How I Became A Serial Entrepreneur

Some entrepreneurs sail blissfully into the sunset after their first big payday. Others — like us — can’t imagine anything more boring. Instead, we thrive on constantly risking it all to build something out of nothing. This condition of serial entrepreneurship is what I call “one-and-not-done” syndrome. We know it will be hard, if not seemingly impossible, and there will be times when we will be overwhelmed with frustration. In spite of that, we know the journey is worth it.

If you’re this special breed of entrepreneur, I feel both sorry and happy for you. More than anything, I welcome you to the club.

There is a magic to what we do as entrepreneurs. We can create a thriving business almost out of nothing. Is there anything more magical than that? This magic is more amazing when 99.95 percent of startup founders don’t receive funding from venture capitalists.

Like most business owners, I have scars from performing this magic trick. I’ve taken missteps, hired the wrong people, mismanaged funds, and denied reality — all of which delayed the vision from coming to fruition. While these things might have delayed the manifestation of the magic trick, it was never derailed.

5 Ways to Fuel Your Next Startup’s Momentum

If there is one thing I love about being a “one-and-not-done’er,” it’s that each time we get the nerve to start a new business, we have opportunities to iterate and optimize the entrepreneurial process. In a way, we have a chance to further perfect our magic trick and shock the world again.

So I welcome you, fellow “one-and-not-done’ers,” with the following lessons I’ve learned along the way of starting a few of my own companies:

1. Generate Corporate Values

Having corporate values in written form allows others to know what is important to you, enables effective hiring, and powers decision-making. More importantly, it creates accountability and sheds light on who should be fired and hired.

Hard-working, effective teams are born from an alignment among company values, individual virtues, and a common belief in the company’s mission. When these three areas are in sync, you won’t have to motivate employees. They’ll consistently put their best foot forward because they know they are trusted and believe in what they do.

That’s what happened at SpaceX. According to one former employee, people worked passionately and were self-motivated. They didn’t need a lot of over-the-top perks to bond with the corporate mission and put in extra hours. Let that be a goal to keep in mind when refining your own corporate and individual values.

2. Face Brutal Facts

Every entrepreneur messes up. But when mistakes happen, fix them fast. Hired the wrong person? Let him or her go. Made a bad business decision? Rectify it. The greatest error is not that you erred — it’s not accepting the mistake and hoping things will turn around. Facing the brutal facts tosses hope aside, no matter how painful it may be.

The most brutal fact of all is accepting where your startup is at at any given point in time. It’s extremely rare — and an unrealistic expectation — for your business to exponentially grow overnight. There will be days of growth followed by weeks of loss. Anticipating these ups and downs and building resilience during slower times are both key for the future of your business.

3. Know Where the Dough Goes

Your survival depends on paying attention to money coming in and going out. Early in your journey, you’ll spend more than you make. Keep calm but also stay on top of your burn rate. My typical rule is to over-fire when times are tough and over-hire when there is proof of traction.

Additionally, make sure to invest funds into the proof points you promised investors. Your ability to achieve those marks will impact future investment rounds. If you pivot — as we all do — that’s fine. However, make sure to discuss revised proof points with your investors so they buy into the company’s new direction.

4. Be Authentic

You can’t fake culture. Gimmicks that stray from your startup’s values and goals can take a critical toll on authenticity.

For example, it might make sense for one startup to have an in-house punching bag if you have a fiery, passionate team. When stressed, the punching bag can take the literal hits. However, a punching bag wouldn’t make sense in all startups, and there’s no use in forcing a specific type of culture onto a company just for the sake of it. Remember, company culture is created by ownership, passed down by management, and exhibited through employees’ actions.

5. Never Quit

If you are a “one-and-not-done’er,” you know what perseverance is. You have lived through the trials of entrepreneurship. However, there are times when you’ll feel like you won’t be able to pull the rabbit out of the hat. When this happens, close your eyes and take a breath. You can get through this. You have before. You will this time, too.

When the going gets really rough, start reading. Books such as Elon Musk’s biography and “Think and Grow Rich” by Napoleon Hill might help motivate you and change your perspective.

We “one-and-not-done’ers” are game for the highest of highs and lowest of lows. We know that making something out of nothing is one of the greatest feats this world has to offer. We leave others in awe because we know something that few do: how to perform magic. And as long as we are always striving to improve, we are sure to be on to the next best adventures and breakthroughs.