A Serial Entrepreneur’s Secrets for Longevity

January 24, 2016, 7:28 PM UTC
Thomas Barwick—Getty Images

As a serial entrepreneur, you could say that change haunts me in my sleep. It’s rare that a week goes by when I don’t find myself lying awake at least one night, staring at the ceiling as my head spins with ideas about a new company I want to start.

At times, it’s a gift. (I get to be my own boss. Life is never boring.) But other times, it can be a curse. The entrepreneurial life is a frenetic one, and in my day-to-day world, I constantly challenge myself and my team to push our entrepreneurial limits while engineering ideas that endure.

Entrepreneurship presents me with an almost constant double-edged sword I may need to one day fall on. But I wouldn’t have it any other way. After founding four startups (not including the paintball company I started at 14), I know that I thrive best in this steely, swashbuckling environment. Here’s how to establish staying power in an ever-changing entrepreneurial space:

1. Hire for the future

I look for employees that are as innovative and as flexible as I am. Potential startup employees need to be OK with the idea that they may be hired to work for one company, but may be asked to contribute to another if need be. It’s also important to look for candidates who seem willing to quickly grow and adapt. My team is successful because its members thrive on change. We constantly feed off of each other’s energy as we work to achieve new goals (and, sometimes, change roles).

2. Find a good “Loss Leader”

Sometimes, you win by losing. As defined by Investopedia, a Loss Leader Strategy is one in which “… a business offers a product or service at a price that is not profitable for the sake of offering another product / service at a greater profit or to attract new customers.” When starting new companies, I have, from time to time, accepted projects for their portfolio-building value rather than their value to my bottom line.

Being able to share such high-profile work with new potential customers has benefitted me in two important ways: 1) I’ve been able to show potential clients that I have fruitful, now-profitable, ongoing relationships with other movers and shakers in their industries; and 2) I’m able to charge a more equitable rate for my company’s services because I have a body of work that demonstrates my company’s viability.

3. Make sure your contacts are comfortable with change

I take care to establish connections with people who will support me through inevitable turbulence. Members of your network need to care about who you are and what you represent, not just about your winning idea. Individuals who are “in it for you” will stick around for businesses Nos. 2 and 3, providing valuable contact-building, support and insight no matter what kind of company you build next.

4. Be the person you’d want to do business with

Establishing business relationships as a serial entrepreneur is like saying, “I’m not certain exactly where this road is going to take us, but I’d really like to have you on the journey. We’ll have some setbacks, a failure or two, and probably some really big successes. At times, you’re going to feel like a Burma reed in a category-5 hurricane. Are you with me?” A serial entrepreneur’s journey isn’t an easy one, so you need to give valuable members of your network a reason to continue to support you. The resounding endorsement of colleagues is a direct result of a steadfast business track record. So, mind your reputation and never burn a bridge. You never know when you’re going to need an advocate.

Mark Fitzpatrick is the founder and CEO of RUHM Luxury Marketing.