Kush Shrivastava is an active angel investor who has been in Silicon Valley for more than a decade. He's worked at large companies, built several companies from the ground up, and invested in many startups. While candidly sharing how he makes investments, he gives authentic stories including some failure stories often not talked about.
Kush Shrivastava is an active angel investor who has been in Silicon Valley for more than a decade. He's worked at large companies, built several companies from the ground up, and invested in many startups. While candidly sharing how he makes investments, he gives authentic stories including some failure stories often not talked about.
Highlights:
[4:17] From building my first company at 13 years old to Google
[6:40] There’s too much data. Is this a problem or an opportunity?
[9:18] Diversification: the best part of investing through syndicates and networks
[15:16] Invite investors to reimagine the world with the solution your startup plans to offer
[23:30] Whether you get a Yes or a No, Silicon Valley celebrates you
Non-profit: Guardians of Dreams
Kush Shrivastava: [00:00:00] When COVID hit, he completely pivoted his company. And that shows you the strength of the founder, his leadership, and how he is willing to adjust and react to market situation. And then they started playing in a month. And I was very excited about.
Gopi Rangan: You are listening to the sure shot entrepreneur podcast for founders, with ambitious ideas, venture capital investors and other early believers tell you relatable, insightful, and authentic stories to help you realize your vision. Welcome to the shore shot on. I'm here with Kush Srivastava and activate angel investor who wears many hats. He has been in the Silicon valley for more than a decade.
He's worked at large companies. He's [00:01:00] worked at startups, started companies and has been an investor in many startups. Let's talk to him to find out how he makes investments Kush. Welcome to the short shot entrepreneur.
Kush Shrivastava: Thank you, Gopi. Really appreciate you having me.
Gopi Rangan: Tell us about yourself, starting with your childhood, where you grew up.
Kush Shrivastava: Oh, that's a great question. I grew up in small town, India in the state of elevation. You be in a city called chassis chassis moonlighted, because that is where the revolt against the British started in India. It's an historic town, small town by compared to the biggest cities that most people in us will know about such as Delhi Mumbai, my formative years.
Learning how to speak English. My mom was a school teacher and she ensured that I have a good education instead of sending me to the schools that she used to teach it. She sent me to a Catholic school and her point of view was that as long as I learn English, get exposed to technology. [00:02:00] I'll be fine.
Fine. So my mom's foresight and my mom and dad's ability to ensuring that the keeping in check, because I was a really wild kid. I turned out okay. I went to school in chassis and lived there for about 17 years of my life. I even started my first company there go be. I think you will also appreciate that living in the.
When internet came and we were all using dial ups to log in, it was a great equalizer for all of us because now you're able to access the information that was otherwise so hard to get really felt empowered. And, uh, quickly coach myself to learn how to code. When I say code, I mean, it's like very standards that were just emerging, but that was enough for me to go to these forums and randomly post that, Hey, I can build a page for you or I can bury a shopping card application for you.
Thanks to PayPal. Start getting some money, [00:03:00] figuring out how to get the money back to it. There was actually a big challenge. I don't think I quite successfully. I will solve that, but it was pretty amazing that a kid in one of our feelings, small town in India can go online, talk to people from all over the world and get exposed to a lot of different cultures.
Understand what problems, success, and try to solve them for my generation. Growing up in India, internet came to be one of the best things ever. Especially, I'm grateful that I got access to internet in my formative years. It may sound like something that we already take for granted. Right. We run around with their internet on 10 devices now, but in those early days it was really, really transformation.
I don't think my son is ever going to appreciate how amazing it did. It was how difficult it was to stay locked in with the internet has really equalized access to information to people all over the world.
Gopi Rangan: I remember signing up the Hotmail. I was probably one of the first users in 1995 [00:04:00] and having access to email and being able to message people across the world and get replies in minutes.
That was very different from many other forms of communication we had experienced. How did you translate all of that experience in India and then moved to Silicon valley?
Kush Shrivastava: Yeah. I started a company and I thought it was the coolest name for a company ever. We call my not a real company. It was just a website.
It used to be called geek for tech. I think that's the best thing a company can have, but I was 13, 14 years old. That sounded really clever. I did a little bit of coding here and there and hired a few people and things were going well. But like every good Indian kid had to go to college. In hindsight, I thought that I probably don't need a degree in engineering.
So I need to learn how business operates, learn about finances, accounting and all that good stuff. So I chose to go to get a degree in commerce and as I was going through school, you get exposed to companies that come for campus placements. [00:05:00] And I got my first job. I was extremely lucky to get a job at Google.
It was definitely my dream company under some of my best work. When I worked for Google and met some of the most incredible and smart people during the eight years that I spent there, the first four years of my career, I was in India working on Google AdWords ads, monetization, trying to sell four lines that we are all familiar with on Google.
Later I've worked on YouTube, where I joined the marketing team and led a campaign for Indian premier league. One of the most popular cricket tournaments in the world. We live streamed it on YouTube. I moved to us. 2011 for an opportunity that I just couldn't pass. It was to build a new content store for the Android platform and Google by and large, it was going to be at that time, the first app store where you can do everything on the cloud and it sinks.
People will probably forget that. But during those [00:06:00] days you have to sync your music. You have to connect iTunes to your iPhone and for us to build something that can just sync over the cloud at that point of time and be first in the market is pretty revolutionary. I came on and the answer at of apps and games, product marketing globally ran some of my favorite campaigns in that role.
I got exposed to pretty much all the popular apps and games that you and we would have access. And we've led the transition from a product called Android market to what the world knows today. As Google play. After that, I moved on to running partnership marketing and a few other things within the same group, as I was thinking about what the next evolution of our industry in mobile is going to be.
One of the problems that started bothering me was that off instead of having access to data, which used to be a good thing, we almost had access to too much. How do you decide what app should I use? Because there are so many [00:07:00] apps of the same type or what game should I play? Which was my problem. So suppose you only bought like a zombie game.
Like we like John DRA, like Fitch, zombie game. Should I recommend to go B, which is on B game? Should I recommend to Kush or somebody else was a huge problem? There wasn't even a good, uh, app store or Google play, social discovery. Wasn't as refined as it is today. I started following a few researchers and a professor at Stanford and met a CTO of a tech incubator who were going to start a company and joined them in 2014 to build this incredible Gotham, which are going to be explained why I'm recommending something to you and that what some people call it today.
Explainable AI was incredible. We sold that company to Pinterest. Seven or eight months later of founding it . And that became the foundational pieces of Pinterest min AI capabilities. And a lot of the [00:08:00] arts infrastructure, a large part of the team, I think is still there. I didn't join Billtrust.
I was compelled to. Caddy on the entrepreneurship journey. So I started another company in the legal tech space. This is something that I think you will relate to as well. When you meet your friends in the valley and you're sitting at a dinner table and suppose there are six people between the six people.
You have like 10 Ivy schools, right? Collectively, but they are so wrong about visa laws or how to get a green card. And these are common immigrant conversations that you have. Hey, so I'm switching my job, part of our transformation. I'm going to my naturalization process. What should I do? I'm going to apply for a green card.
What about my spouse? We all talk about these conversations and that's hard to collectively. No one really knew that, right? So during my last startup, we had built a product graph. I attempted to build a legal graph that can explain given your context, what should be the right solution. We also dabbled with smart contracts at [00:09:00] that point of time because blockchain was emerging to understand.
Can I put something on a decentralized ecosystem and see what kind of responses I'm going to get the startup didn't do as well? But through that startup, I got introduced to Stanford law school, joined them as a fellow and researched a lot on smart contract, blockchain law and policy. During that time, I also got involved and connected with my Google groups and found a community of ex Googlers who are not building companies outside of Google.
And we started supporting them. Supporting each other initially was just in terms of help and advice and reviewing pitch decks, connecting each other with different venture capital companies and investors that we knew about very soon, we realized that we have to take a bet on ourselves. We can invest in each other.
That's where I cofounded a syndicate. And that was my foray into angel investing. As we sit today, that syndicate has made about 40 plus investments and [00:10:00] had many exits some companies, which I'm delighted about for a court backed by Google. And we collectively, they have marketed. Well, north of a few billion dollars, some of the best companies came out of the Google system.
We were just lucky enough to play a small part in the success we do about 300 plus events every year we organize demo day just yesterday. We did our demo day on blockchain. And the goal really was to create an index off the smartest Googlers and Hogan just invest in each other. And the belief was that we're going to end up creating some of the greatest companies the world has ever seen outside of that Gobi UNB started in CRM, which is our business.
Angel syndicate or angel group in the U S that exposed me to a whole different variety of startups. Very different than the ones that I saw from Google, which are largely focused on tech within CRM. There were startups that were focused on fashion and clothing, transportation, and some really, really cool stuff that [00:11:00] has nothing to do with what we do in the Silicon valley.
And that was a great exposure to learn about other industries. After that I joined the horizon through the acquisition of Yahoo. Most recently I was a managing director at Verizon and run PNL law, a group called Yahoo small business, which is pretty amazing because the first GM of that unit was Jeff Rossen.
Who's like a Demi God, in my opinion, the CEO of Y Combinator. So glad that I could step in as a forcep and do some meaningful work while I was at work.
Gopi Rangan: You have had a colorful career over the years, starting at the age of 14, when you first started your first business, then you worked at large companies, and then you started in Dillon mass men groups, like the Zoogler group and the NCR angels along.
More recently, you were at Yahoo small business. Before we jump into the angel side of things, Yahoo small business was also the division that was originally founded by Paul Graham and sold to Yahoo. And it was via web. That's an [00:12:00] important milestone in the journey of Silicon valley.
Kush Shrivastava: Absolutely. That is what seduced me to accept the job offer for most people, it's like the graveyard of internet, perhaps, but for me, it was the history that I grew up with.
Paul gee, when he created via web, that was really the first time. It became easier for small and medium businesses to create a e-commerce store. It was Shopify way before, like imagine Shopify any time before shopping was even born, he was just way ahead of its time. And then through a combination of some other very incredible internet brands like geo cities, we have a few other bits and pieces of the Yahoo infrastructure, and we must also be a huge Amash to Yahoo for building some of the formative technologies that we now know as the big data industry.
They did some incredible research back in the day, which allowed not just like Yahoo to flourish, but by and large, the internet. So Jeff pulled us together in 2003 and the business was growing and it continued to grow until 2010, [00:13:00] 11. And then it was in a state of decline. Yahoo at that point of time had transformed itself into being a media company.
I joined Verizon who had done acquired Yahoo in 2017 or 2018. And my charter was to turn the business around. We did talk last year, the business group, and this was the first time in a decade. The business grew really, really well. Very proud of that and very proud of the team. We have some of the best people who work at via SBE and whereas in computing it of the who you happen to know.
Gopi Rangan: Yeah, Yahoo is an iconic brand in tech. It's great to see that the original story of via web still thrives at Yahoo in the form of Yahoo small business.
Kush Shrivastava: Congratulations. Thank you. And after telling you that the customer loyalty that I've seen for Gale small business products is just incredible. I have never felt that sense of loyalty.
When I talked to some of our customers that feels like I'm talking to. My family members. I really [00:14:00] feel that if I'm not able to deliver on what their expectations are, it's really feels like I'm letting my brother or my mom or my sister down. That is an incredible brand loyal, you know, huge Testament to, of course, the great leaders like Paul Graham and Jeff Paulson on building this business unit the way they did that, it stood the test of time and still is a very profitable business.
And it's back to that.
Gopi Rangan: I wanted to switch to the angel investment side of your career. You've always had very, very busy jobs. Turning around Yahoo. Small business is not an easy job and you accomplished it in the middle of a pandemic. I can only imagine how busy you may have been despite that you make time for angel investments, and you've done that, or you've made many, many angel investments over the years.
What is really exciting for you in angel investments? Why do you invest in stocks?
Kush Shrivastava: I think first I'm not very busy. I just happen or got lucky by hiring some of the best people I [00:15:00] can. That gives me a lot of time to focus on things. I absolutely enjoy. One thing that I enjoy the most is looking at.
Ambiguous market and looking at certain ideas and trying to go imagine with the founders on what the future will look like. It's a three-step process. Whoever is starting a company, and especially you do a lot of seed investments. So you know, this better than most people, which is when I want a founder talks to you all.
They're trying to tell you as, Hey, I'm going to try to do this. The voice looks like this. I'm going to solve some of the problems with this company that I'm building. And third step the world is going to look different today. I really get excited about that simplistic notion of someone taking a bet on building something new.
And reimagining what a certain sector of the industry discipline vertical is going to look like [00:16:00] after they introduce their product. What I enjoy more is being able to offer some of the learnings. I had both as a startup founder and as an operator in large companies, to help them with things like how they should better think about certain things, how they should look at organization designs, highlighting.
And really what the next step should be. If I'm able to think through step one, step two and step three together with them. That's a good sign that I want to invest in that company as an angel and be part of them. If I'm not able to add value item, not as excited, it's a less, even though I feel that I'll try to have a non-mandatory relationship and connect them with someone else who's smarter than me, or have more experience in that particular industry.
But yeah, that's my basis of investing and what excites me. Ambiguous problem and reimagining the world with the co-founders and being able to offer certain guidance, which I think can uniquely help them cut through [00:17:00] some steps or expedite time to market in some way shape.
Gopi Rangan: How many angel investments have you made so far?
Kush Shrivastava:
Yeah, nothing good. 2000 plus that I remember have also done very small angel investments. So yeah, 2000 is a good number that I've personally been involved with very well. And through syndicates, I think there'll be about 50 plus investment. What
Gopi Rangan: Do you look for in angel investments? What stage do you like to invest in?
What do you look for in these entrees?
Kush Shrivastava: So what syndicate, like the Douglas indicate we are a very good co-investor. We really liked because we are all doing this part time. I was very conscious of not drafting the entire investment memo ourselves. And I realize that there are tons of investors in the valley who are much better at investing than us.
So we started co-investing with large investors and we have co-invested with the top brands from into smaller funds. Top angel investors that often featured on the Midas list in different business magazines. So that thesis was [00:18:00] specifically for tubeless personally, the companies that I get excited about or where I want to invest a lot of my time directly, whether it's through Zula, syndicate, NCR, angel.
Or my own investment. The first and foremost is the people what's the vibe like imagining with them. Do I agree with what he's saying? So one of my favorite investments has been in a company called valley matrix, which some of our friends also invested in and they've done really well. The story is so amazing.
This guy. Who's a Stanford PhD starts talking to me about, about fractured mechanics, like speckled recognition that I've never even heard of in my life. And then he wants to build a company that can do stress defect, monitoring, and save billions of dollars of company who may otherwise lose it. If they have to do recalls, my mind is racing at a hundred miles an hour.
I said, oh, why this seems to be such a non-trivial problem. By someone else hasn't solved it. And I looked into it for two days. I [00:19:00] kept talking back and forth to the founder and every time I spoke with him, I got more excited. So that's the first sign. How excited are you about a certain industry and the people investing in the second step is can new meaningfully impact advice and offer help.
You're doing a little bit more than just signing a check, which is the easy part. I knew that I can help, uh, structure. Kimari Levi, the CEO and founder of this company has taught a little bit, help him like refine the pitch stack, make some intros to investors who are better than me, stronger than me and the right people who will be able to like take him.
In the direction where he should go get him some customer development help. And then of course I signed a small check. So those were more like check boxes that I tried to hit. But the most important thing is the people I have invested in some companies. Just meeting someone for the first 30 minutes, just because I thought this guy or girl is super smart and they will just figure it out.[00:20:00]
I probably saw very clearly that I'll be able to offer them a little bit of help, but one of my most successful investments are usually where I spend time. And getting to a point where the founder and me have the same belief and the same ideology and have a decent sense of what the journey looks like ahead of us.
And we can each play a role helping each other become better. Me as an investor and the founder. As the leader of the company, because very soon once you have the money, what are you going to do? You're going to hire how you design your organization, who your first highest are you going to build a team?
Are you going to get your first few customers? All those things are extremely crucial. And most angel investors who just like sit on the sidelines as I did in the past, those investors. And not to work, but if you get a little bit more involved, you're going to have a much more profound impact on the startup.
You will be much more gratified. And at the same time, I believe that you will. De-risk your own investment. Not saying that you need to do the job of the founder. That's not, [00:21:00] you don't need to spend an obnoxious amount of time working on the startup, but you should be able to. Eliminate or at least consider the scenario that you will be able to offer help and move the conversation forward.
Whenever the founder reaches out to you. That is the key for me. When I look at it though.
Gopi Rangan: Yeah. I remember having conversations with Kmart levy. He very spirited entrepreneur, as someone who's specializes in something obscure that no one really knows about. He's a specialist in fracture, mechanics, and non-destructive testing.
These are not topics that typically come up in normal conversations. When you meet entrepreneurs like him, maybe you could give other examples. Also, what do you ask them? What are questions that are on your mind? What answers are you looking?
Kush Shrivastava: I think one of the questions that I started asking recently is if you're not doing this, what would you be doing?
There's no wrong or right answer here. I can probably look at Google or they'll be doing this, but then I've seen most good [00:22:00] entrepreneurs have such a clear view about what they're doing. That they asked me back and saying like, tell me what's better. And I'll do that. That's a very profound thing to say.
Other questions that I usually ask is just try to filter that back down and ask them about their beliefs, where they grew up. Like, why are they thinking about this problem? Who else have they met some just boilerplate filter questions, but the idea is that through this smalltalk, just trying to see, do I.
Gel with this person. Do we have the same worldview when I do like you start getting a little bit more tactical or strategic, whichever way you look at it, thinking about the business more holistically. And once you have those conversations about, okay, step one of the world is this step two, I will do this.
And the world is going to be different. That brings out a lot of emotion that brings out a lot of incremental to leapfrog the ideas. And if I'm able to like get there and I'm able to like, That's a strong filter for me to go ahead [00:23:00] and write a check.
Gopi Rangan: The descriptions that you give sound quite daunting, it feels like they got one chance to impress you and they have to tell the story that resonates with you very quickly.
If it doesn't, is there a second chance? Have you given entrepreneurs a second chance to tell their story and then invested in the company?
Kush Shrivastava: Absolutely every person that I meet, I think tried to articulate it. I tried to have a nonbinary relationship with the founder first and foremost, I think of myself as a cheerleader of the startup ecosystem.
I'll give you a quick story about one of our friends, Tommaso he's founder of a company called Toca, just an incredible guy. He has done significant amount of work in private equity and has turned around many companies. He originally had this idea around Toca too, kind of reminds it on like, Hey, it can be a replacement for business cards, uh, somewhat [00:24:00] of a B2B slash B2C play.
So I love, love, love tomato. I loved this team, but I didn't quite get there with him on the idea that said when COVID. He completely pivoted his company. And that shows you the strength of the founder, his leadership, and how he is willing to adjust and react to market situation. And then they started playing in a market that I was very excited about.
They built an event management platform. I fully trusted Tommaso's the ability to drive sales. He has the right expertise, the right contacts to scale the business even further. Then another person that I admire the most Bob, he joined them and it was a no brainer. So it was easy for me to say no to Maso, even though he's a really, really smart person first time, because I wasn't excited or there on the product market fit with the second time during COVID, which is his last year of [00:25:00] any pivoted us company to a business where I thought I'll be able to give meaningful feedback.
I am excited about. Very easy for me to get behind them and write a small check.
Gopi Rangan: Okay. That gives me a little bit of hope here that there is a second chance and perhaps even a third chance when the right business and the right market appears. Yes.
Kush Shrivastava: The, of angel investors as kingmakers, we are not, we don't read tea leaves.
Good angel investors will be excited about the founder and the idea. That's what I tried to do. If I'm not excited about either. I usually won't invest, but that doesn't mean that you can't leverage the expertise or be shy about asking more questions. Don't think of it as a binary relationship, whether you will get a yes or you will get a no Silicon valley is a very special place.
And what makes us special is that failure is celebrated. No is never know. And it can turn to, yes, like in the example of DACA that I give you more often than not founders should realize that investors more [00:26:00] than that. Have a serious FOMO, which is fear of missing out if you like the angel investor or any other investor.
And even if they don't invest, but you think they can add value. Don't be shy to ask them for time and feedback. They will very likely invest time in you and maintain the release.
Gopi Rangan: Roughly, how many investments do you make in a year if you're taking meetings and especially if you're taking followup meetings with founders, you may have said no to previously.
I really liked the way you phrased it. No, it's never really a, no, it may be a beginning of a yes. How do you make time for entrepreneurs and how many investments do you make per year?
Kush Shrivastava: Don't have a target in mind. I tried this missed investing in this incredible company based out of India called hundred.
And I'm sorry, do the founders, I should have invested. They're great people because I was trying out that, Hey, I'm going to try to hit 12 companies that year and my check size is good. I'll be small, but I don't think that's the right framework. You should invest based on whatever liquidity is [00:27:00] available to you.
You should try to invest in whatever companies that. Excited about, I used to be more aggressive about building a portfolio when I was early on investing, but right now I just want to work with the best founders are probably like four or five investments a year, and then a few with the syndicates.
Gopi Rangan: Well, thank you for candidly sharing the missed opportunity story.
That's very authentic when things don't go well, Angela investment is very risky and it's often possible that startup investments don't go well. What do you?
Kush Shrivastava: Try to find a soft landing or a graceful exit for the founders as an angel investor, I expect to lose most of my money. I also expect that many startups are not going to succeed.
Our job is to just ensure that we de-risk as well. As possible and give our portfolio or the investment that we have done a chance to succeed, but it does not guarantee that everything is going to work out. Usually I try to have a very candid conversation [00:28:00] with the entrepreneur, try to see what's the best landing spot I can get for them.
And therefore their team. Which could be as simple as sending out emails to different corporate ventures or Corp dev teams and seeing if they're interested in talent, acquisition interest in buying certain assets, if that doesn't happen, just ensure that there is a legal claim. What I absolutely don't like as these limbo companies, they're not good for the founders.
They're not good for the investors where the entity is alive, but there is no real work being done. The founder ends up doing some side hustles. In those cases, I've tried to find conversations like let's put a date to it and what we are going to change by that date. If it doesn't change, shut down the entity because we get tax write-off.
But otherwise, for most people that I invest in. Extremely sharp people and are good hires. And so they end up figuring out the next steps. In many cases, they start another company and in many cases, double down on the next idea.
Gopi Rangan: Well, [00:29:00] this is great. I'm glad that you talked about failures and sometimes outcomes are not exactly how we expected, but failure is not a ding on your resume in Silicon valley, especially.
It's good to have that experience learn from the experience and bounce back. I want to switch to the next part of our conversation and ask you about your community involvement. Is there a nonprofit organization you are passionate about?
Kush Shrivastava: Absolutely. There's a nonprofit organization based out of India called guardian of dreams.
That is started by a dear friend of mine called Gloria. She used to work at Google. She left her job to work for another NGO called make a difference and made it one of the most successful engineers in India. And then about a few years ago, I started the guardian of dreams in Ventura. She picks out these amazing programs that are custom curated for kids in different cities in India.
And she tries to be the guardian of their dreams, which is like, what do you want to do? What do you want to [00:30:00] become? Can I fund your education in some way and be the, like a big sister and angel to them? I absolutely admire that someone who had soft fishing jobs. In arguably or one of the best and most sought after companies in the world leaves that company to do something as meaningful and change lives for children who then go on to create more opportunities for themselves, as well as their families.
So I think what she's doing is absolutely incredible and I'm a big supporter of guarding our brains. Go dreams that are please donate if you can.
Gopi Rangan: Of course. Thank you very much for sharing a lot of interesting stories from your experiences through your career and through your angel investments. And you've touched on many topics that are often not talked about, including some failure stories on how to handle them.
Thank you very much for sharing your stories.
Kush Shrivastava: I appreciate you having me.
Gopi Rangan: Thank you for listening to the shore shot entrepreneur. I hope you enjoyed [00:31:00] listening to real life stories about early believers, supporting ambitious entrepreneurs. Please subscribe to the podcast and post a review. Your comments will help other entrepreneurs find this podcast. I look forward to catching you at the next episode.