From Corporate Executive to Entrepreneur

I had an interesting LinkedIn exchange with my old friend Nitin Paranjpe about risk taking and how corporate executives and entrepreneurs view it differently. I was fascinated by the range of responses he elicited and given that I have lived on both sides of the fence, especially as an entrepreneur selling to corporates, I thought I’d share my observations with others who may be thinking of taking this leap into the wide wild world of entrepreneurship!

As I reflected on this journey, it occurred to me that the path I had taken was neither common, nor easy, nor predetermined - but one that could be followed by many more with backgrounds similar to mine. I thought that sharing some of the pros and cons of this journey would provide a perspective to wanna-be entrepreneurs, currently in roles as corporate executives.

Like many of you, I’ve always had business ideas for as long as I remember. Like many of you, I was terrified to leave a job and take the leap. But unlike many of you, I finally took the first step about 18 years ago, and really took a plunge into a challenging venture about 9 years ago. Here are some of the considerations I can share with you:

1. Ideas are a dime a dozen. Getting off your butt and doing something about it is really the difference between a thinker and a doer.
2. There is no right time to become an entrepreneur. If an idea is gnawing at you, and you have done adequate research to scope out the possibilities, take the step and do it full time. There are no half-steps in entrepreneurship - and those who say that are not being honest with the amount of time it takes to get an idea off the ground.
3. Be very clear about your time horizon to give it a real possibility of success. Far too often I’ve seen friends give up promising ideas too early, or stuck with something for too long. But definitely timefence it because left unchecked, you can do this forever.
4. For those of you who are in corporate roles, you have extraordinary “positional power” and influence. Be prepared for it to vanish when you step out on your own and get the “what company are you from and what do you do?” when you try to sell. It is truly humbling.
5. Make sure you have thick skin. I’ve never dealt with more rejection in my life than the past 9 years - investors, customers, potential employees, partners….you need to have the ability to brush these off, learn from them and move on
6. If you thought you had long days/nights/weekends working in corporate roles…you ain’t seen nothing yet! A venture can be all consuming, even when you think you are “off the clock”. You just never are.
7. Be prepared to have people around you NOT share the same passion as you do for your idea. Even your employees. Remember, in every startup, there are only a small handful of “missionaries” who join the journey because they believe in you and your idea. The rest are here for jobs and a paycheck. Don’t confuse the two and don’t expect everyone to be a missionary. You will be disappointed.
8. Look for colleagues who 1) see the possibilities, but 2) also find ways to reduce the risk in every step you take in your big initiatives. Short horizons to prove out ideas with “prototypes”. Build on top of each step, and find ways to confirm with potential customers all the time.
9. Depending on the type of venture you are building, focus like crazy on validating with customers and non-customers. Including detractors. The latter can really blow a hole in your confidence, but you need to listen to them.
10. Raise venture capital only if you must. (that is going to be the subject of another post). I’ve been extraordinarily lucky that my investors are patient, huge believers in our story, and have made a difference. But in retrospect, I would have taken the company much further along and then raised capital than when I did.
11. Invest heavily in marketing, even well before you have a fully functioning product (my all-time mistake, I think). It helps in so many ways that are too numerous to highlight here.
12. While you need amazing and smart people on your team, IQ alone is massively overrated (maybe except for very technical ventures). EQ, ability to execute reliably, and have grit and resilience are way more important. You will go through so many negative experiences that without these attributes, your team will jump ship or not make it work for all of you. Again, I’ve been extraordinarily lucky to have amazing people around me who embody these qualities and have stuck with us through thick and thin. That is really a primary screening criteria for us these days.
13. Don’t shoulder the emotional burdens alone (there are way more hits to your confidence, mental well being, dark days than you can imagine). Find trusted confidantes that can be there for you as sounding boards. (totally failed on this one).
14. Make time for self-care. Family, friends, rest, exercise, fun. (of course, I blew it on all of these!)
15. Lastly and most importantly (!) thank your spouse, loved ones and supporters. ALL. THE. TIME. I have been so fortunate to have an incredible partner in Sujata Joshi during this journey. Without her, there would be no Entytle. Seriously.

So this turned out to be longer than I expected, but I have a lot more lessons tucked away to share along the way. I will do so in subsequent posts over the next few months.

Good luck to those stepping out to become entrepreneurs. It is a journey. But it is an extraordinarily fulfilling one, and I for one am glad I did it.