Do Founders Ever Take Vacation?

There is a raging pandemic that has recently swept the startup community. It has come on so fast, it is hard to know what to make of it or how to slow the spread. But it is undeniable how deeply embedded this disease has become. Of course, I am talking about the VC Work Flex Syndrome.

The symptoms are fairly easy to spot. A VC in the early days of the infection will to go on Twitter and proclaim how hard they are working. This affliction is most readily manifests during the summer, major holidays, and Burning Man season. In more acute cases, a VC may even share selfies from the office in a desperate plea to be seen in the throes of hard work.

Of all the VC memes, this is one of the most maddening of them all. While VCs are flexing their modest hustle, founders are actually working all the time. And when I say “all the time”, I mean over weekends, holidays, the Summer, and whatever cool, hip multi-day experiential life-changing event happens to be going on that all the VCs are tweeting about.

But thanks to those brave VCs for sacrificing the occasional holiday to “be in the arena”.

Before I started my own startup, I thought I worked hard. And there were periods of my life when I was pulling all-nighters like when I had a huge upcoming project deliverable or preparing for a big customer pitch. Probably the hardest I ever worked was when I changed careers to software engineering and poured myself into docs to build my first production system.

It was only after I launched my startup that I understood what the founder life was like. Even though you have co-founders, you are all overloaded. There is no one else or any other teams to delegate work to. You are responsible for everything and no task is beneath you, including all the things you avoided or were no good at. Even Jensen Huang of the now three trillion-dollar tech behemoth NVIDIA said in an interview, “I used to clean toilets. I cleaned a lot of toilets.”

While we had set out to define the roles and responsibilities of each co-founder at the beginning, that did not last long. Soon as we dived in, we all took on a bit of product, engineering, marketing, sales, support, ops, and fund raising. While we each had strengths, big decisions required all of our approval and we often had strong opinions even on non-consequential matters.

The result was that none of us ever took time off. Perhaps it was our fear that the other co-founders would screw something up. The biggest issue was that there was too much work to do and never enough time to get the important matters finished.

Other than an extended family trip for my 92-year-old grandfather, there were no holidays, vacations, or free weekends for the three years of the startup. At most there were half-days of uninterrupted periods where I was not on a laptop or call or other work activity. Even then, work was on my mind. There were plenty of nights when I would wake up from nightmares about the startup.

Everyone has a different approach to work. Every founder I have known or spoken with has all said the same thing. The startup had become their life, consuming every waking and sleeping moment. Even if they managed to take some time off, they were still thinking about the startup. Some even shared how they felt guilty for taking a break, no matter how short.

There should be a warning like we have with cigarettes that startups take years off your life. There is plenty of medical evidence that this type of constant work and anxiety is not healthy. I have rarely met a founder that said they had a better health during their startup than before. Even the comedy Silicon Valley had a running gag where the CEO would visit the doctor about his declining health.

Here is the hard reality though, founders do not have the luxury of taking time off in the early days. This is when it is just a founding team and a handful of employees, you are iterating on the MVP, and getting your go-to-market rolling. As a founder, you cannot afford to check out from work for several days. It is your startup after all.

Is there ever a point when it is ideal to take a break? When your startup is seeing high growth and you have a strong executive team in place, then you are in a better position to delegate. It is still hard to go completely off the grid, but at least there is backup and staff to cover most situations.

Life-work balance is simply not possible for startup founders. However, the risk of burnout is high and there is a point when the mental and emotional toil starts to diminish your productivity and lead to more mistakes. Can founders balance the stress of startup life with the need for rest and recovery?

Here are six ideas to consider based on conversations with founders on how they were able to find time to “tune out” while running their startups in the early days:

1. Set boundaries – Block out times during the day and evening for focused time for yourself. Enforce this by turning off notifications on your laptop and phone and block those times on your calendar so the team is aware that you are not going to be available during those times.
2. Leverage technology – There are plenty of apps that can do a thorough job blocking distracting websites and apps during your focus time. You can also leverage many of the Generative AI apps that can help automate basic tasks and also answer questions on your behalf when you take a break or schedule a longer holiday.
3. Ruthlessly prioritize – There is always more work to do, but not all work is equal. For example, the Eisenhower Method is a way to prioritize where to focus limited time. There are many other methods, but choose one and stick with it to ensure you avoid busywork and only do work that has measurable impact. This way you can free up time for vacation without feeling guilty.
4. Compartmentalize time-off – However shutting off completely is usually not feasible, even for just one day. Designate a block of time in the morning and in the early evening (or whatever works best if you have a remote team) during vacation when you are back on work to catch up with team and handle any escalations or time urgent matters.
5. Start small – The anxiety of being “off the grid” can be nerve-wracking. Give yourself permission though to take a half-day or full-day initially, and over time take larger periods of time off later as you build confidence that things can still operate smoothly without your constant presence.
6. Find community – While not related specifically to taking some downtime, speaking to other founders can give you ideas and the confidence on ways to get more rest, manage your time effectively, manage teams while away, and build in vacation time.

What are some ways you have found that work well in creating space in your busy life for personal time? Let me know, I would love to hear how you managed this as a startup founder!

Mark

Last month, I wrote a post to help founders deciding between bootstrapping or going for VC funding. While there is no one size fits all answer, most startups are better off staying bootstrapped given how hard it can be to achieve the level of scale that would generate a sizable return for investors.

Many people think building a scalable bootstrapped startup is impossible. There are plenty of counter examples however like Dell and Zoho. Then I recently read a post from the founder of Todoist, Amir Salihefendi?, where he shared his own inspiring story of bootstrapping Todoist to $100 million in revenue. I share his post in its entirety below:

Todoist has made more than $100 million in total revenue, which isn't very interesting because many others have reached this number. What's interesting is that we did it in our unique way:

• Fully bootstrapped. Customers have supported us since the beginning, and we've used only our revenues to improve things further.
• Complete independence. Since we are customer-supported, no one tells us what we can or can't do.
• Remote-first. But not only remote-first, we've hired super talented people worldwide who never went to Ivy League schools or worked at Google. Many of the early people who joined Doist have seen a 10x increase in compensation as we've scaled Doist.
• Europe mixed with US mentality. We've achieved this by working 40-hour workweeks and taking 40 days of vacation per year. We only work on weekdays. The three-member CXO team has 8 kids, and we got them while we scaled Doist.

The most critical personal lesson I've learned is that you can do much more than you think. I came from a refugee background and started a real school in the 4th grade. Starting and running a tech company was not even plausible while growing up. But here we are! So start learning, growing, and building! You got this ????

It was so awesome being back in NYC this week for the AWS Summit in NYC! It was an opportunity to meet developers and startup founder in person, help with questions about building on AWS and with Generative AI, and to film a few videos that I am excited to share in a couple of weeks!

Were you at the AWS Summit NYC? If we did not get to meet, I would love to hear your thoughts and feedback on what we can do to make the event experience more enjoyable and valuable.

I am heading back to Asia next week to speak at the AWS Start Day event for our AWS Summit Taiwan on July 23rd! Along the way, I will be in Hong Kong beforehand and potentially a few other spots to meet up with startups and developers. If you are around and know of any cool events, let me know and perhaps we can meet.