For most entrepreneurs, starting and running one successful business during their career is enough of a challenge. But for serial entrepreneurs — those who start, run and often sell multiple businesses — the thrill of startup life is too appealing to do it only once.
These founders have mastered the art of growing a business from the ground up, and therefore have a lot of wisdom to impart to current and aspiring entrepreneurs. Whether you just want to focus on the one business you have or dream of launching several companies in the future, here's what you can learn from 13 successful serial entrepreneurs.
Hannibal Baldwin, co-founder and CEO of SiteZeus (previous company — Baldwin Beach Capital): "I believe the success of progressive entrepreneurship lies within ... identifying and understanding the gap worth solving, the system-level technology or design to solve that gap and the business and financial intelligence to execute with strategic speed."
Steve Gefter, managing director of IDDS Group (previous company — TSG Management): "Serial entrepreneurs have a mindset unlike anyone else; they are entrepreneurs on steroids. A 'get it done' work ethic is the most essential trait. Starting a business takes a lot — financially, emotionally and physically. To start one business requires a 'roll up your sleeves' mentality, so imagine what it takes to start five or 10. You either have it or you don't; and the most successful serial entrepreneurs do."
Devaraj Southworth, CEO of Thirstie (previous companies — Tailfin Ventures, iThinkLabs, 30Seven Design): "I watched [my grandfather] build his own business, Gotham Button Company, from an early age. He loved his business and the people that helped build it with him. What I remember the most was that he was always striving to do things better. I knew the road of the entrepreneur wasn't going to be easy, and that chances of success were very small, but I also knew it was the path I wanted and needed to try. Anyone can have a great idea, but turning that idea into a reality and executing on it is the difference between success and failure. For any entrepreneur, anything is possible, as long as you work incredibly hard, stick to your vision and build the right team."
Georgianna Oliver, founder and CEO of Package Concierge (previously founded and sold two businesses in the multifamily housing industry): "Leverage your connections. Your network can make valuable introductions, contribute financially and most importantly provide realistic, experiential advice. I maintain connections with past employees, colleagues, managers and other influencers in the multifamily space, and even now, I run business ideas and challenges by them for input."
David Goldin, president and CEO of Capify (formerly AmeriMerchant) (previously co-founded Media Connection of New York): "You need to be constantly thinking of how to enhance and grow your business because your competitors are doing the same. Remember that losing is not an option and when you're in stressful situations, you've got to figure out ways to navigate and overcome the obstacles. If it was easy to be an entrepreneur, then everyone would be one. The best entrepreneurs need to be resilient and bounce back from anything."
Charles Michael Yim, CEO of Breathometer (previous companies — Chatterfly, ProBuddy): "At a young age I realized that I needed to keep trying, push myself and experience new things. It helped a great deal that I was also a good listener and learned to accept feedback and seek guidance from people I respected. With Breathometer [which was featured on Shark Tank], I have been able to gain access to people that I always aspired to follow — Mark Cuban, Richard Branson and the amazing people these great leaders surround themselves with."
Dane Atkinson, CEO of SumAll.com (previous companies — Sense/Net, YourDay.com, YourStuff.com, IEnsure.com): "I have [served] as CEO [of] a dozen companies ... [and] the majority have been in service to the small business. I wish there was a single north star, but some advice has fared true through it all. Hire smart, value work and stop meddling when you can. Stay attuned to your own perspective, as a slight change there affects all."
Scott Tannen, CEO of Boll & Branch (previous companies — red5 Capital, Funtank): "We all have a tendency to think that people who seem superstressed and ultraserious are the most successful. In my experience, almost the exact opposite is true. Great leaders inspire others to make them even greater. You can inspire with fear and anger, but your tower of power is really just a house of cards. Keeping things in perspective and lightening up on a regular basis make you more approachable. When you need to get serious, the change in your demeanor will be a great unspoken cue to your team that it's time to buckle down. But, try to smile a lot — it makes you feel better and makes people want to be around you more."
Ben Wong, vice president of marketing at Bindo (previous companies — Versed, NiaSolvo, KCL Investment Club): "There's nothing more exhilarating than starting a new business and building everything from scratch — the processes, the team and the product. Learning new things is what really drives me, and I think there is never enough you can learn when you start your own business. I find the fast-paced nature of startups, and the freedom to make your own mistakes and take responsibility for them frightening but also very exciting. You need to have a personality that never gives up. [You] should not be afraid to wander into unchartered territory and to learn new things."
Ellen Rubin, CEO of ClearSky Data (previous companies — CloudSwitch, Netezza): "Build a solid executive team and board. Strong partners make a strong organization. [Your startup also] needs to consist of several layers of knowledgeable individuals, from the engineering team to sales and marketing. Build [your] team from the best and brightest ... to bring depth of knowledge and skill to the organization."
Jason Hogg, CEO of B2R Finance and senior lecturer at Cornell University's Johnson School of Management (previous companies — HangIt, Revolution Money): "Serial entrepreneurship breeds intellectual curiosity. I like to think about it as innovation versus creation, where innovation is improving upon existing ideas and creation is starting fresh. Societal demands are constantly changing and technology is continually advancing. However, there is a gap that takes place in leveraging these technology changes to properly address new demands. Incumbents have a tough time quickly responding to these shifts because they are dealing with legacy systems and entrenched processes designed to serve their existing consumer base. Meanwhile, serial entrepreneurs are focused on creation and leveraging these technologies to create new solutions optimized to address the market need."
Beerud Sheth, co-founder and CEO of Teamchat/Webaroo (previous company – Elance): "After my first startup, I stopped riding the emotional roller coaster inherent in the startup journey. In startups, the highs are higher and the lows are lower — the emotional swings can drive you crazy. I learned to stay level-headed, even-keeled and focused on the longer term."
Stephen Bradley, CEO of AuthorBee (previously helped build several successful media ventures): "It's thrilling and rewarding to start with a possibility and see your vision come together and turn into something with a life all its own. [But start] one [business] at a time. You really have to be 'all in.' I didn't set out to create multiple businesses — I set out to create a business. You may get to where you feel it's time to move on to the next thing for whatever reason, but until then it takes all your focus. You [also] always have to be prepared for failure. Just because you were successful once doesn't mean you will be the next time. You've got to be resilient and enjoy the ride as much as the reward."
Each entrepreneur quoted is the founder or co-founder of his or her current company, and was a founding and/or executive member of the previous companies listed.