“It gets easier after 5 years”
My CEO sold his company for $30 million at 48 years old, after 8 years of an insane rollercoaster ride. He’s been an inspiration to write a lot of my content on entrepreneurship and success in general. I’ve written about his work strategies, the way he organized his office, his favorite productivity apps, his Google calendar time management template…
But there’s one thing I haven’t covered in depth yet and is very relevant especially now that he’s “made it”. After selling, my CEO stayed at the company for a few months, but eventually decided to resign and “retire”. After that, he focused on renovating his newly-acquired lake house, sailing his boat there, and spending more time with his family. He decided to focus more on life than work, and that’s what this article is going to be about.
A few months ago I reached out to him and we had coffee in the old center of the beautiful town he lives in, near the lake. After half a year of renovating his house and taking some free time, he started his own investment company and he now invests money in young startups he believes have potential. I thought it was the perfect time to ask him about work-life balance and how he will be working moving forward, now that he’s financially free. Here are 4 key learnings I got from our conversation.
My CEO and I both live in Denmark, a country known to promote work-life balance, not working crazy hours in the office, and a place where it’s ok to leave at 3 pm if you have to pick up your kids and then work from home.
While this makes it easier to avoid turning into a workaholic and keep some sort of sanity, it still means you’re going to work more than average as an entrepreneur. When I asked my CEO how he saw his work-life balance now versus when he started the company, his answer was unequivocal:
“It’s night and day. The only thing I can think about that the 2 routines would have in common is family, which is a conendrum. Even when I was working my butt off, I was always trying to make a bit of time for my family. But if I really think about it, when I started out doesn’t even count, because I got tunnel vision back then and I gave my company 100% of my time and energy for about a year. I truly think that when you start off, and if you’re serious about it, there will bearly be any time/room for family. It’s kind of sad but that’s how it is.”
The first year of starting a business is usually a “make or break” one. You have to look for investors, get offices, hire your first employees, get an accountant, and do the first books, not to mention the first fiscal year is usually a joyful mess… It gradually gets easier from there, but most businesses still fail within their first 5 years, hence the fact founders feel like they have no time for family.
In his book The ONE Thing, Gary Keller argues that productivity is about identifying the number one thing that will get you closer to your goal every day, and focusing only on that. He also explains that this means being out of balance with your life when working, and out of balance with your work when spending time with your loved ones.
“The act of living a full life by giving time to what matters is a balancing act. Extraordinary results require focused attention and time. Time on one thing means time away from another. This makes balance impossible.” — Gary Keller
That’s why it’s all about the ACT of balancing, not constant balance.
“The idea of counterbalancing is that you never go so far that you can’t find your way back or stay so long that there is nothing waiting for you when you return.” — Gary Keller
When I asked my CEO what he thought about this approach, this is what he had to say:
“I 100% relate to this idea of never going so far in one area that you can’t find your way back, but I also know from experience that in the sphere of work, it’s so hard to see the line, to know when it’s too much. Many times it’s like: Ok just one more hour in the office, just one more meeting, one more business trip, this and that. And there is a little voice in the back of your head saying: How close are you to crossing the line that’s going to be a point of no return, destroy your marriage, lose your friends, and basically crush everything you took for granted?
It’s normal to give up on some things to be successful in life. But if those things are your health, your social life, and your family, then you’re not doing it right. The act of balancing is achieved by knowing when to pursue the middle and when to pursue the extremes, in all areas, and at the same time. It’s not an easy rope to walk, but it’s worth it.
“If I had to do it all gain I still don’t think I would do anything different, because in the end it worked and I managed to keep my family and my sanity. But I can totally see why many people fail at this balancing game.”
I started at my CEO’s company around 6 years after he founded it. Back then, I remember that although I could tell it was still chaos and there was a long way to go to become a “serious” company, I could also sense the momentum. This was not a 5-people company with tiny offices anymore, it was something bigger. The company had made it past the 5-year mark, something only very few manage to do, so I knew it was a good sign.
“It’s funny you say this, because I feel the same. I remember your hiring was part of this big expansion phase we decided to do, getting a lot more people, and this obviously cost us a ton of money. And I remember thinking “We’re fine now, we’re not going to go bankrupt hiring all those people, I can relax.” Don’t get me wrong after those 5 years it was still intense, but it definitely got better.”
So many founders fail because they don’t have a long-term vision. There will always be people who somehow make it big much faster than average, like Kevin Systrom who founded Instagram and sold it for $1 billion only a year later. Or Peter Rahal who created the energy bar company Rxbar and sold it for $600 million 4 years later (and ended up alone in his $19 million mansion). Those are statistical anomalies, residual data, as there always are. The truth is, if you want to make it big, you’ll have to think long-term in most cases.
This means that unless you find a way to stabilize your workflow, your routine, and to get better at the act of balancing, you’ll burn out sooner than later.
“Once we made it past the 5-year mark I set out a few rules for myself. Things like no more staying in the office later than 6pm; no more phone calls at home after 7pm; no more business meetings on the weekends. I was able to scale back a little bit, knowing it wouldn’t mean the end of the business, and this was a great breather for me. Without that I would have burnt out. The problem is many people burn out before 5 years.”
When my CEO sold his company for $30 million, he was able to keep around $10 million after all the investors got their share of the profit. We live in a world where money often means freedom, and in 2023, $10 million is enough to retire and do whatever he wants with his time. Although he spent $2 to $3 million building and renovating his lakeside mansion, he still has more than enough money to live the rest of his life without ever having to work again. Yet, is that what he decided to do?
“I created my own investment company and already started investing in some startups. Does more money mean more free time? In my case sure, but I can also feel the pull to go back to my previous life. Everyday, I feel how easy it would be to spend more time with the founders on the phone, or set up another company, talk to investors… So I have more time, but I will always have the “entrepreneurship bug”, so unless I’m careful it’s very easy not to have time again.”
Some people make a ton of money for their whole life as a base salary, but since they never stop working they never have much time to enjoy the fruits of their labor. Some other people, like my CEO, get a big payday, have a break, and then try to figure out what to do with their time and money.
My CEO is an entrepreneur at heart, so he’ll never feel like he’s “had enough”. It’s not about making more money, getting a bigger house, nice cars… In fact, it’s not about getting anything nice money can get you. It’s about the pursuit of great ideas, creating something bigger than yourself, and having a blast.
“I don’t even really know how to define entrepreneurship. I know for a fact I’m not interested in making tons of money and all that, for me money is a byproduct of success, it’s a nice bonus. Success is starting a company, hiring people, making great decisions, and just creating something bigger than yourself. And these things take a hell lot of time. So do you have more time when you make a lot of money, yes. But is it easy to make a ton more money than you need and still not have any time because you get tunnel vision? Hell yes too.”
My CEO has already invested over half of his fortune back into other companies he believes in. Knowing the very poor success rate of startups, he may never see a return on his investment, but for him, it’s about more than that. The only nice thing he ever bought is his house and the furniture in it. He doesn’t have an expensive car, doesn’t wear fancy clothes, and his watch is a Garmin Fenix 7. Also, he still wears Nikes.
Money is only one part of the equation, and like every true entrepreneur, my CEO cares way more about the journey than the riches, and I hope this article inspired you to think the same way. No matter where you stand on the path of entrepreneurship, I hope you found some relevant insights in here, and I wish you the best of luck.
Enjoy the journey.