Harpinder Singh On Selling His Company For $800 Million, Then Selling His Second Startup To Rakuten, And Now Investing In Other Entrepreneurs

In a recent episode of the Dealmakers’ Podcast, Harpinder Singh shared his incredible entrepreneurial journey, spanning from his roots in India to co-founding two successful startups.

His latest venture is Innovation Endeavors, a company that invests in upcoming entrepreneurs with funding and training. Harpinder focuses on visionary founders, transformational technology, and disruptive ecosystems, and manages $1.5B.

In this episode, you will learn:

• Highlights of the critical importance of intentionally shaping company culture. Creating an environment of trust, collaboration, and high performance fosters a conducive space for innovation and growth.
• Identifying emerging markets and having a finger on the pulse of industry trends were pivotal to success. His ventures in wireless infrastructure and eCommerce market insights were strategically timed to meet evolving needs.
• A journey through the dot-com downturn and telecom industry challenges underscores the value of resilience. Navigating choppy waters with resourcefulness and determination enabled FiberTower to secure significant funding.
• While initial aspirations may lean towards taking a company public, founders should remain open to strategic shifts. Being receptive to market dynamics and customer feedback can lead to more beneficial outcomes.
• Premium on technical insights that set a startup apart. Identifying ways in which a venture can be 10x better than existing solutions through technological advancements is a key factor in building a successful business.
• The implementation of feedback mechanisms plays a crucial role in ventures. This practice fosters open communication, resolves issues constructively, and contributes to a collaborative and productive work environment.
• Emphasis on the value of education and investment. By teaching entrepreneurship and actively investing in early-stage startups through Innovation Endeavors, he contributes to the growth of the entrepreneurial ecosystem.

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About Harpinder Singh:

Harpi has been an entrepreneur in the internet and wireless space. He was the co-founder, CEO, and VP of Product and Marketing for Project Slice.

Previously, he was the co-founder and Sr. VP of Marketing at FiberTower, a leading independent provider of backhaul to wireless carriers.

Harpinder also held software development roles building internet infrastructure and transaction processing software at Oracle and Bull-Honeywell.

He holds an MBA from Stanford University, an MS in Computer Science from Indiana University, and a BS in Computer Science from the Institute of Technology, BHU, India.

Connect with Harpinder Singh:

• Linkedin
• Crunchbase
• Stanford Faculty
• Dun&Bradstreet

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty well hello everyone and welcome to the dealmakerr show. So today. We have a really exciting founder turned the investor he actually now he went to the other side of the table but nonetheless he’s actually done it multiple times. Very successfully. So and we’re gonna be talking about the full cycle of being an entrepreneur. Thought process going through the idea incubating it building a highper performance team. You know going through the whole thing you know all the way to the exit and I think that you’re going to find his journey quite remarkable and very inspiring so without further ado. Let’s welcome our guest today harpin they sing Harpe welcome to the show today.

Harpinder Singh: It’s great to be with you all. Andrew.

Alejandro Cremades: So originally born and raised in India north of India give us a little of a walk through memory lane. How was life growing up.

Harpinder Singh: So life was awesome I I grew up in shendier which is happens to be 1 of the most planned cities in India and life was great I I grew up playing field hockey cricket flying kites and doing all the stuff that my kids don’t do today um. And I studied computer science I did my undergrad and cs at one of the its and then I came to the us for a ph d in high performance computing you know I wish I had a great answer at that time.

Alejandro Cremades: And what go you into computers to begin with.

Harpinder Singh: I think if you talk to people who went to id in India you take this big entrance exam which is like hard and then you get placed according to your according to your rank. And computer science was emerging one of my cousins was doing it. So I thought it was a great feel. But frankly I did not know a lot about it going going into it.

Alejandro Cremades: So eventually you came to the us and you came for a Ph D program. How was the ah the experience of all of a sudden landing here the land of opportunity the American dream. You know all of that good stuff.

Harpinder Singh: It was it was different um coming to the us was the first flight I ever took at the age of I think 20 or 21. Um, so as you can imagine everything was different. Everything was new ordering a sandwich was intimidating because. In India you get 1 white bread and you know you get 1 cheese which is called paner here. You order a bread and they ask you like you know, do you want like Rie Salurdo french this that and you want this cheese just that cheese and do you want red pepper yellow pepper whatever and I didn’t know half of what any of that meant. So. It was just quite um, kind of transformational. It took me like a couple of months to get a hang of all this.

Alejandro Cremades: So in your case I mean you became a software engineer for a few years and then it sounds like you had an idea of really going into it. You know as an entrepreneur I’d be going into the business side of things but you thought that it was better to go via the and Mba route and you went to Stanford.

Harpinder Singh: Yes.

Alejandro Cremades: So why? why did you take? you know why did you take that approach why going to Stanford you know instead of like maybe going out of out ah out of out of your comfort zone and and and and going at it. You know as an entrepreneur. Why did you feel that an Mba was what you needed at that point in time. Yeah.

Harpinder Singh: Yeah, no, um, great question and I was a software engineer for about 4 years I was at Oracle um, and you know I really love being a software engineer but I felt that okay I kind of maxed. Ah, in terms of what I was going to learn and product managers were telling me what to do and I’m like you know hey I don’t need you to be telling me what to do I want to sort of go do that thing myself. So ah I think that immigrants on this sort of show would kind of appreciate this. But. I was in the middle of my green card process. So I couldn’t just leave and go start a company and going to so going to Stanford allowed me to kind of keep my green card active and use my time to learn something different. So I was super keen on starting a company I had only been a software engineer so I felt that kind of.

Alejandro Cremades: Yeah.

Harpinder Singh: My green card going gave me a way to go learn many many different things meet a different group of people so that’s what led me to Stanford and frankly, that’s where I met my cofounders and it was it was remarkable. Kind of a transition in my life.

Alejandro Cremades: And obviously Stanfordd has played ah an incredible role in your life. You know, not only as a student but then also you became a professor you know which we’re going to talk about in just a little bit now in this case as a student you know, tell us about that process of getting the band together. You know for building what would end up becoming. Fiber tower which started with project shit. You know it wasn’t like a co the fight language for what you guys were thinking you know about doing or what how did that come about.

Harpinder Singh: Yeah, so um, when I was at the gsb um, get it was you know towards sort of the end of dot com days and Gsp is a very very entrepreneurial place. But.

Alejandro Cremades: Um.

Harpinder Singh: And that time was kind of special many people wanted to start companies and you know I was vetting some of the ideas I had I ended up pitching and these ideas to a couple of people who ended up becoming my cofounders so you know in that process. Um. You know we liked how we were thinking and we kind of came back came came together and we were working on an id and storage infrastructure and frankly, three weeks before we graduated, we realized we were too late to the market. Um, so we ended up killing the idea and none of us had cared to apply for jobs and this and that so we’re like okay we don’t have a job. We’re about to graduate. We want to start a company together so we shook hands and decided to spend six months together to incubate something and see if we come up with something that we’re excited about. Um so I had 3 other founders Scott Eric and David and the code name we gave ourselves during the search process was project shed. And so for Scott Herpeetic and David so we would basically call people and say hey we are we are from project shed. We’re a team out of Stanford and you know we are researching this and that would you talk to us so that that was sort of how the team came together. Yeah.

Alejandro Cremades: So how did it go from idea to an actual business. You know what was that incubation process like okay.

Harpinder Singh: Yeah, it was. It was quite a journey There isn’t a script on How do you go about incubating an idea so we had to kind of come up with our own process and what we did was we figured that we needed to go deep. And build enough of a mastery in a few fields so we ended up focusing in 4 different areas. We all took an area each and we would go and talk to product managers and engineers and we would basically ask the question hey. If what you’re working on today is successful. What problems does it create twenty four months out and that was a great way to have a conversation around the emerging problems that people saw. Um so we spent about 3 to four months doing that and we had a long list of problems and ideas that we identified through that process. And we had come up with this matrix. We called it like the attribute attribute matrix that but that we used to basically score all our ideas and it had things like you know how passionate are we about the idea. Can we create a large business does it have barriers to entry ip defensibility things like that. So through that process we. Um, we realized that wireless data was just coming out at that time and it was going to explode and we’ve through some conversations with people at Nortel we realized that there wasn’t enough capacity at cell sites and that was going to be a real bottleneck so there was all these equipment coming out. There were all these handsets coming out and we saw this.

Harpinder Singh: Ah, big kind of bottleneck in between and that’s what led us to start a company in wireless infrastructure.

Alejandro Cremades: So why ended up becoming the business model of Fiber Tower for the people that are listening to get it. How are you guys making money.

Harpinder Singh: So it was um, we were essentially providing very high-speed capacity that was reliable and cost-effective at cell sites. So when you use your cell phonee. Your cell phone is talking to a cell site and all that traffic has to be taken. What is called a switch. Um and that link between the cell side and the switch didn’t have enough capacity. It was expensive. It wasn’t very reliable so we ended up building a combination of fiber and microwave network and our business model was we would charge for capacity just like you would pay for you know. Getting fiber cable to your house now we would our customers were all the big wireless carriers overiz and tmobi a and wireless and so on and we deployed our infrastructure in 13 of the largest markets in the us across thousands of sites and they would pay us. Um. For capacity at the cell sites.

Alejandro Cremades: Now you guys started a company back in 2000 I mean what a wild time to ah to start a company you know because I mean you guys and did push this thing this thing through you know over the course of 6 years until you got the exit but my god I’m sure that you learned quite a bit on on cycles.

Harpinder Singh: Yeah, it was ah um, so we were incubating during 2000 we were fundraising in early 2001 and not only the dotcom was in trouble but some of the telecom companies were in trouble and nobody wanted to fund capital intensive play. And we ended up raising like two hundred and twenty five million dollars over the course of the come over the course of the company. So yeah, we had to kind of get fairly resourceful and creative about how we build the company but there were also a lot of positives. Um I think the distraction level comes down. Um, and we were able to hire really high quality people who were committed and were doing a startup because they really wanted to be in a startup. So. In fact, both the companies I started were during downtimes and I think they are some of the best times to to start something new.

Alejandro Cremades: Why do you think they are the best times to start something new.

Harpinder Singh: I Think the the noise goes down in the ecosystem. Um, it’s I think the fad off you know hey I just need to be in a startup kind of also goes down so people that you’re hiring.

Alejandro Cremades: Um, go.

Harpinder Singh: Ah, really want to be in a startup. So I think hiring becomes easier. Um and I think there is less noise. Overall when you’re talking to customers and partners and so on.

Alejandro Cremades: So First company first Exit Harpee. You know that’s quite a a remarkable you know, achievement now in this case, you know it was ah it was an exit of close to I think a billion 800000000 was reported So what was that acquisition process like you know what was what was the journey of going through. That Inman a you said that crazy Roller coastor of emotions as they tell that and that it typically is when you go through an acquisition. How was that like.

Harpinder Singh: Yeah, it was. It was quite an eventful process. Let’s say in that um I think it happened that the problem we picked became a very strategic problem as the wireless carriers were rolling out their networks. They really needed this infrastructure to work and. And we needed more spectrum and we needed more fiber for our solution to scale and we ended up actually getting an offer from the largest fiber company in the us at that time. Um, and that led to. Another offer from a company that held a biggest spectrum footprint in the us. So we ended up kind of being put in play and with offers on both sides and it was eventful because we had both financial vcs but we also had strategic investors. We had large tower companies that were investors in us. And the tower companies. They didn’t want to sell at all. they’ like you know this is awesome. It makes my cell sites more attractive because you bring high sizepeed infrastructure to those sites so keep on building. Why would we sell? Um, so it was quite ah it was quite an eventful process. It was quite a rollr coaster and um, yeah I think. Through 6 to eight months of getting everybody aligned it ultimately resulted in an exit.

Alejandro Cremades: So make us an insider in there. You know the moment where you’re assigning in King the deal you know eight hundred million bucks your first company. You know an immigrant you know I came here you know to to the us from India how did that feel like what was going through your mind.

Harpinder Singh: Um, yeah.

Harpinder Singh: You know, Honestly, there are so many ups and downs in in building a company and especially when you’re building a capital intensive Business. You’re like you know, okay am I going to be able to raise the next round or you know there’s one s or twice when we felt like we nearly ran out of money. Um. It was frankly just mixed emotions I felt that we were selling early I felt that we should keep on building but it thought at the same time. It was also somewhat of a relief that you know. Okay, we build something valuable that somebody cares about and you know it will get a lot more funding and resources and this will become Big. So I think. Your point I was I was frankly, not even thinking about the monetary side of it I was just kind of like pleased that we started something and you know there was there was ah there was sort of a good outcome.

Alejandro Cremades: So as they say once an entrepreneur entrepreneur always an entrepreneur you know in this case, you know you went you know back into it. You know with sliced technologies. So what was that thing. What was that journey like of now. Obviously the second time at it. You know you have the. The experience already of of really under clarity and the abyssibility into what the full cycle of building scaling financing and exiting looks like and also you did it with the same cofounding team. You know with slice you know once again, you know the band you know gets back together. So what was that process of you guys taking a look at everything and. You know, perhaps you know like figuring and testing ideas and then of a sudden thinking. This is the 1.

Harpinder Singh: Yeah, so um, we felt we worked very well together as cofounders. We paid a lot of attention to the culture we built and the mission we were on and.

Harpinder Singh: I think we had a great time and when we talked to our employees they felt that you know it was sort of this special opportunity and they were in a special place so we exited and we’re like you know, hey, let’s do it again. So we all took some time off. We all took about a year to year and a half off and then went to a similar sort of a project shared approach where we went through an incubation process. Took a little bit longer this time it took ah instead of it taking six to nine months it took like almost twelve to eighteen months I think we were a little bit. Yeah I think we had done it once. So ah, we had cast a wider net we were looking at more things I think we were perhaps more distracted.

Alejandro Cremades: Wow.

Harpinder Singh: This time around but we went through a similar process and we identified this need um around building a company that would provide Market insights for ecommerce. So we built our data analytics company and I love my cofounder that it was just a real kind of a privilege to do it again with them.

Alejandro Cremades: So what was that point where you guys hit Product Market fit.

Harpinder Singh: Um, um it um I think it took us about 2 to 3 years of iteration to hit product market fit because we needed data at large scale to figure out. Um. What people buy online and what insights it would tell so we needed data and then we needed to be able to um, extract this information classify create a taxonomy and then make this data usable so it took us about 2 to 3 years of figuring out. How do we get data at scale. How do we extract insights. But then. Once we did that I think 14 of the top 20 cpg brands were our customers and I think we were solving a real sort of a need in the problem market. So um.

Alejandro Cremades: And how are you guys making money with slice.

Harpinder Singh: We created this business which was market insights for ecommerce. So think of it as like you know I think many people are familiar with Nielsen. So think of it as like Nielsen for ecommerce. So our our customers were you know, big large brands big travel companies and so on so they would pay us for either licensing. And data insights. Um, so so either either raw data that they would use or they would they would buy insights from us. So for example, if you are proter and gamble. You want to know hey how how is dollar shape club affecting Gillette um, or what does subscribe and save mean for my business. Should I have the same packet sizes and pricing as what I put in stores at Target and so on so we were helping the leadership teams at these cpg brands and their boards think about what does ecommerce mean for them.

Alejandro Cremades: and in 2015 there was a shift of roles. What happened there when you became the Ceo.

Harpinder Singh: So yeah, so we were acquired by rakutan which is the largest ecommerce player in Japan and my cofounder Scott was a Ceo and his son actually. Had a medical issue and that he needed to go attend to and we had worked very collaboratively through both our companies. So it was a fairly sort of ah smooth and kind of ah unnoticeable transition. So so that’s when I became the Ceo.

Alejandro Cremades: Got it and in this case I mean for slides you guys raised thirty million bucks so obviously the experience now with investors I mean you guys were well suited you know and and and and well versed on that you know given your experience with fiber tower before so what did you do differently when it came to um. Raising money from the right people with the right reasons. So.

Harpinder Singh: You know so raising money became easier. Um because there was some pedigree. There was some proof but everything else almost didn’t become easier. You know getting customers is still hard getting product. Market fit is still hard. You know recruiting. All these and Nlp engineers that we were recruiting against Facebook and Google and so on was still very hard. So um I think there were certain things that became easier around fundraising and how we thought about culture and um. We knew how to scale businesses. So we knew what it took to build sales team and go to market and so on. But then there was a lot of just um, you know hand to end combat that we still had to figure out on the product and product product market fit and pricing and and things like that.

Alejandro Cremades: And obviously as we’re talking about people here. Um I Want to ask you what about building a high performing team and culture around it. You know like what did you learn you know about about that.

Harpinder Singh: So um, that was something we actually greatly prioritize because of the way we were formed. So um, because we were a team that wanted to work together and didn’t have an idea so frankly, 1 of the first things we did before. Shared agreed to work together was we talked about what kind of a company. Do we want to create what would be our values. What would the company look like so given that it was kind of rooted in that I remember even before. When we got our first term sheet one of the first things we did was we had been working together for six to nine months we sat down and codified and said okay, what kind of a culture. Do. We have what kind of a culture. Do. We want to have going forward so we were frankly, very intentional about the culture. We created about the people we hired my my cofounder Scott he had actually. Built two public companies before um, we got together so he he always talks about the story that um, you know as his companies grew people got hired who he looked at and he said you know hey why are these people here. So we were very intentional about. Ah, the culture and who we hired so we did 2 things actually 1 is we rolled out this thing what we call feedback this is something we learned at Stanford it was about interpersonal dynamics and providing feedback to each other so that we can work well together and also learn from each other. Um.

Harpinder Singh: And that’s been I think absolutely incredible in how we’ve built both our companies it it kind of brings up issues in this without escalating them and you know creates this environment of high performance and low ego. Um, so we were able to use feedback. Ah, in both our companies and frankly it it resulted in low attrition rates. People said what they wanted to say and we we built a trusting and a very collaborative culture. So Um I think just. Knowing and being intentional about what we were trying to create and the culture we were trying to create and also knowing what type of people we hire I think that just served us very well in the long run.

Alejandro Cremades: Um.

Alejandro Cremades: So the company slice ended up being acquired by rakuten and for an undisclosed amount but but a good exit I guess the question here that that I have for you is you know, given that it was the second time around that you guys were going through an acquisition. Ah, what point why did you think it was the right time at that moment you know to do the transaction and when is the right time to do the exit.

Harpinder Singh: So um, obviously I I went through this with both my companies but I also see this across many investments we made I think with slice we actually got an offer from one of the big tech companies here in the valley. Um, so we had been working with them and they loved it enough that they’re like okay we want to acquire you and that actually kind of got the ball rolling and we ended up saying no to them. But Rakuten is another company that we were working with and the Ceo of Rakuten really leaned in and he said okay, um, you know this is what it means for for my business and um, you know I’m going to let slides do what it’s doing but we really want this to be a part of Rakuten. So it actually. We weren’t looking to sell it ended up actually being getting put in play just like with fiber tower and it ended up in a sale. Um I don’t know if there is an answer to what’s the right time to sell I think as a founder you need to be.

Harpinder Singh: Open about that every time you’re fundraising I think investors and founders should pause about you know? Okay, What’s the right next step you know, based on what we’ve learned and the product Market Fit. Do We keep on building. Do We sell? Um I think we we always thought about. You know, taking it all the way and taking these companies public. But I think things happen along the way and you know Market change and you learn about your customer base and so On. So I think it’s best to be um, sort of open minded about those things.

Alejandro Cremades: Now in your case, you know once the company finalized the transaction you know, basically for you the next chapter was a combination of Academia Stanford you know going back at it on the professor side of things but then also going on the other side of the table as an investor with innovation endeavor. So. What an interesting blend there harpee.

Harpinder Singh: Yeah, no I think um ah teaching has been fantastic I teach to entrepreneurship classes startup garage and formation of new ventures. Um, and through that you know we get to sort of work with some of the most entrepreneurial students. Stanford. So I think that’s that’s a treat in itself and then being in the investing side I think it’s such a privilege and that you know you get to work with the best minds and sort of be on the cutting edge of what people are thinking about. So I think it’s it’s it’s an amazing competition. So I really.

Alejandro Cremades: Now with innovation and there were you have been involved as a first venture partner and now as a partner you know for about 14 years I mean this is the investment vehicle where Eric Schmidt you know is also a part of for those that they are not familiar with the name Eric Schmidt you know the Ceo of Google.

Harpinder Singh: I’m grateful for both of those.

Alejandro Cremades: Now alphabet and I mean definitely one of the ah brains you know that allowed for Google to become what it is today. So I guess tell us about how big is innovation endeavors and what kind of companies. Do you look at.

Harpinder Singh: Yeah, so um, innovation at efforts was started about thirteen fourteen years ago by Eric as you said and 1 of my partners draw Berman um, and we are on our fourth fund which is a $500000000 fund. Um and we invest in. Early stage companies so series a and seed stage companies and we invest in 2 areas one is applied Ai so ai applied to some of the big physical world problems. So.

Alejandro Cremades: Yeah.

Harpinder Singh: We’ve done a lot in areas like supply chain logistics Construction life sciences, industrial climate areas like that and the second area is Enterprise Infrastructure. So All the enabling technology. So This is machine learning tooling Data Infrastructure Cyber security areas like that. Um, And. We are usually backing founders who have deep technical insights about a large space and we work with them on product Market Fit go to market so we like being early and ah you know we have a lot of operating experience on the team and we love to sort of meet founders even before they have an idea.

Alejandro Cremades: So Now you’ve been on both sides you know and obviously you were able to understand you know the pain and and the the journey um of of really being the operator on the other side Now you know obviously taking a look from the other side you know with a different lens. You know at the.. Perhaps you know like some of the key ingredients. You know to really make it happen and what it’s Required. So What are some of those patterns that you look for you know what are like the absolute must that they when you see those you know coming Together. You are like we got to make an investment in this company. Okay.

Harpinder Singh: Um, yeah, so I think borrowing a lot from what I what worked for me in my company is one is the team and you know is it? Why does the team want to do what they want to do. Is it a collaborative team is it a team that can scale and grow over time. So that’s that’s obviously number 1 um I think one of the things that I got lucky with and I thought we did write in both our companies was we picked large markets with. Strong tail wins and so wireless infrastructure and then ecommerce and data analytics. Um, so we look for hopefully. Founders that are thinking about large markets and how they can transform them and we’re looking for trends that would support them and it would support this ideation and iteration process if they have to pay it and find their product market fits those are the um, two things we’re looking for and like I said we’re looking for a technical insight around. Why what? they’re doing would be 10 x better than what was possible before are there fundamental advances in technology or raw materials. Um or ai data that is now available that allows them to look at a problem a different way.

Alejandro Cremades: That’s incredible. So I guess saying for the people that are listening Harpe that you know will love to reach out and say hi. What is the best way for them to do so.

Harpinder Singh: Ah, really simple. My email is HarpeHARPi at innovation endeavors dot com or they can reach me at harpe.sync at stanford.edu

Alejandro Cremades: You see enough. Well Harpe thank you so much for being on the deal maker show today. It has been an honor to have you with us.

Harpinder Singh: Ah, Andra it’s been a pleasure. Thank you so much. Thanks.

*****

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