Private Equity Spotlight: Scaling Bootstrapped Success with Vinay Kashyap

[00:00:00] Sean Mooney: Welcome to the Karma School of Business, a podcast about the private equity industry, business best practices, and real time trends. I'm Sean Mooney, BluWave's founder and CEO. In this episode, we have an awesome conversation with Vinay Kashyap, partner with Mainsail Partners. Enjoy.

[00:00:33] I'm super excited to be here with Vinay Kashyap. Vinay, good to be with you. Good to be with you, Sean. Yeah, I've been looking forward to this one for a long time. We're going to be talking about one of the most exciting parts of the world for a whole variety of reasons in the world that you live and breathe in, in the tech world and the software world.

[00:00:51] There's just huge amounts of like historic change going on. So this will be, I think a very interesting one to dig into. But before we go into some of the meat of our conversation, I want to know more about you Vinay. Can you share a little bit like how you came up, how you got into this industry? What's a little bit of your backstory?

[00:01:07] Vinay Kashyap: Yeah, absolutely. I grew up in North New Jersey. About 45 minutes outside New York City, my parents both immigrated to the U. S. from India in the 70s. They were both doctors. Not in finance, and so our dinner room conversations were about their patients and really interesting problems they were solving. But my dad did read the New York Times front to back every day for maybe 40 years.

[00:01:31] And so we also talked about current events and politics. And so. When I went to college, I decided to study economics and international relations, just sort of as a way to better understand how the world works. And so that was my hypothesis with those majors. And as I progressed, got interested in how markets work and companies work.

[00:01:49] And after very short stints in investment banking and in consulting, sort of worked my way into a job at summit partners as an associate in 2006. And so I was. Cold calling executives that were twice my age, trying to convince them to have conversations with summit about taking liquidity, but they're profitable companies during the day at night.

[00:02:12] I was working on deals and reading all the investment memoranda they had. It was all in a drive and there was maybe 200 deals. I could read through, figure out what worked, what didn't work. And I loved it. I learned more at summit in a month than I did in over a year of consulting and half a year of banking.

[00:02:30] And so. With that background, I got really interested in some of the investments that summit had made in the nineties when they were sort of coming up in the industry. And then after going to business school is introduced to the co founders, the Mainsail Partners who also were summit alum, and they were sort of starting it all over again.

[00:02:48] And the thesis they had was, Hey, let's go create some of that success that summit and associates had in the nineties, finding great bootstrapped software companies sort of between the coasts that were profitable growing quickly, but could use some help primarily providing liquidity, but also primary capital and.

[00:03:06] Focus on winning those investments through relationship building and growing big companies and then selling them up the value chain of private equity. So now 11 years later, still here at Mainsail, having a ton of fun, loving my job every single day.

[00:03:19] I love your background and a couple of friends.

[00:03:21] Sean Mooney: I didn't appreciate the summit lineage to Mainsail. So you have two storied firms, two iterations of the story firm in your experience. And that a has to been fascinating. The other thing you mentioned that is really near and dear to my heart, really through the eyes of my kids, is you growing up with kind of a two doctor family.

[00:03:40] My kids go to a school in Nashville that's kind of quasi affiliated with Vanderbilt, and so there's a huge proportion of children there that have two doctor parents who are working at the Vanderbilt Medical Center, and so I just always have to profusely apologize to my kids for the Relative gene pool that they received vis a vis their friends.

[00:04:01] I was like, you're going to, you're going to be fine. You got your mom's genes, but through dad, you're going to be fighting with one arm tied behind your back.

[00:04:08] Vinay Kashyap: Yeah. And it's interesting. It's even their professions. My mom was a developmental pediatrician or she still is. And my dad was an orthopedic surgeon and even they're very different.

[00:04:17] My dad's more mechanistic process oriented, sort of a carpenter. But my mom's, from her, just great empathy, great listening skills, and so you sort of pick up on these things and they influence you over time.

[00:04:28] Sean Mooney: Yeah, you have this kind of scientist mindset, this problem solving set of parents. It's not surprising that that led you to where you are.

[00:04:36] I'm sure the dinner table conversations were pretty fascinating. Were you ever tempted to kind of get into the quote unquote family business?

[00:04:43] Vinay Kashyap: Yeah, my sister and I, I mean, my parents were very open minded and basically told us if you love science and Biology, feel free to go down this path, but medicine's changed a lot.

[00:04:56] Some of it not for the better, unfortunately. And so I think their perspective was, you got to really love it if you're going to do this. And so as we sort of, my sister's in education and administration, I'm in finance, and so they just supported us in any direction we wanted to go. That's great.

[00:05:12] Sean Mooney: But what a great background to have.

[00:05:14] And then it, it clearly. The coaching you received as a kid worked out pretty well, and so, and that inherent kind of like thrust to be curious and kind of find your own journey is also just a tremendous gift.

[00:05:28] Vinay Kashyap: Yes, absolutely.

[00:05:30] Sean Mooney: So maybe peeling back the onion a little bit here, Vinay. One of the questions I love to ask is, we'd know you better if we knew this about you.

[00:05:39] What's one of those things?

[00:05:40] Vinay Kashyap: So I grew up in North Jersey, aspects of my childhood were pretty traditional, upper middle class suburb. I was a lacrosse player. I played lacrosse all the way through college, division three, but really enjoyed the lacrosse program. But I'm up at this small school in the coast of Maine called Bowdoin College is where I went to school.

[00:05:56] And I've always been really into music. And so one fun fact, I guess, is that a friend of mine, he was from the Chicago area. I'm from the New York area. We listened to a lot of. hip hop music, and there was a radio station on campus. And so we actually, for several years, had an underground hip hop radio show in Brunswick, Maine.

[00:06:15] And I think our listenership peaked at about three people, maybe four at various times. We had so much fun just finding obscure, up and coming hip hop artists. They call it like digging through the crates. Sort of looking through the mainstream and finding quality. And that was really fun. I still listen to a ton of music today.

[00:06:37] And most of it's not top 50 type music, but that was a really cool experience.

[00:06:42] Sean Mooney: That's amazing. I always thought about doing that in college and I realized I didn't have good taste, but

[00:06:48] Vinay Kashyap: well, I don't know if we did either, given the three people who listen, but it was just, we had a really terrible slot also being in rural Maine.

[00:06:55] I'm not sure the hip hop listenership overlapped very well with the demographic.

[00:07:00] Sean Mooney: Were you all in the Biggie camp or the Tupac camp?

[00:07:03] Vinay Kashyap: Significantly more Biggie, but early. Yeah. Real early Biggie, and we were just trying to find the stuff where he was more technical and innovative, and as they got more popular and all the money came in, like, the quality of the music just inevitably went down.

[00:07:16] Same thing with Jay Z. Like, the first Jay Z album, Reasonable Doubt, is incredible. After that, Starts going downhill. Sadly,

[00:07:22] Sean Mooney: what was like one of the other kind of like gems you think about like just getting in real early on someone where you were playing their songs or into and then they just like blew up and you're like, well,

[00:07:34] Vinay Kashyap: well, I mean, it's, I can't quite.

[00:07:36] I don't know if I take credit, but like, even like Nas, like his first album, Illmatic, I think is one of the greatest geniuses of music of all time. I mean, that guy was, I think, 17 or 18 years old when you recorded it and you just listened to it and what he was talking about and rapping about and the quality of the music and the beats.

[00:07:54] DJ Premier was his DJ. It was just, it was awesome. Just a lot of the first albums were the best in my experience when they were sort of new and innovative. And it was just really mind blowing.

[00:08:04] Sean Mooney: I went to college in Georgetown in the 90s. You got all of those kind of like Virginia, Maryland kind of college bands.

[00:08:11] And the big one that we got exposed to was Dave Matthews, not hip hop.

[00:08:17] Vinay Kashyap: Yeah, everyone. I went to see him play giant stadium. That was part of everyone's childhood growing up probably in the nineties.

[00:08:25] Sean Mooney: Hey, as a quick interlude, this is Sean here. I wanted to address one quick question that we regularly get.

[00:08:30] We often get people who show up at our website, call our account executives and say, Hey, I'm not private equity. Can I still use BluWave to get connected with resources? And the short answer is yes. Even though we're mostly and largely used by Hundreds of private equity firms, thousands of their portfolio company leaders.

[00:08:48] Every day we get calls from every day top proactive business leaders at public companies, independent companies, family companies. So absolutely you can use this as well. If you want to use the exact same resources that are trusted and being deployed and perfectly calibrated for your business needs, give us a call.

[00:09:05] Visit our website at BluWave. net. Thanks. Back to the episode.

[00:09:13] But I think that's a really cool story. You got to do the college radio story and I like how it Kind of shows you're a kind of a seeker, you kind of find things and go through and you can see where that kind of started from your youth to your radio show experience and then inevitably these curiosities feed kind of who you become in later in life, and that's a really kind of neat connection there.

[00:09:36] And so if we were to maybe take it further, and one of the things that I did when I was in PE was. Inevitably, I started building kind of a scorecard of like, here's what I'm looking for, because you're getting hundreds of sims, and like, you need to have something at least as a starting point. You want to be careful that it's not kind of like, blinding you to opportunity, but it's something to make the world smaller.

[00:09:59] And so, I'm curious, through your experiences, do you have something That you look at when you're getting investment opportunities in terms of what you all think you can do to make that company a better version of itself.

[00:10:13] Vinay Kashyap: Yeah, absolutely. What I really love is, as I mentioned, I joined Mainsil 11 years ago. That scorecard has been very consistent and we plan for it to remain consistent even as we grow the firm and the franchise. And so. We get some Sims, but very few, so most of what we're doing is going out there and proactively initiating conversations with early stage B2B software companies that are 1, 2, 3 million of ARR.

[00:10:38] And we sort of track them over time and the most important, we look at three big things. The first is just growth. Like, we have a saying at Mainsail, the best predictor of growth is growth. We start with just, is this company growing very quickly? And then our filter, because we focus on bootstrap companies that have raised very little outside capital is if the companies are compounding revenue very quickly, then the products tend to be quite strong and they mean that the products are getting pulled into the market, not pushed into the market.

[00:11:11] Usually there's very little go to market dollars, all the scarce resources that the bootstrap software entrepreneur has, they've put into product. And so then we go to product quality, depth of product, durability of the moats, customer value prop, and we really dig deep on the product. How much time did it take to create how much workflow is in there?

[00:11:33] And that leads to our last sort of criteria, which is the entrepreneur that we'll get in business with, because ultimately the software companies are just a Sort of manifestation of code of the entrepreneur's brain, right? And their experiences. And so we're mostly investing in vertical SAS companies where the software is created by an entrepreneur who's coming out of that industry.

[00:11:53] So they worked in the construction industry. They worked in the veterinary industry. They start feeling a problem. They try to buy third party software, nothing exists. So they build it themselves. And that's the sort of entrepreneur we want to get in business with because they're resourceful, they're creative, they're driven, they're competitive.

[00:12:11] And then we want the entrepreneur to also be open minded. And having a learning mindset. And so when we get those three boxes checked, growth, product, quality, depth of product, which leads to hopefully a durable customer value proposition and pricing power. Then we look to, is this an entrepreneur that we want to work with?

[00:12:28] That we want to be in a. Business partnership that oftentimes ends up being a decade. Our average hold period is four to five years, but we oftentimes recap and keep going with these companies. And so that's where the relationship building process is really important. And on average, it takes about, we have it sort of track our sales cycle and Mainsail from first outreach to when we make an investment.

[00:12:49] It's coming up on between three to five years. This year, our four new platforms were five years, and that's wonderful from both sides of the table. We get to know the entrepreneur, they get to know us. We enjoy it much better than getting a sim and having to make a decision two months later.

[00:13:04] Sean Mooney: I really like that approach.

[00:13:06] One, the consistency of principles. I'm sure some of the things you look at over time maybe change as the world changes, but the consistency of the principle and then the long term relationship building, where you're like, We're gonna go on some dates, we're gonna meet each other, know each other, and if there's that mutual alignment of common goals, respect, trust, vision, then that's when the magic happens.

[00:13:30] And I really like as well kind of your mindset on looking at these kind of bootstrappers. And those are the types of companies I was investing in, kind of information data analytics, kind of like scientist run businesses. And when I had this kind of crazy mindset with BluWave. Where people thought I was insane.

[00:13:49] I worked my whole life to become a partner at a P firm. And then I'm going to do a startup to really just solve my problem. And I was like, well, if I'm going to do this kind of like you much more eloquently describe what was in my mind. It's like, I've got to do like the private equity version of venture capital, where we're going to take some friends and family money, but then we're going to be really clever with it and constrain the model, knowing that that drives innovation.

[00:14:11] Like so many of the peers I had who were doing other things, it was just so capital inefficient because they were just thrown. Everything against the wall and seeing what stick in the meantime, they're getting diluted down to during the most dilutionary period of business down to levels that I was like, ah, I just don't like that expected value calculation.

[00:14:31] And so what you're describing, it seems like you're probably getting quite a bit of like ingenuity out of these entrepreneurs as well. They just need now a little more fuel to get over that next hump.

[00:14:41] Vinay Kashyap: Yeah, absolutely. I mean, the culture in these companies is definitively frugal by necessity. And to your point, we find that.

[00:14:48] Bootstrap entrepreneurs have a very heightened sense of opportunity costs that is very useful over time. Cause I mean, as you put the primary capital on the balance sheet, as you build out infrastructure and then you start making longer duration offensive bets, that mindset and that culture persists and ultimately leads to profitable growth, which is what everyone has to achieve eventually.

[00:15:11] And I think our companies are able to sort of achieve sooner just because of that. Founding bootstrap philosophy in the business.

[00:15:18] Sean Mooney: I think that's great. And it's that cleverness that you're almost ingrained in. You have to be it. And you become a custodian of the balance sheet as well as the P and L.

[00:15:26] Vinay Kashyap: Yeah.

[00:15:26] Well said.

[00:15:27] Sean Mooney: So you've identified, you've built a relationship with the business owners. You're know that you're aligned. You think that you can provide some fuel to help them really reach that next level. Cause inevitably. You need that extra fuel just to get to the next level. Cause as I've even experienced here, it's like you're growing fast each year, but that number, the added dollars becomes bigger and bigger and bigger.

[00:15:51] And when you're trying to do multiple things. Across the tech stack and go to market and all those things. Sometimes you just need a little oomph to get over that top. And so I'm sure that's where you all add a lot of value. So you've made the investment. You have that alignment that you've taken years to develop.

[00:16:08] Then what does Mainsail do? What is your approach? How are you adding value in addition to the capital with these businesses?

[00:16:17] Vinay Kashyap: Absolutely. I mean, it's critical and frankly, the funnest part of our job. I love the hunt. We love getting up every morning and. Searching for needles in a haystack. It's really invigorating, but I think if you ask the investing partners at Mainsail, not just the operating partners, the thing that gets us most excited is the business building and taking a company from 5, 10 million in revenue to 50 million in revenue.

[00:16:39] It's just really exciting. And so in terms of how we go about doing that, I mean it starts with Infrastructure and team building and so food straps offer company generally has very little in the way of infrastructure and management team or a board of directors and so we have to start with just putting in place a CRM putting in place a marketing automation system upgrading them potentially up quickbooks onto a more robust ERP and then start measuring data right you can't change what you don't measure.

[00:17:11] And so we're really focused on instrumenting the businesses early in our whole periods and then building out a team on average. Our companies probably end up recruiting something like 5 new executives and 2 to 3 independent board members in our whole period. And we actually have a captive talent agency at Mainsail that does the super majority of that, which is pretty unique.

[00:17:31] And so we found over time. We'd like to just run our own recruiting and have our own talent database instead of relying on third party recruiters and it's been really advantageous but then that team has to gel they have to come together right so we're big believers in jim collins get the right people in the bus they have to start working all together.

[00:17:47] Once we do that, that takes about 12 to 18 months on average, then you can start getting more offensive with the value creation and move from a reactive stance. Most bootstrap companies are reactive, right? They're reacting to inbound demand. They're reacting to customer requests for their product roadmap.

[00:18:04] Now we can be proactive. Now we can build out a BDR function. Now we can actually start spending more money on paid search. Now we can start going to more trade shows. And then now the product roadmap can also start being one years, two years out into the future. And we could start doing add on acquisitions.

[00:18:21] And so it's sort of this posture of building infrastructure, build the stability in the company, do that as quickly as you can. We recruit the management team for 50 million in revenue, even though we usually start at five to 10. And then we can start having fun on some more offensive strategic levers to really drive future growth.

[00:18:40] Sean Mooney: That's Spot on in terms of even my own experience building a company, the things that you feel constrained by is because you're kind of constrained. There's no backstop, right? And so you're opening kind of the art of the possible with these teams. You're bringing in the talent. That's always the more calls we get for AI resources.

[00:18:58] We get a two to one call on people because it's like, it's just, no matter what you need, it's the people that drive these businesses and in terms of you got the talent group within your organization, are there other areas within kind of your operations team that you're kind of bringing to bear?

[00:19:14] Vinay Kashyap: Yeah, absolutely.

[00:19:15] I mean, the way we've constructed our operations team, which at this point it's 24 full time W2 employees at Mainsail from partners down to analysts is we've actually created. A mirror of a software company with our operations team. So all the functional areas of a software team are covered at Mainsail through what we call center of excellence leaders.

[00:19:35] So we have, obviously we talked about talent, we have finance legal, we have go to market, which encompasses marketing sales and customer success, product and technology, and we have leaders of all of these functional areas. A bunch of them came out of the portfolio, doing a tour of duty inside Mainsail, and a bunch of them will end up back in the portfolio.

[00:19:54] So it's a pretty tactical organization. It's less of the McKinsey BCG types. It's more of the practitioners. They've been in the seat. They've done 10 to 50 of ARR before, and then they can serve as a hub and spoke model within the, we have 22 or so portfolio companies sharing best practices, engaging on tactical strategic projects.

[00:20:16] We do annual summits for each of our functional centers of excellence. And so it's really about. Making sure we're innovating, we're learning from each other and being in San Francisco and in Austin, Texas. We also are in the ecosystems here. I'm sure at some point we could talk about AI, but I mean, it's on everyone's mind and having half our team in San Francisco, paying attention to what's happening in that universe, and then being able to push that out to where our portfolio companies are, which they're not in the Bay area, it's just another way where we can disseminate best practices and sort of stay one step ahead of the curve.

[00:20:49] Sean Mooney: Once again, I think that's spot on. And. Not only is it lonely at the top of the portfolio companies as a CEO, but also your business functional unit heads, and that's something I think that's often lost on, and it seems the way that you're approaching it is, not only does the CEO get a sounding board, but so does your head of marketing, so does your good market group, so does your finance group, or whatever it is, they have people that are subject matter expertise that they can use as a sounding boards within your organization, so And not try to recreate the wheel each time.

[00:21:18] Vinay Kashyap: Yeah. One of our entrepreneurs put it, well, they said we don't want to pay the dumb tax. And so that's what we're trying to. Story of

[00:21:24] Sean Mooney: my life. Yeah. My life were up to me, I'd be in trouble. So I've, uh, Frankenstein myself through a lot of ways.

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[00:21:54] Sean Mooney: So maybe with that in mind where you talked about kind of some of these big themes in some ways. At least I think it's one of the most fascinating times that you could be alive in if you're open and to and embrace change, right? It reminds me a little, like a faster moving version of what happened in the mid nineties when the internet was kind of democratized through Netscape.

[00:22:15] And then there was all this craze and all this turmoil, but eventually it started settling into people understood the tactical applications of this new technology that was emerging versus like pie in the sky. I'm curious when I, like, as you think about now, are there some value creation opportunities that you are engaging with that other business leaders you think should also be thinking about?

[00:22:37] Vinay Kashyap: I think you're right in terms of just the pace of innovation and the speed of which these large language models are increasing their capabilities is just, it's mind numbing and it's hard to keep up with. And then the real question is what does it mean, right? To our business here? It means so. So we think about it in three large buckets.

[00:22:53] One is. What does it mean for how we run our own firm right i think we always start with the premise that you got to eat your own dog food and so if you're out there recommending things to our portfolio company we better be doing them ourselves and so we're constantly looking at how can we use machine learning in our sourcing programs how can we start using more generative AI how can we generate copilots for our associates so that they can be.

[00:23:15] Innovative and automate all the mundane tasks that they're doing day to day. And so number one is how do we utilize it inside Mainsail? How do we utilize it in our sourcing, underwriting and portfolio support programs? Number two is how do our portfolio companies use it? We're seeing really interesting use cases right now.

[00:23:33] One of our companies presented at our customer success summit recently and said, we're not going to hire another customer service rep ever. And this company is doubling in size and they think they have the tech stack now between. Five or six different tools that they've stitched together, one of which is open AI, but there's a bunch of others where they're automating so much of the customer service work that they just don't need.

[00:23:58] They're doing it with quality, they're doing it with very high CSAT scores, MPS scores, and really efficient ticket resolution. And so that's a sort of call to arms for our entire portfolio. And that's the real tangible and exciting use case. And then with our companies. AI will eventually really impact code development.

[00:24:20] We're trying to figure that out. What does that mean for copyright? We're in the business of selling intellectual property as a software, as a service set of companies. And so we just have to think through thoughtfully, how do you utilize these tools? Increase developer productivity, but maintain clear IP ownership because ultimately that's what we're investing in.

[00:24:39] And that's what these companies are all about. And then the last thing we have to think about is 10, 20 years into the future. What does this mean for the end markets? We're investing. Which is equally interesting, right? So we're investing in end markets. Like I mentioned construction, maybe a little bit less impact, but we're also investing in end markets, like the legal industry, we sell software to mid market law firms, a lot of impact, right?

[00:25:01] And so we're thinking about it across all three of these dimensions, Mainsail, the portfolio and the end markets we invest in. And I think you're right. I think ultimately. We believe it's a big wallet share expansion opportunity as more and more of these end markets can get automated with technology.

[00:25:20] And so we're quite excited about it, but the pace is fast. It's hard to keep up. And so it's also daunting at the same time. I'd love

[00:25:27] Sean Mooney: to get your perspective on this. The large language models, there's great applications around content, around coding, customer service, creative. If you listen to some of the open AI folks will say it happened exactly opposite in the direction they thought to be robotics then middle and then creative and it was completely the flip side and so same thing if we go back to beginning of twenty three and we were doing our budgeting and the request was.

[00:25:54] Hey, we need three more copywriters for marketing content. And the challenge I put the team was like, well, why don't you try this thing called Jasper and try this thing called ChachiBT and see how that does. And actually, you know, our content production went up 500 percent with two 20 bucks a month subscriptions.

[00:26:11] And the writing was really good. It didn't take the artistry away from our content folks, but it just took the blank page away. And I think it's like, it's somewhere to start, whether you're a developer, whether you're a content writer, and then it's evolving into kind of these customer service agents. I was on, recently on a panel for another private equity firm's kind of internal forum, just because we see so much of this stuff, and this is a smaller kind of growth company as well.

[00:26:38] They had six people in their customer service kind of channel, and by using a self built agent, they were able to reduce that to three. And the response times were better, they were able to respond to more things faster, customer service went up, NPS went up, and so these are things that are going to have profound changes.

[00:26:59] And for the business builders listening to this, I think half the people react, that's really scary. The other half are going to run towards it. And so how are you all working with your companies to kind of make sure their mindset and by nature, I'm guessing because you're in the tech world, they probably have more of that, like look forward mentality, but how do you kind of get them to have that mindset of, we're going to run forward not only with today in mind, but 10 years in mind.

[00:27:27] Vinay Kashyap: It's a great question and I think it goes back to this is one of the advantages potentially of being part of a family, right? Of innovative software companies versus being on an island. And so we just talk about it, right? I mean, we share these best practices. I mean, this forum where this portfolio company makes this bold statement, I'm not going to hire another CS rep.

[00:27:46] I mean, there is so many psychological factors that then come into play in terms of FOMO fear of missing out. It drives. Are very competitive ceos and i mean ultimately if you don't adopt these tools your pnl will be upside down you'll get competed out of business right and so i think generally we're seeing a lot of pull through we're seeing a lot of excitement we're also seeing how can we embed these tools into our products themselves right so we've already done a lot with predictive how do we do more with with with generative ai into the software products given the end markets that we serve other than just talking about it debating it putting it out in the open.

[00:28:25] Over and over again, there's no silver bullet.

[00:28:28] Sean Mooney: Yeah,

[00:28:29] Vinay Kashyap: I think it's

[00:28:29] Sean Mooney: just, for a lot of people, you just have to take a step forward and then another step and another step. Don't even dare to look forward to when we all work for robots. You know, I think that's going to be my, that's going to be my, I think it'll be our kids problem.

[00:28:41] Well, my kids want a robot. I mean, I think

[00:28:42] Vinay Kashyap: even there, us adults, we have so many biases, whether from Terminator or whatever. I'll tell you, all my six year old son wants is a robot, more than anything in the world, in a very wonderful and optimistic way. It's coming right and so we're gonna have to get out of the way at some point

[00:28:57] Sean Mooney: if I can get out of like Sunday chores and like doing Laundry and if Elon can get that robot working 100 percent I'm buying that thing Fingers crossed, you know, hopefully that says it's something in the near future because I'm I'm tired of doing the dishes at my house With this in mind that the world is moving kind of so quickly here in an exciting way.

[00:29:22] And for people who kind of look forward, this is, we talked about, it's one of the most exciting times in the world. The world, though, is in part because of a lot of this generative AI, and just because there's so much thought leadership going on, anyone can kind of now share their expertise. I'm curious, like, rather than maybe asking, what's one of your favorite books, how do you break through and consume the information and Not only on kind of business topics, but personal topics and making sure you're staying up at the latest, but also feeding yourself and your brain and continuing to improve and evolve over time.

[00:29:57] Vinay Kashyap: Yeah, I mean, it's something that I think has been an evolution for me personally. I'd say it starts with I've always been innately curious, but I think that's an overstatement in that my own experience has been just my curiosity. Overtime is waxed and waned and it waxes and wanes on various topics.

[00:30:13] Right. And I think what I've found is don't force it. Right. And at some point, just having a backlog of information sources for me has been incredibly useful. And I guess what I mean by that to make it more concrete is, for example, like, right now, I always like to read some fiction. I think it's really important.

[00:30:34] It fills me up and I'll have something that's maybe a classic work of literature. I'll have something newer. I think it teaches empathy and it's just is a wonderful way to go to bed at night, right? It's to read some really good literature. Then in addition, I'll have 10 podcasts downloaded at any given time across a variety of topics.

[00:30:55] We're on a podcast right now, but I mean, it's just been unbelievable the explosion of high quality content through this medium. And so whether it's. Lex Friedman or Peter, I mean, find your interest area and then just pull the thread and those long form. Three hour conversations. It's going to be really interesting how they compete with certain types of nonfiction books, because I found that it's become a slight substitute for me.

[00:31:20] You go to the source, you go to the author, you get to the crux of the argument. It needs to be long. The content needs to be 2 3 hours, but you can really get into the weeds. I still love reading biographies. And then also, I think you have to get out there. You have to like, go out to dinner, meet friends, travel, and every time you get on a plane and Get to the source of the information.

[00:31:39] This is why we still attend a lot of trade shows. You can't replicate that scuttlebutt from talking to a set of competitors at a trade show. It's just, that's not written down somewhere. That's not on a Tegas or CapIQ transcript. In the investment business, we're in the information asymmetry business. And so ultimately, I mean, in the private markets, we can do this.

[00:32:01] You need to be searching for information that others don't have. That's what we do at Mainsail with our database, 22 years of gathering information on small, privately held companies. And then that's what you should do in your personal life and just. I also am an avid note taker. I use Evernote religiously and I must have 2000 Evernotes or something.

[00:32:20] And it's like, I'll have them on just different people that I find interesting. And then every time they say something, I'll just jot it down and then you can go back and read it and then pull threads. But I do think that the note taking, at least for me, helps me digest what I'm hearing and what I'm listening to.

[00:32:33] And that's sort of my current system. I'm sure it's going to change over time, but it's really fun.

[00:32:39] Sean Mooney: I love that. And it's interesting, I think, as you think about where we are in kind of humanity. And the evolution that we're constantly going on, and I personally think we're just on this long and very purposeful and ongoing kind of progression towards essentially being a cyborg.

[00:32:55] It started, but if you think about it, it's like the internet made it move information possible, the phone brought it with you, the iPhone, but an awful interface. The AI is distilling it much faster. And then eventually, now you got the glasses, I still won't wear the Apple goggles, it's getting closer and closer, and so your ability to digest and consume is much greater, but also your requirement to do so is greater.

[00:33:22] And so, I was talking with an educator recently, and they were saying, in also in concert with like business, like, there was a long Trend toward specialists and there's a big question about is it really the liberal arts education back in vogue now? Because as people who are trained to think and use tools and digest I think the people that can, what you're describing to me as I, I perceive it as kind of like, it's not, or I'm not going to do this or that.

[00:33:50] I'm going to do. And

[00:33:51] Vinay Kashyap: yeah, and then to your point, it's the synthesis of those data points that gets really interesting, right? When you're like, oh, I just listened to this on this podcast and read this and even this old novel, and then it connects to this conversation I just had. And then that's where the, there's some connectivity between the neurons, but.

[00:34:06] The other thing I think, though, is in this information age, you have to find the time to be quiet, right? And so I have a meditation practice. I've been doing it for a long time, and I don't know how people don't, because I think you need that foundational, whether it's walking quietly, take the headphones out, right?

[00:34:22] I mean, you just can't have this constant noise coming at you. And then I think you have to filter out the nonsense. And so there's newspapers I can't read anymore that I used to read 10 years ago, just because it's become nonsense. And so you have to find the right sources and then get rid of everything else.

[00:34:37] Sean Mooney: It's so interesting you say that, because I completely agree. Now the world is a wash. You can have information and content anywhere you go at any time, and it's all fascinating, but you gotta find that time to be quiet. So I too, when I was in P. E., my brother in law, who was in the U. S. military for a long time and did kinda interesting things, he's just like, man, you gotta learn to quiet your brain.

[00:34:59] And so he had been a big proponer of that in the field that he was in. And so he put me on to it and I was like, well, but I don't want to do like flowing robes. Cause that was my mindset on it. He's like, no, you don't have to do it. Like just get the headspace out. Start there. That has had such a profound change to me.

[00:35:18] There was a social media clip that came across my stream. The algorithms are very good. And it was someone describing like, yeah, we didn't have meditation in the 90s as a Gen X 90s person. We just had something called like, go outside. So but you didn't have the information. You didn't have this constant influx here.

[00:35:34] The earbuds in your ear, you go outside and

[00:35:36] Vinay Kashyap: everyone's got the earbuds in their ear, right?

[00:35:38] Sean Mooney: It's just no, you're gonna go outside and you're gonna be alone with your own thoughts, which is incredibly scary for me to be alone with my own thoughts. But I think that's, that's really such a good point that.

[00:35:49] You gotta have balance in things. You can't just be consuming 24 7. Your brain is in some ways a muscle, and if you're not letting it kind of rest, at least mine goes a little haywire. So I appreciate that. One more tap down on the content. Is there any type of fiction that you like? What kind of things do you kind of dig into?

[00:36:08] What's interesting to you now, I

[00:36:09] Vinay Kashyap: guess? Right now I have on the bedside table Brothers Karamazov. They're classics for reasons, and the writing, it triggers something in me. Both profound and I find it very humorous, which I enjoy. He's just, it's just the true masterpiece. And then I'm reading another great book right now by John Boyne, the hearts, invisible furies.

[00:36:32] It's a beautiful book about someone who's gay growing up in Ireland in the mid 1900s. My sort of feeling on reading is the same in that I also start and don't finish lots of books or I come back to them. And so I think, again, for me, the journey has been don't force it. Follow your curiosity. I'm often in the mood to read fiction at night, and I'm often in the mood to read nonfiction in the morning.

[00:36:54] I don't know why. It's my biological clock. So I sort of follow that, and I don't force it. So you just sort of feel your way through learning in a way that's, I think, authentic and natural, and it makes it really enjoyable and fun. Don't make it a chore.

[00:37:07] Sean Mooney: It's such a good mindset on that, and you know, similarly, I probably have 20 books on my side table, and my wife thinks it's insane.

[00:37:15] And it is. To be fair. But it's like you read a chapter here and then you dabble there and then I'll do a podcast and I have this concept that I call broccoli with cheese on it. And so it's like it's good for you, but it tastes good. So I also love historical fiction. The way I first became really kind of enthralled and familiar with the school that you attended was through this great book called Killer Angels, Pulitzer Prize winner about the Battle of Gettysburg.

[00:37:42] And one of the main characters was a professor at Bowdoin. And so it was, it was such a great book. So the institution you attended always had like legendary status.

[00:37:52] Vinay Kashyap: It's a true liberal arts school. And it's very interesting. The president of Bowdoin was in San Francisco last week. We had lunch with her and they're grappling with, What are we doing to prepare these students for the age of AI?

[00:38:03] Her daughter works at Anthropic actually, which is really interesting. And so you may be right that it's the classical foundation of multifaceted education is most important, but I mean, they may also need to learn certain things have to become core curriculum, like the ability to work with data.

[00:38:20] Manipulate data, write certain queries, whatever it may be. But I empathize with being a sophomore or junior in college in that I would find it exciting, but also, as I said, daunting, just because they're entering into an age where certain professions may not exist in 20 years, the internet was disrupted, but I'm not sure to that degree.

[00:38:40] I mean, obviously move things around and democratize information, but you know, I know she's thinking about it a lot. And so it'll be very interesting.

[00:38:48] Sean Mooney: Interesting is the right word. And exciting, but daunting all at once. You'd rather have it that way than the opposite,

[00:38:55] Vinay Kashyap: so. Yeah, maybe we live in interesting times, right?

[00:38:57] We are living that saying, so.

[00:38:59] Sean Mooney: Vinay, this has been a really interesting conversation. I've learned all sorts of things that I wish I knew before. And so that's a, A, a tremendous gift, and B, super appreciated, so. Thank you very much for spending the time and sharing your insights, perspectives, and teaching us more about what you all do so well.

[00:39:17] Vinay Kashyap: Thank you, Sean. Thanks for having me.

[00:39:28] Sean Mooney: That's all we have for today. Special thanks to Vinay for joining. If you'd like to learn more about Vinay Kashyap and Mainsail Partners, please see the episode notes for links. Please continue to look for the Karma School of Business podcast anywhere you find your favorite podcasts. We truly appreciate your support.

[00:39:45] If you like what you hear, please follow. Five star rate. Review, share, all that fun stuff. This is a free way to support the show and it really helps us when you do this, so thank you in advance. In the meantime, if you want to be connected with the world's best in class, private equity grade, professional service providers, independent consultants, interim executives that are deployed and trusted by the best business builders in the world, and you can do the same, give us a call or visit our website at www.BluWave.net. That's B L U W A V E and we'll support your success. Onward.

Private equity insights for and with top business builders, including investors, operators, executives and industry thought leaders. The Karma School of Business Podcast goes behind the scenes of PE, talking about business best practices and real-time industry trends. You'll learn from leading professionals and visionary business executives who will help you take action and enhance your life, whether you’re at a PE firm, a portco or a private or public company.

BluWave Founder & CEO Sean Mooney hosts the Private Equity Karma School of Business Podcast. BluWave is the business builders’ network for private equity grade due diligence and value creation needs.