Ian Sandler, COO of Insight Partners and co-founder of Riley’s Way Foundation, engages in a deeply personal and wide-ranging conversation on leadership, venture capital, and building meaningful impact. Ian reflects on his unconventional career path, his philosophy on building organizations, and how a personal tragedy shaped his mission to empower the next generation of kind leaders. He also shares practical advice for founders and young leaders on dreaming big, understanding themselves, and building networks that matter.
Ian Sandler, COO of Insight Partners and co-founder of Riley’s Way Foundation, engages in a deeply personal and wide-ranging conversation on leadership, venture capital, and building meaningful impact. Ian reflects on his unconventional career path, his philosophy on building organizations, and how a personal tragedy shaped his mission to empower the next generation of kind leaders. He also shares practical advice for founders and young leaders on dreaming big, understanding themselves, and building networks that matter.
In this episode:
[00:58] Ian Sandler’s background and upbringing
[03:59] From law to “wimpy entrepreneur”
[06:05] Building and scaling at Insight Partners
[09:27] Balancing venture capital with purpose
[12:35] What makes great investors today
[17:12] The story behind Riley’s Way Foundation
[31:33] Advice for young leaders: dream big, self-care, network
[36:17] The future of Riley’s Way Foundation
The nonprofit organization Ian is passionate about: Riley’s Way Foundation
Ian Sandler is the Chief Operating Officer at Insight Partners, where he oversees the firm’s non-investment operations and helps scale new strategic initiatives. Over a career spanning roles at Morgan Stanley, The Carlyle Group, and Citadel, he has built a reputation as a “builder of businesses” who specializes in identifying talent and turning ideas into scalable platforms. In parallel, he is the co-founder of Riley’s Way Foundation, a nonprofit dedicated to developing kind, community-driven young leaders.
Founded in 1995, Insight Partners is a global venture capital and private equity firm focused on high-growth software, internet, and technology companies. The firm manages over $90 billion in assets and has invested in more than 875 companies worldwide, supporting founders from early-stage growth through IPO. Its approach combines capital with hands-on operational support through its “Onsite” team, helping companies scale revenue, build talent, and execute go-to-market strategies.
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[00:00:00] Ian Sandler: Dream big. I'll use my own personal storytelling. When we started Riley's Way and had no idea what we were gonna do. In my head it was this multi-generational, massively impactful nonprofit like Teach for America or the Peace Corps, which the average life of a nonprofit is three years. Like there was no rational basis for me to have that view, but I don't have a moderation button in me. That's just how I'm wired. And I was like, "Well, if we're gonna do this, let's freaking do it."
[00:00:36] Gopi Rangan: You are listening to The Sure Shot Entrepreneur - a podcast for founders with ambitious ideas. Venture capital investors and other early believers tell you relatable, insightful, and authentic stories to help you realize your vision.
[00:00:58] Welcome to The Sure Shot Entrepreneur. I'm your host, Gopi Rangan. My guest today is Ian Sandler. Ian Sandler is the chief operating officer at Insight Partners. He's also the co-founder at Riley's Way Foundation. We're gonna talk to him about his career, his life perspectives, and his priorities on how he spends his time on both the investment side and also on the foundation side. Insight is a very large venture capital firm with multiple different strategies.
[00:01:30] But more interestingly, I'm curious to learn more about Riley's Way Foundation. Ian and his wife run Riley's Way Foundation. It's a nonprofit organization that empowers young leaders to create meaningful connections and create some positive change in the world. What does that mean and how does he do it?
[00:01:48] We're gonna talk about all of that. Ian, welcome to The Sure Shot Entrepreneur.
[00:01:52] Ian Sandler: Oh, thank you so much. Such a pleasure to be here and talking with you.
[00:01:56] Gopi Rangan: We'll start with you. Tell us a little bit about you, starting with where you grew up. You grew up in Long Island, right?
[00:02:02] Ian Sandler: I did. I had a idyllic childhood. My late father was from South Africa. My mother grew up in Texas. So my dad came over to get a PhD in nuclear physics, and then he became a serial entrepreneur, so he ended up moving to Long Island because that was close to where Bell Labs were. So I spent all of my childhood in a town called Dix Hills, and far enough away from the city that you really couldn't get into trouble, but close enough that you kind of felt the pull of it.
[00:02:32] Gopi Rangan: Now you come from an academic background: strong research, PhD and all that.
[00:02:37] Ian Sandler: Mm-hmm.
[00:02:37] Gopi Rangan: But you majored in political science and English and business-
[00:02:42] Ian Sandler: Yeah.. ...
[00:02:43] Gopi Rangan: For your undergraduate, and then you became a lawyer.
[00:02:46] Ian Sandler: Yeah. I was fortunate enough to grow up in the '90s and I wasn't really a great student. I was a good standardized test taker and I would do really well in the classes I liked and really poorly in the ones I didn't. And luckily I aced my SATs and got into the University of Michigan. And I came on campus and thought I'd be a business school student until I arrived in my first semester and took intro to accounting, and I absolutely hated it.
[00:03:11] And I met a guy who was a senior. I was pledging a fraternity. He was a general studies major, and I was like, "Oh, what do you do? " And he's like, "I take any class I want. " And I said, "That sounds amazing." So I called up my dad and said, "Hey, I'm gonna drop out of this business school thing and be a general studies major."
[00:03:29] And fortunate enough for me, in South Africa, everybody gets a liberal arts background and then they specialize. So he was like, "Oh, that's fine, boy. You'll go to grad school." And and he was right. So very fortunate that he was supportive because I fell in love with learning at Michigan and I, to this day, remember the political science and art history and English classes and jazz classes I took and did really well, but was totally unemployable after graduating.
[00:03:59] And so, again, relied on standardized test taking got into the University of Pennsylvania Law School and went there after Michigan.
[00:04:07] Gopi Rangan: Do you think of yourself more of a businessman or a lawyer?
[00:04:12] Ian Sandler: I honestly think of myself as neither of those things. I think of myself as a wimpy entrepreneur. And what I mean by that is my late father, he was a real one. He came over to this country with nothing and he started company after company, some of which turned out to be highly successful. I do it the wimpy way. I love building things. My talent is finding talented people and putting them together and having a rough idea of where the world's going and saying, " let's go over there. Let's go do something." But I do it the wimpy way. I get a cushy job at Morgan Stanley or the Carlisle Group or Citadel or Insight. And then I build things there by taking a COO role where I go to my owners or the people who run the business and I explain to them that any problem you have, I'll solve. I'll cover the defense side.
[00:04:55] But I always wanted to be a revenue generator. I picked that up from very early on at my early days in Morgan Stanley and I never wanted to be a cost center. And so I don't think of myself as a businessman. I don't think of myself as a lawyer. I think about myself as somebody who has a really good eye for talent and has a good sense of where general trends are. And then I'm just completely overconfident and am able to convince people to try things with me and a bunch of them have worked out okay.
[00:05:23] Gopi Rangan: Well, you can support entrepreneurship in a few different ways. You can build your own company. That's obviously one.
[00:05:29] Ian Sandler: Yeah.
[00:05:29] Gopi Rangan: But you can support founders in multiple different ways. You can be an investor providing other kinds of support as well, or you go into public policy and try to build better infrastructure for entrepreneurs to thrive.
[00:05:41] Mm-hmm. So I see that you're right in the middle. You call yourself a wimpy entrepreneur, but what you actually do is you spot talent and give them the space to let their ideas bloom. Yeah. That's fantastic.
[00:05:53] Ian Sandler: Think that's right.
[00:05:54] Gopi Rangan: Okay. You've had a long career in multiple different roles at Morgan Stanley, at Carlisle, at Citadel, but now you've been at Insight for 10 years.
[00:06:05] What is your role at Insight? Sure. What are you responsible for?
[00:06:09] Ian Sandler: It's the same blueprint everywhere. I'm the chief operating officer. So all of the non-investment side of the house rolled into me right now, the technology side of the house doesn't because we've just gotten so big. And so we brought somebody in who works with my onsite group and he manages that.
[00:06:25] But I manage all other aspects of the non-investment side of the house. But as I've mentioned, i'm a wimpy entrepreneur. Before I came to Insight, I worked at Citadel and I really became enamored with how impressive public markets investors are and the way they model and the rigor at which they look at markets.
[00:06:44] And so my first four or five years at Insight, I was recommending to my owners that we build a public equities and late stage private business that would be highly complimentary. The idea was simple was, bring in a small talented group of people. They would help us make better decisions on the series Es and Fs and Gs, make better decisions when we bring companies public.
[00:07:05] And then if we could build a big business as part of that would be wonderful. But the table stakes was hire a team and have them make our private market investors that much better. And that's a group that we started in 2020 called Insight Partners Public Equities. It's a crossover business. It's liquid public only business. And then it's a series of focused investments in some of the most interesting late stage private names. That total business is now about $3 billion in addition to what they've deployed there. That was the group that came up with the firm's idea to make a big investment in Databricks.
[00:07:42] We have about a billion dollars of capital invested that's probably on paper, worth another billion dollars from there. So that's led by a guy named John Wolfe, who's been a business partner of mine from the beginning. He's a Harvard baseball player who luckily couldn't hit the slider. And so he went into investing to my benefit and he's just a wonderful team guy and a great business builder.
[00:08:02] And just an example of what I do, I come up with an idea, I hire people much better than myself, and my job is to figure out how to make them better and then get out of the way. So I think about that across all the different aspects of the firm. And then, the other thing I spend a lot of time on is I've got a wonderful owner group and, making sure they are getting all the things they need to be successful.
[00:08:25] And it's been a decade that I've been at Insight. The beauty of my time at Insight is I showed up after I had left Citadel, which was the only job I ever took for money, and I didn't have to really work after that. And so when I joined Insight, I went to my owners and I said, "This is not my priority. My priority is Riley's Way, and obviously I'll care deeply and I'll do all these things, but my number one focus is really building and growing my nonprofit. So you may see me leave on a particular day to go talk to college students or go work on our programming". And they couldn't have been more supportive.
[00:08:59] The whole firm's been so supportive of what we've built and the irony is spending the last decade working on a nonprofit that's focused on kind leadership and servant leadership, you eat your own cooking and actually become a much better leader and it's really helped us. We've scaled the organization from 80 to 450 people for me to wake up every day and say, my job and my team's job is to make everybody else better and really understand what that means.
[00:09:27] Gopi Rangan: It's great to see that you've thoughtfully designed your professional life in a way that it allows you to focus on things that you truly care about. Insight is a multi-strategy firm investing in early stage, growth stage, late stage in multiple areas in the private market. Why is venture capital or private market interesting to you?
[00:09:50] Ian Sandler: Well, listen, I've never come through the front door of any job I've had. And so I wanna stress that I think I have a toolkit, and it was the same toolkit I walked in when I left the law firm and I joined Morgan Stanley back in 2003 that I walk through now 23 years later, I always try to be a pineapple in a sea of apples and oranges.
[00:10:08] And what I am as a connector and a business builder and somebody who can spot trends and can figure out how to really scale organizations. That's what I like doing. And so, I started doing it at Morgan Stanley first on the trading desk and then as the technology COO for the entire firm, which was a huge opportunity, a job I was woefully unqualified for, but I built a business, I had sold it. And John Mack and Mitch Petrick thought I could go do this job, and that was my big break. I went to the Carlisle group, same thing. Mitch hired me to go help him build a business. We scaled it from $9 billion to $ 45 billion, but again, Mitch hired me as a COO and chief legal officer. I didn't get a job through the front door of Carlisle.
[00:10:48] Ken recruited me to be the COO for global equities. I ended up co-running that business and then when I came to Insight, it was the same thing. I couldn't even spell SaaS when I showed up. I didn't know that much about Insight, and Insight didn't know that much about me.
[00:11:00] And I think that's been a little bit of the happy accident, is that we have 450 people, and most of the people walking the halls are better investors than me and know the intricacies of our business better than I do. But I've always been a generalist. I certainly know more than enough to be dangerous, and I'm able to float, whether it's this public equities business, I've led our secondaries business now in terms of doing continuation funds.
[00:11:24] We hired an amazing team to actually go on offense and build a fund around that. All these different things that I do, I know enough to help. And then I keep using the same skillset, And I learned this from Ken Griffin, quite honestly, at Citadel, your job as an executive is to hire and develop talent.
[00:11:43] Your job in your 20s is an individual contributor. As you move up, you're not judged by what you do, you're judged by what your team does. And I think the sooner people in leadership positions realize it's not about them, but it's about the organization, the team, the better they'll be at their job, and the better the organization will be with them in a leadership spot.
[00:12:04] So, what attracted me to Insight was it was a different challenge, and they hadn't had a COO in 10 years, and I really liked my owners. Like, when I met with them, I was lucky I had three or four different things I could have done. Rolling back all of those opportunities would have been really successful ones. So I definitely created during my garden leave some great opportunities, but nothing as good as this opportunity at Insight, and I thought it'd be a challenge. And I thought I was gonna be there for a couple of years, not for a decade plus.
[00:12:35] Gopi Rangan: It'd been 10 years. And now, there's a big SaaS apocalypse happening right now, so maybe you don't need to learn a lot about SaaS today. The whole world is changing because of AI.
[00:12:46] Ian Sandler: Yeah. The whole world's changing, but I think there's a lot of misconception there. I think that the marriage between AI and software and where these software companies are really companies that have deep relationships and deep business process understandings.
[00:13:01] And I think a lot of the public markets and I learned this and learn it every day from my team it's shoot first and ask questions later. I think what you'll find is there are going to be plenty of great software companies that pivot and have agentic solutions and are able to really be successful going forward. And then there's gonna be companies that come along and they're AI native disruptors and those folks are gonna win. And I think it's way, way too early to figure this stuff out. But that's not what Insight is. What Insight really is at its core it's a world-class sourcing machine. That's what Insight does. We cover every technology company on the planet or try to, and we create as many shots on goal and as many opportunities as possible. And then we've had an investment committee. I'm very lucky to work with my partners and watch them every Monday at work and see what they do. And what they do is if their teams come up with the right opportunities, we're able to be able to pick the best companies to invest in time and time again. So we're deploying Fund 13 and it looks amazing and it's companies that are so well positioned for what's happening because Insight from a growth perspective, that's what they do. That's what they've been doing for 30 years.
[00:14:13] So it's been an amazing decade. And for me, at this point in my career, my hope is that I'm able to both help some members of my team become the best versions of themselves and then to build some of these things and leave lasting components that I've put my hands on because the guys who built this firm the four people who built it, they're just incredible at what they've done.
[00:14:34] Gopi Rangan: You brought a lot of public market discipline into the world of private markets, especially investing in small companies with very little data to analyze and due diligence. It's important to have some kind of discipline that makes sure that the team can collaborate and make good judgments.
[00:14:51] What, in your point of view, are two or three things that investors can do in the current market to be successful? What's a good way to build discipline?
[00:15:02] Ian Sandler: I think right now and you're seeing it with the way we're approaching our investment pace is they really need to be great opportunities.
[00:15:10] And so I think the discipline comes from understanding what the fundamental business opportunity is, what their competitor landscape is, what does their customer base look like, how sticky is the business? One of the things we spend so much time on is what does retention look like in a business and how leaky is that bucket?
[00:15:29] And you can see and learn a lot. If you have a fast growing business, but you're leaking a lot of oil, boy, that's gonna be a hard business to scale. We spend a lot of time thinking about the margins of these businesses, but listen, in growth, you're betting on where these things are gonna be five, 10, 15 years out.
[00:15:47] And I think really doing the work, developing the relationships, what Insight does differently than anybody else on the planet is we're starting relationships with companies and investing in them sometimes two, three, four, five, six years later because that's when we get the opportunity and you've proven to the founder and the management team that we're going to be a growth partner.
[00:16:12] And what I mean by that is we have the finest organization in terms of how we support our companies. Our onsite team is unparalleled in the business and what they do. So we don't go into companies and say, "Oh, we're gonna fire the CFO and bring in the director of finance and make money by squeeze." No. We look at these companies and say, "Wow, look how great your business is. " And you do it with three sales reps, or you do it with the founder as the person who's driving this. We're gonna bring in our sales center of excellence, and we're gonna show you what we can do and how we can add value.
[00:16:44] And we do this even when we own 10 or 15% of a company. And a lot of the reasons why we win deals is because we've done deals in the past in ecosystems like Utah, Salt Lake area or Israel has been another area where we've just been really successful. And some of the best entrepreneurs who we've worked with, they say Insight is just as good a partner as you're gonna have. And that's really when you're trying to get into the best deals, that's how you get them.
[00:17:12] Gopi Rangan: I can see why sourcing is so good at Insight because you get connected with founders quite early and you perhaps even help them well before you invest in those companies. This must be a fascinating job for you, but in addition to this, you spend a lot of time with Riley Way Foundation. What is Riley Way Foundation?
[00:17:34] Ian Sandler: Sure. So Riley's Way is a national nonprofit that focuses on empowering the next generation of kind leaders. We started it almost 11 years ago. My daughter, Riley, was nine years old, and Riley was the greatest friend you would ever find. And listen, she was nine, so she never got jaded by all the things that could have happened when she grew up. But, like she was one of these kids who loved connecting her friends, loved meeting every person she could. She was having the summer of her life at sleepaway camp. Fiction is never as cruel as real life. We had all of our bags packed. We were picking her up the next day. We got a phone call in the middle of the night. My camp director was on the phone and she, in a panic voice, had said that Riley had collapsed and they were taking her to a hospital and I needed to get up to her. And I was four hours away and my first thought was, let me get a helicopter until I realized at 12:30 in the night that I didn't have access to a helicopter and that there wasn't one that was readily coming.
[00:18:40] So I did the next best thing, which is ... I called an Uber and I put in an address on the Upper West Side and I explained to the Uber driver who was a parent of four children himself that what had happened to my daughter and he turned off the fare and he drove me up to Albany and one of the kindest things anybody's ever done.
[00:18:57] And Riley was too far from the hospital. Her throat had closed and she was gone before I got to her. I had to tell my wife, Mackenzie, who was a couple hours behind me because we had to get somebody to look after my son, Brody, who was six at the time. Then our daughter was gone and I spent three days with Riley in the hospital trying to donate as many of her organs as we could.
[00:19:21] I learned that a nine-year-old's kidney can go into a 61-year-old grandmother, and we started Riley's Way then, and raised a lot of money because I work in finance, and we are overpaid, and this is every parent's worst nightmare. And I did what I do with everything. I got smart amazing people together, and we focused on who she was and what we could potentially do with the money we had raised, and we focused on friendship. We focused on who Riley was. And that work has really evolved over the last decade into working with high school and college students, and providing them with the scaffolding and support to be kind leaders. And the way we execute that is through our core program which is the Call for Kindness.
[00:20:07] It's a national micro grant campaign. These are for young people aged 13 to 23 who run social impact organizations. We give them grant money, they become part of a fellowship, we fly them all together, and they get programming for a year, and then they continue to graduate on and become senior fellows, and we continue to support them in that work.
[00:20:26] And then our other core program is a youth leadership retreat that we host at a sleepaway camp, just like where Riley was when she passed. And we bring in high school juniors and seniors who are interested in this notion of kind leadership and bringing it back to their community. And we fly these kids from all over the country.
[00:20:42] We had kids from Alaska, from Hawaii. They spend a weekend together and they form lifelong relationships. Some of them become college roommates. Some of them start nonprofits together and the theory of change behind our work is really simple. It's not a political statement, just meant to be an objective one. The face of leadership in this world is broken. History says that young people are always the ones who make change in this world. And our theory of change is that if we promote this notion of kind leadership of servant leadership, this idea that when you get into a position of power, you look after your team, you look after your community, you don't use this as an opportunity to grab for yourself, and you do that over and over again.
[00:21:27] We've worked with over 6,000 young people now. They've given out more than six million dollars in grants and program making. The impact of those 6,000 young people and their programs is in the hundreds of thousands, if not millions of young people that they've impacted, that you change the world. They all go into leadership positions. They all take a different view towards it. And it may take another 20 years to do so, but you have this opportunity if you can continue to push on this movement that the world that we're delivering to our kids could look a little bit different or could look a lot different. And that's what we're gonna be shooting for.
[00:22:03] Gopi Rangan: You share this story with a lot of poise, both the sad side of the story, which is shocking for any parent. It's a tragedy and how you turn that around into bright future for young adults and the impact that has on our local community and the world at large is massive for many decades to come when young leaders are groomed this way.
[00:22:28] This is absolutely inspiring. It's fascinating to hear how you're spending your time and how you're finding the right kind of people to coach and groom. Can you give some examples of people who are in the program?
[00:22:41] Ian Sandler: First I'll talk about just some programs. One of the ones I like to talk about is an organization called Purple America, really simple. Just young people from red states, young people from blue states, get them together and start talking. And I mentioned that just because I've had a conversation this morning with an amazing human who's much more on the political right than I am. And we had this incredible conversation about how we need people to be talking to each other because there's silent majority that I think agrees on a lot more and the social media and media in general, I think has just fan the flames.
[00:23:11] That's one quick example of an organization. We've got a young man who started with us when he was 15 and had this idea that he would give away computers, this idea of digital equity. We all have machines lying around, corporations do, we do at home. And he said, "I'll handle all of the wiping, the cleaning, I'll get you a tax donation, and I'm gonna give them to people who otherwise wouldn't have access to these devices."
[00:23:36] We started with him when he was 15, giving out his first computers. He's now given out over 200,000 computers on his way to giving out a million computers. There's an amazing organization called Tunes for Kids where a member of our community, a young person saw that the musical instruments that she so readily had access to weren't available to so many kids and went on this massive drive to go about finding instruments, raising money for this and then the life altering power of music.
[00:24:05] And I can go on and on. We have a young person who started with one of our chapters, one of our high school programs when she was in ninth grade in New York City and that was this very smart but somewhat shy young woman, found her voice through the work we were doing in terms of what breaks her heart and how to actually drive change. She went off to Cornell, got a degree, had multiple job offers and came back to work for Riley's Way because it was so impactful to her and the work we're doing. I have 11 full-time staff at Riley's Way and each one of them they're the heroes. Those are the heroes. The teachers are the heroes, the doctors, the nurses, the first responders.
[00:24:44] Society's got it somehow all wrong with people in finance and the things we do. And so those of us who work in some of these fields where there's just too much that goes to us, I'm still a capitalist and I think then it just becomes, what are you gonna do with it? And we all only need so much. That's a lot of my pitch when I speak to my friends and the pitch is very much that these are the young people, this is good business. These are the young people you're gonna wanna hire. Think about AI and the fact that the machines are gonna win the IQ test over and over again. So what actually is gonna matter going forward? It's gonna be EQ. It's gonna be people who can understand how to connect with different people. Sales is probably the last thing that's gonna get automated fully, although the tools to work around it certainly are gonna continue to be optimized. The skills that come from kind leaders, from servant leaders, from those who actually know how to work with and amongst one another's.
[00:25:45] And these are tools and skills. It's not like some people have them and some people don't. And so just from a business perspective, these young people that are part of the Riley's Way community, when I talk to my friends who run investment banks or law firms or accounting firms, like these are the people you wanna support because they're gonna be your future leaders.
[00:26:05] So I get tired of saying this because I think, the world unfortunately keeps making the argument louder and louder for the work we're doing, but the world keeps making the argument in every way that this is work that really does need to be supported. And the challenge we face at Riley's way is from a business perspective, we have product market fit. We are turning down over nine out of 10 young people that wanna be part of the work we do. And so that's, it's why I still work. It's why I speak so much about what we're doing and about our team and how we scale it because we can't move quickly enough to, instead of saying no to nine out of 10 kids, I wanna be able to say yes to 10 out of 10, and we have a lot of things we need to do to get there.
[00:26:50] Gopi Rangan: This is incredible. I can see the type of people you attract and what you do to them, and it's heartwarming to see that some of these people actually come back and join your organization. What happens in the program? What kind of things do they get in the program that helps them?
[00:27:05] Ian Sandler: So, the main one is our Call for Kindness Fellowship.
[00:27:08] What happens is you are a leader of a social impact organization in your community. That could either be something you've been running for years or it could be a brand new project. This year we had around 400 completed applications. We had another 800 that were like on the way. So about 400 social impact organizations, they apply, we pick 50, and they get to be part of a year long fellowship. One of the first things that happens is we get them all together. So we fly them to a city, they spend a weekend, we do something in the community and there are some discussions from what I call old people like myself, but the bulk of what they spend that weekend doing is peer-led workshops and then really it's getting to know other fellows.
[00:27:58] There's so much power that comes from being focused on climate in Alabama and meeting somebody who's doing the same work in Washington and you can see the, "Oh, I'm doing this and yes, and we can do this. " And so that weekend becomes incredibly powerful, but then we have 11 full-time staff, they're working with these young people as well as our board and our broader community on all the things they want help with.
[00:28:27] What they generally want help with is how do they raise money, how do they manage communications, PR, how do they network? I have a thing tonight where we have about 80 young people getting together where we have a bunch of adult mentors and we do speed networking and talk about this because I'm a big believer that your network is your life.
[00:28:47] There's an interesting tension with these incredible young people because they wanna do so much good and yet they're so kind that you have to explain to them, "You're not bothering me or you're not doing something wrong when you wanna get on a Zoom with Ian Sandler and have me open up my network to you, " right?
[00:29:06] That's actually the work I want to do because I want all of these young people to elevate into leadership positions, but they love the community of Riley's Way so much that you have to spend time with them because they don't, they're like, "Well, I don't wanna like ask for something and taint all the greatness that is."
[00:29:22] But we're running programming with them, a lot of it's virtual, but we're doing it on a year long basis. And then anyone who's been a fellow has the opportunity to then continue to get funding through our senior fellows program, which we keep growing. And what we found is there the investment is on the people as opposed to the project.
[00:29:42] So like you could come to us and have a fellowship for a community-based program that you run in New York City, but then you could end up going to Vanderbilt University and wanting to do something around just getting people to talk to one another. And like we can pivot the work that we're gonna support if we know this is a kind leader that we wanna grow with.
[00:30:05] And then those people who become senior fellows, they come back to our retreats, they come back to our events when we fly our fellows together or our fall programs, and they serve as mentors both at these things, but also virtually. And so you have this incredibly cool flywheel where you have an adult community and their network available to these young change makers.
[00:30:25] But you also have young people who are a few years older than the current fellows. And as somebody who's got a 17-year-old, like I can talk to my son and he'll listen to me sometimes, but like he'll really listen to a 20-year-old who he believes has gone through what he's gone through and is much more authentic. And so what we've found is we've given our organization over to our young people. We have young people who sit on our actual board, we have a youth advisory board that they do. Our strategic planning is driven by young people. When we judge our Call for Kindness, our main program, 80% of the voting comes from young people 25 or younger.
[00:31:04] We've hit our stride by really being this place that doesn't tell young people, "Oh, we know and we're gonna tell you", but rather, "We don't know. We're here to support you. How can we help you? " And just that pivot in how we approach things has been the magic for us.
[00:31:22] Gopi Rangan: Over the years, you've supported about 5,000 young leaders with various types of resources, funding and leadership development programs and peer support communities as well.
[00:31:33] What is your advice to young leaders? What are two or three things that they should keep in mind as they develop?
[00:31:38] Ian Sandler: Well, my teams used to hear me say this, which is dream big. I'll use my own personal storytelling. When we started Riley's Way and had no idea what we were gonna do, in my head, it was this multi-generational, massively impactful nonprofit like Teach for America or the Peace Corps, which the average life of a nonprofit's three years.
[00:31:58] Like there was no rational basis for me to have that view, but I don't have a moderation button in me. That's just how I'm wired. And I was like, "Well, if we're gonna do this, let's freaking do it." And I encourage young people to really think not just incrementally about what they could do, but what would their biggest dreams be and to truly go after it fearlessly.
[00:32:23] What I found is if you dream incredibly big, even if you don't get all the way there, where you end up landing is a pretty remarkable place with a pretty great view. So my first push is to dream really big. My next push, and again, a lot of these pushes, because I think that's really all we can do as humans is from my own learning.
[00:32:44] I only survived the last decade by learning who I am. And by that, meaning how do I become happy? How do I become productive? What is my personal formula? And not the formula that society tells me, which is make a lot of money or that my parents wanted from me, but, like, what is my own formula? What I realized for me was I need to really lean into physical fitness in order to be in the best possible place from a mental perspective.
[00:33:13] I gave up booze in 2020. I was never a big drinker, but what I realized was I just wasn't metabolizing alcohol well, and I'm an all or nothing person. And at the very beginning of the pandemic, I'm like, "Well, I'm either gonna go through my thousand bottle wine collection or I'm not." And so I stopped and I really leaned heavily into my physical fitness. And for me personally, it's been one of the best decisions I've ever made. So figure yourself out and it sounds selfish, but put your oxygen mask on first. If you can wake up every day, because the only person you compete against in this life is yourself. So if you wake up every day and look in the mirror and really like that person and be proud of that person, you're gonna be able to do great things for your family, for your friends, society at large. And if you don't feel that way, it's really hard to do amazing things. And so dream big and then put your oxygen mask on first and really look after oneself before you do that.
[00:34:10] And then, my last push would be this notion of building your network. And I think young people look at that and they're like, "Oh, like, how do I meet an old person who is in my field and how can ... " It's not that. I mean, those are wonderful people to add to your network. But what I've actually found is, like, I'll talk about the University of Michigan. I'm a devoted fan. I love this guy. I go back every semester to guest lecture. I care deeply about it. And I do because I found myself on campus in Ann Arbor and I found, like, what my formula was. And so I get a lot of pleasure out of giving back and talking to young people and doing it. But, like, what I've found is I've made such great friends that have been so helpful in my personal life and my professional life through that network or other shared networks and area of interest. And so, I've got an incredible friend group. I love my friends. I probably would not have survived the first year without my wife and my family and my friends and how supportive they were.
[00:35:12] You think of your friends as this group of people that are there so you can have fun times with until life actually hits you. And then you realize these are the people that are gonna keep you going. And figuring out who those people are and it's just like a bank, you're putting money in, and hopefully you never have to withdraw. But if you spend your life curating that network and really looking after people and being kind and thoughtful, life's gonna hit you. And when you gotta pull that money out of the bank, it's nice to have it there. And so those would be three things I'd really focus on. And if you can do those three things pretty well, you're gonna have a pretty good life.
[00:35:51] Gopi Rangan: Dream big, self-care and build a network.
[00:35:56] Ian Sandler: Yes, sir.
[00:35:57] Gopi Rangan: This advice is relevant, not only for young leaders, I think, for the larger community as well. The Riley's Foundation now is about a decade old, a little more than a decade. What is your plan for the next decade? Yeah. How do you see the foundation evolving?
[00:36:17] Ian Sandler: Well, remember, I'm a growth ... I work at a growth equity software firm, so there's only one answer, which is just massive growth. I also mean that because there's huge pull from our young people and everything, the combination of the failure of leadership on a global scale and really like I said, we're judged as a society by what we deliver to our children, and we failed our children at this point.
[00:36:44] And everything that's coming with AI and the importance of EQ, like, I just think the world is aligning that we need to be working with tens, if not hundreds of thousands, more young people and figuring out how we can help them be kind leaders and servant leaders as they move forward in their lives. And so I plan on this being a decade of massive growth and hopefully correspondingly massive impact from our young change makers.
[00:37:18] Gopi Rangan: Ian, I am inspired. I wish you luck, and I am very grateful and thankful to you for sharing this story. You've shared a lot of insights on your career and how work happens at one of the most iconic investment firms: Insight Partners, and more importantly, how you spend your time shaping the future by supporting young leaders through Riley's Way Foundation.
[00:37:44] I look forward to sharing your nuggets and your stories with the world. Thank you very much.
[00:37:49] Ian Sandler: Thank you so much. I love the conversation and very much appreciate all you do.
[00:37:55] Gopi Rangan: Thank you for listening to The Sure Shot Entrepreneur. I hope you enjoyed listening to real-life stories about early believers supporting ambitious entrepreneurs.
[00:38:04] Please subscribe to the podcast and post a review. Your comments will help other entrepreneurs find this podcast. I look forward to catching you at the next episode.