What most people don’t know about being a startup CEO/founder

Techblogs tend to paint a glamorous picture of how easy it is to raise a billion dollars in funding and build a startup. Reality is very different – it is hard work, a long journey and compared to a job, you are never really off the job.

As a startup founder for 20+ years and counting, 10 years as an angel investor, and lately  a Venture Capital investor through BootstrapLabs, I have seen a number of interesting patterns in startup founder’s/CEO’s behavior.

One thing I think a fair bit about is the ‘obsessive’ behavior of successful founders that I advised and invested in for the past 10 years (and I see this trait in myself as well…).

Startup CEOs are working super hard, and not always at the office. They always seem to be preoccupied, which drives spouses and family members crazy sometimes.

It’s not that they are literally working 90+ hours a week in an office, doing work tasks such as coding, recruiting, selling, etc. Once they start to grow their team and begin getting traction, to be successful they need to shift into how to really drive the business. And they always need to be thinking about the next big thing, and how to get the company to the next level or stage of growth.

The reason for this is that startups are not really executing a business model, they are in search of a hyper scalable business model. And that search continues until they get escape velocity, die, or divest for other reasons.

So on the journey of a startup CEO you don’t have a quiet moment in your head most days, you are constantly thinking about your ‘baby’, and trying to figure out how to solve problems 24/7 around the clock 365 days a week (or sorry, I mean per year).

As I tell many founders that pitch us at BootstrapLabs, you need to surround yourself early on with a team that shares this ‘obsessive’ behavior to drive your startup forward. And your most important job is to find those people and make them excited about the being part of the journey.

So even when having dinner with friends, or taking care of the kids, or in the morning shower, the founder/CEO is thinking that to hit that $5 million annual run rate to raise the “A” round, you need to ramp up hiring of the sales force and marketing teams. And you need somebody that has experience in X and skills in Y. Or that a particular piece of the product is inhibiting the growth, or is not good enough to drive Product Market Fit, etc.

When launching a new startup: You usually start in a search & discovery mode – that seems to be all over the place for many of the people around you. But once you start to get data points and validation of what you do, you need to quickly shift into a very different approach that is laser focused. At the same time you need to stop every 2 weeks or so and question just about everything and make sure that your assumptions are still valid.

From early assumptions to Laser Focus: Once you have found what to zoom in on, your most scarce resource is actually neither money or time, but personal attention span – which is why most startup CEO’s go into a reductionist mode to create a clear focus on the most important things that need to happen to bring the company to the next level. If you focus on the right things at the wrong time, your company dies.

This is why there are a few key things you need to learn early on as a founder/CEO of a startup:

• You need to recruit co-founders and team members that give you leverage (execute things independently better than you) – this will increase your attention to other things you do better.
• Early on and for the core team, you need to find people that share your obsession & passion.
• You need deep domain skills for the core things you are trying to do within the team, for everything else you need great advisors that can give you sharp insights a few times a month.

Because of the shift from discovery to reductionist mode, the early team is extra hard to build, as very few people are capable of shifting successfully between these two operating modes. In part, this is why it is so hard to find co-founders, since this prerequisite skill is so scarce.

After you have found a focus it becomes a tad easier, but you still need to build a core team with an almost obsessive drive to take things to the next level, and then work really really hard to become a Unicorn.

“No sleep for the wicked”