of things to be done before that point.

Our only focus was making Campground Booking work.

And it did.

During our first year of focusing on it full-time, we grew the business by 5X.

It’s very interesting what can happen when you treat something like a real business. I think back to a conversation I’d had with Nathan Barry, founder of Convertkit. Nathan said that most founders make the mistake of believing a startup could fit into a 40-hour workweek. He felt from personal experience and observing other founders that in the early days of a company, it takes a sickening amount of work to bring something to life.

In my mind I wanted to have a real business, but it wasn’t until we quit treating it like a side hustle that we created one.

Going All-in on Campground Booking

Why work 40 hours a week for someone else when you can work 80 hours a week for yourself?

My days in 2019 were spent mostly at the office. Wake up. Eat. Coffee. Walk to coworking. Come home at night. Rinse. Repeat.

The work-life balance we’d created on the road went out the window. We were building a company. There were no other options.

Even when I wasn’t working, I was thinking about work.

While we were RVing I felt less pressure to make Campground Booking successful. Even if the business tanked, I hadn’t sacrificed all that much (other than time). I was working on it in between hikes at Banff National Park or while we explored the coast of Maine. I hoped it would be successful, but I was hedging my bet in some ways.

When you work on something full-time and give it your whole self, you care if it works out. You care a lot. 

A lot of people talk about the sunk financial cost, but I hear less about sunk emotional costs. When you have something that takes an exponential amount of your energy, there’s pressure to see it through. Otherwise, all the time you put into it was wasted…or at least that’s how it felt.

I was all consumed. It was also starting to spill over into my relationship with Alyssa.

Early into 2019, we’d signed on a decent-sized customer who wanted to open up for reservations at midnight Pacific time (2:00 AM Central). I stayed up all night long handling support calls from people. A lot of people were able to book online, but so many were trying to fight over the same sites it was causing problems. While Alyssa slept in the next room I had to quietly try to calm down campers who chastised me for ruining their family’s RV vacation.

This particular customer had support calls that bled over into a vacation I’d booked with Alyssa and my sister-in-law’s family. We were in the Bahamas enjoying time on the beach and I felt awful having to drag out my computer to answer emails and steal away time from a trip we’d had planned for months. Yet, I didn’t see any other option.

There were a number of situations similar to this one over the course of this year.

This is the part of the story where I should probably mention how it was all worth it and sacrifice is essential. Maybe that’s true, but I look back on this time and just remember it being hard. Really hard.

Growing a Team Beyond Two Cofounders

When Paul and I went full-time in the business we made two part-time hires (shoutout Scarlett and Sean!) to help with sales and support. I felt immediately lighter. No longer was I the last line of defense for support calls or demos. It was a good feeling.

There was still a lot to be done, but now I wasn’t alone.

As we grew, it became clear that Sean and Scarlett couldn’t only work for future stock and we needed to pay them (and ourselves) a living wage. We needed money. In 2020 we decided to open a round of funding. The business had been entirely bootstrapped for four years, but we couldn’t take it any further on our own.

The company was making some money, but not nearly enough to pay ourselves a market rate. Plus, we’d hired even more contractors who were doing an awesome job and we wanted the ability to bring them on with a real salary.

We secured $750K (shoutout Greater Colorado Venture Fund!) and it quickly went from being Paul and myself and a couple contractors to a team of ten full-time employees! Similar to how it felt in 2019 when we’d decided to quit our side projects and go all in, the stakes were elevated.

In every way that I’d dreamt about, we were running a real startup.

This had been a major goal of mine. Find a need. Build a product. Scale something bigger than myself and then eventually sell it. It was exhilarating to reach the point where we were supporting real businesses and creating jobs. It was also much more responsibility. The risks were elevated. It was more than a lifestyle business. We had investors and employees and their families who were depending on us.

My friend and our COO Garrett later told me that after we’d raised money that I “looked heavier.” Not like I’d gained weight, but like I was carrying more weight on my shoulders than before. I didn’t recognize it in the moment, but looking back I would agree. I’d gone from full-time RV life with Alyssa and Ellie to leading a team of 10 employees with a monthly payroll of over $60,000. Our software was managing millions of dollars for small businesses who relied on us to be there 24/7.

This was exactly where I thought and hoped the business would be when I started it years earlier. It was exciting, but it was far from the lifestyle business we’d been running to date.

An Unexpected Acquisition Offer

2021 came with an unexpected twist.

On April 1st of 2021, we announced that we’d sold Campground Booking to Camping World/Good Sam.

The acquisition process had been going on since January, but it wasn’t public until April. Not only are there a lot of things that can go sideways in an acquisition conversation, but you’re selling to a publicly-traded company there are more reasons to be private.

The offer came only months after closing our round of funding and wasn’t something we’d planned to pursue in 2021. However, we felt it would be a win for our customers, team, and investors, so we said yes.

Because our company was still relatively small in size, a lot of our deal was dependent on our team coming on board in the acquisition. It wasn’t quite an “acqui-hire” as we did have an existing product and business, but in many ways, the excitement was more of what we could bring to the table with our experience as people in the RV space.

Giving up Freedom

One of my favorite books is the Subtle Art of Not Giving a F*$&. There’s an idea Mark shares about the power of choosing your pain and how our lives will never be pain-free. When you’re poor, your pain point is that you don’t have money. When you have money, your pain point is that you don’t know what to do with it or you’re stressed about losing it. Regardless of where you are in life, there will always be pain.

The best we can hope for is to choose the pain that we’re okay with experiencing. An even better frame of mind is to ask yourself the question: “What are you able and willing to suffer for?”

The narrative in my mind during the acquisition process was that after years of scrapping, I was okay with trading a season of freedom for a season of stability.

When I was introduced to the Camping World/Good Sam team, Alyssa had literally just come up and given me a hug to tell me she was pregnant. We were going to be parents of two babies and whether the story in my head was right or wrong, I longed for the ability to be present with my family and not miss out on any more moments.

When Ellie was born, I took off for maybe a few days before I started diving back into emails. It was during the hustle period of 2019 and I gave myself a terrible paternity leave. It pains me to say that I don’t remember much of the days of her being a  baby. My mind was somewhere else.

What people don’t tell you when you start a business is that your mind rarely turns off. Maybe it’s just me, but when I’m working on a problem, I don’t leave that problem with my laptop. It’s in my mind for hours. When I should be sitting down with Alyssa to eat dinner and be present in conversation, I’m thinking about that problem. I know that’s a personal issue and something I need to work on, but the point is that I struggled to balance building a startup with living the life I wanted.

My Transition from Entrepreneur to Employee

I think my biggest fear about transitioning from entrepreneur to employee was more around the identity I’d created for myself than anything.

I was an entrepreneur. I’d boldly told the world this for years, on my podcast, this blog, and to anyone who would listen. The idea that I had to shed this identity and work full-time felt more damaging to my ego than anything.

The truth was, I was ready to be surrounded by a bigger team. I was ready to lift this business off my back and create stability for our employees. I knew that we’d be able to hire more developers to build better features for our customers. However, ego doesn’t always care about rational thought processes, so the fear was still there.

So, how has it actually been going from entrepreneur to employee? What has been the good, the bad, and how aligned were my fears around losing my freedom?

The Good Parts about Transitioning from Entrepreneur to Employee

#1 I no longer wake up at night stressing about the future of the company. 

There was a period of time when I struggled to sleep through the night. I’ve never had a problem sleeping in my life. In fact, the opposite is true. I’m a notorious sleeper. I’d sleep anywhere—a restaurant booth, on a friend’s floor, on a boat. Yet, at some point after we’d raised the money, I quit sleeping well.

I’d wake up with my mind running about how we were going to get a feature out the door or in fear about a competitor creeping up on us or if we were going to have to raise another round of funding. Not all of these thoughts were rational or true or needed to be sorted out at 2 AM, but my mind didn’t ask me.

Post-acquisition, this is not the case. It’s not that I no longer care about our customers or the business, but we’ve scaled up our team significantly. We have the support and team in place to know that our customers will be taken care of and it feels good.

#2 I feel lighter.

When Garrett told me I looked heavier, I felt it. At times we’d have a customer complain or churn and my monkey mind would immediately start thinking about how we could lose it all. The first domino had fallen and the rest would be history…but it never happened.

I no longer carry this weight. When friends have asked me how I’ve felt since our deal was complete, lighter is probably the word I’ve used the most.

I actually don’t think we are at our best when we feel heaviness. A little pressure is good, but too much can break you over time. The work I’m doing now I feel is genuinely better and I’m enjoying it more than I did during that heavy period.

If the business is no longer fun, that’s when burnout becomes a real internal risk. If you aren’t enjoying what you’re doing but just powering through each day, how are you going to compete with someone who is having fun and feels a sense of lightness?

Our best decisions don’t come when we’re overwhelmed or exhausted.

#3 Our product, service, and sales are better and our business has 2X’d in less than a year.

Since joining the Good Sam team, we’ve made several strategic hires and leveraged a large enterprise to fuel our growth. We’ve been able to do things I wanted to do while bootstrapping the business but could never afford to do (like scale up our development team!).

This week I shared with Alyssa the map below which has pinpoints of all the parks that are now using the booking platform we created. As an entrepreneur, one of the driving motivating factors for me was freedom but I also wanted to grow something larger than myself that made an impact.

When I was trying to decide if I wanted to sell CB or not, money and freedom were major factors. But there was also the question of if selling would do right by our customers and make the product better. Now, our product is more stable with infinitely better support so we provide a better all-around customer experience.

My Biggest Fears About “Losing Freedom”

The biggest fear about transitioning from an entrepreneur to an employee was around the element of losing freedom in going back to a “real job”. However, how much freedom do you actually have when you eat, live, sleep and breathe your startup? In the past three years, I started working more and more, missing out on time with family and stressing over the company when I should’ve been focusing on what’s most important to me.  I recognize in retrospect that if you want freedom, a tech company may not be the best path towards having it.

Today

Today, I’m lighter than I was a year ago. I’m a much happier person since we sold the company and have no complaints. I was stressed and anxious most of the time. Now I’m not.

Our son, Eli, was born in October and this time around I had a very generous paternity leave, which I will forever be grateful for. During my three months of leave, we spent over a month visiting family and friends, even making a spontaneous trip out to Disney World.

Plus, now that I’m not the last line of defense to keep the company alive and breathing, Alyssa and I can travel again without feeling like I should be somewhere else. I thought when we hit the road in 2014 that I would never be an employee again. Being entrepreneur was a badge of honor to me. But it’s given me a lot of peace after years of hustling a little too hard.

I will always be an entrepreneur. Even now, within a bigger company I am helping spin up new business ideas. After so many years of scheming I’m not sure I am capable of doing anything else. While my official title as changed from CEO to Senior Director of Product Innovation (yes, it’s very long and important sounding), I’m excited for how this chapter rounded up and for the opportunity to provide value to a larger company.