The hard thing about startups

There is a joke I sometimes share in my talks about startups. It goes like this:

"When I was a startup founder, I slept like a baby. I woke up every two hours and cried."

The quote is from the book “The Hard Things About Hard Things” by Ben Horowitz. While most know him as the co-founder of one of the top VC firms Andreessen Horowitz, he was once a startup founder. The book recalls his experiences and lessons learned from launching, scaling, and exiting his startup Loudcloud / Opsware.

I usually get plenty of laughs from the crowd. For the founders in the audience though, the joke gets nervous chuckles. They know all too well what a grind it is to build a startup.

In my own startup, every day felt like I was putting out fires. Sometimes implementations went sideways. Other times, it was a hot deal going cold. Then there were ongoing battles with our outsourced development team and even among ourselves about priorities and money. Even seemingly simple things like color schemes for our brand guidelines or placement of buttons on our UI sent us spiraling into endlessly time-consuming fights.

Through the 3 plus years of the startup journey, the one constant was the sense of exhaustion. Even the lone two-week holiday I took felt tiring as my mind went to thoughts about my startup. What was haunting me? Questions about whether I was doing enough to enable us to succeed.

It took me a few years after my startup to understand what matters when it comes to nudging the odds of startup outcomes. I saw these same things play out across dozens of startups that I advised or invested in. The three most important factors that stood out for me include:

1. Making fast decisions, taking action, and learning quickly
2. Having passion and persistence through difficulties
3. Being lucky on market timing and opportunities

Luck is not something you can predict or control. It falls your way because you do enough things that luck opens up more possibilities and increases your optionality. As the saying goes, you make your own luck.

Passion is your entrepreneurial fuel, but it is volatile like rocket fuel. Most startups that die do so not for the typical reasons cited like lack of capital or poor market fit. They crash because the founders simply ran out of energy or they ran into seemingly insurmountable obstacles. Instead of fighting through the challenges, they quit.

What most defines startups is the hustle and speed of execution. You could even think of startups as perpetual motion machines. They are constantly pushing out features, gathering feedback, and iterating. The faster you can do this, the better chance you have of finding product-market fit. This constant cycle of iteration though requires work, and a lot of it.

There is a debate that rages across social media every so often about the startup grind. On one side are those that glorify the hustle culture as a virtue. Others mock the advocates of the grind as hustle porn addicts.

This reminds me of a Twitter thread some time back by a former Microsoft engineer. He was on the team that built Internet Explorer 3, the product that helped Microsoft finally compete against Netscape in the browser wars. In the middle of this thread however, the author shared an odd confession:

“Sadly, there were divorces and broken families and bad things that came out of that.”

Immediately Twitter went nuts. They declared it a toxic culture, a den of spoiled tech bros, an offensive attack on worker rights, etc. Seeing the backlash, he backtracked. Admittedly though, any job that leads one to get divorced or normalizes 2 AM foosball contests in the office is probably not a healthy culture.

What most people missed though was these engineers wanted to join the team. A spot on the IE3 team was a coveted opportunity. As the author of the thread shared:

“Most Microsoft engineers made $1M+ then, regardless of team. But thousands wanted to join the IE3 team just to do their best work.”

They signed up to the grind.

That is what you are doing when you launch a startup. You are signing up to do whatever it takes to get an idea off the ground and mold this idea towards a scalable and repeatable business model.

When I mentor first-time founders, a common complaint I hear is how much work it is. These are often accomplished professionals that went to top universities and worked in some pretty intense jobs like banking, consulting, or law. And they all admit that they have never worked as hard in their lives as when they launched a startup.

It is hard to explain this to people that have never gone through the experience. You do not have other teams to offload work. There are no processes or systems to handle tasks. There is just you as the founder, your co-founders, and maybe a few employees or contractors to do the work.

As a founder, there is no job or task that is beneath you or beyond your scope. I had not coded in years, but rolled up my sleeves anyway to build our MVP. I was not a designer, but I created our brand kit and website. Everyone on the team did whatever was necessary to move the startup forward and make progress.

The other thing about startups is that a most of the journey is unpredictable. You have no idea what issues are going to come up or challenges you may face. A problem comes up and you just have to solve it, because there is no one else to turn to and it is not going to magically go away.

You simply have to do the work. As hard as it might be, you agreed to the mission. That’s why many startups go nowhere. Very few founders will ever admit it, but they did not realize what they signed up to. You need a high threshold for uncertainty and tolerance for pain in order to survive for any length of time.

This is why all the talk about work-life balance in startups makes no sense. In an established business or scaleup, there is an abundance of people, capital, and processes to help. As a resource-constrained startup, you do not have the option to offload the work. And when things blow up, you just have to deal with it.

What is more important in a startup is the vision and the culture. The people that join early on do so because they see alignment in values and have the desire to build something meaningful. They have motivation that runs deeper than pure financial gain, personal ambition, or short-term rewards.

Don't get hung up on work-life balance or the grind culture. Instead, be clear at the onset about the vision and culture of your startup. Build a team of true believers. And recognize that burnout does happen, so give everyone on the team permission to take the necessary time to rest and recover. That includes yourself and your co-founders. The best way to keep the passion alive is to take time away from the grind to gain perspective, explore ideas, be creative, and reset your mental and emotional state.

Did you struggle with the question of work-life balance in your startup? How did you handle issues of burnout in yourself, your co-founders, or employees?

Mark

Are domain names still relevant in 2024? Apparently so, and some startups are shelling out big bucks for the best domains! For example, one of the big news items recently was the huge sum paid for “friends.com” which elicited quite a few comments from the Twitter crowd, like this one response:

A few founders then chimed in with their own domain name acquisition stories like the $150K the founder of Loom paid and $33K the founder of Ghost shelled out. At least in these cases, those were some seriously great domains, and the stories of how they acquired them for under market value were impressive.

Should you be hung up on getting the right domain name however? If you have a ton of VC cash to blow, it probably makes sense as long as you budgeted for that in your raise. For early stage startups though, it is better to focus on a good name and then use hacks for getting a close enough domain if the .COM is too expensive or already in use.

By “close” domain name, you want to pick some domain that includes your startup name, but uses either a different extension or added qualifier. For example, you might try “[NAME].co“, “[NAME].ai”, “use[NAME].com”, “[NAME]hq.com” or something similar. You still get the value of your name in the domain for SEO purposes and discoverability, but let's you punt the decision on getting the .COM for when you have traction and can make a valid business case.

It is worth noting that even Facebook did not start with “facebook.com”. For those that were either around at the time or watched the Social Network, the original domain name was “thefacebook.com”. Quite a brilliant way to get started!