Having worked in corporate environment in Silicon Valley, Seattle and India for 12 years prior to founding ShopClues, I can say it with high conviction that whether you are a first time or serial entrepreneur, it is among the most demanding, challenging and difficult career choices you would make. While it may sound counter intuitive to many, I strongly believe that being a serial entrepreneur is so much tougher than first time entrepreneur because you have inherited legacy issues, some time have lesser patience and falling in love again has never been easy.
So here are the five critical factors that in my view are super important to be a serial entrepreneur:
Perseverance and Resilience
While you are first time entrepreneur or serial, perseverance and resilience are hallmark of success for being an entrepreneur. However, these traits are more important second time or in your subsequent ventures because having gone thru once as an entrepreneur, you can lot many times can see many things before they occur, you may have some time sense of entitlements or you may have your own legacy issues/thinking serving as a big hurdle. Hence, perseverance and resilience are the only way you will come back and come up!
Be ready to fall in love all over again
Does not matter, whether you had successful exit or outcome from your last startup or not, the next startup needs all of your love and attention. So if you are unable to move on from your first love, you will likely have issues building a new life with your new startup. This is not practically and emotionally easy but one must move on and fall in love all over again. Every new venture needs 110 percent or your love and attention and it does not matter whether it is first time or 5th time.
As a serial, you are loaded up with rich experience and grip on so many topics. However, most if not all of your team, may still be doing things first time. It is better to have patience and let them do things and even fail vs. behaving like grandfather or grandmother we and kill the empirical learning and newness for others. So, in my view, one needs to be a bit patience and let everyone graduated on their on from those learning that you likely graduated in your prior venture (s).
Learning from mistakes
One should become serial entrepreneur only when they can learn from their mistakes, evolve and be ready to make new set of mistakes. If one does not learn from mistakes, then he will likely make same mistakes again and again and likely may not evolve. Startups and investors have lots of tolerance for mistakes but it becomes increasingly less tolerant when you make same mistakes again and again.
It does not matter whether it is your first startup, second time or fifth time, you always need to have long term approach and solve business with innovative approaches, strong fundamentals and build to last type of mindset. In my view, it takes 6-8 years to create from scratch a world-class business and not keeping a long-term approach will only hurt.