‘I think mentoring is overrated,’ says Ram Gupta, Silicon Valley veteran

By Dipti D
November 07, 2015, Updated on : Thu Sep 05 2019 07:25:23 GMT+0000
‘I think mentoring is overrated,’ says Ram Gupta, Silicon Valley veteran
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As the average age of startup founders in the Indian startup ecosystem touches the ‘thrilling 20s’, there is an increasing need to have a safety net for them. A good way to achieve this is when senior entrepreneurs and other startup stakeholders walk with young founders on their entrepreneurial journey.


Silicon Valley veteran Ram Gupta, who has a rich career spanning 25 years running startups and large public companies, believes what young entrepreneurs need is not a know-it-all mentor, but a “friend, guide, a sherpa.”

Ram Gupta has expertise in technology strategy and execution at fast-paced innovative companies like CastIron Systems, PeopleSoft, WebMD, Silicon Graphics, IBM, and Tata Consultancy Services.

At present, Ram serves as a Director on the boards of Progress Software(PRGS), Aryaka Networks, Simplilearn, Haptik, Unmetric and FusionOps. Since 2007, Ram has served as director on the boards of various public and private technology companies like S1 Corporation (SONE, acquired), Platform Computing (acquired), CastIron Systems(acquired), Persistent Systems(PRST, IPO), AccruentInc (acquired), Knova Software(acquired), Plateau Systems (acquired), and Geek Net(GKNT).

From 2005 to 2007, Ram was the President and CEO of a startup, Cast Iron Systems, and then from 2007 to 2010, he was the executive chairman of Cast Iron Systems. It was then acquired by IBM. Before that he was executive vice president of Peoplesoft and helped grow the company from a market capitalization of $3B to @10B and its acquisition by Oracle. Prior to that, he was Senior Vice President at WebMD and helped to take it from a startup to $2B IPO.

In an email interview with YourStory, Ram delves deep into how young entrepreneurs can and should seek out their guiding stars.

YS: With such a rich career spanning 25 years, you must have experienced both sides of being a mentee and a mentor. Looking back how do you see those learnings merge, thus empowering you in both your professional and personal life?

RG: I have spent all my life learning. There is never a point in time in life where you stop evolving and learning. The mentors have changed, but the learning continues.

As far as being a mentor, I think that being a mentor is overrated. It has almost become a profession and at the end of the day, I do not think that you can really mentor anybody. All you can do is share your experiences. If you are born a pigeon, nobody can make an eagle out of you (smiles).

I do not think of myself as a mentor at all. I think of myself as a Friend, a Guide, or a Sherpa. I have had my own journey. The people that I ‘mentor’ are on their own journey. Maybe they are at a crossroads in their journey that I have been through. All I do is to share with them where each fork may lead to. And then they make their own choice.

More importantly, the entrepreneurs that I am working with are teaching me new lessons all the time.

YS: Looking at young entrepreneurs today, what areas do you think they need to focus on to help them move ahead in their venture?

RG: Cash Flow and Profitability. I can’t tell you how many businesses go out of business because they are not focused on cash flow and profitability at the unit economic level. In the bubble that we are in where ‘growth masks all the sins’, it is even more important. Like all bubbles, this one will also burst. And the survivors will be companies that focused on cash flow and profitability.

YS: Because they are young they not only have pressures related to lifting their startups and ventures off the ground but also struggle with stress, handling family, and even in some cases depression. Do you think they should look for different mentors for different areas of their life?

RG: Very good question. I think that there is no such thing as a mentor for work, a mentor for health and a mentor for family. Either you are their guide on this journey or you are not. The first thing I ask the people that I work with is, “Do you exercise regularly”? And if the say no, I am after them to get into exercising. I know all about their families and do my best to meet with them. And of course, I get involved with their work.

My advice to them is that at any point in time, you are juggling three balls. One is your health, one is your family and one is your business. The health ball is made of glass. If you drop it, it could become impossible to fix it. The family one is made of clay; if you drop it, it is imminently fixable but it will take a lot of hard work. And the business one is made of metal. If you drop it, it will get dented but it is relatively the easiest to fix.

YS: How does one go looking for a mentor? 

RG: (Smiles) I do not know. Maybe I can talk about what to look for.

All of us meet a lot of people all day long. Some of them will leave you with an impression that they really care about you, not just your business. Has their journey made them humble? Do they profess to know everything or do they talk about what they do not know? Is ‘mentoring’ a profession for them, or they do it because they expect to learn new things?

What you’re looking for is someone with tumultuous life experiences, humility and a good sense of humor.

YS: As a mentor yourself, how much of your corporate learnings do you bring to the startup's table?

RG: Once again, I do not consider myself a mentor. I consider myself a friend, a guide, a Sherpa, a fellow traveler.

Having worked with tens of startups and a number of public companies, I do bring quite a few scars to the table.

And all of them are valuable lessons. All these lessons are available to the founders and CEOs to learn from. But at the end of the day they take some lessons, and other lessons they end up learning on their own by making their own mistakes. You can tell someone all day long not to touch a hot surface. But they are going to touch it, get burnt and learn on their own (smiles).

YS: Usually, single founders are more vulnerable to internal and external pressures, what advice do you have for them? 

RG: Do you mean unmarried founders (smiles)?If yes, I would tell them to find a partner and spend quality time with them. If you mean the companies that have only one founder, indeed they have it harder. And it is even more critical for them to have a guide, a friend that they can reach out to, hang out with and talk about things that are on their mind.

YS: What qualities should an ideal mentor possess, and how can mentees evaluate that the person they are seeking help from is the ideal one for them?

RG: Tumultuous life experiences, humility, and a good sense of humor.

It is critical to find people that you connect with on an emotional level. Do not try to find a teacher. Try to find a friend that has been around the block a few times before you.

Can you talk freely? Can you share your fears? Can you talk about everything and anything? Can you laugh together?

YS: Could you share some examples of the difference a mentor has made in the life of an entrepreneur?

RG: Hmm…. Most of them are exercising and taking better care of their health and family (smiles). And, of course, their businesses are running far better. (But that is the easy part).

Here is one that comes to mind. This young entrepreneur friend of mine was here (in the US) running his startup and was at a critical junction in the business. At the same time, his father fell really sick in India. He was torn about what to do. Should he keep running the business or should he go and take care of his father? I insisted that he go back and take care of his father.

Finally, he agreed and went back. While he was there, every day we chatted about his father, his mother, his family and what was going on with him and his business. I even talked with his father and his mother. Unfortunately, his father died despite all his efforts. But for rest of his life, my friend will have the satisfaction that he was there with his mother and father and he did the best he could.

After his father passed away and he had settled his mother, he came back and continued to run the business. A year later, his mother came to visit him in the US. He told me she wanted to meet me in person.It brought tears to my eyes.

And guess what? As of now, his business is the strongest it has ever been.