If I Had to Start All Over Again, I Would…

I started relatively young – 16 years old working in telemarketing and then onto Insurance by 18. At the ripe age of 25 and a half, I started my first tech business with some friends.

We were part of the trend of web shops opening the city – a little too early – as it closed doors after not being able to sell $99 websites – a common roadblock, “why do I need a website.”

I created it because I couldn’t find a job at that young of an age within the tech / ad world. Heck, I struggled to find even a low paying job!

As you probably can guess, it failed and, eventually, I went on to do other stuff and accomplish a few internet firsts.

From creating a digital creative agency to a software application.

What I learned too late in my career

I’m really good at a lot things but I’m really good at driving awareness.

It doesn’t matter what industry a brand is in, I can drive traffic to it and make it popular. And best of all, I can do it without ads.

But because I can do one thing well, it doesn’t mean I can create a successful business. I still need amazing people around me.

For example, when I started working with Rebecca Herr, our business started to take off.

She’s the CEO of our brand community agency, LeFace

Rebecca is not your typical CEO, as she is really good at building connections and finding the right people. Best of all, she can do so on a budget.

That is her best skill!

And working with her I realized that no matter how smart you are, you’ll never build a company unless you have a talented team.

People help you scale and grow fast. With more brain power, assuming you are picking good people, you’ll solve your problems faster and see revenue roll in.

So what would I do if you started over again?

Well, the lesson above is one of the hardest lessons I had to learn. And I learned it too late in my career.

It’s obvious, but when you start out as an entrepreneur at too young of an age, you make mistakes (sometimes huge ones) that you more likely wouldn’t have made if you had started your entrepreneurial journey a bit later.

So, what would I do?

Well, I would spend the first 9 years of my entrepreneurial journey in the workforce.

The first 3 years I would spend my time at a startup. And ideally, one that doesn’t have too much venture funding and isn’t taking off like a rocket ship.

The reason I wouldn’t pick a fast-growing startup is that the hardest part is making a company work and then growing it. By working at a company that has amazing traction because of timing or luck, or something that they couldn’t control… it teaches you to be creative, scrappy, and how to fight to win.

You’ll learn a lot from the startup life.

After my first 3 years in a startup, I would then spend the next 2 years working at a mid-size startup that has raised at least 10 million dollars and is growing up and to the right like a hockey stick.

This will help you understand what a fast-growing company looks like. And let me be the first to tell you, it’s not sexy… it’s very messy.

So many things go wrong and keep breaking because you are growing so fast. You’ll end up finding things like your economics may not be great, or you may be working with mediocre people because you just need to hire for the sake of filling in empty positions.

And after those 2 years are done, I would spend 2 years working at a mid-sized company. One that generates at least a hundred million a year in revenue, but less than a billion.

The struggles that mid-size companies face are different than startups and large corporations. But by being in the mix at one of these companies for a few years you’ll learn everything from dealing with politics, to how to make a slow-moving company grow, to even thinking about the big picture. Such as how bigger companies look for huge markets because they know that it is easier to own 5% of a multi-billion-dollar industry than it is to own 50% of a multi-million-dollar industry.

Last, but not least, I would spend my last 2 years at a large corporation. When I mean large, I’m talking about a company that is worth over 10 billion dollars and potentially even publicly traded.

What would you do after your 9 years as an employee?

The whole purpose of working for others is to get the right mentors and to learn how the real world works.

Entrepreneurship isn’t as glamorous as most people think. Success isn’t easily achieved and it doesn’t look like what you might think considering what so many “successful” influencers might sell you on social media.


brand community success startup

By working with others, you’ll learn what works and, more importantly, what doesn’t work.

No matter how smart you are, you will make mistakes. Just look at people like Elon Musk and Mark Zuckerberg, no one is perfect. Even the billionaires make mistakes.

But once you’ve worked for a handful of companies that are all different sizes, you’ll have a good understanding of what it takes to succeed.

You’ll have a much better understanding of common mistakes people make, such as how to avoid hiring bad people, and if you do hire them, how you need to fire them fast.

In essence, you will have learned what you should do for 9 years straight, which means if you skip all of that, it will be harder for you to be in a position to succeed for lack of experience in the real world. Sure, there is always the possibility of success without all of the experience, but it is much more difficult to become a reality.


Entrepreneurship looks great and is amazing. I wouldn’t trade it for the world. But before you go off and become an entrepreneur, learn from companies of all sizes.

It’s not an easy road and the last thing you want to do is fail on someone else’s dime because your reputation is all you have.

By putting in 9 hard years into other people’s companies, you’ll increase your odds of succeeding.

And when you are ready to go out on your own, hopefully, you would have met a few amazing co-founders along your journey because it takes too much time and capital to do it all by yourself.