Ep 54 – To IPO and Beyond: A Techpreneur’s Take

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About Vinita Gupta

Vinita Gupta is a pioneering entrepreneur known for being the first Indian-American woman to take a company public in the United States. After a successful career in engineering,  she co-founded a tech company that initially focused on hardware and later evolved into a hardware-software company.

Despite early challenges, including her partner’s departure, Vinita’s resilience and innovative approach led the company to profitability and an IPO in 1994. She eventually re-privatized the company in 1999,  driven by the changing internet landscape and the collapse of the internet bubble. 

Post her entrepreneurial journey, Vinita has continued to make significant contributions through her involvement in various non-profit boards, including the Mathematical Society, Stanford Medicine’s South Asian Health Research and Education, and the Palo Alto Medical Foundation. She is also an accomplished bridge player, a writer, and a painter, finding fulfillment and continuous learning in these pursuits.

Episode Highlights

  1. The critical mistake to avoid in building your startup team: lack of transparency and trust.
  2. How to choose the right co-founder for your startup
  3. The fail-safe way to validate market need for your startup’s offering
  4. How to successfully navigate the funding-growth labyrinth
  5. Finding and keeping an all-star team
  6. The changing landscape of  capital markets and how they influence your startup journey
  7. Challenges and rewards of going public 
  8. How to make the tough calls about company ownership
  9. Know when to hold ’em, know when to fold ’em
  10. Keeping the inner light shining bright

Links and resources

Interview Transcript

Shubha K. Chakravarthy: Good afternoon Ms. Gupta. We’re so happy to have you here with us today on Invisible Ink.

Vinita: I’m looking forward to it Shubha.

Starting the Journey: Motivation and Early Steps

Shubha K. Chakravarthy: I want to talk about a bunch of different things, maybe three main things. First and foremost is you’re the first Indian American woman to start a company and take it public in the United States.  I’m  going to ask you a bunch of questions about your journey of starting, running and exiting a tech company.

So what did the company do and what was your motivation to start this in the first place?

Vinita: Let me start with what the motivation was when I dived into it. I think I was ready for a major transformation and transition. Transformation in my professional journey and transition meaning I was not happy doing what I was doing. The combination of that was, what else can I do? And sitting in Silicon Valley, it wasn’t so unnatural to think of being an electrical engineer. It wasn’t so difficult to think that maybe I can start a company. And I didn’t have that in mind but I gave myself three months if I found myself after I quit without having concrete plans.

I felt like if I don’t find something to do in three months, 90 days, I gave myself a hard line. I’m going to start a company because the path to start a company was not so obvious at that point in time. So that is what was the motivation. It was as much as I say what led me to do it. I would also say, definitely making a lot of money was not a motivation because we all know that very few companies succeed. When you start as nobody you always think about not succeeding but you don’t let yourself drown in that fear. So it was not to make money. It was to do something which was more purposeful.

Shubha K. Chakravarthy: Help me understand. You’ve just quit your corporate career. You’ve given yourself 90 days. Is the 90 days to find another interesting job or is it to come up with an idea?

Vinita: Both. If I look back, decision making for me has always worked out better when I pursued two alternatives, not too many but not only one because then what choice do you have? So yes, the answer is I was going to look for another job which I could have found in a similar competitive space in the Valley very easily.

I didn’t want to jump from a pan to fire. So I decided that I’m going to look for a job, which was making a transition into something. And at that time I could only think about engineering to marketing. And it wasn’t easy in those days to make that transition if you haven’t done it before.

Shubha K. Chakravarthy: Got it. So you’re looking for motivation. You used the word “purpose” which is hard to kind of combine with engineering, at least to my brain. I know you have filed two patents or you have two patents. So were you looking at those patents as a source of inspiration? Were you looking at what the market was lacking? Where were you looking for ideas for your business?

Finding the Right Idea and Partner

Vinita: Where I was looking for ideas and where the idea ultimately came from were two different things. One of my friends who had worked in the same company that I left. He came to me and he said “if you ever think of starting a company, give me a call”. He had about the same experience as I did. I gave him a call and then we both sat down.

It was like “let’s think about two alternative ideas what we start the company in”. I was working in something which would have required a huge amount of capital and he had a very niche idea of what we could make. He had seen that because that’s what he was working on in those days.

We ran with his idea rather than my idea which we said, “we don’t know how to raise capital. So how are we going to go and raise capital?” That gave me an impetus to do something because we were there for each other to encourage each other because you need a lot of encouragement as you take your initial journey.

It was his idea. He was the engineer. I was the rest of the company sweeping the floors to accounting, to marketing, whatever it takes. It didn’t feel small to do that. I mean we do what it takes.

Shubha K. Chakravarthy: So how much would you say there was an overlap between your domain expertise and the core of what was needed for this company’s engineering part?

Vinita: Core expertise was very similar but for the product idea was that I had a grander product in mind. If you look at a shelf full of equipment you can make the whole shelf with everything in it or you can make just one card in the shelf and we were a piece. That was more manageable and that is what actually led to our success because then we expanded and built a full blown system as they say.

Initially we started with a hardware based company but when we reached the system level, we had a lot of embedded software. Then it was a hardware software company but that was an evolution.

Shubha K. Chakravarthy: Got it. So then you’re looking at both the ideas. Clearly capital was the tiebreaker to say, “Hey this is something we can start sooner versus this requires a tremendous amount of capital. So it won’t go this way”.

Did you do a formal market analysis? Did you figure out how much demand there would be or what you could charge for this? At least at a high level what did you evaluate?

Vinita: We evaluated because our runway was small, he put in money, I put in money. We were self starters. Our runway was small. We did our business analysis. How long will our money last? We knew how much it would take to develop the product. There were two aspects which I now get reminded of. We borrowed a Gartner research report, marketing research report from another colleague who had left the same company but he had gotten venture funding.

He could afford to buy all those marketing researches. We couldn’t so we got  the marketing research from him. The rest was what I would call going to trade shows and looking at competitive products not disclosing to them that’s what we intend to do. That makes no sense because we didn’t know where we would end up being. We were a little cagey in doing that, going there pretending as if we were potential buyers which we were not.

Shubha K. Chakravarthy: I can imagine. I can practically see the scene. Did you also have certain milestones especially given you had a short runway, right? Money was going to run out at some finite point. How did you set up any milestones or checkpoints to say, “Are we on the right track? Is this succeeding?” What were those milestones and how far apart?

Vinita: The problem that time was we knew we will be on milestone. It’s like when you have to get something done, the milestones are ingrained in your head. You don’t have to think about it. You don’t have to look back.

Learning and Growth

Vinita: But what’s important was we were two engineers starting a company. We knew how to build a product. We could even learn manufacturing pretty quick because you go through external manufacturing people. But what we did not know was how to market and sell the product. What we didn’t know was that there are distributors through which you do go through or you have to battle door to door with customers who are business customers.

It will be B2B business. You can call up customers but who to call, what person to call in a large company. They were Fortune 500 companies that we were selling to. We became very creative. We asked for the directory of Nortel networks which is where we worked. We asked a friend, not really directory but we wanted to get names of their distributors, people who were selling Nortel’s product.

We approached them and we asked them if they would sell our product. So you’re discovering how to sell. That is an unknown road. Nobody can predict what your sales are going to be and how soon. But we were motivated. If we got the one end of the thread, we chased it down. We took it and that worked out really well for us.

Shubha K. Chakravarthy: So in those early days especially given that you’re learning something that you’ve probably never done before, was there ever a point where you felt like it is really dark and you may have reached potentially the end of the road?

What was there like a big moment like that was hugely challenging to you? Not because of the technical challenge but just because of the unknowns and the fact that you don’t know these skills.

Vinita: There were downs and there were a lot of ups. Ups is what kept us going. In terms of what we discovered after five months, I looked over my shoulders to say, “What am I doing here?” Because nothing was happening the way we expected.

Some things went better than expected. Some things were like learning through a firehose. I learned so much in six months that I hadn’t learned in the previous 12 years. In every area you are learning how to interact with people, how to do accounting, how to do marketing, how to create a market for your products or how to sell your own product.

Then would come the phase when we would start looking for VC money, when will we grow out of two people, how will we manage, how much faster, when will we run out of energy just working harder and faster. Everything was such a huge learning experience to pinpoint my finger and say, “Oh, this is what was the most difficult thing.” And in the beginning for the first four years there was a different challenge that had to be overcome.

Shubha K. Chakravarthy: And that’s a fair point.

Fundraising and VC Experience

Shubha K. Chakravarthy: You mentioned that through this process you came to a point where you had to raise funding, reach out to VCs.

Can you talk a little bit about what your experience was in the fundraising process? Was it very different as a woman founder then? Do you think anything has improved today? Can you just walk us through how it felt to go ask for money?

Vinita: The money raising environment was very different 30 years back or I should say 40 years back. Money raising environment was extremely different. In fact, what happened was that we used to place small ads somewhere about our products. You have to sell your product. A few companies contacted us wanting to talk to us and they wanted to buy us.

At the same time I used to be on the board of my husband’s company. The VC who funded his company was somehow tracking me. You know, it’s not so hard to track the space but he knew who I was. His company and he contacted us. And when they found out that there was an interested buyer, they basically said, “well, why would you want to sell the company? We’ll give you money and you can run your company for as long as you want and make it much bigger.”

This is like  two and a half years through the journey. It was a very different environment. I think there were other venture capitalists who came to see my company and I don’t remember how I contacted them. But when they came, there were some big names in the Valley. Because we were in the internet space it was considered a very hot space to be.

So there was a very interesting company. Roy Rogers, he was a big father figure in those days in the Valley. He came to visit me and my partner had left by that time. He still was holding 50 percent of my stock because that was the agreement as he had put in half the capital. I had put in half the capital. He came and advised me that I should buy his stock. But I had very little money. He never ended up investing but he gave me very valuable advice and they were very respectful. I never felt like they treated me any less because I was a woman.

Shubha K. Chakravarthy: So different from some of the stories I hear today. And it’s so good that it was good back then. I hope it’s good to get back to those days.

Vinita: When you have a little like I initially started the company. I had some success to show. So there is a difference. If you have a person with an idea they don’t know you. If they don’t know you unless you have done a company before. If they don’t know you and you are a person with an idea then you are amongst thousands of other entrepreneurs who are pitching. In that time I can imagine biases might creep in but I had a proven track record of building the business from very little capital.

Shubha K. Chakravarthy: This was your track record after you quit corporate. This was your track record as an entrepreneur.

Vinita: Exactly. Nobody cares what you did before. All they care is that you didn’t get fired. Maybe these days it is a good thing to get fired. But I had worked for two companies in 12 years. That was a very good track record.

More than that they were only interested in what space I was in, why was it, was I in it, what do I think would happen. I had a little more knowledge than them. And in new space and technology especially entrepreneurs, their lives depend on that. They dive in. In fact, VCs are learning from entrepreneurs and that happens all the time even today. So be mindful of it.

Don’t put yourself too much below VCs to pitch to them. They are going to get value out of it. That’s why they are talking to you. And you are going to get money from that. It is like if you’re not going to get money from them, don’t be so desperate. That would be my only advice.

Shubha K. Chakravarthy: Good counsel.

Navigating Partnership and Leadership

Shubha K. Chakravarthy: You mentioned that your founder had left by then and he had still got 50 percent of the stock. What led to his departure and how did that affect your motivation and your direction in terms of leading the startup? What impact did that have on you?

Vinita: That is a very interesting story but I will not drag you through that story. The long and short of that was that being a partner in a business is like a marriage and you can get on each other’s nerves. He felt that I got on his nerves and he just couldn’t stand me. That is a pretty damning thing when you hear that from your business partner that you think you’re doing everything right.

And suddenly he says, “You know, I can’t tolerate you and I’m going to quit.” I was down for a few days but then I got myself going. My husband was a big support behind. He kind of mentally helped me get back into the bandwagon and roll the dice again.

Shubha K. Chakravarthy: Was there one thing like a pillar or anything that helped you anchor through that experience that said, “This is why I’m going to come back as hard as it is” after that setback.

Vinita: Frankly speaking, I think I’m a fighter. If something looks difficult or impossible that’s what I want to do. I wasn’t going to give up. It is a very humiliating thing that you start a company and you don’t succeed.

People don’t realize that. I wasn’t going to shut the door but then a year after I started, I was going to give it another shot. I didn’t know I’d succeed, obviously. But I was going to give it another shot somehow. I did put myself together.

Shubha K. Chakravarthy:  So now you’re back on track. You’ve got a different trajectory because you’re now a solo founder. Essentially you’re doing this on your own. What are you now thinking about in terms of fundraising & in terms of future path? What is the next step in the growth of this company?

Vinita: Growth was the thing. How do you grow and being in the hardware business you do need money. I didn’t need money because we started making money. We were profitable pretty early on because we wouldn’t have survived if we did not become profitable.

But to give yourself a professional outlook you have to have a business partner like a VC. So my motivation in getting VCs at the time was not as much money which brings me back to the earlier statement that I was not so desperate to get money. I wanted to take it to a different path rather than being on an everyday struggle which is what I was on. Little did I know that path will continue the struggle part.

Building a Strong Team

Vinita: That is what the money did because suddenly after we raised the funds, we were able to attract senior executives to build the company so that I was not involved at the ground level running everything. I could think at a higher level. And now my challenge was how to manage the business & direction through them. Because now they are a source for new ideas. They were in some ways much smarter than I was.

That didn’t prevent me from hiring them. The biggest question I asked is why did the giant join this tiny little company? One guy came and he was the VP of engineering. He came and he said, “Oh, when I first walked into the digital link it felt like I was walking into a doctor’s office. A little front entrance and something happening in the back doors. That’s what I was looking for at the time”.

I said, “Oh, really? That’s what people look for.” People forget that not just the founders but people who come and knock on the doors of startups and apply for the jobs. They are also superhuman beings that think very differently because they know that the risks are high, rewards are unknown and they are not as much in control of the situation as the founders are.

I think in Silicon Valley people do not give credibility to the people who come and work for startups.

Transitioning and Delegation

Shubha K. Chakravarthy: So two questions on getting this new team members in place. One is, how did you hold them together? How did you keep them on board and keep them kind of coming along with you?

And then secondly how did you transition because you’re used to doing everything especially after your partner quits. You’re doing accounting, you’re doing this, you’re doing that and now you have to hand off things to other people who maybe didn’t do it as well as you thought you could. How did you make that transition successfully?

Vinita: Transition was like a sigh of relief because I didn’t have to do everything in that way. But keeping the team together is something that not everybody does well but I did it very well. And again I recently heard the statement, it is information sharing that builds respect and trust.

So that showed them that I respected them. That I shared all the information, what the VC said in the board meeting, what happened here, there. I never held back anything from them. And in return they gave their best to me. They stuck together with me for a very long time.

Shubha K. Chakravarthy:. Do you think how much of that is due to the fact that you’re a woman because there’s the understanding and belief that women tend to be more collaborative. Do you buy that? Do you think your gender had something to do with your style of managing your leadership team?

Vinita: They were all the people who happened to be white males that I hired. At that time Indians in the valleys were not at that level. I think in the first 10 years I probably had a director level person who was an Indian otherwise we did not have anybody in the team which was Indian or woman but not a VP.

All the VPs were white males. And there was nothing that I ever felt that they were not willing to work with me because I was a woman. One individual whom I hired as VP of sales was probably 15-20 years older than me. I was still debating whether to hire him or not. He asked me for an interview again. He asked me and he called me back. He said, “I want to come and see you for an hour”.

He came to my office and said one sentence which I will never forget that he said. He looked at my eyes and he was a salesman. Yet he said, “If you are thinking that I will not listen to you, believe me I will”. And that made me hire him. The age could have been perceived as a barrier and he somehow sensed it because that was exactly what I was thinking.

Shubha K. Chakravarthy: A perceptive guy. So clearly the right person to be in sales. Do you think that this is the case today? Like it’s such an interesting juxtaposition of where you saw things when you were building the startup versus what you observed today as an investor or just a person in Silicon Valley.

How much do you think that has changed? I’m just curious. Do you think that’s still the case that there’s this lack of bias and this openness to seeing. Like I’ll kind of judge you on your merits and not by the color of your skin or your height or the accent in your voice. How would you contrast the two?

Vinita: I think the bias in Silicon Valley is if there was X amount of bias in those days like 40 years back, it is X by 10 now. It has reduced dramatically the bias against this. There is more talk than actuality. When it comes to entrepreneurship, people are only interested in what would make them money outside people.

Founders are looking for whatever they are looking for. They are not looking for money by and large. But investors & everybody want to see companies succeed. They buy products from you because your product will save them money, make their job easy.

They are not doing favor by buying from you and they don’t care how you look, what your accent is, whether you’re a man or a woman. I would say that by and large it is more rational. I wouldn’t say that it is totally absent but by and large, I would say an entrepreneurial journey is a more puristic journey than trying to fit ourselves in the corporate jobs.

Shubha K. Chakravarthy: That I can certainly agree with but I’m definitely going to test what you’re saying because it’s very different from what I’m hearing from others.

But obviously you come from a place of experience. So there’s a tremendous amount of weight I would place on what somebody like you would say. Thanks for sharing that. Coming back to your journey. So you’re doing all this stuff, you’ve got a leadership team in place.

Going Public: The Big Decision

Shubha K. Chakravarthy: I know at one point you decided to go public in 1994. What drove that? Is it just the fact that’s what you normally do in the stage of growth for that? Or is it just the fact that the markets are starting to heat up leading to the 1998-99 hype in internet businesses? What drove that decision?

Vinita: Like you said it is the growth. If you are growing and you can go public that is a way to provide liquidity for your investors. You can sell the company if you find a good buyer at a good enough price or you can go public.

Going public was considered a better alternative. And since we could go public, the markets which I did not understand at that time, IPO markets open and close so that sometimes investors are more willing to go up to buy stocks of IPO of initial public offering.

Navigating the IPO Process

Vinita: IPO stands for Initial Public Offering and sometimes they are not easy. And our VCs were a big set of advisors for guiding us through that process. It was like since you can go public, let’s go public now rather than wait another year.

Shubha K. Chakravarthy: And what was your thinking? So first of all, did you consider an acquisition at all? Or was it just, “Hey, it’s a hard market. So let’s just do it”. Where was your mind on that?

Vinita: I didn’t know anything about how to provide liquidity but I knew that the investors will look for liquidity. And since we trusted them, I did not go shopping .

In those days acquisitions were not as popular as they are now. There is a reason for that but in those days people did not acquire companies. Landscape on that front has changed. Going public was a very good alternative at that time.

Challenges of Being a Public Company CEO

Shubha K. Chakravarthy: And what was the biggest learning leap for you in terms of transitioning from a private company CEO to a public company CEO and just going through that whole IPO process?

Vinita: The biggest surprise was that it’s like wearing another hat. You have to communicate, meet the expectations and button down. Before that we ran the company and when the orders came in, we shipped the product. When they didn’t come in, we said, “Oh, this month is going to be soft.”

And yes we will not make as much money or we might lose money which we did not any month. We kept moving forward. But now you had to meet. It is for the CEO. It is one more thing which is very important to do because you have to beat your drums as a newcomer in the public market space so that after it is after the initial offering the stock can dive sometime because the CEOs just disappeared in running the business.

You couldn’t do that. And besides doing the work it was the change of focus and running the company from managing investors, their expectations, giving your quarterly calls, talking to the analysts all the time who are asking you how the quarter is going and how do you communicate. SEC rules were very strict rules, What you could say, what you could not say. So you have to learn.

Learning wasn’t a big thing, but just day in day out interacting with investors was consuming me.

Shubha K. Chakravarthy: How did you feel? You sound to me like a very entrepreneurial person who likes running things and solving problems. It’s a very different set of activities.

Vinita:  It is. You are very perceptive. It felt too restrictive because I couldn’t say some things and what I said, I better be right about it.

In entrepreneur businesses, you just handle new challenges every day. But once you have been a public company and have enough revenue that you have some leeway in what you can do and what you cannot do, it’s a different thing. But in the beginning companies get very restricted by the market.

Shubha K. Chakravarthy: So did you feel constrained at all? Did it make you rethink your career?

Vinita: It did. It did.

Shubha K. Chakravarthy: So what was the result of that?

Reprivatizing the Company

Vinita: That is what led to the privatization of my company. I reprivatized the company after taking it public because markets were changing and public markets are not very permissive. The financial markets are not permissive.

That “oh, I have decided this quarter to spend the money in developing or for next two quarters money into this product”. How is that going to, why did you not tell us on the quarterly call? Because we didn’t conclude that.

So you have to operate in their time window. And we felt that our transition was going to be very hard into newer areas if we continue to stay this way. In some ways at a very different scale that’s what Elon Musk is doing with Twitter now, X. He re-privatized the whole thing.

It is a huge risk when you do that. I took that huge risk, which I don’t know if any company in those days who was in technology space who was doing reprivatization of the company.

Shubha K. Chakravarthy: And how did you pull that off in terms of the financial wherewithal to reprivatize the company?

Vinita: That is what we had to kind of lean on the banks. The company had the cash because we had done IPO but to buy the shares and we have to buy everybody’s shares and then privatize the company.

So depending on how much cash you have we had a gap. We had to get the gap filled by a bank so we had to take a loan. It is very complex how to do privatization. And I went through that. I mean much more difficult and much more complex than taking the company public.

Shubha K. Chakravarthy: I think you took your IPO and your company public in 1994. Then you privatized in 1999 if I recall correctly. That’s a pretty short window.

So it sounds like almost like you went public and then you’re like this is not going to work out. I’d better take it. So how long did it take from the time you went public till you decided this isn’t going to work and we need to be back in the private.

Vinita: I think it took us a year to actually figure out how we can do once we figured out the process. I knew that it was a huge risk. I knew and my husband knew and we were the ones who were buying it back. So we were taking all the risks that were going forward hoping that there would be a big reward at the end of it.

But that reward did not happen. It may look like a short period of time but we had been in existence for 15 years. We started in 85 and to almost 2000, was a long period of time in between.

We had a window of raising a venture fund, then developing products, taking the company public, and then dealing. Internet space was changing at an extremely fast pace. It was like it wasn’t giving us a lot of leeway or for room when we can do work.

We had to act when we saw the public market well and employees used to get all disenchanted if the stock price fell. So privatization of the company was also partly to keep employees happy. The valley was so hot in those days that employees were leaving for greener pastures.

Shubha K. Chakravarthy: Dot coms, yes.

Vinita: All of those combined, it was becoming really difficult to run the company. And that’s why I’m saying that starting a company is one thing but the whole journey is the hardest thing one would ever do. But is also is the most exhilarating thing that one would do.

Shubha K. Chakravarthy: Got it. So now you’ve taken your company private, you’ve taken these huge risks. What happened to the company after? Can you walk us through the time post privatization.

Impact of the Internet Bubble Collapse

Vinita: Basically we had to exit the company eventually because the markets had collapsed. I took the company private and the internet bubble collapsed. When the internet bubble collapsed it not only impacted us, our customers which were like WorldCom SBC or all large telecom companies were our customers both domestically and internationally.

British telecom, Deutsche Telekom, Air Canada were the customers. Everybody started tightening the belt. They not only cancel the orders on the books. They’d said that they’re not likely to buy any product for next two quarters because they didn’t have visibility.

When that kind of an atmosphere happens, life doesn’t give you many choices and you have to decide whether to hold or to fold. And for variety of reasons, I decided that the better path to take is to exit the company, to fold the company, fairly treat the employees and the vendors. We could have declared bankruptcy but I’m so proud that I did not. We basically dished out money from our pockets to compensate people’s salaries and everything.

Yeah, every time you get tested what you should be doing.

Reflecting on the Entrepreneurial Journey

Shubha K. Chakravarthy: So then looking back how do you reflect on this whole journey? You started with a certain point of view and an aspiration and expectation, a vision. You went through all of these challenges you grew, you learned a bunch of stuff.

You took decisions that you didn’t anticipate whether it’s going IPO taking it private. Looking back, what is the one thing that stands out in this whole journey to you as a person?

Vinita: The learning.

Shubha K. Chakravarthy: The learning. And what about the learning? Is it the process of learning?

Vinita: The learnings were the experience that you go through at every step that shapes you, changes you, builds you up for the rest of your life. That learning changed me in such a dramatic way that I wouldn’t have changed if I had worked for somebody else for 15 years.

And there is something about running a company that I think that people miss out on is the owner’s mindset. You do everything. There is nothing, no pomp, no show. It is reality. You do it with an owner’s mindset.

Even now when I sit on a number of not for profit boards, when I said, “let’s think about what the owner of this company would be thinking about, not what makes us look good, what makes the next year look good”.

So the owner’s mindset is what I have which I would have never learned. When you are in that hot seat for 20 years, how can you not get it?

Shubha K. Chakravarthy: And then looking back, is there anything that you would have done differently knowing what you know now?

Vinita: I actually think that I was looking back, I was daring and I did the right things by continuing to roll the dice. I rolled the dice three times starting a company, then privatizing the company and then shutting the company. It was a journey and I think a net net. I came out far ahead financially.

I could have come out more ahead had I rolled the dice the second and the third time but it did not. You are going to suffer falls anytime and you brush your knees, you get up. Sometime it takes longer.

Some experiences are worse than the other experiences but you learn to get up and get going again because and overall it was a journey that I would not give up for anything.

Shubha K. Chakravarthy: It’s great to hear. I want to kind of link it back to something you said in the beginning. You said this is about purpose, right? And we talked about all the different decisions you had to take. It’s very clear that you placed doing the right thing by people very high on your list of priorities.

Can you comment on what you think was the sense of purpose that drove you early on and has that changed over time? What is the one thing that kept pulling you through all of these experiences?

Vinita: I would say the one thing if I examine my own life I’ve learned is that you have to take a deeper dive within and find what that purpose is at different moments in time. What are you trying to achieve? What is bothering you? All these things have to culminate.

For example, for the last 20 years, 19 to be more precise I have been not working for money. But you can’t be just sitting and not doing anything. You still need a purpose in life and I’m a fighter. I am highly competitive. So I need to find something which is going to keep me excited and I don’t want to lose my goodness in doing that.

It takes a long time to build your reputation and one bad choice can kill your reputation in one second. You have to preserve your own integrity. It should be a high priority in life and we all are instilled with that I would say.

Given all that I think listening to yourself & to your instincts is important. I put it also in terms of women in general are not taught to do that. They are always looking for the endorsement of other people. We say they lack confidence but what is this confidence? The confidence to me means that we can do it. Listen to yourself.

You are not going to work your life with somebody else’s brain. You got one brain and one only brain. So that’s how I work. That’s how I operate my life even now.

Balancing Identity and Purpose

Shubha K. Chakravarthy: And I want to come back to that in a few minutes but before that I want to touch on this aspect you mentioned of being a woman, being South Asian, being an immigrant. How has that identity impacted your choices and your journey as an entrepreneur?

Vinita: I grew up in India. I was 23 when I came here. The initial years, they leave a huge imprint on you. So the culture, the upbringing at home and what we were learning, what was emphasized, what was not emphasized.

My Indianness doesn’t go away no matter how long I’ve been here 50 years, 23 years back in India. I would say that even though I’ve been here 50 years, I am so much formed by the Indian value system.

What the biggest lesson in India we have always heard is that do the work and don’t worry about the results.

And that is a reminder whenever we come to the juncture, just do the hard work and hopefully results will come is the message. And U.S has given me a lot too and I value that. I value the work ethics of American culture.

Contrast in Work Cultures and Its Impact

Shubha K. Chakravarthy: I want to probe one thing, right? So this whole point you brought up of, two things actually. One is, to do the work and don’t worry about the results. And the other thing is to be seen and not heard right?

So in some sense they are antithetical, I would argue to the American way of doing things which is to be results driven. Everything is about the outcomes which is very different from doing the work and let the outcomes be what they are.

Was that ever a conflict? And how do you reconcile that?

And then secondly to those of us who have been brought up in the be seen and don’t be heard, don’t rock the boat, be humble, be self effacing. How do you overcome that inner programming and find out who the real you is versus the conditioned you?

Especially if you’re being brought up in a culture or an environment which says be humble, don’t rock the boat.

Vinita: Shubha, you are asking very complicated questions. I’ve reflected on these things quite a bit so I do like them. What can I say about it is seen and not heard who is the real you and who is the outwardly you. I think as we go through our experiences we learn about who the real me is. It does tell you.

And I think the ultimate is becoming who you are. You know you have arrived when you feel comfortable in your own skin. Then you know that you have gained the confidence for which you were striving for. You know that the only person you recognize and can retain in your internal and outwardly outlook is the real you.

The pretend goes away. It was a varnish which entered your head. It gets ingrained by different people whether they are your parents or teachers or society, your co-workers, all those things. I think the art of listening to your instinct is what we need to develop. And the only way we can develop in my mind or the way I developed is by saying, “Whose brain am I going to think with? My brain. That’s all I have”.

That has been powerful, but it is not easy to practice.

Shubha K. Chakravarthy: Are there tips that helped you do it better than otherwise?

Vinita: I think I tend to hang little cards on my desk and write things that I need to incorporate in my personality. They change from year to year. It’s like my new year’s resolutions but it is more not what I’m going to accomplish. They used to be that way but as I have grown and I understand life a little better, they are more about how I can become a better person.

Shubha K. Chakravarthy: Got it. Very inspiring. Thank you.

Advice for Aspiring Entrepreneurs

Shubha K. Chakravarthy: I want to shift a little bit and talk about a couple of other aspects of being South Asian or an immigrant woman being a founder. What have you seen in terms of the trends from kind of when you were building your company today?

What are some big trends that you see with women who are trying to start companies? Are there things that have gotten more difficult? What has gotten easier and what counsel would you give somebody like this looking to start a scalable startup to improve their odds of success?

Vinita: I think the South Asian women today, the numbers are hundredfold compared to when I was there. They obviously always had the ability. They are going more into STEM education. They are not afraid to take the leap. They are not as dependent as you know, that they will marry and that is how they are going to make their food come to the table.

All these little things that have transpired in Indian women’s life back home as in India as well as here has inspired them to probably do better and examples don’t hurt.

You always think, “Oh, that is my person who looks and smells like me and the person has done this”. You have removed one barrier in the mind that you can do if this person can do it so can you.

Shubha K. Chakravarthy: Do you think there’s any negative to that? Because now that in theory there are fewer barriers. I wouldn’t say no barriers. There’s a risk that if you haven’t done it therefore it’s your own fault. Whereas that might not be the case. I mean in some cases the barriers might still be there.

Vinita: I was saying you are absolutely right. It is your fault if you haven’t done it. It was your fault before and it is your fault now. So take the ownership of what you are doing which is what you said effectively.

Shubha K. Chakravarthy: You finished your journey with the company. How did you redefine your purpose? How did you redefine your direction and how do you now frame your life in your post startup journey? How did your startup journey influence that?

Life After the Startup Journey

Vinita: It has become far more interesting now than it ever was. I say that because I am involved in a number of boards. They are all not for profit boards but one is a mathematical society, one is Stanford medicine. They have a specialized South Asian health focus. I’m involved in their board. I’m involved in the Palo Alto Medical Foundation board which is a local healthcare provider very huge one with 2,000 doctors & physicians. So it’s a huge organization.

And then there is something called Asia Society. I meet different sets of people and they are all very accomplished board members on these. So just rubbing shoulders with them, being able to contribute to the strategy of the organization. These people are from different walks of life than what I have gone through. They are not technology companies. I’m not on technology boards.

My learning and enrichment as a result has been quite dramatic and I enjoy every moment of that.

Then I play bridge which takes 30 percent of my time and learning bridge is as hard as the journey of being an entrepreneur. The learning never stops. It takes decades, generally 20 years before you become a real expert in bridge if you were playing full time. So it is a very difficult journey. 

In a game of mind none of the computers have been able to defeat expert bridge players and I have won three national championships. I have progressed quite dramatically but that progress has taken a lot of hard work and hours and money in that way. I play bridge desk we talked about and then I do writing which is another journey which I have really gained a lot about how to be more organized in my thinking, how not to just rattle out things, how to concatenate the words to form sentences which are easy to understand.

English wasn’t my first language. So that was another step up for me. I never thought I would be writing. The fourth thing I do is painting. I always call it like a pillar where I’m not doing anything. I’m painting and let the hearts settle down in my brain and I always enjoy having a painting on the aisle.

Shubha K. Chakravarthy: That’s fascinating. Would you recommend that for founders who are building their companies today, Would you recommend any of these activities to enrich?

Vinita: Having some creative aspect to them like doing any kind of artwork whether poetry or writing that has a lot of creative elements. Engineering or research for example which a lot of us have done tend to be more unidimensional.

This gives you breadth of thinking, creative thinking, where you don’t have to have preconceived notions on how to paint, how to write a poem for example. I think that the other activities require time.

They are entrepreneurs and people in the hot seat and professional careers. They do not have that much time and women especially are running their family taking care of children. Primary responsibility still happens to fall on the women. They lack the time to do anything but creativity is something you can do rather than worrying.

You can do that and get your mind more organized. And of course meditation. Some people find that as a tool to do the same thing but I have not been a meditator.

Final Words of Wisdom

Shubha K. Chakravarthy: So in conclusion what words of wisdom would you offer to either a younger version of yourself or to other women just starting out this journey?

Vinita: Be you. You just try to be you.

Shubha K. Chakravarthy: What does that mean? I’m going to challenge you on that. What does it mean to be you?

Vinita: Be you means don’t do anything which looks artificial that you have to struggle to portray yourself. If you are projecting yourself the way you are, others will come to you or engage with you.

I think engagement is something we need in professions as well as social life. If we can be ourselves, people find us more interesting. People believe us more. They trust us more and the job becomes far easier.

Shubha K. Chakravarthy: One last question on that. Where do you split the line between learning new skills that feel uncomfortable or new ways of thinking about things?

For example, taking risks when you don’t feel comfortable taking risks versus figuring out who is the real you, which is as you can see this is a repeating theme that I’m struggling with as well. Any words on that?

Vinita: I would say there are two different things that being you is who you are. And part of us as humans need success to feel that our life was worth living and we did something which was worth doing.

I think striving to do something, to accomplish something is natural and should be done and that is part of life that you should not back away from. So being you doesn’t mean that you become easy on yourself.

Shubha K. Chakravarthy:  Well said. On those words I want to thank you. This has been amazing and a very enriching conversation to me. I’m very sure our listeners will feel the same way as well. Thank you so much for being generous.

Vinita: Thank you very much, Shubha. I enjoyed talking.

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