Episode 1: Matt and Swati of Incite

Come on into The Room. The Room is a series that lets you get a view into the room where it happened. I'm Claudia Laurie.

And I'm Madison McIlwain, your co-hosts. Recently dubbed Silicon Valley's new power couple. Matt Rogers and Swati Mullavarappu are partners in every sense of the word. Growing up together in Gainesville, Florida, they had been friends for years. It wasn't until the two reconnected via Facebook many years later that their friendship grew into something more. In those years apart, Matt and Swati were busy putting their mark on the world. Matt started his career at Apple, launching the very first version of the iPhone. By 2009, he left Apple to start Nest with his former boss, Tony Fadell. A vision for a smart, connected home began with a thermostat. Thermostat that tracked consumers' temperature preferences. Just 5 years later, Nest was bought by Google for $3 billion. Meanwhile, after graduating Harvard and Oxford as a Rhodes Scholar, Swati was busy herself at Google and then Square leading international development. Going on to learn the ropes of venture capital from Kleiner Perkins, Swati felt there was a need and an opportunity to build a mission-driven investing firm. Thus, Insight Ventures was born. Through personal hardships, the joy of raising two kids, and the commitment to a better future for our country and planet, Matt and Swati truly have a special partnership to be revered. In today's episode, we'll explore themes such as the power of patience, distilling a grand vision into one product, and what it takes to be a servant leader.

It's really fun to get to have both of you, Matt and Swati, on today. You're our first official dual guests.

Awesome.

Thank you for being here.

Oh, we're excited.

Just to set the stage for our listeners, in February, Vox published an article titling you and Matt as Silicon Valley's new power couple. That is quite a title.

I think Teddy came up with that out of his own creativity.

Well, certainly from our research, it seems to be true. And kind of, you know, given this status, this name bestowed upon you, We'd love to actually start with your founding story, how you both met and came together. I think there was middle school somewhere in there.

There was definitely middle school and high school there. I think my earliest memory of Swathi was probably around our 6th grade. So we were like 11, 12 years old. She was a very short, very big-haired girl. Like her fro is larger than her body.

And curly hair in a very humid climate.

Yeah. Oh my gosh.

This is Gainesville, Florida. Do I have to say that?

Gainesville, Florida.

Yeah.

So we grew up in a small town in Florida, which would be basically just a swamp if it wasn't for a large university there. It's kind of like the Ann Arbor of Florida. Big college town, but not much else there. Otherwise, quiet residential place. It was a great place to grow up in that a really actually diverse community of people because of the university and access to a lot of educational facilities that we normally wouldn't.

Really good public schools in those days. Then the rest of it was kind of a typical millennial love story, if you will. We went our separate ways for college and grad school, but Facebook generation, so we were able to kind of stay in touch without really talking to each other and both ended up in Northern California to work in tech-related things. I mean, Matt was one of these very prescient young people. I think when we were 13, he knew that he wanted to work at Apple and had his grandparents take him on a road trip to visit campus in Cupertino. And I was a little bit more, you know, a roundabout path, a liberal arts degree, traveled the world, studied development economics. And of course, that naturally led me to a job at Google. But at any rate, we ended up out here, would kind of see each other once a year because there was a small group of us from high school that would hang out. And one year, it just made total sense for us to date each other. And the next thing we knew, we're married, we've got two little kids, we get to work together and build to build a life together. So we're partners in a lot of different ways. And I would say it's the single best decision I think I've ever made.

Best decision.

That's adorable and really refreshing to hear. Claudia and I are both figuring out our own love lives alongside our careers. And it's inspiring to hear that you guys have been able to do that together now. And we'll touch more on your partnerships in multiple aspects later in today's episode. But we'd love to start with Matt's story in founding Nest after Apple and kind of all the way to Insight today, because I feel like it's 50/50 on our guests of people who knew they were going to be founders and build something super cool, or people who never thought they'd be founders and then here they are. And so I'd love to start there.

Sure. Actually, it's funny you should say that. Like, the word founder has developed all this additional meaning in our culture the last decade or so. I always knew I wanted to build stuff. Even when I was a kid, I wanted to build stuff, but I wouldn't call that entrepreneurial DNA. I love building things and that's what led me to build a career at Apple and building iPods and iPhones. And actually, that's what drove me to leave. So I was at Apple almost 5 and a half-ish years, was leading teams on the iPhone, iPod, and iPad. I had this really weird feeling kind of late 2009 as we were working on iPhone version 4. That was a really good one, by the way. A lot of other folks were having the same feeling, and it's actually, it's a very millennial feeling. Wow, we've got all these fantastic talented folks together and we're effectively making a platform so people could play Angry Birds or Fruit Ninja. And actually, people don't really play those games anymore, but—

The prime of the iPhone App Store.

Totally. Is this the best use of our talents? That's what got me itching. Reached out to a bunch of friends and mentors and Sat down for lunch with my old mentor who was my boss at Apple, Tony Fadell, and the two of us started talking about what we could do. And we were super attracted to this idea of making our homes smarter and more efficient. We could build a product that saves energy, is good for the environment, and makes people feel really good at the same time. And that's— we just jumped right in.

That vision seems to be very true to your story, both with Nest and all the way through now to Insight and what you and Swati have built. I would love to touch more on your years at Apple, just because I think those are some pretty iconic years. I heard a rumor that you were maybe the youngest intern Apple's ever had. Don't know if we can substantiate that.

I don't know if I was the youngest intern, but I was definitely the youngest manager at Apple at the time. I interned at Apple in '04 on the iPod team. Was working in the printer cube outside Tony's office, which was right place at right time. I didn't realize it was the right place at the right time at the time, but it certainly was in hindsight. Was fortunate to be on the best team in the company. I lucked into that. I applied on the internet through the apple.com job site and somehow got placed as an intern on the best team at the best time in the best location. It was just great. I learned kind of end-to-end product thinking. Jumped in as an intern working on manufacturing, and they tried to get me to quit school and just keep going, but my mom would've killed me. The Jewish mother would be very unhappy about me skipping out on school. I came back after I finished, was the junior firmware engineer on the team. And of course you throw the junior guy on fixing bugs or the project you think that isn't really going to happen, which ended up being the iPhone.

Wow. Yeah.

At the time, let's call it—

Last project.

Yeah, how about that? It's late 2005 Apple. iPod was killing it, 70% of the company's revenue, super high-flying at the time. Tony and Steve started this super skunkworks team, codenamed Purple, walled off. No one knew what they were working on. It was like 4 people at the time. They needed a software engineer to start helping out. All right, let's throw the young guy on it because he doesn't really know better anyway. And if we cancel the project, we didn't really lose much. So yeah, that was me. That's how I got started.

Being in the Gen 1 iPhone team is pretty crazy. It's iconic to be one of these young innovators here and As you mentioned, one of the youngest, maybe the youngest manager Apple's seen. But even at the top, you felt like there was more. And you mentioned this, you wanted to build products that really helped to change the world. So that's when you left to start what would become Nest. But it didn't look quite as glamorous as maybe that sounds on the surface.

It really wasn't that glamorous.

There was a garage. They were sweeping leaves and fighting squirrels.

Yeah, totally. The traditioned Valley tale of early-stage hardware teams in garages in Palo Alto, we did it not because it was like a legend, but because it was cheap real estate. We rented a small little garage behind a psychologist's office on Alma Street in Palo Alto. It was great. The best place to start. I miss those days of all being together in one room. One, we can't do that anymore. And yeah, two, actually it was, it was a super productive time.

With that though, your vision to start was building the connected home of the future. Which is a tall order. And you were able to narrow that down into the thermostat, which was Nest's first product. I think a lot of our listeners are founders, either on the hardware or software consumer side, asking, "Wow, I see so much opportunity and areas for change, but I don't know where to start." Walking us through how you and Tony narrowed down Nest's first prototype into this one item.

I love this one, 'cause actually this speaks to the skills we brought to the table and like the tension between the two of us in terms of like ideation. Actually, Tony's brilliance is that narrowing and focus. Believe it or not, I actually had brought the big picture. I really wanted us to do this expansive smart home, connected home vision and do all these products. Tony basically said, "Matt, you're an idiot. That's not how you build a company. You start with one discrete thing and do it really, really well, and you use that to then catalyze an ecosystem and build it one product at a time." He was spot on. Leaving that conversation, we spent a few months actually surveying the landscape of all the things that we could do. What's the right first product that could captivate people's imagination? It was very clear we had found the right one in the thermostat. We actually looked at other ones, we looked at irrigation systems and all these other areas of the home, and what we realized is we wanted a product that everyone could have, that they could see every day, that would make them feel good using because they could save energy and be be good for the environment, but at the same time, a product that could pay for itself. So there's a rational component to it too. And there are so few of those in our lives that really can play on the rational and emotional sides of our brain. Once we had done our research, we had so much conviction, we had to go do it.

I think it's a really important theme and it's a little bit of, you know, I think part of what you're stitching together is also what Matt took out of his time at Apple and how that sort of played out in the Nest context. It's also oftentimes the conversation that we're having with our Insight founders. Especially at the earliest stages when they're building a company. And a lot of these are founders that are motivated by a big-scale world problem. So the reminder on our part is have the discipline to focus, pick one thing that you're going to do really well, but you gotta walk and chew gum at the same time. That one thing has to be credibly extensible such that if you nail that one thing, the path to doing all of the other big stuff in the opportunity is a clear one.

Yeah, there's a big difference between a feature and a company. And some companies, like, they have a really great idea for a feature or a feature for a product, and that's what they go, go and do, and they never really grow and scale from there. We always knew from the beginning we had a big vision, but yeah, you got to start with something that's real and tangible that could catalyze a business and captivate people's imagination.

So Swati, if I have it right, your parents came from South India in 1983, and as we mentioned before, you grew up in Gainesville, Florida, where you volunteered for Democratic campaigns as a door knocker. Then you went on to Harvard.

With Matt, actually. That was something we used to do together in high school.

Oh, no way. That's incredible.

We did like door knocking and sign holding on street corners for Al Gore in 2000.

2000. That mattered a lot.

We should have knocked some more doors, frankly.

The world could look different.

Yeah, gosh, it's very frustrating.

And given that the election is next week, that's a very topical anecdote.

4 days.

Swati, you're also the co-founder of Arena, which trains and supports the next generation of campaign candidates and staff. It seems like you've always had a passion for politics and social change. Would love to dig into what drove that early interest for you.

Yeah, although it's interesting, I know it reads that way, but the truth is there was a good 15-year break there where I didn't do anything political for college, grad school, and the time that I was spending building tech companies and working in venture capital. And then like so many, probably, of the folks that are listening to this podcast, the November 2016 election happened and Matt and I both felt like, you know, a huge door had slammed on a lot of the core things that we valued and we woke up thinking, what is going on in the rest of the country while we've been out in Northern California doing this tech thing? We started to learn more and one of the things that we learned really quickly at the end of 2016 was, oh my gosh, this ecosystem that has burgeoned in Silicon Valley and taken off across the country where entrepreneurship has become super accessible. The idea of building a startup is something that people everywhere in America were tuning into and getting access to and learning more about. It was actually easier at that point to figure out how to build a startup than it was to learn how to run for office or be involved in Democratic politics. And we were like, wow, this is a huge imbalance. We have totally got to do something to fix this. And because the only thing more fundamentally American, I think, than entrepreneurship really is democracy. So we started Arena as a program that went around the country and encouraged young people to run for office, to work on campaigns, and not only encouraged them, but actually gave them access to the experts and the tools that they needed for free, at no cost, with digital toolkits that were super accessible for a new generation, and have really participated early on in building the new progressive ecosystem that I mean, now everybody's tuning into. So we helped get new candidates like Lauren Underwood, a member of Congress, Lena Hidalgo, dozens of people like that running for office who now we can wake up and sort of look at in the news and say, it mattered that we helped elect those people because they are changing the way that democracy works in America. So that's the work that I've been up to at Arena, and that has been my day job alongside the venture investing at Insight. What I'm most excited about is the way that that work plays off of each other.

So it seems like there is this really strong relationship between entrepreneurship, starting a tech company, and then also campaigning and becoming a politician to some extent. So after Harvard and Oxford, you made the cross-country trek to California. And you mentioned that there was a bit of a winding path to get into tech and start at Google. Could you tell us a little bit more about that journey specifically?

For me, the strong orientation has always been studying big and pressing problems in the world. So in school, it was a lot of time on themes of economic development, which, you know, if you cast in a different way, is really the study of how people and communities and societies look to improve their livelihoods over the course of time. I got really frustrated in a PhD program. I was like, I don't just want to study problems, I want to go and do something about them. So let me go and learn how to build things. At the time, you know, the mid-early 2000s, the few brave Ivy League educated folks were venturing out to the West Coast. Some of them were starting companies like Facebook. Others like me weren't quite that bold. But I took a job at Google because at the time Google had just gone public. Its founders and its early employee community were really curious about the ways in which they could build things that mattered in the world. And so they were starting this group called Google.org, which ended up becoming this really fabulous learning grounds for working alongside some of the best thinkers in technology and some of the best doers who were building great products. And we brought in folks that had economic development expertise, public health expertise. So after Google, one thing led to the next. There's never been a shortage of opportunities out here. And eventually ended up going to Square to sort of bring some of my international experience, some of the experience I'd had incubating early product ideas in a tech company to really help that company figure out how they were gonna build a business outside of the US.

And then you went into venture. I think next on the, on your resume is Kleiner Perkins. Talk to us about that transition, being a builder to being a funder.

Yeah, so at that point Matt had exited Nest and we knew that our life circumstances were changing. And one of the things that I was really interested in getting smarter about was, you know, you could create and build individual products and companies, as an operator inside of them, but there was also an opportunity to impact entire ecosystems by making capital allocation decisions. What ideas are worth funding? What teams are worth believing in? We wanted to learn more about that with the ambition of eventually doing that with some of our own capital. So we had this idea for what would become Insight, but wanted to learn a little bit more. Kleiner, you know, had such a fantastic track record, had been around for a long time, and We had really great working relationships with some of the partners there. They were early believers in Matt and the team at Nest. They had been placed early bets at Square. We really loved some of the values-driven partners there, like Randy Komisar and John Doerr. So I went there for a couple of years really to learn. Man, I geeked out. The operations team at Kleiner is still one of the best in the industry, led by Sue Biglieri. They sit on decades' worth of historical venture data, which for an economic historian like me was just fascinating to go back and unpack and understand this is what drove returns in this wave and generation of funds. This is how the ecosystem has changed to really understand how the economics of the, of investing worked.

Where did you start to think that you might become a founder or you might start a fund yourself?

I didn't, that was really Matt's influence. I kept coming home with all of these ideas of where I saw opportunities to do things differently. And Matt said, you know, the best way for you to demonstrate that is to do it. We could do it and it would be a lot of fun. The world needs more of these kinds of platforms. And I think your point was also as an entrepreneur, right?

The reality is if you see things that you want changed, just got to get out and do it. If anything, showing initiative could blaze the trail for others to follow. That's kind of our philosophy is if you want to see the change in the world, just make it happen. Others will follow.

And Matt had this really wonderful experience where when they were originally casting Nest, when Brandi and folks at Kleiner expressed interest, they bought into the impact that the company wanted to have as well as the huge market potential, the idea that they were building Nest to reduce energy consumption and to have a green angle. One of the things that Mac kept saying was that we need to have more investors out there that have that kind of a focus and orientation because for him and Tony as founders and builders, it made a big difference to have somebody on their board and on their cap table that was in it for that. Objective.

Mission alignment was critically important to us. And actually, as we added folks in subsequent rounds, mission alignment ended up being one of the decision factors for us bringing people in. And at least 5 years ago, there were all too few mission-driven early-stage investors and I guess even operating partners. So we saw it as an opportunity to come in and help with that.

It wasn't a linear path, but then this was how Insight was born.

And there we all have it.

Insight was born 2017. This was, as you mentioned, the year after the 2016 election. The interesting thing about Insight is a couple of unique aspects for a typical, air quotes, venture fund. You do invest across business opportunities and social and political movements, and your core structure is not like most venture capital funds in the sense that you are its limited partners. Do I have that correctly?

Correct. We've got the responsibility to do that, responsibility and privilege to do that. But at the same time, by doing it ourselves and not bringing in outside capital, it frees us a little to be a little bit more— I'll use the word reckless, but like to take a bit more risk.

We take risks.

Yeah. Take more risk.

And you're taking risks that others, because to your point, and we like to think our podcast is for people who might not know the industry as well as Claudia and I do, is to say we're not going to take an endowment or a children's hospital's money. Such that if our risks don't pay off, these people who really need the capital don't get it. You're saying it's our capital, we've decided we don't really need it. And so our hope is that in taking this riskier bet, when it pays off 10 to 15 years down the line, or maybe 20 on climate change or other social issues, you are okay with that kind of uncomfortability.

[Speaker:DAVID] We've even actually taken it a bit further, talking about innovation around risk-taking. For our more kind of down the fairway, middle of the road, venture investments, we do it much like another venture fund would do. But actually, for our most risky, maybe if the company is so early that there's still science risk, for example, we'll actually invest off of the balance sheet of our foundation. So either A, we're really smart investors in that the foundation's corpus will grow, or we're really good philanthropists in that we're effectively writing a grant for important climate science. And if it doesn't pan out, then that is okay. We wrote a grant.

That's really interesting. And that kind of dovetails into the 3 vehicles that you've built into Insight, which is the Insight Ventures, which is a fund looking at mission-driven enterprises, Insight Labs, nonprofits that provide grants for charitable, educational, scientific purposes, to your point. And then finally, Insight Politics, which is more a personal involvement of you 2 supporting candidates. Can you just talk us through a bit more of those 3 arms and how you think about building that kind of fund?

Yep. So one of the core motivations for starting Insight, Matt just articulated, it was this idea that we believe that more people that are building hard things require capital that's willing to go the distance and take those risks with them. But the second insight was that, and now you're starting to understand why we call it Insight, it's a play on words, but the second insight was that founders who build really hard things, sometimes they're starting companies, but sometimes they're starting nonprofits and sometimes they're actually doing really bold things in the political space. If we had just formed an LLC for a venture fund, we could only back companies. If we just started a foundation, we could only fund nonprofits. Or if we were just giving personally, we would only be doing stuff in politics. We wanted was an entity that had the flexibility to build really hard things irrespective of what form that entity takes. So that's why Insight set up to be able to fund across these three categories. We do venture investments, We back political causes and candidates. We fund philanthropic work.

And the cool thing is actually like from a day-to-day, actually the problems are the same. This is like key insight that we have that more of the Valley can pick up on is this idea of being an angel investor or being a venture capitalist, joining someone's board, the skillset and the kind of value you add is the same regardless if it's a company or if it's a movement or a new nonprofit. Advice on hiring and HR work, raising money, raising money. How do you scale? Yeah. How do you get the word out?

How do you do branding and message development?

It is so— there are so many common themes. As a board member across the gamut, the stuff that we do is about the same regardless of what the company is working on.

And I think something that we love, a sign that we're doing it right, is we regularly get all of our Insight founders together. And to see the synergies and just the jiving that happens between our climate nonprofit folks and the folks that are building our green tech companies, there's all kinds of good stuff that comes from that sort of community development. I think it allows our really creative entrepreneurs the flexibility and space to have mind meld and realize, okay, we're actually building impact in this holistic way, even though my company is addressing one specific part of it, or my nonprofit is addressing one specific part of it. So we happen to think that our happy hours are really, really the happiest of ours.

It does seem like you're touching on an important aspect of venture capital that often does get overlooked, which is the community building component and how amongst portfolio companies and investments, you can really nurture strong relationships amongst other CEOs by being, being able to say, I think you would really enjoy meeting this other founder because you guys are just going to be able to jam on this idea around sustainability. But within that, both of you have worn many different hats through— it is very clear— both of your paths to Insight. For Matt, this is his first time, I would say, formally doing venture, and Swati, this is maybe your first time being formally a founder. What are some surprises for each of you along the way of switching hats?

Ooh, my favorite/least favorite one is one of the same, is about influence. So like, as a founder, as an executive, if you want to see things happen, you make it happen. And there's some like authority and responsibility that goes with that. As an investor or board member, you have influence, but no authority. If portfolio company CEO or founder is running into a brick wall at full speed and you know it's coming, you could give them the insights that the wall is there, but if they don't veer, then there's nothing you can do. All too many times, actually Randy used to use this phrase at Kleiner about soft-mouthing the ball to be able to give insight and influence, but without shocking the system too much. And that's an art I've not perfected yet, I got to tell you.

I would say mine is focus. When you start out to found and build something, I mean, I'd say besides your marriage or your personal relationship, it is the most significant singular commitment that you make to, to kind of create this thing. For me, that's always been a challenge. I have what I love to call intellectual ADD. I thrive when I'm juggling multiple things. It's a lot harder for me to focus on just one. And a great example is 2 years after we started Insight, I decided that I would also chair a presidential campaign. So I was doing that alongside the Insight work. But lucky for us, we had Matt to carry the football on the Insight side for most of last year. So still work in progress, but I'm learning the benefits of focusing.

On the note of juggling many balls, most founders, and especially early founders, are probably trying to figure out, okay, how do I still make progress on building product while I'm fundraising and also I'm trying to hire folks? Do you have any tactical advice on keeping focus and calm even though there's a ton of different roles up in the air?

Yeah, from my perspective is around being even-keeled. Even when there's chaos in your brain or there's chaos around you, like projecting calm and stability and focus focus to your team is critical because presumably you've hired well, and if you've hired well, there are people that are owning each of those areas and are focusing on them. Even if there's lots of chaos, you're jumping from a fundraising meeting to a sales call, always level setting and knowing that for your team, they're picking up on your emotions, your attitudes, and your focus. Actually, most critical thing. When I meet with founders, they're all in a tizzy, they're all over the place. Their teams usually pick up on that too.

That's your vibe, Matt. You might just be the cool, collected person. Swati, do you feel like you have that strength or maybe you have other strengths?

I think I'm really good at structuring big amorphous stuff. We joke about what that means in our home life, but at work, it's been really great actually as we've transitioned to a pandemic work environment because we, we use OKRs, for example. I've always used them on the teams that I manage and run in companies. But we're using them now at Insight, and it's great because we might have, you know, our 4 or 5 team members are all working from home on slightly different schedules, managing childcare and stuff at home. And I'm also so proud of the fact we are an all-woman team plus Matt, which I love. But we use OKRs. So we say, you know, every quarter, these are the things that we want to get done. These are the specific measurable indicators of progress. These are the key people that own and drive decision-making on it. And then it helps me avoid micromanaging and it empowers everybody on on the team to go and do the best version of what it is that they have ownership over.

I just want to clarify, OKRs are Objectives and Key Results. When I first did my internship at Rent the Runway in college, everyone kept talking about our company OKRs, and I was like, what are, what is this acronym?

It's worth a podcast solely on OKRs, by the way. It's a super, it's a great management tool and goal setting tool for an organization.

As past product managers, we definitely would not have gotten this far without leveraging them.

Not in the slightest. And so talking about these tech terms and these tech ideas and structures, Swati, it's been a, I would say, a sweet spot and superpower of yours to take this and translate it into a more archaic and less innovative field of campaigning and politics. So you mentioned that you chaired a campaign. I know which one. Would you mind telling our listeners who?

Yep. I was the national finance chair for my friend Pete Buttigieg's presidential bid during the Democratic primaries last year.

And I love that you say friend because it's a 10-plus-year relationship with Pete. You wrote him a check in 2010, right?

More like 18 years. Pete and I went to college together, and we were Rhodes Scholars together.

I have so many embarrassing photos. And the cool thing about Google Photos, once you tag a face, it shows you all the photos of the face. Oh, man.

On the first iPhone, Matt, are those photos from?

Yeah, yeah. Totally. Yeah, exactly, right?

Embarrassing because I mentioned before, but I always had pretty out-of-control hair for most of my youth. Pete and I have known each other for a long time. We shared some pretty important formative experiences. I am all about building the bench of rising progressive talent in public leadership around the country, making it more accessible to more folks. And I— when he decided to run for president, he called and said, listen, I think I'm going to need your help because you understand this new evolving ecosystem better than most. Can you help me? So I stepped in early. And in those days, it was a book tour. We weren't sure how much traction it was gonna take. I mean, I think the first time we had him here in San Francisco, Matt and I couldn't even get 20 people into our living room to hear Pete talk for free. And in 3 months, like, our house could not even fit all of the people that wanted to contribute money and come to a fundraiser with Pete. So it changed really quickly. That was like being on the fastest growth startup that I have ever been a part of. We had to scramble to help him hire up a team and put his senior advisors in place and kind of figure out what the course of that campaign was going to look like.

This is a great anecdote of kind of the thematic ties between starting a company and launching a campaign. What specific skills, lessons you've learned from tech and brought over into being in the campaigning and fundraising room?

Yeah, well, one of the really important insights that for me was so shared was, you know, something that I think really wonderful product-oriented companies do in, in the tech ecosystem is they figure out, it goes back to what we were talking to Matt about that he learned at Apple, do something super duper well, make it incredibly simple and easy to access. I mean, at Square, we talked all the time about how important it was to have a seamless and fast onboarding experience. The idea that you could within 5 minutes get a Square reader, sign up for an account, and swipe your first credit card. Apple is notorious for this. I think Nest nailed this for what would otherwise have been a very complicated product with the thermostat. We had to figure out some version of that on our campaign with Pete because to go from zero to a known entity nationally meant that we were only successful by empowering other people to feel ownership in the campaign, to build a really rapid organic volunteer ecosystem where people could evangelize who Pete was, what he stood for, and what they liked. You know, there were little ideas like that that were about empowering a distributed grassroots movement. And I think there was a genesis that we had that I observed from what I had seen work really well in fast-growth consumer brands and tech companies.

You talk about like mission-driven companies. The companies has a mission orientation to their DNA. A political campaign should have those values at their core, but actually often it's very much about the issues, about the person. And I think what, what Swathi and Pete put together was, it actually was a mission-driven campaign.

Having known Pete for 18 years and sort of seeing his potential and his values and his mission, you continue to help him and invest in him as a person. And so kind of like zooming out to some advice for founders, I think a lot of founders who are especially trying to tackle those larger problems that might take 10 or 15 years to realize, they might feel, oh, this year we didn't really hit our milestones. Maybe we should pivot. Maybe this is a little bit too hard to go after. It's easy to get lost in a 15-year journey. What advice do you have for founders on sticking to their gut and keeping pushing through it for the long run versus actually stepping back and saying, "Hey, no, this is— we bit off too much that we could chew. This is not working.

We should actually pivot for valuable reasons." [Speaker:MADISON McILWAIN] So I think there are two really important ingredients for them to keep in mind that I really am so proud of and observe in Pete and his experience in that campaign. So the first is, You have to be bold. If you are going to go into this work of building something that matters and doing something really hard, be bold. Think really big. I think the size of the undertaking isn't necessarily the challenge. I mean, a year and some months ago, the mayor of the fourth largest town in Indiana decided to throw his hat in the ring to run for the highest elected office in the land. So let's just kind of pause for a moment to consider the boldness of that undertaking. It also could have been easy to get bogged down in, no, there is a 16-year path for you to take to get there. You should run for this office first and then do that and then do that. I think there was boldness in the undertaking and that actually is really important. But the second is Pete has a self-discipline and a desire for self-improvement that is tremendous.

I think the Valley has built this archetype of the ruthless asshole founder. Maybe it's because of the success of Steve Jobs at Apple or others. But actually, if anything, like embodiment of servant leadership, I think is actually the more likely path to success and the way you bring people along on your journey.

I love that. I think that is incredibly powerful, and I hope that I get to continue investing in founders who have that mentality as well go forward.

We talk about it at our weekly insight meetings. I mean, we're a little bit more direct about it, but we've got a strict no assholes policy. And in general, I think more folks in the Valley would be better served if we talked more about the values that that people have and what they bring to the table as a whole. And a decision to back a company is also a decision to back the values that the individuals behind that company stand for. Yeah.

One of the things that we don't talk about in Silicon Valley a lot, but it's actually forefront in our brain having been through it ourselves, is when you're making capital allocation decisions, when you're deciding, hey, I'm going to invest in this company, effectively what you're saying is I want to invest in the future wealth creation potential of these individuals. If when you start using that kind of more values-driven moral or ethical lens, like, are these the people you want assigning capital in the future, maybe you make a different decision.

You've been able to leverage your network, high net worth individuals who grew up alongside you in your founding days, to be a part of these now political movements and political fundraising moments. What's it like being in those rooms versus the tech rooms?

It ends up being a lot of the same people. In some respects, the folks who are in those rooms and are willing and able and excited to start to start giving back or, you know, paying it forward. Just being in that room means they're already heading in the right direction. The problem is those rooms are pretty small. A lot of the tech community doesn't sit in those rooms and doesn't think about giving back and paying it forward.

In both circumstances, we think about the success of our work as the ability to change the composition of who is around the tables in those rooms and making those rooms bigger.

It's been so awesome hearing about the story of you two working together to create this incredible organization that is supporting such awesome and world-changing causes. We mentioned earlier in the podcast that you guys met in middle school and you've been around together for everyone— each other's major career moments and major life moments. It probably has been a period of a lot of wins, but also struggles. Can you tell us a little bit more about what it was like transitioning from having your independent careers and being incredibly successful there to working together? And what it was like supporting each other along the way?

It actually wasn't that hard. You hear a lot of that, it's hard to be work partners with your life partner, but actually I think it's really easy. It's all about building that trust and relationship. And I think about what makes the best co-founder relationships is that deep, deep, deep trust. Where could there be more trust than with your spouse?

Do you have any tactical advice on working together as a couple for founders out there who are considering starting something with their partner?

We are super flexible with our own time and with our own structure. And as Swati said, When she was chairing the campaign, I knew I had to be a bit more diligent on the financial planning side and the investment side and the grantmaking side. At the same time, like, if things are ramping up for me, I still need to step in more. Just having that fluidity and that flexibility is really critical.

For us, a really important part of our relationship is we are equal partners. Everything that we undertake, whether that's building a family or, you know, Matt's got a new company venture and I know that it is like I participate in supporting him to be successful in that undertaking. And we work together on our Insight side. So I never feel like it's either him or me. In the end, when the pie grows, we're both benefiting from that. So it's really helpful when a baby is screaming and a toddler is coloring on the walls. And, you know, rather than playing the blame game of who's responsible for what, it's kind of like, okay, I'll get the diaper, you wipe the walls. We go at everything knowing that we're on the same team and that that's everything.

I'm super inspired by this.

Very encouraging. And I think something, I guess a topic that Silicon Valley and tech doesn't really talk about that much. And so it's awesome to hear those insights.

We think it's important in the scheme of telling these amazing, successful stories to say, hey, it wasn't always up and to the right. We'd love to ask, I'm getting some emphatic nods from you guys. I'd love to just challenge you both to share a moment where struggling to see the future or the vision and how you were able to turn that around, continue to get out of bed and make the vision happen.

Sure. So I, in 2018, in May, so about 6 weeks before Matt and I were expecting our first child, I was having a hard time breathing and went in to get a scan and found out that a cancer that I had had 10 years ago, which wasn't supposed to come back, was back and it was back in a very bad way. It was a very rough year. I really kind of dropped most everything. We had family move in with us. But the biggest thing that got me through that was actually Matt. I mean, Matt literally dropped everything. He went on family leave from Google the very next day. He was for 6 months changing diapers and feeding our newborn and then running my antibiotic transfusions, scheduling my chemo appointments. Doing blood draws because we couldn't find really great at-home nursing care. So he did everything in those 6 months to literally keep me alive so that I could show up and continue to do this work that I love doing. So that was a really hard moment for us. I mean, we'd also only been married for a couple of years. We had all of the stresses of starting a family. I mean, imagine being newly married and basically having your in-laws move in with you for the better part of a year. Right?

All—

and then his work, which was such a big part. I mean, he was Nest Mat, such a big part of it. Had to put all of that on the shelf to be at home first. So that was really, really hard.

Yeah, really hard from a lot of perspectives. But at the same time, this is one where I refuse to take no for an answer. And when doctors around the country said, "Hey, there's nothing we can do for you guys," just no. And I'm going to keep hunting and keep searching. And that same kind of entrepreneurial perseverance can apply to all sorts of things in your life. We never gave up. I'm not a doctor, but certainly could learn. Did. I mean, like, as she was saying, like running IVs and stuff, did it at home. Couldn't get a good home nurse to do it, so fuck it, I'm going to do it myself.

Part of what makes Matt such a remarkable human being is he has this boundless energy and enthusiasm. I mean, when he walks into a room, the room just like explodes. And there were days where I would wake up and look at him and say, I don't think I'm going to make it. Like, literally, I do not think I am going to live. Past the end of this year. And he would just say, no, you are absolutely going to get there. And there were times where, I mean, I talked about how amazingly lucky we are to be— I am to have him on my team, but he was literally dragging me over the finish line that year. And in that case, the finish line was staying alive.

Thank you so much for sharing this part of your story with us. It's really— it's more than the word inspiring to hear how your true partnership, both personally and professionally has been what's helped you survive some of the hardest years of your life. We're really glad to hear that you are in remission now, Swati, and it sounds like you're back. And man, I don't— I'm kind of at a loss for words. I just think it's, it's just, it's just really, really inspiring.

So when things are really hard and dark, you know, the key is to have someone in your life who could give you hope and keep pushing you forward. It's true in life. It's true in business. It's true in all these things. Having great partners is what keeps things going.

And it's also very clarifying the people that matter most and the work that matters the most, which is why we wake up with more resolve than ever in our work at Insight that you've gotta build stuff that matters.

Another question that I have for you is, as we kind of wrap up this podcast, we have a hero question that we ask all of our guests. I would love to know for both you, Swati, and also Matt, Who was a woman in your life that has had a profound impact on your career and life path?

There are so many, you know. If I had to name one, it's a woman that I've actually never met. My dad's mom, so my paternal grandmother, passed away when my dad was really young, so I never met her. But this was a woman who was born in India in the 1920s. She was a renowned tennis player. She was the first woman to graduate with a physics degree and a math advanced degree from one of the top universities in the country. And she, in in those days married out of love instead of marrying somebody that her parents had sort of chosen and arranged for her. She taught as a professor while having and raising 6 children. You know, she did those in that context at that time. And for me, it's always been an example of this idea that as a woman, there's nothing that's off the table for you. And at the same time, she also lived an incredibly hard life because she was in a cultural context that maybe didn't empower her and proactively support her as much as I benefit from having now. And so I know that we've got a long ways to go, and I am so in this work to break down even more glass ceilings. And trust me, I've experienced them. Thinking of her example always gives me strength in knowing that I have every advantage to live this life now, 100 years later.

I'm going to go with the most corny, but frankly, the most true. And it's actually Swathi. I could spend all of my day deep diving into some core technology or something that's really interesting, exciting, and she continuously reminds me to step up and reflect on values. I am certainly a values and mission-driven person because she continuously pushes me to do so.

I can think of a few people who have definitely, you know, prioritized their career and as a result, you know, haven't prioritized finding a significant other or starting a family or really like investing in the causes that they're passionate about. It's really awesome and refreshing to hear a story where, no, like, you can build a really strong partnership and you can work on the things that you care about.

I think oftentimes, especially as young women, we talk about these things like they're antithetical to each other. Like, I got to choose my career or having a personal life. Our relationship is such a blessing to me because it's been the ultimate lesson that sometimes 1 1 is greater than 2.

I don't think we have anything else to add.

For listening to this episode of The Room. If you enjoyed our conversation, please like and subscribe. Stay tuned for next week's inspiring guest airing Tuesdays at 7 AM Pacific. See you soon.

All opinions expressed by Claudia Madison and podcast guests are solely their own opinions and do not reflect the opinion of The5EC. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.