Serial Entrepreneur: How is it different the second time?

Posted: October 27, 2009 in Business, entrepreneur
Tags: , , ,

Yesterday I was filling out the registration form for the TiE Summit in Mumbai, coming up this December, and where I needed to describe my entrepreneurial status. Of the many options offered there (e.g. early stage entrepreneur, growth stage entrepreneur etc.), there was the one that seemed most correct for me, viz. Serial Entrepreneur. Yeah, I guess I qualify for that! Having co-founded and ran from 1998 to 2007, before divesting our stake and exiting, now this new venture, Social Wavelength, started in April of this year, is certainly a “serial” venture!

So how is it different the second time around? Is there still the same passion? The madness to think that you can make the world different? Or is it all tampered with time?

I thought about it, and realized that for me, this second time is certainly different. But for all the right reasons! Well, except the age. Really, I wish I could have started my entrepreneurial career at least 10 years before I did. Oh well. (Maybe this last bit of thought is the direct consequence of having just passed the 46th birthday. Part of that philosophical churn that accompanies the passing of a birthday, especially in the 40s age bracket!)

Coming back to the differences between being a first time entrepreneur and a serial one, I would pick the following key factors:

  1. There is more fire in the belly. I must qualify this. I remember a talk by Kanwal Rekhi at IIT Mumbai, earlier this year. Where he clearly contrasted second ventures of very successful first time entrepreneurs (and how they were not doing that well, as comfort zone had set in) and how he valued the not-so-successful-first-time-entrepreneur’s second venture. Because if the first time had meant lesser success due to a myriad of circumstances, but not for want of trying, then the entrepreneur has a bigger motive this time. To show others but most importantly to himself that he is no less, and he can be successful. That brings in more hunger and more determination.
  2. When an employee walks away without giving adequate time, you are upset but not shocked. And words like ‘betrayal’ do not exactly come in the head. You have seen enough and more. That there are all kinds of people. After doing all that you can, to make life good for your team, and more importantly, give them the freedom to speak candidly to you about leaving etc., people may still behave peculiarly. Suddenly the ‘father may get seriously ill’ or ‘the family may get transferred’ or they may ‘develop a disease that requires hospitalization’ and due to which reasons, they have to leave the job right away. You almost want to tell them that ‘do away with the charade’. But you don’t. And accept this as one of those things that happen. In spite of everything that you do. And you go ahead and look for replacements and life goes on!
  3. There is excitement and enthusiasm but celebrations don’t start before the cheque actually clears in the bank! You have seen enough near-misses to know that being almost there is not good enough. A great client contract, an investment or any other such good news is only true and worth celebrating, after the deal is done or the contract signed. Or whatever.
  4. In my case, specifically, there is a lower dependence on the valuation story and more focus on making and running a good, profitable business. The first time around, we actually stopped a profit making activity after we raised venture money, and pursued only a valuation game. This time around, there is clarity that profits and cash are king, and must be nurtured and protected and grown. And valuation, if it happens (and it will!), it is good, but it should not be made the be-all-and-end-all of the business activity.

Well, so here I am, serial entrepreneur. On this second journey. More exciting than the first in many ways.

What’s your story? Are you on your first? Second? Fifth? Done and retired in Bahamas..? What??

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