Home Article and Opinion 4 first-time CEO mistakes to avoid at all costs

4 first-time CEO mistakes to avoid at all costs

Recently founded a startup or planning to soon? These are some of the most common founder mistakes to avoid, including how to avoid burnout.

When I was only 23, I started my company by myself, with no outside funding or support. In a few years, I scaled the company into a multimillion-dollar business with over 50 people working for me. But then I burned out hard.

After a creative retreat, I figured out how to pivot and increase my business’ profitability, while spending significantly less time managing it. These days, I’m focused on investing in smart founder’s building interesting SaaS companies with high growth potential. I also rediscovered my passion for surrealist art, and started rapping and fashion designing, among other creative pursuits.

As a startup advisor, people often ask me for help scaling or optimizing their sales and marketing efforts. But here, I wanted to share some broader business advice for first-time founders that I wish someone had shared with me.

Thinking the hustle will someday end.

I used to dream of hitting certain business milestones because I thought things would get easier if I met them. But every smart experienced entrepreneur will tell you, some things get easier, but then you find new, harder problems to solve.

The first million dollars in revenue is so exciting, but once you hit that, you’re thinking about how to get to $5 million, $10 million, and suddenly $100 million.

Entrepreneurship is a path to endless hustle. It’s like a rollercoaster; there are always ups and downs. Make sure to enjoy the journey on the way, instead of only obsessing with hitting the next milestone. If you can’t do that, the process will exhaust you.

Trying to get everything done on your to-do list quickly.

I’m super “Type A.” I never procrastinated in school and I’d always try to get everything done as soon as possible. But this mentality is the startup founder’s path to burnout.

It’s literally impossible to cross off all your to-do’s when you’re running a company. Instead, you need to ruthlessly prioritize how you spend your time. The startup accelerator Y-Combinator teaches this a lot, but it’s so true: “Work smart, not hard.”

In other words, no matter how much energy you have, or how much sleep you’ll sacrifice, you only have 24 hours in a day. Effective time management and pacing yourself are the keys to business success and a happy, healthy life.

Neglecting your personal brand.

Every young entrepreneur wants their company to be a huge success, but most startups fail. The good news is even if you don’t end up making a lot of money directly, you can use it to build your brand.

I know many entrepreneurs who created companies they no longer run. But many of these people leveraged their brand to create other opportunities. I’m sure they’d probably prefer to have made millions or billions of dollars from a huge exit, but they’re doing well enough, even if their companies weren’t huge hits. They have paid speaking opportunities, bestselling books, profitable consultancies, and online courses that make them recurring revenue. Some used their brand to get lucrative jobs in the C-suite at bigger and more successful companies. Others even used the brand they built with their old company to launch new ones.

I don’t recommend doing a startup just to build your personal brand. However, having strong personal branding as an expert in a particular field makes it easier for you to create other opportunities, including starting your next business.

Hiring your friends.

This is one of the biggest mistakes I’ve ever made. One of the worst problems is that you’ll probably hesitate to fire your friend, which can lead to all kinds of issues if they start slacking or just not being a good fit for your business.

And even more terrible: firing them may cost your friendship. One of my earliest hires was an old friend who no longer talks to me because I had to fire them for shoddy work and repeated missed deadlines.

As tempting as it may be to work with your best friend, it’s almost always better to keep work and fun friend time separate.


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