Sriram Gollapalli. Exited Tech Founder Who Loves Investing
Episode - 20
Sriram Gollapalli. Exited Tech Founder Who Loves Investing
Sriram Gollapalli. After selling his software as a service business 8 years ago, he spent 6 years working with an acquirer before embracing his new found freedom. His calling? Investing and fostering a community of like minded investors. This episode delves into Sriram’s post exit journey. Including an introspection retreat, angel investing and the challenges of estate planning.
What We Discussed:
00:01:10: Introduction
00:01:19: Discussing Sriram's sale of Ilab's operation systems.
00:02:20: Life changes after the exit
00:03:55: Structure of the exit
00:05:08: Post-sale transition to being an employee
00:07:39: Developing new business ideas
00:09:06: Conceptualization and growth of LongAngle, Sriram's current project
00:14:54: Verification and vetting process for LongAngle
00:16:53: Sriram's approach to parenting and estate planning
00:17:16: Sriram's ventures in angel investing
00:19:50: Understanding the Concept of Time and Benefits of Working Out
00:23:17: Private Equity Placements, Real Estate, and Simplicity in Investing
00:25:33: The Fun and Stress of Active Stock Picking
00:28:13: Intentions to Contribute in the DC Tech Scene
00:29:08: Discovering One's Purpose and Legacy
00:31:01: Reflection on the Responsibility and Freedom that Comes with Wealth
00:36:10: Regrets Associated with Selling the Business
00:38:35: Challenges of Meeting Customer Expectations in a B
00:40:33: Gratitude towards Parents
00:41:27: Challenge of Firing People
00:43:17: Vegetarianism and Prayers
00:44:13: Spiritual Growth and Personal Growth Strategy
00:45:16: Advice for Someone who Just Sold their Business
00:47:19: Biggest Mistakes after Selling the Company
00:49:36: Importance of Health Care
00:50:35: Current Level of Fulfilment
00:52:43: Importance of Intentional Relationships
00:55:26: Aspiring the Next Generation of Builders
00:55:57: Legacy and How to be remembered
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Sriram Gollapalli: [00:00:00 - 00:00:05]
Fulfillment is relative, based on time and space of where you are.
Anastasia Koroleva: [00:00:05 - 00:00:28]
Sriram Galapalli. After selling his software as a service business eight years ago, he spent six years working with the acquirer before embracing his newfound freedom, his calling, investing and fostering a community of like minded investors. This episode delves into Sriram's post exit journey, including an introspection retreat, angel investing and the challenges of estate planning.
Sriram Gollapalli: [00:00:29 - 00:01:05]
Everyone in the community has to show proof of assets of at least 2.2 million investable assets. Do you really need that sweater? Do you really want a $200 jacket? Whereas the other side, you're making these wild bets. Either a $25,000 angel investment or it always feels like different pots of money. It was a mix of silent meditation, a mix of nature solos, a mix of breathing exercises. I do see myself continuing to find ways to build, touch and feel things. I think legacy is important. Would like to be remembered for inspiring the next generation of builders.
Anastasia Koroleva: [00:01:10 - 00:01:11]
Hi, Sriram.
Sriram Gollapalli: [00:01:11 - 00:01:13]
Hi there. Good morning. Or good afternoon.
Anastasia Koroleva: [00:01:14 - 00:01:15]
Very excited about this interview.
Sriram Gollapalli: [00:01:16 - 00:01:19]
Excellent. Me as well. One of the first I've done. So excited.
Anastasia Koroleva: [00:01:19 - 00:01:30]
So let me jump right in and ask you to go back to that moment when you sold Ilab's operation systems. And how did it feel?
Sriram Gollapalli: [00:01:31 - 00:01:45]
Oh, good question. It was a mix of relief and a little bit of anticipation of what might be next. And also, most importantly, actually, how were we going to be treating the people that we had been really shepherding over the last ten years?
Anastasia Koroleva: [00:01:45 - 00:01:48]
Fantastic. So you bootstrapped it, didn't you?
Sriram Gollapalli: [00:01:48 - 00:01:56]
We did. We did. We raised a little bit of friends and family back in the mid two thousands. And, yeah, we got it all the way through a strategic exit ten years later.
Anastasia Koroleva: [00:01:56 - 00:01:59]
So would you say it was a life changing exit for you?
Sriram Gollapalli: [00:01:59 - 00:02:09]
I think so. You know, life changing is always relative, but it was definitely bought us a lot of freedom to decide how to spend the next several years of our lives.
Anastasia Koroleva: [00:02:09 - 00:02:19]
Okay, so how did your thinking about the exit change over time? Because it was eight years ago, wasn't it? You had a chance to process your experience by now.
Sriram Gollapalli: [00:02:19 - 00:02:20]
Okay, so how did it feel?
Anastasia Koroleva: [00:02:20 - 00:02:23]
Or how did, how did it change over time?
Sriram Gollapalli: [00:02:23 - 00:03:55]
So I think at the beginning it was sort of like, and one of the things we heard as we were doing some of the research around then was don't change too much. Like, be thoughtful after the exit, buy a dinner, splurge on this or that, but don't do anything completely out of the ordinary. So we didn't we say that because we didn't change too much. I remember still getting the check in the mail, literally both to the company and then my share and just kind of seeing that sharing with my parents. You can't share this with too many people because for all the reasons that I'm sure you know, so I'll never forget that.And then after that sort of excitement subsided, it was sort of like trying to understand well, what happens, how do we approach, how do we think about it? What are the kinds of steps that we should do? Should we do anything differently? Whatever we bought. And ultimately, Anastasia, I think what you buy with that kind of experience is freedom of time and how you approach how it's, you have a responsibility to be more intentional about the time that you have and how you can approach it. And I'd say I continue to feel that today, even eight years later, on choices I make now, I bought myself a freedom of, I can spend weeks or months or even several years not having to worry about necessarily the day to day, but focus on what I want to do now. I don't do that well, but I have an opportunity to be thoughtful from that perspective.
Anastasia Koroleva: [00:03:55 - 00:03:59]
How was your exit structured? As much as you can share, obviously.
Sriram Gollapalli: [00:03:59 - 00:05:07]
Sure. It was a 100% asset purchase agreement. What that means is Agilent Technologies is a public company. They purchased all the assets of ilab. We were fortunate through the process. We actually, we were approached by private equity and strategics. We had a whole process. Happy to dive into that. But we went with Agilent. They were a fantastic fit. They're still a fantastic fit today. They've taken extremely good care of our staff. I was shocked actually. I left formally about a year and a half ago or a little over a year ago, and I was writing my goodbye email, Anastasia, and I think it was when I was trying to look through the directory of the people that were still there. This was six years after I left. I want to say like 75% of the people were still at Agilewood after we left. And that just really warmed our hearts because we're so great to find a place because I know I hear horror stories and things like that. Having said that, the exit was pretty much an asset purchase agreement for cash. And then there was about 25% stock than what was left for being higher equity holders.
Anastasia Koroleva: [00:05:08 - 00:05:12]
And you joined the buyer, didn't you? For quite some time?
Sriram Gollapalli: [00:05:12 - 00:05:18]
We did. All of us joined the buyer. I stayed for, as I mentioned, just over six and a half years almost.
Anastasia Koroleva: [00:05:19 - 00:05:19]
Oh wow.
Sriram Gollapalli: [00:05:19 - 00:05:28]
With them. Yeah, it was a journey. There were four years of the proper best and then afterwards continue to find interesting things and how to make an impact.
Anastasia Koroleva: [00:05:28 - 00:05:34]
How did it feel to suddenly become an employee, essentially, after you were a co founder?
Sriram Gollapalli: [00:05:34 - 00:06:28]
I think there's a one part relief of not having to make all the decisions and worry about payroll and worry about approving expense accounts or things like that, necessarily, or wondering about where the different investments we're making, but also one part ensuring you still have that entrepreneurial. It's hard to ever let that entrepreneurial happen. I've been an entrepreneur since I was like the late, late nineties when I was in high school. So losing some autonomy from a decision making process can be challenging, but it's also, sometimes it's relieving also, like someone's telling you, here are the things you should do, and I can tell you if you're doing a good job or not. And that's always, sometimes, you know what my wife says, decision fatigue sometimes can be challenging. And if you have some time to turn that part of your brain off for a little while, that can sometimes be a different kind of way of use your mind.
Anastasia Koroleva: [00:06:29 - 00:06:32]
So I understand that ilabs, you ran operations.
Sriram Gollapalli: [00:06:33 - 00:06:46]
I did. I ran a number of things. So I started as a tech. My background's technology helped code the first few lives, which I was just looking, actually, two nights ago, for whatever reason. But my code is still being used nearly 20 years later in production.
Anastasia Koroleva: [00:06:46 - 00:06:48]
That's a huge compliment, is it?
Sriram Gollapalli: [00:06:48 - 00:07:10]
Or something? And I ran. I have a fondness for the ops side, whether it's HR ops or streamlining ops or things like that, getting things off the ground and finding the right people to kind of manage those things. But I'd say my heart straddles the technology side, because that's where a lot of my training came from, as well as the operations side, where appropriate.
Anastasia Koroleva: [00:07:10 - 00:07:13]
Would you call yourself a creative person?
Sriram Gollapalli: [00:07:13 - 00:07:17]
My friends definitely would. I don't know that I'm the best, but yes, I would say so.
Anastasia Koroleva: [00:07:17 - 00:07:39]
So I'm really curious to understand how your motivation changed over time, because obviously you continued creating new businesses, how your motivation was different between when you started ilabs and when you started your next business after you stopped working for the buyer.
Sriram Gollapalli: [00:07:39 - 00:09:06]
I would say, look, creativity comes a lot. It's true. Mother is. Necessity is the mother of all inventions. And I think even from. I was just hanging out with my parents house not too long ago, and they brought one of my first inventions out when I was in elementary school. I built this wooden structure with a shelf, a small piece of wood, and a pole hooked up to it. And I'd written a name on it and I spelled it g e t o w e l. It was called the get towel. So it was a tool that I had used. Apparently when I was in probably elementary or middle school, I built this thing out of wood and to literally get towels off the high shelves. So I would say creativity has always been there. I think there has been a need to solve problems in whatever I might see day to day. In the beginning, it was around this whole b two b space for cancer research hospitals, which was pretty fascinating, finding a way to help them streamline operations and then through the ideation phase, trying to solve personal finance challenges, children's organizational challenges that we kind of stumbled through. And then what we do today with longing goal kind of on the community side. But I think creativity has always played a role both in parenting. I have three small children, but also in how you kind of form the genesis of some of these business ideas.
Anastasia Koroleva: [00:09:06 - 00:09:09]
How did your idea with the second business come to you?
Sriram Gollapalli: [00:09:10 - 00:09:13]
Well, you have to define second, Anastasia, because I've had several seconds.
Anastasia Koroleva: [00:09:13 - 00:09:18]
Okay. Okay. So tell me about all of them. Tell me about the journey you had.
Sriram Gollapalli: [00:09:19 - 00:09:21]
Yeah, I don't know how much time we have.
Anastasia Koroleva: [00:09:21 - 00:09:23]
I know those you disclosed.
Sriram Gollapalli: [00:09:23 - 00:11:05]
Yes. So, yeah, in high school and in college, my partner, who I'm still completely friends with, Tad, he and I started our last one with. Together we run through a number of businesses, everything from helping set up a social space for friends online in the early two thousands, keeping our high school class together, which obviously sounds familiar now, to helping people find and source raw diamonds for people. We thought we built a whole website to help people identify, help to kind of streamline the diamond buying process. We learned a lot through that process out as time will tell. But it was fascinating to go through that journey today. Even before we started longing goal, Tad and I were going through a number of different ideation phases. Everything from helping investors streamline k one s. For those of you that have investor, those of you that have private placements, having an organizing k one s is a highly frustrating process, which should be much easier. So we kind of designed something around that. Two things, kids related. You know, even today, Anastasia, if you go through an airport, going past security, it is very hard to find diapers and baby formula. It's shocking. I was with my nine month old and four year old at the time. We were flying back from New Zealand. We were in an airport, we were past security and we had checked our diapers in or something similar, and we couldn't find diapers. So we kind of ideated a whole process around a vending machine for diapers and baby stuff. And long story, we didn't launch it just for tam reasons and other complexities around regulations, but there are always these kinds of problems that we're trying to crack.
Anastasia Koroleva: [00:11:05 - 00:11:08]
Did you do all that while you were working for?
Sriram Gollapalli: [00:11:09 - 00:13:26]
Yeah, we had some nights and weekends, opportunities to kind of, you know, we definitely, at agilent, there were a lot of interesting ideas to solve with the buyer, both helping them kind of break into the next generation of software and technologies and solving problems at that corporate level. And we gave that our all. And I think it was a fascinating place. That's a fantastic place to work. I would recommend it both as a buyer, as a seller, as an employee, great culture and everything else like that. But I think for us, in our stage of our lives, we knew we were kind of thinking about, after giving it a go, what could be next, and are there opportunities to go next? Trust me, we would have been probably fine staying there another 510 years, maybe. There are people there that we met that were there for 30 or 40 years, which is nearly unheard of these days. So that really is a testament to them. But for us, we thought maybe there's another go. We started a personal finance multifactor hedge fund that we ran for about three years, working through a very interesting analysis of our funds and things like that. We shut that down. And then with long angle, though, that was also, again, a personal need. Back to creativity. Is there a safe space to ask questions of friends who are fortunate to have an exit or just be fortunate to be younger good savers or be in an industry that affords you to have more wealth when you're younger and having a safe space to ask questions of each other in a community like environment without fear of being solicited to? A lot of questions we had after the exit still shocks me today, Anastasia. After the banker or whoever goes you through the process, or a buyer buys you and goes through the process, they give you these large amounts of money, small or large, depending, but that's pretty much it. There's very little financial education that comes after that. And we said there really needs to be something to help you with that. Asking questions like, do you get umbrella insurance? Do you superfund your kids 529s now, how much are you paying for taxes? Who do you go to? How much does your trust and estate plan look like? What level of acronym soup do you want to put in place for your kids? There's so much online, it's hard to distill everything. So we kind of said, let's kind of create a safe space for a dozen friends who are going through processes like that together and share information in a judgment free, objective place to have those conversations.
Anastasia Koroleva: [00:13:26 - 00:13:28]
So how old is Lorna Ingle now?
Sriram Gollapalli: [00:13:28 - 00:13:32]
It is officially probably three and a half years old.
Anastasia Koroleva: [00:13:32 - 00:13:34]
Okay. How is it going?
Sriram Gollapalli: [00:13:34 - 00:13:42]
It's going really well. It's going really well. We started, like I said, with a dozen friends. We wanted to create a vetted space for this community and today we have over 2500 people.
Anastasia Koroleva: [00:13:42 - 00:13:43]
How do you vet people?
Sriram Gollapalli: [00:13:44 - 00:14:29]
Great question. Everyone goes through an interview, so everyone goes through an application process, but we keep it streamline but objective. So everyone has an interview either in person or over Zoom. And we also really look for character, wanting to give back to the community, want to share insights, want to learn from each other. You might be a very novice, you might be an expert, but you're there to learn. And especially not solicitation. I mean that's obviously the most important thing. But unfortunately, as you probably know as well, this world is full of people trying to make a business, which is fine, but trying to navigate that. And then lastly we do wealth verification. Everyone in the community has to show proof of assets of at least 2.2 million investable assets, liquid or illiquid.
Anastasia Koroleva: [00:14:29 - 00:14:31]
How many members do you have now?
Sriram Gollapalli: [00:14:31 - 00:14:32]
Just over 2500.
Anastasia Koroleva: [00:14:33 - 00:14:36]
That's great. That's very fast growth. I think in three.
Sriram Gollapalli: [00:14:36 - 00:14:52]
Yeah, yeah. Especially with the vetted spot. You know, we went back and forth on vetting and doing all that stuff, but we got a lot of feedback from the community members that it's important to interview everyone, especially when Tad and I were doing them. So yeah, Tad and I each together have nearly met 1000 people each.
Anastasia Koroleva: [00:14:52 - 00:14:54]
Oh wow, that must be taking a lot of your time.
Sriram Gollapalli: [00:14:54 - 00:15:20]
It is, yeah. Actually just before this call I met a fantastic hotel operator in Honduras trying to figure out what might be next or last week it was an oral surgeon and then obviously the tech, early tech employees. It's been fascinating to kind of find and see the diversity of wealth, especially when we're younger. But I've now learned also a lot that wealth comes can be generated a number of different ways. Tech exits are obviously a common one, but not the only way.
Anastasia Koroleva: [00:15:20 - 00:15:22]
Do you have regular meetings?
Sriram Gollapalli: [00:15:22 - 00:16:01]
Yes. So with long angle we actually do quite a bit. So we do happy hours in most of our major us and global cities about three times or four times a year. We do zoom events three times a week actually on a whole list of topics. So last week it was related to healthcare, longevity, travel, home building. I think this week we're doing one on mental wellness and oh, tax loss harvesting, asset allocation strategies. So we're binding topics that the community is interested in and we kind of create basically small zooms or breakouts, both hosted as well as just with community members.
Anastasia Koroleva: [00:16:01 - 00:16:03]
Great. So what does it give you?
Sriram Gollapalli: [00:16:03 - 00:16:53]
Personally, I would say it's fascinating. As Aja, knowing what I know now today, I think there's just such an interesting opportunity to help this demographic. Most of us, the thirties and forties, most of us have two kids under ten. And most of us, some of us have wealth advisors, some of us don't. And most of us have like this sweet spot of five to 50 million. So we have, call it four or five or who you talk to, seven or eight or nine decades ahead of us still and really helping us find intentional ways to think about what might be out there and discovering the unknown unknowns. For me personally, for example, we're just going through our personal estate trust in estate planning. So how do people approach that? It's not a question that you can very easily ask a set of peers, but with the community we are, we're able to kind of go through that. How do you approach a lot of kid related stuff?
Sriram Gollapalli: [00:16:53 - 00:17:13]
How are you approaching like college counseling or how do you approach sort of things like that? How do other people do it? What is the right place to invest that money in time and what are other places to do that? Travel is another big topic. You know, my wife and I want to do some extended travel this summer, maybe. So how do you approach kind of travel with those periods with kids?
Anastasia Koroleva: [00:17:13 - 00:17:16]
So you do lots of angel investing?
Sriram Gollapalli: [00:17:16 - 00:17:17]
I do.
Anastasia Koroleva: [00:17:17 - 00:17:23]
How does that work for the community? Do you do it with the members of the community?
Sriram Gollapalli: [00:17:23 - 00:18:41]
No. So actually it's a good point. So before I started loving angle, while I was still with the buyer, I lived in Boston. I lived in Boston about 15 years actually. So we just moved back to DC area to close with a family in Boston. I had gotten together with some friends and we had all had exits of different magnitudes and we really enjoyed angel investing. So we said, let's kind of create a space for us to share angel deals, vet them together and maybe go in together. That actually turned into another group that I run. I volunteer and I run that group on the side. It's called TBD Angels. It's now one of the fastest growing east coast angel networks, New England based but east coast leading about 300 people in the community there. We invest in angel deals about once a month we vet deals probably twice a week on every single sort of domain. It's really just looking. And that group is made up of formerly operators or people who have expertise in the industry. So I personally probably have, gosh, like 40 or 50 angel investments across the board. I just invested in one last week. It was a high school or, or grade school ed tech for computer science, actually.
Anastasia Koroleva: [00:18:42 - 00:18:48]
Do you think angel investing is a good financial strategy?
Sriram Gollapalli: [00:18:49 - 00:19:50]
No. I tell anyone that gets into angel investing, do it because you love helping the next generation of entrepreneurs. Do it because you want to have a pulse. Think of it as a paid education. If you break even, you've done amazing. I honestly believe that, yes, you might find the Uber, I think. I was just reading another story about someone who exited for, I think it was like 300 x in two years. Highly possible. But you could also go buy a lottery card and potentially do something similar. I first have not had the exit, so I can't speak like that or that perspective from an angel. But it's just been so rewarding to speak to the next generation, figure out how to help them, connect them with the right people as a portion of your financial strategy. If that is something for asset allocation purposes, go with a true angel fund that has been proven to get access to that. Otherwise, making individual investments, it's incredibly educational, but I would not say the smartest financial strategy.
Anastasia Koroleva: [00:19:50 - 00:19:54]
Do you think for you it was a good way to spend your time?
Sriram Gollapalli: [00:19:56 - 00:21:15]
Um, spending time is an interesting question in general. Right. A limited time. I asked myself the other day, like, what would I do with another hour of the day? And it's related to working out because I just don't work out anyway. So, um, I, I'll admit that I, the, the time I spend today is probably a little bit around mentoring, a little bit about deal flow sourcing, but it's not as much time as I used to do at all for a number of reasons, both raising children, running long angle and things like that. But again, it depends on what stage of life and what stage of career and what kind of things you want to do with your time. After an exit, I think it's a great, great way to spend some time to get a pulse of what's going on because you get to almost get a paid consultative seat across a number of industries, most likely with an exit. You have access to either peers or can get access to a wide variety of things. So you can quickly dabble across a number of industries, whether it's, you know, one of our best investments was a women's champagne brand, for example, or B two B SaaS or social or crypto or health tech. You can quickly see all these things and realize, okay, well, I have a passion for this space, so let me go deeper now here. So I think it's a reasonable space, a reasonable place to spend time as a post exit investor founder person. But it's certainly not for everybody.
Anastasia Koroleva: [00:21:16 - 00:21:52]
It's definitely a very popular activity postexit, as I'm sure you know. But I think people regret doing it later because I think their expectations were different from yours. They actually did expect a big financial outcome and often doesn't happen. Or they expected to not spend time on it, and then they realized that without spending time on it, lots of startups don't quite have the experience they would need to succeed. So these people end up spending more time than they bargained for. Would you agree with that?
Sriram Gollapalli: [00:21:52 - 00:23:17]
It's interesting, especially as an angel. Depending on where you're playing, you're generally playing in the pre seed space and the impact you have then can be high. But as they grow, you may not be the right person. You're also most likely, you're very small on the cap table or the founder. Them being the founder, yes, they're appreciative of you, but they don't really always have the time to give you the update that you're seeking or what have you. And the last thing I'll mention is it's a long game. There will be those few diamonds in the rough that exited within, call it 18, 24, 36 months even. But most likely if they exit, it's at least five, if not 7910 longer years. And the second thing that you sort of setting yourself up for is probably putting more in over time as new fundraising comes in. Are you willing to ride that journey completely or let your slice continue to get diluted? Both answers are actually potentially fine. You have to make the bets correctly for the post exit founders that find themselves feeling like they're spending more time. I would ask them, are they getting the return on that time, or did it feel like the return is actually there? Because chances are your time is likely better spent unless you really have an official relationship with that.
Anastasia Koroleva: [00:23:17 - 00:23:21]
So how do you invest your wealth outside of angel investing? What's your thinking?
Sriram Gollapalli: [00:23:24 - 00:25:29]
It's definitely ebbed and flowed in a number of different ways. The early post exit days, I was very much, I did some boglehead sort of brought based index strategies, but I also said, look, I'm young enough and I think I'm smart enough that I should just be able to buy my own tickers and kind of equity positions and do that. I did fine. I didn't do amazing, but I definitely, the beta was, the alpha was actually fantastic. I doubled, I think, a lot of the proceeds within three to five years. Now, again, nearly anyone could have in that time period of 2017 to early twenties, but again, you had to kind of be in the right spaces across almost any industry and any investment. You could have done that. And like I earlier mentioned, I now get 50 or 60 different k one s, a lot from the Angels, but also a lot from a lot of the private placements that I do. I'm sort of biased towards some of the secondary offerings that private market offerings that are out there. You know, the unique fund structures that have a unique space to arbitrage and find unique private equity placements. Getting access to those which we've been able to do through longingle and other places has been a, has been a growing portion of my portfolio. I have a little bit of real estate and then everything else. I'm actually now trying to simplify a bit more into broad based indices like the BTI ZBO, a little bit of Bixs, maybe some international exposure. I still have several individual ticker symbols. I bought a share of Berkshire A after the exit for fun, and that's phenomenally well, fortunately. So I think there's a reason to get some more simplicity. My accountant would love if I had more simplistic approaches. My wife would probably love it if I had less places to log into. So I had a fun eight year journey in that process, and now slowly realizing I want to spend time in other places. So I can simplify that realizing the return profiles along with the private equity placements are likely going to be more than fine, and then offering myself to kind of invest in other areas.
Anastasia Koroleva: [00:25:30 - 00:25:32]
Do you find investing fun?
Sriram Gollapalli: [00:25:33 - 00:25:35]
Investing in what? That's the question.
Anastasia Koroleva: [00:25:35 - 00:25:40]
The process, just the process of investing, comparing to the process of building a company.
Sriram Gollapalli: [00:25:40 - 00:28:07]
I would say it was fun. Especially when you got to see some of the thing about investing that I think can be immediately fun and also give the adrenaline hit are some of the immediate wins. Like very rarely can you buy, like Nvidia, for example, and then watch what happens to it within days, weeks, months, years, and then realize, okay, well, that was phenomenally to go on that ride, and there was an immediate return for that minuscule amount of time, depending on how you did the research process. Having said that, I now know, and no one needed to tell me this, that active stock picking is really best left to probably no one, honestly, broad based indices largely over time, everyone will tell you 99 times out of 100 will beat any sort of active manager. So fun. Good things I knew about at the time, but I'd say building. And there was also the first probably five years I was that person checking the portfolio every other day just because I could, and watching things go up and down. It was stressful, but it was also, and it was super fun. It also came into the calculus when I was making decisions on things. When you watch portfolio swings in like five digits, sometimes six digits, it really puts a perspective on when you're making your day to day buying system. Like my wife would say this also, she's like, you're spending so much time thinking about buying this for a, you're watching your entire portfolio swing by tens of thousands of dollars. And it's very sort of counterintuitive because we grew up from humble household. You're taught to be thoughtful, you're thought to be, let's be weighing those decisions. Do you really need that sweater? Do you really want the $200 jacket or whatever it is? Whereas the other side, you're making these wild bets either call it $25,000 angel investment, or it always feels like different pots of money. But it's fascinating. So a longer way to answer your question, also a shorter way, rather, is that I personally feel like I now have a lot more fun building. Whether it's building and investing time in the company, in watching the kids grow, and investing in the pursuits that they have, I think now I'm realizing investing in one's health is really important. I still don't spend enough time on that. Yeah, I think I answered that.
Anastasia Koroleva: [00:28:07 - 00:28:13]
So what other activities you find meaningful besides building and taking care of the kids and family?
Sriram Gollapalli: [00:28:13 - 00:29:06]
You know, I am trying to get involved, for example, more in the we'll see how it goes out. But in like the DC tech scene, wanting to give back in whatever that means, giving back both from a perspective of the next generation of entrepreneurs or trying to help build up DC as a tech city. We have a lot of history here. How do we grow it? How do we make it kind of bring it back to some of its luster. And then I'd say personally on the health side, spending more time with the family, trying to get date night in, which still appears to be a challenge for whatever reason, and then investing in even the next generation of entrepreneurs. Like I mentioned, my daughter investing in her. She's ten. Teaching her about the pursuits of generative AI. She just launched a coloring book on Amazon. So realizing that making small differences can really have longer impacts.
Anastasia Koroleva: [00:29:06 - 00:29:07]
Do you have a sense of purpose?
Sriram Gollapalli: [00:29:08 - 00:30:45]
So one of the workshops we run at long angle is, or we're going to run actually we're just in the early stages of planning, is a concept around ikigai, which is a lot of what it is around purpose Ikigai, and I won't claim to be an expert around this at all, but it's really around identifying how one spends their time and how you kind of approach that appropriately. It's an exercise I haven't gone through formally. We're going through some of that. I've personally gone through some other exercises called a centenarian exercise, which basically when you. It seems simple, but in practice turns out to be very reflective when you turn 100. How did you want to view remembered per decade? Not generally, but what did you want to remember vividly in your thirties, forties, fifties, sixties, seventies, eighties and nineties? And what are the kinds of things that you have done in those periods of time, in those decades? I say all that to say that I have homework and books on my bookshelf as I speak, as I'm looking at right over there, and I've not done all the investment there. So I would say the purpose today does revolve around a lot around family and then helping to build out the long angle platform and community. I feel very satisfied and happy and excited on those pursuits of current purpose. Whether those will be my pursuits and purpose if you had this conversation with me a few years from now, I can't tell you, but I feel extremely excited about these kinds of things that I miss.
Anastasia Koroleva: [00:30:45 - 00:30:47]
Whom do you want to be when you grow up?
Sriram Gollapalli: [00:30:48 - 00:30:50]
You did not give me any prep questions.
Anastasia Koroleva: [00:30:52 - 00:31:01]
No, I wouldn't have, because I want this face on the screen right now when you're thinking about it.
Sriram Gollapalli: [00:31:01 - 00:33:19]
Who do I want to be when I grow up? I appreciate the question also because it also implies that we have not grown up. And I think that that's an interesting perspective, especially with our age demographic. I think the question of how long, and I don't say this in a very Sci-Fi sort of way, I do think there's a realistic thing that we, our generation needs to be ready for in terms of a potentially a longer time horizon that we should be thinking about what that might look like. I think for me, I would like to, I would like to continue to be a builder. I don't want to necessarily put a name on a Persona or an individual as to who I want to be when I grow up. But it's hard for me not to imagine myself building now. What that means, I think will always evolve and the grandeur of whatever it might be building could be. But I think I see myself creating and building. One of my first careers was in consulting with one of the big four back in the early two thousands, which I absolutely adored. It gives you a broad perspective. I recommend consulting, especially in your twenties, to almost anybody because you get the perspective across nearly any discipline, provided that you are entering the right kind of space. And I have a lot of appreciation and respect for people that continue to stay in that, especially in their thirties and forties. The one thing I will say that was somewhat challenging about that space, though, was not feeling like you have a tangible legacy left from that. It was a lot of recommendations, a lot of areas to leave impact on. The organizations that you were working with, don't get me wrong, but I wasn't building that widget. I'm working on a Lego set, for example, with my middle daughter. At the end we will have the end result. It'll be something that you can see, touch and feel. So I do see myself continuing to find ways to build, touch and feel things and leave that as part of what I continually want to do as I grow up and legacy wise and need to kind of reflect on that a little bit.
Anastasia Koroleva: [00:33:19 - 00:33:21]
That's a beautiful answer. Thank you. Very cool.
Sriram Gollapalli: [00:33:21 - 00:33:23]
So we'll see. That totally got me off guard.
Anastasia Koroleva: [00:33:24 - 00:33:30]
So it sounds like building things is what motivates you in life right now.
Sriram Gollapalli: [00:33:30 - 00:34:01]
You know, I have. I recently went on a, for the first time, a self reflective kind of retreat, I guess, so to speak. And it really did a lot of that came both that and then being more intentional about family time. I think that is something that I feel like I do an okay job of, but there's always room for improvement. But I do. I love the idea of building and it's going to be hard for me, even presuming there's a post long angle days not to be building something.
Anastasia Koroleva: [00:34:03 - 00:34:08]
Tell me more about this reflective or introspective retreat.
Sriram Gollapalli: [00:34:08 - 00:36:08]
So that was two and a half days in the Catskill Mountains run by, I guess he was another former exited founder, Peter Corbett. And I had no intention of ever doing anything like this before. It was posted in one of the groups I was in and I looked at it for a second and I was like, huh? I don't meditate today. I don't really do a lot of personal investment in myself at all. And anyone can tell you that knows me. And I saw it and I was like, look, this is two, I think it was two nights, two and a half days, give or take. And it was for whatever reason, the timing worked out, which logistically, especially with three kids that I had, traveling, you know, dual career household. So I talked to my wife and was like, okay, yeah, why don't you go try that? And never done anything like this before. I would probably do something like this again. In fact, I told him and others that I would not only want to do that again with my wife because I thought that can be particularly reflective as a couple, but also as a family. I think those kinds of experiences are rare. And being in an environment like that to both, you know, and it was pretty simple stuff at the, at the same time, it was, it forces one, you know, mindfulness and things like that are ones that it's hard to make time for. But when you make the time, realize you should be making more time. Just like a number of things in your life where it was a mix of silent meditation, a mix of nature solos, a mix of breathing exercises, and it was good. It allowed us to kind of talk about a number of things and force ourselves to think about a number of things. And from that, it also gave me a little bit more clarity on all the things I mentioned for the last half an hour or so around spending more time with the kids, spending more time with my wife, but also being intentional about the long angle journey, what we're building as well.
Anastasia Koroleva: [00:36:08 - 00:36:10]
So did money make you happy?
Sriram Gollapalli: [00:36:10 - 00:38:12]
I guess it's interesting the way you asked that question, because I think there's did, which means, like you're referring to an exit, or the exit, I presume, versus does just generally. And the way I sort of approached that question is probably more around, again, back to the time, what does it actually allow one to do? And I think it really is around the freedom of time. And it's almost, it's more responsibility to think about, yes, we have a nice house, and I'm not in nice vacations of those things. I think those have been and adding to be life's experiences and allowed us to be things like that. But I think there's also components of it almost adds a lot of responsibility around both raising the younger generation in a certain way. How do you be more intentional about. My wife and I talk about this all the time, bringing different realities to them, sharing different experiences with them and things like that, where money allows a number of those things and allows you to kind of bring a lot of those experiences to bear. And it kind of allows you to multiply a lot of the things that one can do if being intentional about it. So does money to the event make it happy? Yes. I think it was a great sort of realization of the goals of spending the last ten years. We hadn't necessarily expected something to go that way. We were having a fantastic time working with our friends. We would have kept doing it if we had to. It was stressful, I'm not going to lie about that. But it was good, it was fun. We were making an impact. We had built something. We changed the lives of many of our employees and our team members, which we fondly have great memories of. So I'd say it was happiness from the perspective of going through the journey, keeping them in a safer space, not having to worry about stressing about them as much, and allowing us to give the freedom to make some more choices in the future. But I think just money being a happiness factor is probably not the way I would totally look at it either.
Anastasia Koroleva: [00:38:12 - 00:38:15]
Do you ever regret selling your business?
Sriram Gollapalli: [00:38:17 - 00:38:34]
Probably not that one. I think it was a good time. Like I said, I don't know enough about your journey, but most entrepreneurs, you kind of hit that point. We were doing well. It was a very healthy cash flow business.
Sriram Gollapalli: [00:38:35 - 00:39:04]
People were great. But it is anyone in the business of building product and service, it can be. You're always building a product and service, and there will all be. I think that the most challenge, one of the most challenging things about that, especially in a b two b space where I was, is being the kind of person that I was. And many of our team was also. You're unintentionally always letting people down in some perspective. Like, there's always someone asking for this feature or that feature, or wanting to see it do this way or help them solve this problem.
Anastasia Koroleva: [00:39:04 - 00:39:04]
Oh, yeah.
Sriram Gollapalli: [00:39:04 - 00:39:30]
And there are only so many things you could do. And that was sometimes challenging. It was also invigorating because it said there were so many challenges to solve in the space for that particular problem that we had found. But I think it was a good run. It was a good ten years of my life, as most of my twenties and my early thirties, and I think I would not have done it any other way and allowed us to kind of figure out what the next chapter could be.
Anastasia Koroleva: [00:39:30 - 00:39:37]
No, of course. Did you feel that you needed to go through therapy after the exit?
Sriram Gollapalli: [00:39:37 - 00:40:33]
No. And I think for two reasons. One, culturally, therapy is not as common and is never really even seen as a. As an, I wouldn't say option. As a toolkit or part of your toolkit. Yes, as common, especially then. Now I think the stigma is changing and a number how you approach it's changing. And then two, I had some time to pause and reflect, but I didn't really have that much time to pause and reflect. As you go through the transition of being integrated into a larger multibillion dollar organization, kind of going through that process. Process for the first few years, then you're kind of trying to make a name for yourself within the organization for the next few years, and then you're trying to figure out, is this the place I want to stay and ride the next ten years of my career journey, or do I want to approach what to do next?
Sriram Gollapalli: [00:40:33 - 00:41:26]
And I think a lot of it had to do with having an extremely strong support system. I'm beyond thankful for my parents sort of, quote unquote, allowing me to even go on the first part of that journey after going through investing in schooling and everything like that and doing really well at my consulting opportunity, to then come to them and say, I'm ready to quit. Go live in a small townhouse with six guys and drop my salary to nothing after just going and spending all that investment on my college education and leaving a really well paying big four job, I think having the support of my parents to say, that's fine, we trust you, you'll be fine. That has a major, that had a major impact on just de stressing the whole thing. And then after the exit with my wife, she was working, and again, my parents being supportive of how to approach it.
Sriram Gollapalli: [00:41:27 - 00:42:07]
And even when I was reflecting on how to quit, two things I'm terrible at is acquitting and firing people. Firing people is one of the hardest things to do. Of course, whenever you do it, you always wish both you and that person wish you did it earlier. That's a whole different story for another topic, another podcast. But I'd say allowing that and allowing both having the support structure, I was gonna say, with my wife, my family, I think, and my business partners, of course, I shouldn't say that. I never really had time to even think about do I need, quote unquote, therapy as an option.
Anastasia Koroleva: [00:42:07 - 00:42:35]
I'm not surprised, actually, because my observation is that people who continue being busy feel less mentally sick, in a way, but those who immediately stop working after they sell their business, that's when you get hit by that emptiness, and people start questioning their mental health quite a lot. How about spirituality. What are your thoughts on that?
Sriram Gollapalli: [00:42:36 - 00:43:17]
I would say I am. I was raised. I'm born Hindu, practicing Hindu. I'd say Hinduism. We are highly culturally aware. We observe many of the festivals. Hinduism is sort of an interesting religion as a study, even. It's sort of prescriptive, but also freedom of choice, at least the way we've interpreted it. So, you know, I'd say spirituality has a place in our home. We, like I said, observe many of the traditional festivals, raising our children to observe culturally, a lot of the dangles we practice.
Sriram Gollapalli: [00:43:17 - 00:44:06]
We've been practicing vegetarians since birth in our. Myself, my wife, my whole family, and my kids and things like that. And then I'd say, you know, before going to school, before the school starts at the beginning of the year, having some basic prayers for having a good year, preserving certain good days and not good days and things like that is probably. And, you know, hitting the temple for some specific kinds of events, whether it's, like, for the children again, first time, reading and writing and elements like that, first locks of hair. So I would say, me personally, I would say I'm highly culturally aware and am spiritually aware.
Anastasia Koroleva: [00:44:06 - 00:44:11]
But is spiritual growth part of your personal growth strategy?
Sriram Gollapalli: [00:44:13 - 00:45:16]
I believe that there probably will be. I like to have it as part of a toolkit that I recognize, but I also recognize it's there for me when I need to have that as a focus opportunity. And it's probably one of those things, as I think about it. I'd probably be more intentional about later in life. I think I have areas that I'd like to invest in now. Knowing that that is an area, at least for me, this is completely my opinion. I'm personally okay with investing in later because I will have the ability, and I think I will have the ability in mind space to get what I need by investing in that later. Yeah. So I'd say it's always there. It's been there as an opportunity, but it's probably not forefront.
Anastasia Koroleva: [00:45:16 - 00:45:25]
So if you talk to someone who just sold their business, what would be your normal advice? Because I'm sure you talk to these people a lot.
Sriram Gollapalli: [00:45:25 - 00:47:18]
Yeah. First and foremost is do nothing like basically, really, you hear this a lot. You see this a lot. You know, splurge on the things you need to splurge on, you know, but don't. Don't splurge on something crazy. Splurge on things where the mistakes are, you know, can be made. But also do recognize it, you know, do appreciate that you did do something. You know, you shouldn't feel, feel like the accomplishment that you just did. Most likely is you're in rarefied error. And whether that exit was for tens of thousands, hundreds of thousands, or tens of millions, you still did something to kind of create something that then yielded some sort of exit opportunity on our side. So one of the easiest things to do is to not actually recognize that and just like literally do nothing. Like, don't do that. For example, I think we celebrated a few small minor wins. Like we went to an extreme Lake Favicon dinner that we never, never would have gone to otherwise. I think there are a few clothes, purchases, things like that, that again, just felt non traditional. And then of course, we had some larger purchases around homes and renovations and things like that. But after being a little more methodical and what we could afford, I think the other thing that we were kind of reflective on is still at least the mindset that we were in is live in an affordability zone. Never overextend yourself. Even with this exit, you don't know if this exit will happen again, treat it extremely such that way, and then really reflect on, like I said, learning more about this process called ikigai. If anyone looks it up. It's a pretty straightforward, pretty elementary thing. But even spending that time to kind of reflect on how you might spend your time just really, again, it opens your aperture in terms of how you might want to be thinking about spending the next whatever stage of life you might be left with.
Anastasia Koroleva: [00:47:19 - 00:47:23]
What are the biggest mistakes you think you've made since you sold your company?
Sriram Gollapalli: [00:47:23 - 00:49:36]
I have too much of a bond position. I tell you that straight up. Everyone said buy bonds. Whether I did it wrong, I can't tell you Anastasia, but that was probably my first performing part of my portfolio without fail. Fortunately, it wasn't. Yeah, I don't, again, a number of things. I think all the investing side as well never really invested as much in real estate as I think. I don't know. We could have, should have, would have, or what have you. For a number of reasons, no good reasons, maybe time, maybe what have you. But I think the zero interested rate environment that really the world lived through, especially the US, is rarely gonna be back. It was nearly a once in a lifetime. We might see that again in the future. So taking advantage of those kinds of good debt opportunities are rare in one's life. But it was also early in my post exit career, so. And the debt is such a foreign concept, at least for us growing up as well. It's hard to really latch on the idea of good debt. I think other than that, again, health will always be there, and we're seeing it again today. I think there's never a good time to not invest in your health. It was never a good if I said that. Right. So even to this day, how do you think about really incorporating health? You know, I did do. I was very proud of myself. I did invest in Boston. There's a really big cancer awareness bike ride that I participated in. I did the 50 miles version of what's called the Pan mask challenge a few years ago. I just signed up again, this is three years later, to do it again. So kind of forcing you to kind of do that writing and things like that. I'd say the other thing, usually, as a founder, I was terrible at kind of investing in health because you're kind of investing in really every other part of the business and the life and things like that. The other thing I would tell a post exit founder is really do spend that more time on healthy. It's rare to have, especially you do open up time. And I say it, I preach it, I don't do it. So it's easy for me to say it, but I'd say that's probably one of the areas I continue to wish I'd do more.
Anastasia Koroleva: [00:49:36 - 00:49:50]
Yeah, no, I absolutely agree with you. I actually think it's the very first thing that an existed founder should do, because we are quite traumatized, and our business always takes quite a big toll on our health.
Sriram Gollapalli: [00:49:51 - 00:50:07]
There's always a priority, and there's never, quote unquote, a good time that'll quickly catch up on you. Like, I'm just learning to play squash, for example, and, like, you get injured now and you don't get recovered, you don't recover the next day. Like, it takes days or weeks or months, some cases, to get my heart rate.
Anastasia Koroleva: [00:50:07 - 00:50:35]
Yeah. But also talking about mental health and therapy, what I noticed is that sometimes people just think they have mental health issues. Well, in reality, they're just very tired physically, and they need to take care of their physical health, and mental health will follow instead. They don't do that. They try to get therapy or medicine to address that, just to realize years later that that was not the right tool for the job.
Anastasia Koroleva: [00:50:35 - 00:50:41]
So on a scale of zero to ten, how fulfilled are you?
Sriram Gollapalli: [00:50:42 - 00:50:48]
I would say right now, I would probably give myself a seven and a half.
Anastasia Koroleva: [00:50:48 - 00:50:49]
Okay.
Sriram Gollapalli: [00:50:49 - 00:51:52]
Yeah, seven after eight. I feel pretty good. Like, I think I'm. I'm reflecting for a moment. May have answered quickly, but I think fulfillment is relative based on time and space of where you are. So I'd say for where I feel like I am today, I feel pretty good. Like I feel fulfilled. I feel like there are elements that I want to invest in, as you've heard me say a number of times over the last hour on health and wanting to do more, but I think having and spending, but I feel like these are so small dials. I still have within my power to adjust. Nothing's out of my control. So that's on me to do, which I'm not saying it's easy, but it's on me to do. And I feel like I have the tools that I need to do it. It's just waiting on me to make that choice versus. Because there's sometimes you feel like you can't do something for some trickle reason. Yeah, I don't feel like I have that.
Anastasia Koroleva: [00:51:52 - 00:51:57]
So you think it's in your control to take it from seven and a half to ten?
Sriram Gollapalli: [00:51:57 - 00:51:59]
Yes.
Anastasia Koroleva: [00:51:59 - 00:52:03]
And you would need to work on your health more than anything?
Sriram Gollapalli: [00:52:03 - 00:52:43]
Yeah, health. And especially with a life of a family of three kids and parents and in laws. We have a very fantastic, great joint family growing up relationship here that we've built around us. And I think continuing to spend more time focused inward and being intentional about that, I think we'll pay back in spades. Stronger relationship with the kids, stronger relationship with my wife, with my parents and my in laws, I think has been just being intentional in all those different vectors would be. It's in my control. And I think taking that step to do that, I think it's just important to kind of be reflective on.
Anastasia Koroleva: [00:52:43 - 00:52:47]
So how do you choose the people you surround yourself with?
Sriram Gollapalli: [00:52:47 - 00:55:23]
Yeah, you know, like I mentioned, we're fortunate, we're extremely fortunate to have my parents, my grandmother, my in laws, my three kids, my wife. Like, around us, everyone I just described is around us nearly 24 hours a day, actually. And that is, we kind of built ourselves around that. One of the reasons we moved to DC was for that reason, the DC area. And that has fortunately taken up a lot of our time to kind of build ourselves in a multi generational household with our children. Just the other night, we had dinner with my grandmother, which is my kid's great grandmother. We were cooking together. We were learning from each other. I think that's such a rich part of the history and cultural tapestry that we want to be kind of giving back. Other than that, though, like I said, I do a lot during what I call school hours, which are effectively nine to three here. So I am constantly, as my wife will say, meeting new people for lunch or dinner or breakfast in the area. I've been fortunate to meet a number of post exit founders here in the DC area. I've been meeting people through long angle. Like I said, we've built this community. Younger people trying to figure out their next journey in life or in their wealth journey, realize how to be better stewards of that, whether it's someone looking to expand their horizon, build the next business or things like that, VC partners, general managers at funds. I think I've ended up, as I reflect on your question a bit more, I'd say during my working hours, I spend a lot of my time both interviewing new members at long angle, which kind of naturally leads me to this interesting set of people, thirties and forties, younger, very high net worth individuals. But then I find myself also craving the in person. So I'll find myself doing, I don't know, two or three lunches a week. That seems like a lot, maybe like one lunch a week. I've been trying to pick up squash a bit more. Like I mentioned, meeting young professionals who are, you know, there are a few of us that have some of that flexibility during the day, not as many. And those that do who are younger have gone through some exit or have more flexibility in their schedule that allows them to do things like that. So I'd say that's been a lot of. Yeah, I'd say if I had to classify that full group of people, it'd probably be younger investors, post exit founders, people who want to invest and be intentional about the next parts of their lives.
Anastasia Koroleva: [00:55:23 - 00:55:26]
Yeah, it makes a lot of sense. So you have common interests with them.
Sriram Gollapalli: [00:55:26 - 00:55:52]
And time, you know, very few people have that time during the day to have the flexibility to have conversations as well. And then, of course, a lot revolves around the kids friends and kids parents and things like that. I'd say otherwise kids activities for sure, but I've been fortunate to kind of build a network and continue to build a network, especially in an area as rich as the DC area. We've been fortunate to kind of continue to find new people.
Anastasia Koroleva: [00:55:52 - 00:55:57]
So you mentioned that question before, but I have to ask you, how do you want to be remembered?
Sriram Gollapalli: [00:55:57 - 00:57:47]
Yeah, I think legacy is important. I would like to be remembered for inspiring the next generation of builders. You know, I've never had to put that pen to paper. Anastasia, you're one of the first people to ask me that and I appreciate the question. I think as I reflect on that through this conversation, it would be around a lot of that, especially going through this journey with my daughter right now. I think it would be to, yes, be remembered for inspiring, accelerating and encouraging the next generation of builders and how impact can be done. I think intentionality for us is so important these days, how we think about what our means can provide and focus those things, whether it's different career ambitions that aren't otherwise encouraged or the next few startups. In fact, just two or three days ago, I met someone who knocked on our door, and he was running, he had started the high school entrepreneurship club, and he was trying to, he gave me a quote for washing my windows so that I could raise funds for their next meetup. And I said, I'd be happy to do that. Let's negotiate a price for that. But also come talk to you. I'd love to see what you're all doing in this generation. And he was already talking. He's like, what, 15, I think, talking about digital currencies and whatever generative AI might be bringing and how do you kind of those kinds of things. So how that manifests itself, I think time will tell. Fortunately, I think I have a fair amount of time to do that, but I think that would be a fair place to sit.
Anastasia Koroleva: [00:57:47 - 00:57:54]
Sriram, thank you so much. I really, really enjoy this conversation. Thank you so much for joining me today.
Sriram Gollapalli: [00:57:54 - 00:57:56]
Yeah, I appreciate it. Thank you so much. Anastasia, thank you.
