Bipul Sinha is the founder and CEO of Rubrik, a leader in zero-trust data security used by enterprises to defend against ransomware and to create global cyber resiliency. On today’s episode, Jon Sakoda speaks with Bipul Sinha on his unusual path from India to Silicon Valley and his unique mindset as a startup founder.
Bipul Sinha is the founder and CEO of Rubrik, a leader in zero-trust data security used by enterprises to defend against ransomware and to create global cyber resiliency. On today’s episode, Jon Sakoda speaks with Bipul Sinha on his unusual path from India to Silicon Valley and his unique mindset as a startup founder:
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BIPUL SINHA: One thing that I was very clear on is that starting something is never a risk. The risk starts once you start that. So think about the act of jumping out of the plane is not the risk. The ability to build a parachute along the way so that you have a safe landing is the risk.
JON SAKODA: Welcome to the Decibel Podcast. I am excited to welcome Bipul Sinha, the founder of Rubrik, to the show. He was a successful venture capitalist who became an entrepreneur. And his startup, Rubrik, has become one of the fastest-growing success stories in data and cybersecurity. He has a very unique founding story and has great words of wisdom for founders. And I am excited to finally have him on our show.
Bipul, thank you so much for coming on the podcast.
BIPUL SINHA: Thank you so much for this opportunity. I’m really excited to talk to you and also provide some things that I’ve learned along the way to your listeners.
JON SAKODA: So, can we start at the very beginning? Where did you grow up? Tell me about the house that you lived in. Tell me about what your parents did. And tell us the journey about coming eventually here to Silicon Valley.
BIPUL SINHA: So I grew up in India, northern India, initially. And my dad was a farm entrepreneur, and he it didn’t work out for him. So we lived in a household with a lot of financial difficulties, food security issues. We were all living in one room and everything. That was the bedroom and living room and study room and everything in between. And that experience and my dad’s influence on me has really made what I am today in terms of the ambition, the entrepreneurship. In some ways, I like to think that I’m my dad’s spokesperson, and his ambition is getting expressed through me.
JON SAKODA: I’m glad you’re telling this story. And I think many founders out there can relate. Many people I know who have started successful companies came from similar unconventional backgrounds. Their parents were amazing people like yours, but perhaps didn’t have resources. Still, though, had incredible influence. Would you mind sharing some of the wisdom that your dad taught you along the way?
BIPUL SINHA: The biggest thing that he taught us was if you can dream and imagine, you can get there. So you are what you imagine yourself to be. And you are only limited by your imagination and thinking. And that seed of thought at an early age really became the factor, the propulsion that drove a lot of things I did in my future life, because the local obstacle didn’t matter, because you were running for or going for something big, something fantastical—something that you can’t even describe or measure. And that focus on something huge and then maximizing right now to maximize all the current sort of opportunity that is in front of you right now, really became this kind of framework for me to think through life, entrepreneurship, and everything else.
JON SAKODA: This kind of advice at an early age can be so powerful. And I know it was a long time ago, but do you remember any specific moments or stories he told you that inspired you to really dream big? This must have been quite memorable as a child.
BIPUL SINHA: So there was no one specific moment when that discussion happened, but it was through osmosis over months and years. But I distinctly remember, when my dad was trying to start his second company, and he had absolutely no money, no family support, nowhere to live. And he had to motivate himself. And he had to go to the state government for a loan to start the company. So he wrote down on the wall of our one-room house that hard work and long-term thinking, strong determination, is the key to success. And he wrote that on the wall. And all of us will see it every day. And that was his way to motivate himself, and his way to for us to learn what it means to live life, and how do you think about life.
JON SAKODA: And one of my favorite stories that you’ve told about growing up is that you decided to drop out of high school to focus on taking an incredibly important exam that would possibly change your life. So would you mind telling that story?
BIPUL SINHA: Absolutely. So I was not a good student, since I grew up in very, very small town where there was no like, good educational infrastructure. So I didn’t have a good elementary school or middle school or high school education. And whatever education that I had, I didn’t have good grades at all. So when I came out of high school, my dad said that, “Given your grades, you can get admission in a local college just to get a degree. But it’s not going to take you anywhere. And unemployment rate is so high in India that you’ll most certainly not get a job. And then you’ll essentially have to start a small little shop on the street corner and sell something to make a living. Or you could not go to that path, drop out, and prepare for IIT. And if you get through the entrance examination, they don’t look at your grades. They just look at the results of that entrance examination.”
And back in the day, it was a 12-hour-long exam over four sittings. And if you can get through that exam, everything else is kind of immaterial. So, first time when they gave the exam, I failed in every exam. And I had insisted that I will also take the state college entrance exam. And I failed in that too. And when I failed, even in the state exam, my dad brought sweets and told me that, “I’m glad that you didn’t get through the state exam, because if you had gotten through the state exam, you’ll never go to IIT.” And think about the situation where somebody has no educational excellence record, or somebody has no prior history of anything out of ordinary. To have that level of confidence that you will get through IIT, and I’m glad that you didn’t go through the state entrance.
And everybody thought, all our relatives thought that this father/son duo has gone crazy. [Laughter] And they are dreaming of something which is almost impossible. But he had a strong conviction and confidence. And he asked me to drop out again and not do anything else, just sit at home. So I did that. And then next year, I got through. And that really changed the trajectory of my life and career, and as well as my family’s financials, as well as other situations.
JON SAKODA: I really love this story, and I’m so glad you’re sharing it. I do wonder, while you were going through this process, when you failed your first exam and your dad kept dreaming that you were going to pass an even harder test, looking back, was there some tension in the house over what you were supposed to do? What did your mom think of this?
BIPUL SINHA: It was not a great situation in the household back then. My mom was very sick back then. And we didn’t have like, money to take her to a good doctor. So in some ways, it was the choice between her health and medication and buying books, so we used to alternate. And she was equally ambitious. And for some reason, she had the confidence that I will do something in life. And there was no real basis of it. Both my mom and dad, their belief was never wavering.
JON SAKODA: Are you still close to your mom and dad?
BIPUL SINHA: Unfortunately, both my mom and dad passed away. But I was very close to them. They were my guiding force, and in some ways, as I said before, I’m here purely because of them.
JON SAKODA: I am so sorry to hear that they are no longer with us. But I do really appreciate that you’re able to share these stories with us. They seem like amazing people. Maybe to finish your story, what was it like getting into IIT after all that hard work? They must have been proud. Was it what you thought it would be?
BIPUL SINHA: So, one of the experiences that stayed with me was this feeling of an outsider. Because when I went to IIT, my communication skills were not great. I was not very confident in myself. Because where I came from, I felt like I got lucky and got in, and I truly do not belong, in the sense that I was there, but I had this outsider perspective. And that outsider perspective stayed with me. In some ways, when I first came to America—and I came to America as an economic migrant, because I wanted to earn money to support the family. Because even when I came to America, my parents were still in the basement where they were living while I was in India.
So that outsider perspective, that economic migrant angle when I came to America, in fact, when I landed in America, I felt that I belong here. And that was a very unreal feeling, because I never had like, the middle class socioeconomic situation in India. As a result, I started as a software engineer, and really love learning business, learning technology. First 10 years was software engineering. And that 10 years gave me the network and confidence that I’m not going to slip into the poverty where I came from. And then starting mid-2000s is when I started to think about what is next for me. And am I more interested in business or just the technology? And that’s when I started to change.
JON SAKODA: When you look back, was there ever a moment when you said, “I’m gonna someday start a company”? Or did you have any early plans to be a founder of a startup?
BIPUL SINHA: I do not plan for long-term at all. So I do not know what is the next thing I’m gonna do. I only have this feeling that I wanna do something big and fantastical and attain my full potential. But I can’t define my potential. As a result, I don’t worry about timeline or switching into different things. And so, I never thought about becoming an entrepreneur. Even when I joined Wharton, I never thought about becoming a venture capitalist. Essentially, four months before becoming a venture capitalist, I never had thought about becoming venture capitalist. And also, six months before starting Rubrik, I never had thought about starting a company or becoming a founder. So I’m living almost day-to-day.
JON SAKODA: I know we’re gonna talk more about living in the moment. But before we get there, would you mind telling us the story of how you eventually made your way to the US and here to Silicon Valley?
BIPUL SINHA: So, when I first came to the US, I joined a company called American Megatrends. And American Megatrends was a federal manufacturing company that used to supply servers to different OEM partners. And they hired me in their R&D. And I was writing the server management software. And from that, I wanted to come to Silicon Valley, because I thought, since I’m in technology, and Silicon Valley is the center of universe, I wanted to come to Silicon Valley.
So I applied to many companies. Oracle gave me an interview. And I came to interview at Oracle. And that was a software development job. But they felt that I was not ready to be a software developer. So they gave me a job as a QA engineer. And it was a big decision for me because I was really doing well at American Megatrends, where I was in Atlanta, to come to Silicon Valley, particularly taking a software testing job. But I thought, I’m coming to Silicon Valley. It does not matter where I am. And it allows me to be at the center of the software universe. So I joined Oracle. And within a year, I got a job in the software development. In fact, the manager who gave me an opportunity to be a software developer, he gave me all the books around operating system and distributed system and algorithms to learn about computer science, because I was an electrical engineer. And I didn’t have any formal education on software, particularly writing database kernel.
And that year, when I read all these books and really taught myself as how to write or how to think about larger scale distributed system, was really the foundational kind of platform that I built. And over the years at Oracle, I became manager of the team, which I joined, then director of the team. I worked with really really smart people across the data and systems technology that I was a part of. In fact, after becoming a venture capitalist, I funded a number of companies started by people in and around this area.
But those years at Oracle, I used to think that I stayed at Oracle for way too long. But looking back now, I feel that those were the most important year of my life and career, because it really taught me how to think about hiring people, building teams, setting the technology focus, thinking about building a product for market. Because Oracle, the software engineering manager used to have a lot of leverage in terms of product to build, think about the market. And that focus on the engineering is the way to succeed in the marketplace, really ingrained in me as how to think and build software products. And that really built the foundation for everything that I did after that.
JON SAKODA: And what eventually inspired you to become a venture capitalist?
BIPUL SINHA: So, at Oracle, at some point, once I felt like I’m not going to slip back into the poverty where I came from, I start thinking like, what is next for me? And I used to have that feeling that I’m doing well at Oracle because Oracle is really good to me. Starting 2005, I was starting to get pings from recruiters and other places. So I went and interviewed at four or five big companies, what you’d say like big tech. And I got job at all of them. So then I started to change my thinking, saying that it’s not that Oracle is really good to me. Maybe I’m good. Maybe I have something to offer that is maybe different or valuable.
And that change of perspective, where you don’t exist because of the world, but world exists because of you, that perspective change was pivotal—and it didn’t happen in a day. It happened over a span of few weeks to several months—really changed my thinking about risk, my thinking about what’s next for me. And then I started thinking about like, I want to go to business school and get some foundational knowledge about business. I wanted to switch into looking at businesses more holistically.
And back then, I had this strange fascination with mid-market private equity, because I used to think that applying my technology understanding and business understanding, I can help really transform some of these mid-size company growing. And after my first year of business school, somebody told me that there’s a venture firm in the city they’re looking for somebody to join. And I looked at them. And then I thought about, maybe venture capital is the right way. But that was just three months before getting a job in venture capital.
And I applied. They had a lot of candidates back then, and I didn’t have a real background in finance or deal-making. But I kept calling them, kept calling them. And they eventually relented. They said, “Hey, come join us as a consultant, and we’ll see how you do before we offer you a full-time job.” And I said, what do I have to lose? I went and joined them as a consultant. And within a week, they actually offered me a full-time job.
JON SAKODA: And many people don’t know this part of the story, but you invested in some amazing companies as a venture capitalist. And you were well on your way to becoming a Midas List investor. But then you chose to become a founder in the middle of all this great success. So tell us that story.
BIPUL SINHA: I didn’t know how I would be as a venture capitalist when I started on this journey. But I always thought about like, I want to be the best at it, like fantastically top. So I came across many companies and situations which really went on to become very large companies. And that really gave me a framework that how small things become big. You know, seeing is believing. And that, small things getting big, I got a fascination with it.
And then the second thing that happened was, I was looking at my life and situation and venture capital. And I thought, me being a venture capitalist itself is a 2-sigma event. I was not supposed to go to IIT. I was not supposed to come to America. I was not supposed to work at Oracle. I was not supposed to be in venture capital or go to Wharton. Since I’m here, is this the end of me, or how far I can push my luck?
And the other thought process that came to me was that everyone knows Microsoft founder. Nobody knows Microsoft’s investor, whether it’s first investor or second investor. So that thought process, that how do I go create impact and build something that outlasts me, that really was the kernel of thought that started me on this journey. But it didn’t start for many, many years. It started literally six, seven months before I left the job and started Rubrik.
JON SAKODA: You have famously said that starting a company is like jumping out of an airplane and then building a parachute on the way down. It’s one of my favorite quotes about startups that you’ve shared. And I’ve always been wanting to ask, did you feel like Rubrik was like jumping out of an airplane? And did it feel like you were taking a big risk?
BIPUL SINHA: See, one thing that I was very clear on is that starting something is never a risk. The risk starts once you start that. So think about the act of jumping out of the plane is not the risk. The ability to build a parachute along the way so that you have a safe landing is the risk. So, do you have a clear understanding of what are the mitigating things that you have to focus on? And only those things that you have to focus on to really have safe landing. And are you focused on those things? And are you relentless about those things? And 99% of the people do not focus on mitigating things and being relentless about it.
So the risk is not being able to be relentless and be able to identify the risks. The risk is not the act of starting something. And I was very clear about it. So I had this clarity in my mind that what really matters is what do you do after you start.
JON SAKODA: And while we’re here talking about the moment of inception for Rubrik, what was the initial idea and the thesis? Tell us about the first few months, when all you really had was a PowerPoint?
BIPUL SINHA: I have always believed in attacking an existing market, as opposed to creating a new market. Because creating a new market with venture dollars is very, very hard. So you are adding an additional thing of the market risk, in addition to the product and execution risk. So I always was a believer that as new company, you want to reduce risk. And then risk reduction is really about going after an existing market with existing buyer and existing budget, and really change the game of the market.
So that was the thought process. And the way I saw it was that backup and recovery was an underserved market. The incumbents were making a lot of money, so $20 billion, $25 billion-dollar market. The incumbents were making a lot of money with almost no innovation. And as the world was digitizing more and more, the enterprises had only one data strategy, which was backup and recovery. And as the world was digitizing more, the cyber attack and cyber strategy around data was missing. So can we build a new platform that will be the enterprise core data strategy?
And in fact, when we were in the stealth mode, we called ourselves World’s Data Management Platform. So that was our vision. We didn’t know what would be the killer application on this platform once we actually transform it. And that killer platform turned out to be cybersecurity.
JON SAKODA: Your initial success as a company was truly incredible. I believe, famously, you went from zero to $50 million in sales in your first year. This clearly was not by accident. You engineered product-market fit in a very specific way. And I was wondering if you could demystify that process for people. How did you engineer that type of explosive start?
BIPUL SINHA: So, in my mind, you have two really huge risks with a business. One risk is the execution risk. And the other risk is the financial risk. So whether you will have enough money to continue to execute. And execution risk is that, are you creating enough of a signal for next investor to give you money to build? So these two things are closely related, but both are equally important. So the thought process was that speed is the startup’s biggest asset and biggest weapon. So how do you create a high velocity company by changing the rule of the game on an existing market? So that was the thought process.
The challenges with many startups are that when they start and try to explore the product-market fit, they execute serially. They build product, talk to some customers, and then hit like a 60-65% product-market fit, and then take one or two years after first product GA to really hit the 80-85% zone. My benchmark is that if you talk to 100 people, and if 85 people say, “It is interesting, let’s have a second conversation,” then you have a product-market fit that you can scale. Below that, the cost of sales is too high.
So, my idea was that how do we get to that 80-85% zone in the fastest possible time? And we have to also eliminate tire-kickers. Because you will find a lot of people who are not really believers, but they will show interest, and they’ll waste your time. So what we did was, we created a pitch deck as if our product is ready today to sell. And we created a one-pager—we called it Early Access Program—where we said, “Hey, if you are interested in trying our product, our first beta product, you have to pay us $3,000.” And the contract was simple one-page contract with three bullets about what you are going to test and how do you determine the success. And you will get six weeks to do so. So we’ll go pitch to the customer. And if they show high interest, we’ll send them this contract, saying, “Sign this contract for you to be ready to test our beta product.” Did 60 to 70 calls while we were building the product. And then we send this contract to whoever showed interest in trying our beta product so we could eliminate nonbelievers. Because if you can’t get $3,000 contract by your procurement, you’ll never buy a $100,000 product from me. And that allowed us to focus on the right set of people. We had 22 beta customers who signed up with Rubrik, and we converted all of them. And that really time-compressed our product-market fit and gave us early signal to be able to spend dollars in marketing and sales. In fact, pre-GA of the product, we hired sales team all around the major marketers in America.
JON SAKODA: This is one of the more incredible parts of the Rubrik story. And as I recall, you also had some very unique approaches to recruiting your initial founding team. Would you mind retelling some of those stories?
BIPUL SINHA: So, because of my venture capital job, it taught me a few things about talent and capital. So on the talent front, I knew that the best chance you can give a new company is to hire the best people. And sometimes founders fall in this trap that, “Hey, we are an unknown company. No great person will join, so hire a mediocre person. And when we have a little more signal, then we can hire the top people.” That, in my own thinking, never works out. Because once you start compromising in the startup in the early days, you’ll have series of compromises that will lead to not so great outcome.
So, our goal was to hire the top quality people from day one. But getting the top, top quality people is hard. I thought that I’m this hotshot VC. I will leave my job. 50 people will follow me, and 20 people, I’ll hire on day one. 45 days later, I had zero hire. Because people that I knew from my life as venture capitalist, some of them were not ready to do a change because of professional, personal life situation. And the others who were ready to start, my co-founders will reject them, saying that they are not meeting the quality bar. And that was the first two tests of entrepreneurship. Because I remember, 45 days later, I would get up with sweat, 2:00 in the morning, thinking, “What did I do with my career? These guys are not hiring anybody. We’ll not be able to build the product. And I had this good venture capital career. What did I do to me?”
And so, I distinctly remember, after a few 3:00 wake-ups with sweat, I told my wife, saying that, “Hey, forget about me for the next 90 days. I’m going to not eat breakfast or dinner at home.” I created a pitch deck to pitch to engineers, just like you pitch to the salespeople. I would go sit at a coffee shop next to Google on Facebook offices. And all day, all I’ll do is cold call people and pitch them. Literally from 7:30 in the morning. And I would do a coffee meeting till 9:00 in the night, every single day. And the next 45 days, we hired six people. And we would actually recruit folks or interview folks recruit folks or interview folks parallelly over the weekend.
And so much so that we actually threw baby shower for one of our candidates that we were interviewing, because his wife was not comfortable with a startup. So we literally threw a baby shower and got them at our small office to convince her to allow her husband to work with us. And I’m proud to say that she did. And the founding engineer is still with us.
JON SAKODA: These early stories are so raw and emotional. They’re a part of the fabric of every startup story. And I know that you have many, many stories when your back was up against the wall. You dropped everything and just willed your way to success. I’m curious, now that Rubrik is bigger, do you still find yourself activating that same tenacity?
BIPUL SINHA: 100% feel that that relentlessness in you is what drives this company. Because as a founder, you are the lead dog, and you have to set the pace and set an example. And so, you have to have that day one, day two, day whatever nine years later. You have to have that. Once you lose it, you should get out of the way. Because the thing that you are creating is bigger than you.
JON SAKODA: That is so honest and such great advice. It takes me to another one of my favorite Rubrik stories. You guys started out disrupting the backup market, and then along the way, found another killer app. You used backup as a really unique way to create cyber resiliency. And would you mind telling everyone the story as to how you stumbled into that use case?
BIPUL SINHA: So, when we started our business, we built our architecture that now is called Zero Trust, but we didn’t have the nomenclature. But we built our architecture in a highly secure way. But nobody was buying security. So we started selling a better backup, automated backup, hybrid cloud solution, all of that. But I remember, starting 2017, one of our first customers got attacked, and everything was down other than Rubrik. And they had a ransom note that they didn’t have to pay. And they called us, and they said, “Bipul, you guys saved our hospital.” And I had no idea why and how. So we sent our engineers to investigate a little bit, as what has happened.
And what we discovered was that our unique architecture that we built for cyber, it really makes the platform immune to attacks, because it’s a full authenticated platform. And that really started this whole motion in us saying that, hey, we have this unique technology, unique platform. How about we build a threat intelligence directly into our own software? How do we build an event response in our own software? We started doing that in 2017. Nobody was talking about cyber or or ransomware. So we were like three, four years ahead. But we had this vision that this market needs data security. And then we got lucky. The market came our way, and number one use case became cyber recovery. And we have the most comprehensive solution.
JON SAKODA: Finding success in security was more than just luck. Your product clearly was well-architected to solve more than one problem. But I’m curious, your competitors and customers really historically only focused on either backup or security, not both. So how did you go to market in both domains as a small startup?
BIPUL SINHA: The thing that happens to a new company is to set the agenda of the market. So as a new company, you have to set the agenda of the market, which is different from how incumbents are playing. And so that you force them to play by your rules, and then you disproportionately win. That’s how startups start and grow. But when you have to switch to yet another rules of the game, and in this case, was data security, then in some ways, you can confuse your existing customer or your prospects, because now you are trying to be defining new rules of the game.
So we had to really kind of do that in a way that we don’t leave our core customers behind, and take them on this journey, and make them realize that they really need a comprehensive data security platform. Because it is all about being two miles ahead of your customers, not 200 miles ahead of them. If you are two miles ahead of your customers, then every interaction that you bring gives them something interesting to think about, and that could be applicable to them, as opposed to, interesting, but hey, come back to me five years later, because you are way, way ahead of me.
JON SAKODA: Now that you have created such success, I think there are now many founders out there who are running their company to someday be like Rubrik. They want to try and engineer their company for the same level of intensity an hyper-growth that you’ve seen. What are some of the most important words of wisdom that you’d share to founders who want to emulate some of your success?
BIPUL SINHA: The most important thing, at least the mindset-wise, is that do not think that doing $2 million in the first quarter or $5 in the second quarter is impossible. You’ve got to challenge your team, particularly in the early days. You have to set impossible goals and celebrate failures. That’s the right state to be in, that every time you fail, you set a new benchmark, a new standard of growth. So, teaching that team and teaching yourself of not being happy with what you got, and go for a bigger and bigger outcomes, where you’re always failing and always succeeding by inserting new benchmark, that’s the kind of foundational fundamental thinking.
JON SAKODA: I know that a lot of founders right now are wrestling with the concept of high growth, while also finding high efficiency. Do you have any advice for founders or lessons learned that you can share with anyone who’s struggling with these conflicting priorities?
BIPUL SINHA: It was not that from day one, we were very efficient. We made our own mistakes along the way. But at some point, what we realized is that the business, at certain scale, has to have what business ought to be. So the business is built to generate cash flow and generate free cash flow, because that’s how the businesses are valued. So how are you setting the company to generate free cash flow and a lot of them in future? And that thinking has to come in in terms of how you design your business.
See, a lot of times, what happens is that when something is working, you feel like, do not touch it because it is working. And in some ways, it is true that do not touch it because it’s working. In other ways, this becomes a limiting factor, because that psychological safety that you have in supporting what is working, it becomes the issue when it comes to making sure that you have a part to building a long-term business that is generating cash.
So, thinking about and fighting your own psychological safety, and staying in this time of conflict all the time, where you have to make decisions about how are we going to really make it a profitable business? Is this particular situation going to lead us to an outcome? But you can only do that if you have this fantastical maximal thinking. If you are trying to find an exit for the business, then you can have a very different optimization, because you want to show growth, because you’ll get acquired based on how many customers you have. But if you want to build something long-term, something fantastical, then you have to kill your psychological safety and really go for this conflicted mental state, where you are trying to grow and optimize at the same time.
JON SAKODA: You have brought up this term in the past, which, if you don’t mind, I’d like to unpack it now for everybody. Psychological safety. I think it’s one of the more important mental coaching tips you have for founders. What is psychological safety, and why, as a founder, do you need to push yourself to avoid it in your startup?
BIPUL SINHA: See, the thing is that human beings have evolved to reduce the cognitive dissonance. So when we see a new situation, we immediately try to box that situation into something that we can understand. And that’s what the consumer marketing and other marketing do. They try to box everything for you so that you can easily understand. And what happens is that when you resolve the cognitive dissonance, you have psychological safety because you can operate now with a framework.
But in a high-risk situation or in an uncertain situation, that psychological safety’s your enemy. Because for psychological safety reasons, you make decisions which actually goes against you. I’ll give you an example. So if you have a sales rep, and then if you ask the sales rep, “What is your forecast for the quarter?” So they’ll give you X number. And then if you ask them, “Show me the deals,” they will have deals that will never close for the quarter. But they will have it there because it gives them psychological safety that I have enough of a pipe. But that psychological safety is against them, because if they take those deal out and say that, “I do not have enough deal for the quarter,” then they will fight hard to bring some other deals into the quarter or build pipe for the next quarter. But if they linger on on deals that are not closing, then they will not work hard for the next quarter or to bring something new in this quarter. So, for an uncertain situation, you have to not go for psychological safety, but live in the psychological upheaval.
And same thing is true for founders. The answer is always conflict. Answer is not a resolution.
JON SAKODA: I want to ask you about some other unconventional wisdom that you’ve shared in the past. And this is about the value of experience, or perhaps what I call the wisdom of experience. Would you mind talking about the trade-off in your mind between people who have a lot of experience, usually seasoned executives, that want to import that wisdom into a company, versus a founder’s own intuition about what is right for their company in the moment?
BIPUL SINHA: See, the thing is that as a venture capitalist, I used to always think that the founders constrain the management team by over-managing them and being obsessive compulsive about it. So I took the approach of completely hands-off. But what I realized then was that a lot of people who have been successful in the past come up with a framework that have made them successful. And it is also related to psychological safety. So they are safe in that framework, and they impart that framework into a new company, which almost never works. So you have to help the management team become uncomfortable in a new situation and learn. And if you leave them alone too much, then they are not learning, and they are going for psychological safety. So you have to bring the team together with a context of the current company and a framework of execution for the current company.
And I say it is based on intuition because this is what you have learned about your own company over the years. Nobody else will have so much thinking and knowledge as you. You may not be exploiting everything, but you have a framework intuition. So you have to apply that framework intuition and make sure that your management team or your executives are not applying psychological safety framework; they are uncomfortable and learning in the current context. And that is the most important thing. If you just listen to them and take a step back, saying that, hey, these people know what they’re doing because they have done so much in the past, or they have this success or that success, that will ultimately not work out.
JON SAKODA: So, two questions on this point. One, how do you recruit for people that can embrace this concept? And then how does that also show up in your management team meetings?
BIPUL SINHA: So, while you’re recruiting executives, you have to ask questions to ensure that they show self-awareness and learning in terms of what they have done. So what I typically ask is, “Tell me what has surprised you in your last job that you didn’t think about going in.” So, trying to kind of understand that what did they learn? What was the framework going in, and what did they learn? Ask these questions to see, are they self-aware, are they learning? Those are the most important things. And then, in our executive team meeting, if somebody says, “I know it from my past experience,” we almost always reject that.
JON SAKODA: In this current environment, there’s a lot of people that are uncertain. And I know that you have a lot of thoughts about operating in times of uncertainty. So, tell us a little bit about your framework for how you guide the company through moments of uncertainty.
BIPUL SINHA: The most important thing in uncertain times is to first accept the uncertainty. See, a lot of people, when they operate, they either have good memories or regrets of the past, or worry about the future. And they are fighting today. They are not accepting the situation today. And they feel like the situation will get better tomorrow, so I should not make that decision. So I’ll give you an example.
So, if you see that economic situation, macro economy is bad, or your customers are not buying, instead of fighting that thought, for psychological safety, again, accept it, saying that the situation is bad. And now that you accept the situation is bad, what do you do to really get out of it, as opposed to fighting it, saying it’s temporary, it’s because my team has not done . . . It’s like you are trying to always find an answer to satisfy yourself that things are not too bad. So, acceptance and maximization. That’s all you can do. Everything else is not in your hands, and you can never control. But tomorrow is a reflection of now. As long as you maximize now, tomorrow will be all right.
JON SAKODA: I know you don’t like to look back, but it would be great if, for a moment, you could for us. Would you give any advice to your younger self?
BIPUL SINHA: What thing that I’ll tell myself if I have to—I’ve had that opportunity, is to be more confident in your own thinking. Just be more confident. Because here is the thing. We are all, as founders, living at the edge of known and unknown. Known is what everybody knows. Unknown is what we are trying to create. So at the edge of the known and unknown, nobody knows the future. Nobody knows the unknown. So your own intuition is as good as everybody else’s intuition. However many years they have spent in venture capital, or however many successful companies they have created as founders, nobody knows.
So when nobody knows the future, your own intuition is as best as anything else you can get. So really be more confident in your own thinking, and don’t let other people overwhelm you, is what I’ll tell myself.
JON SAKODA: I know that you are a friend to many founders, and you give a lot of advice. What’s some of the most common advice that you’re sharing now with founders?
BIPUL SINHA: A lot of times, folks ask about, “How do we know there is a product-market fit? How do we allocate capital? How do we think about acceleration?” And those other kinds of questions folks have. The most common thing is, and that I fundamentally feel, is everybody’s trying to learn to much. It’s like, I’m listening to this podcast, I’m listening to this. Ultimately, what you have to really think is for your own unique situation, what are the unique mitigating things that you have to mitigate to really move the business forward? And nobody knows that other than you. There is no amount of knowledge that can help you. So have some framework in mind, and just go for it.
JON SAKODA: Do you feel sometimes that good is the enemy of great in a startup?
BIPUL SINHA: My thinking is that there are some good companies, good, successful companies, there are some great successful companies, and then there are companies who are at potential. But then here is the crazy part. There is no company with ad potential. And it is something that you have to strive to get to. It’s like infinity. You can never become infinity. You have to strive to get to infinity. But having that thinking, that we are not going to be satisfied, and we are going to go better and better and better, what it does is it creates some detachment from your current situation, because you’re not happy with your current situation. You’re not like, accepting success. You are saying that, hey, this is my temporary state. And I’m going to be bigger and better and bigger and better.
So that transcendental experience that you have, mentally, it really opens up the possibility. Because all of us define constraint by trying to be good or trying to be great. But you unconstrain yourself by trying to be at potential, because you know you can never be at potential. You can never be satisfied. You will always be detached, and you’ll always go for this fantastical magical maximal outcome that you’ll never achieve in life. But you’ll create new records.
JON SAKODA: I think this is definitely one of my favorite things you have ever said. You should always strive to be at potential, but you will also always be dissatisfied.
BIPUL SINHA: In my mind, searching for happiness is not happiness. Accepting the conflict is joy.
JON SAKODA: It is really hard to top that one. Accepting the conflict is joy, said like a true founder. I love you, man. Can I give you a hug?
BIPUL SINHA: Virtual hug.
JON SAKODA: Oh my god, that is so good. Bipul, you have been an amazing guest on this show. Thank you so much for coming on.
BIPUL SINHA: Thank you so much for this opportunity. I really appreciate it.