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I made $50 million before turning 30. Here are the 3 biggest mistakes that shaped my career - and what you can learn from them.

Erik Bergman   

I made $50 million before turning 30. Here are the 3 biggest mistakes that shaped my career - and what you can learn from them.
Strategy8 min read
Erik Bergman

Erik Bergman

Erik Bergman.

  • Erik Bergman is a cofounder of Catena Media, a company that went from zero to over 300 employees in five years. Under this journey, Erik made more money than he will ever need in his life, but at the expense of burning himself out, as well as both his business partner and his fiancee that also worked in the company. Now he has started the company Great.com. This time, the focus isn't extreme growth but rather well-being, transparency, trust, and flexibility for the team and where 100% of the profits will be donated to help the environment.
  • Before founding Catena Media, he had launched six different businesses that all failed. He believes it's important that all entrepreneurs and professionals know that mistakes happen and are OK.
  • Three mistakes he believes everyone should avoid making are overthinking decisions, keeping ideas to yourself, and not asking for help.
  • "'Do you think this is a good business idea?' is one of the most common questions I get from entrepreneurs," he says. "They're looking for validation - for someone to nudge them in the right direction. My answer to these entrepreneurs is always the same: 'I have no idea if you'll succeed, but you should definitely try.'"
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On February 11, 2016 - my 28th birthday - we entered the Stockholm Nasdaq Stock Exchange with an affiliate marketing business, Catena Media, valued at approximately $200 million. I made more money that day than I'll ever need, and I'm incredibly thankful for that.

If the story ended there, you might think that I'm some amazing entrepreneur who has it all together. Heck, I have over 60,000 followers on Instagram right now who look to me for entrepreneurial advice.

Unfortunately, the reality is: I didn't and still don't have it all figured out.

I launched six different businesses before Catena Media, and they all failed. I made countless mistakes that left me embarrassed and with strained relationships, and cost me time and money.

I say all this to illustrate that entrepreneurship is not about being perfect; you're going to make mistakes. I've made my share of them and will make plenty more before it's all said and done.

But, if there's one thing that you take away from this article, it's that you can still make mistakes and come out the other side successful.

However, let's not pretend like we want to make mistakes. If you can avoid them, you definitely should try. Here are three of the lessons I've learned from mistakes in my life, in hopes that you can avoid them on your journey as an entrepreneur.

Mistake #1: Overthinking, overreading, and overanalyzing

I'm dressed in all red, standing in front of a door twice my size. This was the last place I wanted to be, but I'd made a commitment.

I took a deep breath and pressed the doorbell. As the footsteps on the other side got closer, my heart pounded louder.

The door flung open, and a grumpy middle-aged man was staring back at me.

I gathered my courage and began to sing.

"Jingle bells, jingle bells, jingle all the way …"

I was four years old in this story, and my brother had dragged me out to sing Christmas carols in our neighborhood. The main reason we were out there wasn't what you might think. While making grumpy strangers smile was nice, my brother knew that if we were cute enough, these strangers might give us a small tip for our effort - which they did.

I love telling this story because it illustrates the simplicity of business so beautifully while also detailing a familiar feeling for many entrepreneurs. I doubted my brother's idea originally and would have rather been playing comfortably in my room instead of awkwardly singing to complete strangers. But, when we bought hot fudge with the tips we had earned, I couldn't have been happier.

I had no idea at the time, but I was embodying one of the biggest entrepreneurial mistakes - hesitation.

"Do you think this is a good business idea?" is one of the most common questions I get from entrepreneurs. They're looking for validation - for someone to nudge them in the right direction.

My answer to these entrepreneurs is always the same: "I have no idea if you'll succeed, but you should definitely try."

We're all afraid of failing. Whether it's in business or our personal lives, fear of failure is an all-too-familiar hurdle. Unfortunately, many entrepreneurs let fear keep them from trying.

This fear of failing manifests itself in the form of overthinking or overanalyzing our ideas. We mistakenly focus on resolving issues before they arise, waste time seeking validation, or simply talk ourselves out of ever trying.

Instead, we must be willing to take calculated risks - even when it's uncomfortable.

I'm thankful that I learned this lesson when I was young because it instilled a higher level of confidence in me. This courage helped me start my first business at 13 and eventually led me to play poker professionally. It's also the catalyst for starting Catena Media when I was 24 and spending $900,000 on my new charity project (Great.com).

If you're on the fence about an idea or contemplating whether to take a chance on a decision, I encourage you to take a leap of faith and invest in yourself. No matter what, you'll learn from the experience and avoid the dreaded "what if."

Mistake #2: Keeping your ideas to yourself

I have to be honest - this next mistake isn't something that I've faced myself, but it is an issue that I see many other entrepreneurs make.

Growing up, I always yearned for personal affection and affirmation. This eagerness to be liked made me a bit of a social butterfly. So much so that I eventually earned the nickname "Radio" because I never stopped talking.

While I wasn't that popular with the teachers, it did make me incredibly well connected with my peers.

Learning how to effectively talk and listen to others helped me grow into a successful networker and salesman. It also showed me the value of brainstorming and how powerful feedback is when working with a new idea.

As I got older, I used this same openness to work through business ideas with intelligent and inspirational people. Unfortunately, many entrepreneurs are afraid to share their ideas with anyone else for fear of someone stealing them.

While there is certainly the risk of someone stealing your idea if you share it openly, in my experience, it's highly unlikely. Even if someone does steal your idea, can you out-execute them on it? If not, you should be focusing elsewhere anyways.

The downside of talking about your ideas with others is obvious, but it's also quite small when compared to the benefits that come with others' input and vantage points.

When we started growing Catena Media, I had no issues opening up about our ideas and strategies with anyone that would listen. Heck, I'd even discuss our ideas with competitors.

You know what I learned? When I opened up, they did, too. We shared insights and tricks about what we were doing and what worked, and they began to discuss their own strategies with us.

As a result, in 2012, we implemented an email-capturing strategy using a popup based on a conversation we had with one of our competitors. This simple change led to a revenue increase of more than 10%.

Critical discussion is a powerful tool for businesses, but it's difficult to do if you keep your ideas a secret. I truly believe that it's important for entrepreneurs to seek feedback for ideas and be willing to share openly with others.

This heightened level of transparency has helped me optimize my ideas, gain new inspiration, collaborate with brilliant minds, and find business investors.

I encourage you to avoid secrecy in your business. Consider sharing your strategies and ideas with others and actively reach out to thought leaders in your industry for feedback. Who knows, you might actually land a mentor or receive notes that can help you take your idea to the next level.

Mistake #3: Not asking for help

I'm 19, standing outside a club on a Friday night. I'm watching a group of people slowly walk away, disappearing into the night.

This was one of the worst nights of my life.

I had just started a party-planning business and rented out a nightclub in our town. I hired a DJ and told everyone I knew that this was going to be an unforgettable night - unfortunately, it was anything but. The entire night was a complete failure. A few people showed up, but they left shortly after because no one else was there.

After a few hours of watching people come and go, I eventually left in tears. I was humiliated, broken, a failure.

I spoke to some people a few weeks later about the party and many of them said the same thing - they ended up not coming because they heard from others that nobody was there. This is obviously a cyclical problem. People are not coming because they hear it's empty, therefore it will continue to be empty.

I then realized that I could have alleviated this entire issue by simply asking my friends to arrive early and fill out the club. In fact, before the night, I wanted to ask my friends to come early, but I never did. I was too proud and didn't want to inconvenience them.

I eventually discussed the party and why it failed with several friends, and they all said the same thing: "Why didn't you just ask us to come early? We would have loved to help out!"

When I'm struggling with something in my personal and professional life, I always think back to that night outside the club and how things could have gone differently if I had just been willing to ask for help.

This lesson was tested a few years later when Catena Media was just getting started. We had a dispute with our landlord who was suing us for almost $500,000 - which was well beyond anything we had at that time and would have effectively ended our business.

I remember lying awake at night, stressing about what to do. I eventually asked one of my friends, who was a lawyer, if he could take a look at the dispute. My friend's legal fees were more than we could afford, but he was willing to help us anyway. He guided us throughout the entire process and eventually helped us settle for roughly $100,000. Without his help, Catena Media probably would have folded, and there's no telling where I would be today.

As an entrepreneur, it can be incredibly valuable to seek help from others. Not only can it provide immediate support for whatever struggle you're dealing with, but it can also help you develop relationships with others who might be able to help you in the future. Asking others for help is not a sign of weakness - it's a sign that you're willing to grow.

Mistakes come with the territory

There is no blueprint for becoming a successful entrepreneur. Everyone's journey is different, and the struggles I faced will not mimic the ones that you do.

However, if we take a step back and look at the big picture, we can see the true message of this piece. We all make mistakes. It's not always about avoiding these mistakes, but rather your willingness to learn from them and to grow personally and professionally.

I wish you the best on your road to building a successful business and am always happy to discuss your ideas, struggles, or victories on Instagram @smilingerik!

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