5 Tips from Those Who Thrive Doing Multiple Startups

Knowing all too well how hard it is to start a single new business, I’ve always wondered how several well-known entrepreneurs, including Richard Branson and Elon Musk, have managed to successfully lead dozens of startups to success, and thrive on the process. These special people are called serial entrepreneurs, because they have figured out how to do it over and over again.

In a very real sense, they seem to succeed at everything they try, just like the rest of us wish we could. I learned a lot about the mindset and actions required from a classic book, “Serial Winner: 5 Actions to Create Your Cycle of Success,” by Larry Weidel, a serial winner in the financial services business world over a forty-year career, while helping other people do the same.

Although Weidel’s focus is more generic, I believe his five principles and actions are extremely relevant and can be more specifically targeted to aspiring entrepreneurs as follows:

1. Make a decision, any decision, and move on.For entrepreneurs starting a new business, the world is fraught with risk and there are no sure bets. Yet making no decision means you never start, or you quickly lose. Serial entrepreneurs embrace the risk, gather the relevant facts, and move forward. You have to move forward to win.
2. Don’t just build a business, change the world. Every great startup begins with a vision that is much larger than just making a profit. Serial entrepreneurs understand that the business culture today rewards going beyond profit, to helping people and the planet. They set big goals, challenge limits, and have a mindset to exceed every one.
3. Be prepared for many pivots, but never quit.Winning in business requires surviving many setbacks. Many experts believe that the single biggest cause of startup failure is that the entrepreneur simply quits too soon. Serial entrepreneurs take every setback as a positive lesson learned, alter their course accordingly, and charge ahead again to win.
4. Trying is not enough, you have to deliver. Serial entrepreneurs focus on surpassing every objective, and they don’t even think about excuses, like economic downturns, culture changes, and running out of money. They have the mental toughness to keep their head down and charging until they have achieved one hundred percent of the goal.
5. Each success incents a dozen greater ideas. The best entrepreneurs capitalize on the momentum of each success, and can’t wait to aim even higher the next time, based on lessons learned. Once they have mastered the fundamentals, they are never satisfied, but are driven to continuous improvement and streamlining the process.

It helps to have limitless energy, and unshakable determination. Elon Musk is known for his hundred-hour workweeks, and his endless curiosity. It’s also important to surround yourself with the right people, who can complement your vision with the necessary execution skills. Smart entrepreneurs also make good use of domain experts as advisors and mentors.

Don’t forget that today’s innovative “social economy” requires an emotional attachment that links customers to products, as opposed to competitors, translating into sustainable growth. Serial entrepreneurs have found that multiple simple inspirational product and brand messages are far more influential than ones which highlights product features and functions.

Serial entrepreneurs certainly understand the high probability of failure, but they don’t necessarily like to gamble. Instead, they take calculated risks, stacking the deck in their favor. They must have enough confidence in themselves, supplemented by expert knowledge, solid relationships, or personal wealth, to see the risk as near zero.

For serial entrepreneurs, the next step is often to be the CEO of multiple early-stage startups concurrently, or a parallel entrepreneur. The hot new term for this practice is “multi-table” entrepreneurs, which no doubt is derived from the common online gambling practice of playing multiple poker games at the same time. There is no end to the fun of being a serial winner.