Investing Beyond the Day Job

Brandon (00:46) I have my brother with me, Andrew Lindsay. We've known each other for ages. We are alum of the illustrious Howard University, also HBS and an HLS guy as well. More importantly, he's just an incredible guy with, and I always I always joke all the time that he's had one of the most interesting lives of anyone I've known. We're not gonna tell the Kanye story to Shignize. We're not gonna go to any of these stories right now. Today, we're gonna break down ⁓ how do you approach

Private market investing when you are an executive who's busy, a family man. ⁓ how do you think about you know building this private market portfolio outside of your day job? So with that, Andrew, I appreciate you joining us. We're gonna dive into your story, but you just taking the time is is is incredibly appreciating. And al always, Brandon, this is an incredible community. I love what you're building with Gravy. I love the community and

this time is time very well spent. So happy to do it and appreciate everybody for listening in right now. So you came to mind because you know, I had to like go through my mind and say, like, we have obviously heavy hitters, you're a heavy hitter. Your day job is running AI and cloud platforms from Microsoft. So we're talking about the guy who's in the room for, you could argue, the most important technology of our of our lifetimes. And you're the one that's there with your team.

Brokering deals, brokering partnerships. This is a job that is a big, big job to say the least, right? ⁓ number one. So thank you for taking the time, you know, outside of all of that to spend time with us. But the reality is, you know, when I thought about who are the folks that I know that have taken a very thoughtful approach to building a private market portfolio as they are busy in their day job and with family, you came up and you know, we've done deals together, direct deals together.

You build a real estate portfolio in the Bay Area, which almost seems like a oxymoron. ⁓ and then interestingly enough, you actually don't own your primary residence. So you own multiple units in the Bay Area, which you chose not to own. And we'll get into all of this stuff. But before we before we get into all the details, just walk us through a little bit of your professional journey just so we get to know who is Andrew first. Yeah, sure. Look, ⁓ my professional journey is one that's been driven by

Intellectual curiosity, searching for impact, trying to marry together innovation and growth with being on the cutting edge of new technologies. That's been the core through line of my career. I actually started out back at HU, and you know this, Brandon, back studying biology, right? So from going from biology and pre-med through to AI partnerships at Microsoft, it certainly wasn't a straight linear line. It was a very

indirect path to say to say the very least. And the path has been checked with going from studying biology to going to investment banking in New York and learning about finance and getting my introduction to business. Then from there we're really going to law school and business school because of the intellectual stimulation and building up that skill set and the breadth of kind of capabilities that come with that kind of graduate education, going to McKinsey for several years to kind of have a finishing school around business, going to

Early stage startup wanting to help companies grow and being very early at the intersection of data, AI, and hardware at a company called Jawbone that was venture-backed, going from that to enterprise software, whereas at the CRM and ERP and trying to build a platform for the front office. And then most recently and right now at Microsoft, where, as you mentioned, I lead partnerships. ⁓ I was very fortunate to have a team where we look across the platform from data centers and land and power.

And silicon all the way up through to ⁓ AI platform with big partnerships with companies that everyone knows, like OpenAI, Anthropic, xAI, and so on, and making sure that ⁓ Microsoft stays at the center and at the forefront of this AI era. So that that's been a few seconds my career. There's a lot that I could dive into into that, but I know that's not the focus of the conversation. Well, translation, you're not getting much sleep because I'm not getting much sleep. You can't open up.

Yeah, at least I can't open up, you know, the news and and not see three or four huge developments in the AI space every day. Every day there's something, whether it is ⁓ what we are doing by buying capacity for GPUs or a partnership with silicon or something that we're doing with the government. I have a whole team that's focused on how Microsoft engages with the government and the Department of War, or it is what we're doing with our competitors, or what we are doing with the model labs. There's something every single day.

I I don't wake up in the morning and not see something in the news that throws you. And even when you're even when you're not doing a deal, you're f closely following every deal that's happening. So literally everything that's happening, you're covering. But this is about a private market, you know, conversation. And so one thing, you know, when I think about you, you've been in some rooms, right? And it's it's funny I kind of joke that you're kind of like the forward we talked you being like the forest gump. You've just been in in rooms socially, professionally.

That very few people kind of get to be a fly in a wall in. And so I'm curious for you specifically. And you know, also we didn't talk about the fact that you sit on the board of Asana, a public company. ⁓ you obviously have a very big corporate role, you live in a Bay Area, you've done fund investments, you've done direct investments. But what is your philosophy at the end of the day, when we kind of think through all the experiences you've been in, it's informed like the culmination of some view that you have around deploying your own personal capital.

Can you articulate kind of how you think about that right now? Yeah, I think about deploying capital the same way that I think about the totality of my life and career and that it intersects with what interest do I have around wealth preservation and generation. That's certainly a priority, but it's also communities that I want to support, loyalty to individuals who I believe in, who believed in me, and I want to back them and support them in their growth.

⁓ as well as things that are just interesting for me that I want to have a finger in and I want to learn more about and be a participant of. Those are all considerations when I make investments, which is a little bit different than some other folks, right? Like when I make investments, it's not only about the DCF of this investment. There's a whole series of other implicit calculations that I make. I don't have a strict criteria, I don't have a set framework that I walk through. Frankly, I don't have time for that. And so as things come in.

And it's mostly opportunistic. I'm not out looking for opportunities. As things come in, I run them through those filters and I think: is this something that I want to participate? Given the limited time that I have and my ability to actually participate in terms of capital that ⁓ that needs to be deployed. Those are some of the calculations that I that I make. That's actually a a very wise kind of perspective because.

Basically, what you're saying is by having a very clear framework in terms of your values and what you stand for, it's easier and faster for you to make decisions. It is. And they're not purely capitalistic decisions, which in many cases, for the average person looking at deploying capital, you're thinking like just whatever returns the highest amount. But it's a lot more complex than that. It's a lot more complex. That's right. Well, the one major filter is I don't want to know that I'm going to lose my money. Right? Like that's that's one.

And that binary of the is this a high risk? I have very low confidence in this opportunity in terms of the return. If that's the case, then I'm not gonna participate. But if I have some level of confidence that I'm likely to get my money back, and then some, and then it's an additional filter, how do I decide amongst those? Right. And a major part is do I have the time to assess it? If it requires a lot of time and analysis, then I'm not gonna put.

I'm not gonna do it. I just don't have the bandwidth. I don't the cycles for that. And it is it's interesting because knowing you as a person, I think you take a same approach to how you spend your time. And so, you know, as you've been always busy in your different professional moves, you've always carved out time for things that are important for you. Family, I know you just got back from a a weekend with your daughter, just daddy-daughter time. And I, you know, you've recently tapped me to to to to to serve on the board with you for the Howard University Digital Business.

center and I'm I'm excited about that. But these are legacy things. If you're clear about what you stand for, then as you spend your time and as you spend, you know, or invest your personal, you know, funds into investments, it kind of reflects who you are at the end of the day. I absolutely that's a that's a great way to put it, Brandon. Where I put my capital is very similar to how I think about where I want to put my time. Both of those are investments that I'm making and I think about them

Very similarly, if I don't want to put my time behind this initiative, if I had it, then I probably don't want to put my money against it either. Okay. There's reputational elements to it. There is ⁓ learning elements to it, there's impact on the world elements to it that I do take into account. So let's talk about the portfolio construction part of it. And it is nuanced for you because you literally live and breathe AI every day. And if look at the vacuum that is AI as a sector within

venture investing, it's all going to AI, right? And so you have a lot of exposure, you have a lot of information. How should someone think about when they're in a position where they're getting as much information flow, they they have to kind of represent or re acknowledge the fact that they are in certain rooms. How do you lay all this out in terms of what's available to invest and and how you're thinking about placing additional investments outside of what you're already exposed to? Sure. Well I do get a a

Of proprietary information around what's happening in the AI world, what's happening in cloud, what's happening in infrastructure. And that would give me a massive informational advantage around making investments. But I also have a very bright line about not investing in places where it intersects with my day-to-day work in a way that could lead to a conflict of interest. And that that very easy decision is it simplifies a lot of my investing. I don't invest in places.

where I also work day to day. Right. And that removes a lot of opportunity because I do get lots of opportunity to invest in companies where I partner with them, I work with them. I don't want to do that because at the end of the day, that is necessarily going to lead to a conflict that I can't disentangle myself from, that is just not worth it for me for ha potentially being on the wrong side of making a decision because my loyalties are divided in ways that I can't manage in the way that's

keeping with the integrity that I want. So I just don't do that. And I started that ⁓ back when I was at I was at HubSpot Prior to Microsoft. I started a venture fund, a corporate venture capital fund. And we made lots of investments, but lots of times companies would come and say, you know, I'm not sure I want HubSpot investing for a variety of reasons. Sometimes founders don't want to have corporate venture on their cap table, but Andrew, I want you to invest. And I have to say like I appreciate that. It's an honor. But I I can't do that.

'Cause that's gonna create a conflict that I don't wanna have to have to sustain over time. And so that's like a very clear key key bright line for me. And it and it echoes what we talked about before, which is if you're clear on your your framework, right? Yeah, you actually are eliminating headaches later, right? Because it makes it easy to make decisions. And so I know sitting on board sometimes, you know, has conflicts and and whatnot. So if you just stay away from it, then you're able to just

move on to the next thing with the with a clear mind, not having to worry about balancing these delicate, you know, intricacies across the board of your portfolio. It it's very simplifying and that saves me on time for analysis, time stress later. It doesn't maximize returns. I know that. I know my returns would be higher if I use my informational advantages to seek out the best investments and filter the best investments. But it's just I'm not that's not the game that I'm playing. Right. And and and

Net net at the end of the day, you're choosing that because the totality of your situation is what works best for you. That may not be the case tomorrow, and you'll have a lot of assets that you can, you know, you potentially tap as you think about what's next. But in all, this is you're kind of protecting the golden goose, so to speak. Okay. So this is just kind of one part of it. But let's get into your portfolio. Like to the extent that you are comfortable being transparent about this, what is like your overall public to private kind of like split?

Like how are you thinking about that? Yeah, it is it's mostly public equities. That's still where the vast majority, three quarters plus of of capital is. ⁓ of private, it's ⁓ about ⁓ half, a little more than a half is real estate.

And then the other half is private investments, ⁓ private equity debt investments into companies. Okay. So let's get into a little bit because ⁓ knowing you, I know that you own multiple units as as I mentioned before in the Bay Area, right? Yeah. ⁓

When you ultimately kind of found yourself in this situation, was this an intentional move to say I'm going to amass multiple, you know, kind of units in the Bay Area? Did you just have an opportunity that was too sweet to pass? Like, what was the genesis of the real estate component of the portfolio? Well, so the the genesis of it was if I look back at the the real core, it was growing up, my parents and I grew up in Toronto, parents were Jamaican immigrants.

they always had an eye on real estate. I remember Sundays after church, we would go look go to open houses and they would think about real estate and they think about do they want to buy a second home and use that and rent it out. So that was always something that was just ⁓ kind of ingrained in me from a very early age. Same thing with my wife. Her parents, ⁓ her dad was in real estate, ⁓ was in broker. And so we had both this growing up, both of us.

And the initial entree into real estate was for our primary home, our our residence. And we were living in San Francisco and we were renting an apartment and decided, look, this isn't financially, this isn't the best ⁓ way to to spend our capital. We should we should we're gonna be here for a while. Let's buy a home. And let's buy a home that we wanna live in. And how do we do this? Real estate's ⁓ expensive in San Francisco. It's ⁓ arguably the most expensive.

market in in the United States. And ⁓ I did a lot of research. I spent a lot of time trying to find what would be our entry path into real estate ownership in the Bay Area. And there was move further out from San Francisco where prices start declining the further out you go from the city, or there are parts inside of the city. And I got I got quite excited in doing my research in that I wanted to be court of the city still. And I wanted to be in a

community that I believed in that I wanted to put down roots that I wanted to invest in. Well it wasn't just a home, but this is my capital as a way to invest in the things that I care about. And there's a neighborhood in San Francisco called Bayview. And if you'll all indulge me for a moment, I'll tell you the story about Bayview. So if you go back to World War II, ⁓ at that time one of the largest naval bases in the country and certainly on the West Coast.

was on the east side of San Francisco, this community called Bayview Hunters Point. And it was incredible integration of races, of communities that came from across the country to work at this naval base. And ⁓ at the end of the war, all of that integration it kind of disbanded where you had ⁓ folks moving from that neighborhood up into San Francisco.

Right, especially the non-black folks were able to move into the core of the city, they used the earnings, there's a big post-war boom, and they bought real estate in San Francisco. Right, some of the most expensive parts of the of the city right now. Our community didn't have that opportunity because of redlining. So instead, they bought homes very close to that naval base, and that's the Hunters Point Beige neighborhood. And so that neighborhood for the past

80 years has been predominantly black. And people don't realize that this neighborhood exists inside of San Francisco. And it's changing and there's some gentrification happening. But that those families that bought after the war, they're still there. ⁓ And it's actually the highest rates of home ownership for the residents of anywhere in San Francisco. When I learned this story, and I learned about these homes and I learned about this community, it's like that's where I want to invest, and that's where I want to live.

And most people who are transplants like me to San Francisco don't know that Bayview exists. They don't know that it's just a mere few miles from the heart of the city. Most people aren't going there because it doesn't have the hottest restaurants. It doesn't have some of the, doesn't have the big companies that are based there, but it was a neighborhood that I feel very comfortable. It's a place where the communities are very strong. We bought a home, we got to know our neighbors. And that was the source of our of our first of our first purchase. Now, that's why we decided to.

buy in the location we did. The second piece was we were of modest means and we couldn't afford a 20% down payment. And so I had to look through what are different ways that I could structure this investment. And I talked to tons of banks, talked to lots of people. And as a first time home buyer, there were programs for people who wanted to buy into certain neighborhoods. And part of this was the Community Reinvestment Act,

legislation was to support home ownership in some communities that had been historically ⁓ underinvested in. And Bayview was one of them. And the zip code they were looking at was one of them. Which in some ways was just coincidental for us. And we were able to buy the home with ⁓ it was three and a half percent down. All right, so we didn't have to put down the 20%. We put down the three and a half percent and we're able to borrow the rest.

And so that was how we were able to afford the first home that we bought. Right. And it was also like the other thing I should note, it was ⁓ it was certainly a project where the home with it was the who we bought it from, they'd been in the home for decades. It required a lot of work. Well, I'm not afraid of getting my hands dirty. It became a nights in a weekend project where we were the ones scraping off the the carpet, pulling it up, scraping the glue off the floor. We did that on our weekends w when we

⁓ we were staying in the home when there was no kitchen. We were doing a lot of work. It was a real elbow grease to get this place in a in a situation where we could be really proud of it. But that was that was part of the fun. And that was the first home. So, you know, you found it in cra you did your research basically. You did your research on again aligning with values. What type of environment do I want to be a part of? I want to buy into the community. It's not just a purely economic decision. Yeah. Found your neighborhood, believed in it, looked at opportunities, found an opportunity.

Did a bunch of research on what is the best way to acquire a property, found an incredible deal that just happened to align with the neighborhood you had already chosen. You didn't choose it because of the financing. And then it all kind of came together. So I think it's kind of preparation meets opportunity type type of situation here. Now you had won, right? But you didn't stop at that one, that one property, right? You know what what happened to get you to now go from like we own this house.

Right, which most people in the Bay Area would say that's a win. Your ambitions grew from there some kind of way. What what what was that about? Well, so it was I became a very strong advocate for Bay View. And anybody who would talk to me about moving to the San Francisco moving to San Francisco or homeownership in the Bay Area, I'd say like this neighborhood in Bay View is the place to be. And started attracting a community. And other people bought into the neighborhood, other people who my friends started living there as well. And

started looking at different ways to invest. And if I want to help build this community up, if I believe that San Francisco is the center of innovation and technology, and this is well before the AI era, but the the San Francisco has a singular place in kind of the future of the economy for the country and certainly the and certainly the bit the kind of California, but extending to the world, then I should want to invest in this.

And so looked at do I want to buy a commercial along the commercial corridors? Do I want to buy mixed use? There's a lot of ⁓ learning curve that I had to get up for that. So I wasn't quite ready for that. But there was another home that I had my eye on for a long time, which was a three unit building ⁓ a few blocks away. And ⁓ I always thought that's a that's a that's a great place where one, it's the size of it, the fact it's a corner place. ⁓ I would love to live there one day.

And I just kept my eye on it every few weeks I look by. I spent time on Zillow, Redfin, just waiting to see if it ever became available. And then it became available. And went and looked at it and decided like, you know what, we should we should look at moving into this place and having it's kind of like our urban compound, if you will, where it's three units, it could be multi-generational, could have

our fa my wife and I family living there as well. We could have friends. It would be fantastic to do this. And so we we ended up buying that place as well. And buying that place, we found another opportunity ⁓ with a bank that would ⁓ provide us the a a path to putting only five percent down. Right. So I couldn't get to three and a half percent, but could get five percent down, which is pretty unusual, especially for multifamily, but talking to banks, talking to people, understanding what opportunities exist.

it paid dividends and being able to finance the home in this way. And we're not going to fast forward past this because what was the rate that you liked to in for that that multi-unit? That rate was about three and a quarter. Okay. So we put five percent down, three and a quarter to get a generational asset, multiple units in the Bay Area. So let's unpack this a little bit because I want to get kind of tactical here. Yeah. The first thing is you did your research. Most people would kind of just go with their kind of existing

banks or maybe their the the bank that they bank with for their checking account, whatever it might be, how much value would you just put on the process of exploring different opportunities and what would be the best practice you would recommend for someone who is looking to acquire a property or any other thing that would require financing? I think it is ⁓ there's l there's opportunities that aren't widely advertised. And it takes doing deep research and now there are tools, right? You can go on

To co-pilot, you can go on to ChatGPT Claude and do the deep research, helping you uncover these opportunities that aren't widely known for financing advantages. And spending the time doing that and just talking to people because the amount that you can save with a few basis points over the life of an investment is pretty extraordinary. And the opportunity to get into the market.

If you do not have the full capital for the down payment, is also pretty extraordinary. And it's just but it does take that work. There's no way we would have been able to to to land these investments without me having done that that research. The other thing though is ⁓ that's how we identify them, that's how we finance them. The other piece is actually winning the deals. I I put a lot of time into getting to know the agents.

Getting to know what the factors they were looking at. Price is one of them, but sometimes the sellers also have considerations beyond just price. Spending time with them, like real deep time with them outside of the open houses to understand how we could win these assets. And I think that was ⁓ this was all pre-kids, so I had more time than I do now. ⁓ but that those were those were some of the tactics that we did. Well in in some ways, the deal making kind of.

attributes, right? Because you're a you're a B D guy. Yeah. ⁓ you're bringing that into your personal life. You're absolutely looking at what's out there, you know, you're you're building relationships, you're realizing that it's more than just numbers. It's about people making decisions and emotions behind this stuff. ⁓ what will be the two or three questions you would now that we have Claude, right? What would be the two or three questions that you would recommend someone ask if they just want to be kind of familiarized with some of these types of programs. We're

Where would you start as far as questions go for these types of programs? Well, so we can start getting into like prompt engineering. But ⁓ the way I would start it, it's not it's not one or two prompts. It is having a conversation with ⁓ with it with a with an agent and having a conversation ⁓ with AI around identify what it is that you're trying to do. Right. So start out with ⁓ you know, I am a

I'm a resident of San Francisco. I am looking to put X amount of dollars into a home. I ⁓ I looking at these neighborhoods, I want to identify the best opportunities for advantageous financing. and this is the zip code that I'm looking at. You are a real estate ⁓ you're a mortgage broker with a

Deep expertise into opportunities in the Bay Area. Where should I start thinking about this? And you get a response. And then from there, you start, you just have a conversation, right? Like this is an advisor to you where you have a conversation and you keep dig digging and looking into different corners and looking into and can kind of like pull the string as more opportunities become available and you look into like every dark corner of opportunities. Like the programs that I found, again, were not programs that were heavily advertised.

There were programs where I like one of them the they had advertised it years ago and I found ⁓ through some like the tenth page of a of a Google search, there was a PDF of it of they had a open house about at some point. I found the bank I found the the banker's name on it. I emailed the banker and said the program does it still exist. They said yes, but they're not prioritizing it. So that's how we found out about it. So basically there's no way to get around the elbow grease. Even you know.

You could make the argument that if you use LLMs, it will be helpful in some ways, but maybe potentially gloss over other opportunities. You gotta put the work in. But but you still gotta put the work in with the LLMs. You still gotta put the work in. You can't just ask the first prompt and stop at that answer. And you've been in the Bay Area for how long now? 15 years. Okay. Yeah. You place these bets, and we've seen the Bay Area go up.

go down and who knows where it is right now, which is kind of the point of this next question, which is how has your real estate portfolio benefited you? Obviously it feels great to be an owner. ⁓ lock in incredible rates and terms for acquiring it. We know that you kind of bake the win in again like a good deals deal person. You bake the win in coming into it. But talk about tax benefits, talk about the appreciation that you've observed. Like what are your reflections and what have been the benefits of owning this property over the last

⁓ you know, seven, eight years. Yeah. The ⁓ so to finish the story on the the multifamily, the intent was for us to move in. But in doing some research, found that ⁓ one of the tenants who was supported by the Section 8 government program that subsidized their rent were able to increase their rent significantly. That would come out of the government subsidy, not out of the tenant themselves. And it changed the calculus for us because now

they were willing, they were able to pay more than it was kind of worth to us. And so we said, look, maybe we shouldn't move in right away. And that was many, many years ago now. So we actually haven't moved into that home. We never moved in. They're still there. And it pays for that home's mortgage. It it helps the other home that we were ⁓ initially bought, it it pays against some of that as well. So overall, the real estate portfolio more than pays for itself.

Right. So that's like that's number one. And those low interest rates help tremendously with keeping the keeping the cost structure down. There are tax benefits against some of the ⁓ against some of the costs that come along with it. I'd say we haven't maximized those yet and talk about like areas where as a portfolio I could do a lot more around optimizing. There's lots of areas and it's just one of the things on very long to-do list that I just haven't gotten to yet.

⁓ and having tax advisor work with me through all the ways that we should better optimize. ⁓ there are so those are it it the fact that it pays for itself, the regenerate some income from it.

It is a source of pride as well, being homeowners in this community that we care deeply about. and ⁓ there is some work that comes along with it that we don't have property managers for it and across across any of them. And so between my wife and more more so her than I ⁓ do collect the rent and when something goes wrong, call the handyman and so on, but we have

pretty good relationship with most of the tenants. And so it makes makes it pretty easy. And it's interesting because, you know, we had AJ who you know well. He joined a last Owner Mode Summit and he got his effective tax rate down to the low teens. Excuse me. He's cool. I'll tell you he's cool. Like he has done the optimization that I have not done. Right. And so l listen to AJ on that stuff more than me on that. But but some of it is lifestyle design, right? You know, at the end of the day, to unlock the the biggest tax benefits, you have to have a real estate professional in the household. Yeah.

And the reality is not everybody wants that to do what is necessary to be considered a real estate professional, right? And seventy five seven hundred and fifty hours a year, right? And more than fifty percent of one's time. Right. So need to be able to satisfy that. Right. And and not every household w has someone in it who wants to do it or can do that. And it's okay because you're you're optimizing for what lifestyle you ultimately want to have and peace in a home. Okay. So

Thank you for diving into that because I think a lot of people could gain a lot from this idea of this is possible while you're working, intense jobs. Obviously, this was pre-kids, but putting that work in because basically, even now you're like, there's ways I can optimize it in the future, but you lock down 80% of the win, which is you have the optionality to optimize further, but you lock down permanent things that will benefit you over the long term, giving you the luxury of just sitting with that for a while.

And potentially doing some more stuff with it later. And I'll see the other thing for me, and sorry to interrupt you, Brandon, is that I enjoyed that. Like those processes, like I am a deal person. And so identifying which assets do I want to buy, how do I structure it, how do I build those relationships, that didn't feel like work for me. And when I had cycles to do it, I enjoyed doing that in my nights and weekends. I I it brought me a lot of satisfaction. That's not everybody. It's kind of an advantage that I have.

That instead of watching TV or on social media, I do like thinking about these opportunities. And so it didn't feel arduous to me at all. But you don't currently own your own residence or living in. What is this? What is the deal? How did that happen? So ⁓ COVID, ⁓ we had had a we had our first daughter in 2017. ⁓ our second daughter was coming August 2020.

So right in the beginning of COVID. And ⁓ the home that we were living in was gonna be just insufficient for four people, plus ⁓ working from home, plus ⁓ not having the opportunity to go out into the community during COVID as much. She said we need to move out of our of our current home and for a period we're just gonna rent. And we're gonna have to do this quickly. And because it's COVID, we're not gonna spend a lot of time. We can't.

We just don't have the time to buy. And we're not sure we want to buy in this market right now. We don't really want to like eight months per or seven months pregnant, don't really want to go into a lot of different homes and expose ourselves to the chances of catching COVID at that time. And so ⁓ we decided we're gonna rent for a period. And that started in July twenty twenty. So I remember this because it was a month and a half before ⁓ my daughter Issa was born. And

Rents were pretty depressed at that time, right? Landlords were not in an advantageous position. It wasn't easy to get tenants. People were wondering, is this the end of San Francisco? Is this the end of cities? We decided we're gonna stay in San Francisco at least for another year, and we rented a home. And the home was significantly larger, it had exactly what we needed, loved the neighborhood, and we locked in a great rental rate. And that was now what, six years ago.

And just stayed there. It ended up being advantageous to keep renting. And my deal loving self is constantly looking and saying, ooh, it would be great to buy a different place in San Francisco. But then when I look at just what it would cost in taxes and what it would cost in insurance, let alone everything else, it just doesn't make sense. Financially, it doesn't come close to making sense. So it's like it's better to keep renting.

Now the calculation gets a little bit more complicated of I don't have the certainty with the rent that that could change at any moment. But it helps with the relationship with the landlord and the the house that we are in. They've owned it for generations. Don't think they're particularly trying to maximize rent. We're good tenants and we have a lot of sensitivity and compassion for what it's like to be a landlord and how to make their lives easy. And so I think we're doing our best to make it comfortable for them.

And so we decided just just keep renting. And and basically kind of the the translation is you had no brainer situations before based on the terms, your conviction on the neighborhood, et cetera. If it's not, you know, I've heard someone say if it's not a hell yes, it's a no. And so for you, you're happy paying a nice rent in a nice place and owning, having exposure to real estate as an asset class in a much more, you know, ⁓ advantageous situation, which is what you've done. Okay. So

Well the I say the other thing that ⁓ that I wrestle with with all investments and really all decisions is ⁓

Again, why am I making these decisions? I just just the kind of the introspection around it. And there is a source of pride that comes with home ownership. Right. And there's a source of of of like ego fulfillment of like, I own this home, like this is my trophy. Right? Like that that brings some joy. And I I wrestle with like, it's better to rent financially and for everything, but I don't get that. And that's not a really great reason to buy a home.

Right. And like I I keep pushing back against that. it'd be so cool to own this home. Like that's not a good reason. It's kind of reflexive, but I gotta like intentionally push back on that on that orientation. Which is fair, but at the same time, you also know you own, right? Some people, they're having that conversation, but they own no real estate at all. And so the additional I just need to own some real estate, right? 'Cause obviously the prices are going up, et cetera. So we've we've done some deals together, you know, ⁓ we've invested in

in the NBA Africa together through ⁓ a mutual connection. ⁓ the Gravy Capital Syndicate brought the Harvard Business School Development, where you went to school right across the street. And hopefully for your reunion, you brought the family and pointed to that building. I own a piece of that. My point is your network, your circles have been able to bring you access to investment opportunities that many, many other people would never ever see. Right. And you can make the argument that in some cases they're not even the best

Financial investments, they're like prestige investments. They mean something, which kind of goes back to this concept we were talking about before. What are your reflections on access? How important is it? ⁓ what has been your experience in terms of just being in the center of deal flow coming through your job, through networks you're a part of? How much does that matter when it comes to deploying capital into the private markets? It is critical. And the reason it's critical is

When you have an opportunity to make an investment, especially in private markets where it's an inefficient market, like that's what private markets almost definitionally are, you have to ask yourself, why do I have this opportunity to invest? Right? If you think about money as money and investment and capital in as kind of a commodity, why is it that I am being presented this opportunity versus somebody else? And if it's being presented to me because I have a relationship with this person?

And they think that they need to raise capital and they are going to their kind of the inner part of their concentric circles of their network, and I'm part of that, that's a good reason because I have an advantage over everybody else based on that relationship. Now, if I'm getting presented an opportunity and I don't know this person and it is somewhat random, and I'm getting presented the opportunity because they just need capital.

And they're going to any source of capital that they can get. I have to ask myself, why are they having, why are they coming to me? Are they coming to me because they can't raise capital elsewhere? That could be okay if they don't have the network, if they don't have the community. Or are they coming to me because they can't raise capital elsewhere? Well, that's not a good reason. Right? And so having the inner circle where I get a ⁓

exclusive deal flow for what should be selective and exclusive opportunities is a massive advantage versus things that are ⁓ kind of generally available. Like I see people sometimes present me opportunities. Again, I was I was pre-med, so I have sometimes doctors say, hey, I saw this thing on this doctor message board ⁓ to invest in. I'm like, that's that's probably not a great investment. Right? Because if it was a great investment

They probably wouldn't be blasting it out to the world for everyone to invest in. Just generally, that's what I that's what I find. So let's let's break it down a little bit more. Let's talk about access because now we have to talk about vectors of access. Yeah. You have a relationship because of certain places you've been, platforms you've worked at, schools you've gone to. Yes. Have these relationships with people who ⁓ more often than not will have a caliber of deal flow that you would value, right? Yes.

What are give us the the vectors of access that you think matter and and if someone doesn't have the prestigious platform or the prestigious ⁓ you know, kind of school behind them, what are some other places to get, you know, what I'll consider to be, as you mentioned, the legitimate deal flow coming in, not because you're just the only option or the last available option, but because people actually, you know, are strategically looking to, you know, give you access for some reason. Yeah, I mean, you didn't ask me to say this, Brandon, but I think gravy is a

Is a great opportunity. It's being part of communities where that community it entitles one to access to deals that they wouldn't otherwise see. That the k that the the general investing public doesn't otherwise see. And there's a reason why it's being presented to this community. Because it's based on some relationship some representative of that group has, or if it's based on ⁓ the kind of the community having characteristics that people want, right? Those are

Those are the the bases if it's not based on kind of the individual network. I'm fortunate between McKinsey and Harvard Business School and Harvard Law School and tech jobs and ⁓ being in the Bay Area, those are all in Howard, those are all communities that are sources of deal flow for me. And I'm fortunate in that way. Not everybody has that, but people have to l they want to privately invest privately. They have to be able to develop those kind of communities and develop those kind of relationships so that

They are not the investor of last resort. They're the investor of first resort. You have to be an investor of first resort in order to get advantageous deals and get things that are going to return well. So let's talk a bit a little bit around, you know, you you put out a lot of bets, you know, you planted many seeds. What has been a really, really good investment you made and maybe one that that has not been a a good investment? And what have you learned? I look I look at the real estate investments and I look at how much I had to put down and the return on that capital. It's extraordinary.

It's absolutely extraordinary. Right. It's not realized yet, but even well, it means with the rent with the the cash flow and the kind of profit that I generate on it is it's pretty extraordinary. So those are those ones are are the strongest. On the others, ⁓ there are some I've made some angel investments in companies that have done well. I am you know, very lucky that I have a cousin who's like a brother to me who

⁓ is now gone into investing. He now has his own venture fund, Maple VC. And he I've invested in him. And you know, it comes back to ⁓ who do you want to invest and what do you want to believe in? I I believe thoroughly in Andre Charoo ability. And I also want to see him succeed. And I also have a vested interest in his success, let alone the financial investment. I want to see my cousin win. Right. And so that that helps a lot. And he has brought me he's brought me deals.

And when he brings me those deals, like that is proprietary deal flow that I have, right? ⁓ those are some of those have been very good investments. When you are thinking about the shorthand, because you're short on time, you're you're you're handling a lot at home, off the court, on the court, you have to process it through some filter as we talked about before. You mentioned like, can you return my capital plus more? And is there some reason that I will want to do it beyond the capital reasons? But I know, for example, Bonita Stewart.

with back ventures. ⁓ she's actually a judge in our pitch competition, which is happening as part of the Owner Mode Summit. ⁓ you invested in her fund, for example. So there's direct investments and then there's fund investments. What's your shorthand for both? For for fund investments, it is really an investment in the people. Do I believe that Bonita is going to be a powerful and successful steward of capital? I do. I believe her and Jackson and

everybody associated with that fund are very astute observers of the market, very strong ⁓ deal flow themselves, and I feel like I'm gonna get an outsized return in back. I also believe deeply in having these leaders who started the Black Angel Group having capital and deploying it in a way that is ⁓ it's not necessarily only into our community, but it's thoughtful about our community, right? And ⁓ I believe in that. So that's a

In some ways it's a kind of the double bottom line for me of good return and doing something that I care about. Right. Operator Collective is another one where it is a collective of LPs who are ⁓ Mallun Yen who started it, ⁓ focused on bringing together ⁓ exceptional operators, ⁓ especially women and minorities who historically have not participated in adventure to invest together.

And into this fund, and the in the operators then help the portfolio companies be more successful. What an elegant model. Right? And I believe in that. And the returns are also extraordinary. And then I mentioned Andre and Maple VC. Like, I'm gonna invest in that. So sometimes it's investing in people, it's investing in the philosophy behind the deal, and it's having confidence in the return. So those are the funds. And then on the direct investments, it is.

Sometimes who is bringing it to me? How much conviction do I have in that person's assessment of it? sometimes it's something that they are doing themselves. I think about a mentor of mine from very early in my career came and said, he's raising capital for an investment that he is making. Look, this guy is somebody who was pivotal to my career decades ago, completely changed the trajectory of my career and very smart. And when he came to me with this opportunity, I was like, this is a no brainer for me.

And as a no-brainer, not just out of obligation, but because I think he's going to make a very good investment. And I don't have to spend the time looking through it deeply because I trust him. That goes a long way. Goes a very long way. And if it doesn't work out, because you know, making a direct investment, sometimes it doesn't work out. It's okay because I I invested in the person I believe in. And while it may not work out this time, I don't have any regrets about supporting them.

And they're even more invested in this than I am. Like I an analogy for me is I ⁓ you know, I have a bit of a thrill seeker. And ⁓ I've done things like hang gliding in Brazil and ⁓ over over Ipanema or skydiving, but I do it when it's a tandem jump. Like I'm not jumping off the plane by myself, I'm jumping strapped to the expert who knows how to do it. And I

Yeah, there's some risk associated with this, but that person I'm jumping with is taking just as much risk as I am. And so I'm happy to do this in a tandem with the expert because and I'm and I'm giving a lot of trust into that person, but it's a lot less trust than if I were to do it ⁓ myself, right? ⁓ and so, you know, I make investments, it's similar. Like I'm jumping off the plane with them and they have just as much invested, if not more than I do, in somebody I trust. Great analogy.

All right, I'm gonna ask you two last questions. The first is a look back question. So let's go back fifteen years. If you were to look at your portfolio and kind of reflect on how you would do things differently knowing now, knowing then what you know now, what would you do differently?

I made some investments, Brandon, where I was honored that I had the opportunity to invest in a business ⁓ because I was like, this is cool. Like angel investing is what you do. When you're in tech, you wanna write a check and be an angel investor, and that sounds neat. And I it was in in things that I ⁓ you know, if I was being deeply critical of like, well, I'm not sure this is.

the best opportunity. And it wasn't in people who I knew directly and I had a deep wellspring of trust in them. There's people who either were friends of friends or they came in through some other network. And those were not great investments. Like some of them didn't work out. And when they didn't work out, I think like, what did I get out of that? ⁓ yeah, I I kind of it was a lottery ticket. I was just kind of gambling. That's that's not a good way to put my capital. I I could have put that into somebody

Who I do care about. And if it doesn't work out, like at least I bet in their dreams versus bet in some random person's dreams. Right. And so ⁓ I wouldn't have done those. Like those that that was that was a big mistake. And I I think ⁓ you know, a lot of people make that mistake, where something comes along and they say, it's I want to diversify into private cat and private investing, and here's something, and it just kind of like checks a box versus being deeply critical of it.

and kind of fact based about it, or doing it based on some kind of relational advantage that they have. So that's probably the number one mistake that I made. Okay, the next question. Last question for you. And this is horrible. You just happen to be in the epicenter of what might be the most revolutionary transformational technology of our time. It feels like B C A D, right? Before AI, after AI.

And a lot of the folks in the audience are successful, right? They have good jobs, good companies, they they've done everything right, but there's some insecurity now because, you know, the reality is the knowledge worker layer seems less important than it used to be for reasons. Yeah. And so they're thinking, what do I do? Right. And Raby Wells' idea is look, you need to have an ownership strategy. That can include private markets, it can include figuring out your entrepreneurial pathway, making some money on the side, whatever it might be.

To take control of your own destiny. You are sitting in the power, you the epicenter of the power seat of AI. You know what it can do. What would be your perspective to someone who is just trying to process what's going on? What is the true north? What should you know their philosophy be if they're looking to be on the right side of this thing? And that can be a private market, you know, ⁓ you know, idea or it can be a personal, how do you manage your life idea? But just give us some game in terms of what you're seeing.

What are some moves? What would you advise people to be thinking about and doing? I think the the number one thing is nobody knows how this is going to play out. That I do get to sit in the room with the leaders of these companies, the people who should be able to see the future and around all the corners. We're moving so fast right now that it's impossible to predict what's going to happen three months from now, let alone three years from now. And

The best thing that people can do in to future proof themselves and be in a position to win in this era is to engage deeply. Engage thoroughly, be unafraid, and just be brave enough to just jump right in, use all the tools, understand the workflows and how they can change, understand what this can mean right now for how you work, and being able to track it is I think the most important thing. The if if you're

People are doing that, then they will have the insight around how it's shaking out to be able to make decisions for themselves. If people are making decisions based on reading what's happening in the news alone without actually using the tools, then it's hard for them to apply it in their own lives. It's hard for them to think about what what does ownership look like in the future if you want to start a company, if you don't know how to use the tools to start a company. Right? I I

I met with a venture investor friend of mine, and he was telling me about a friend of his who has a billion-dollar company. It actually ended up being written about in New York Times. Billion dollar plus revenue a year, a single individual. Right? And they were able to do it because they harnessed all the tools in very creative and very powerful ways. Anyone can do this, but you just need to be able to engage deeply. And what I hear a lot of people say is.

I'm afraid of what AI is going to do. Or I think it's going to take my job. Well, how do you prevent that? You actually make yourself more valuable and more powerful by using the tools for your own purposes. Like you become the superhero in AI versus the AI coming and the robots taking over. You control the robots yourself. And everyone has that power has that power. I love that because it it kind of is a philosophy that encompasses.

the corporate risk piece, but also even on the investor side. You're basically saying you'll be a better investor in this movement if you're actually using the tools and understand what the dynamics are from a ground level versus just kind of hearing the buzz and the noise and and kind of falling in line with, you know, kind of whatever the narrative is that's being spun. Any last words you would give for folks as, you know, we're all about the earner to owner movement before you, you know, what would you leave folks with as as parting words? I ⁓

Question. ⁓

From a from a owner mentality, I think people should be ⁓ com and from a capital investment, understand how much capital you want to put at risk. And so don't invest, you go get upside down when you put more capital in than you can afford to get out. And remember the time horizons around these. And the time horizons can be long and they can be illiquid. But when you take that into account, don't be, don't be afraid.

to to jump in on something that you feel like personal conviction about. And there's some learnings. You might get it wrong the first time. I'll give the examples where I I did it wrong with my first few Angel Investments. But jump in and get started. You need to that occurred to people. Get in that thank you to the audience. Let's give Andrew a round of virtual applause. you you definitely shared a widespread range of of very relatable circumstances that many of the folks in the audience are, you know, are dealing with now. So thank you. We're really appreciate you joining and

and kind of opening up and letting us know what your journey's been and congratulations on your success as, you know, as you're in a seat that is going to in many ways define the future of humanity. So ⁓ you know, with that being said, we're glad that we have someone like you kind of in this in this seat, you know, and bringing perspective that is going to benefit, you know, everyone ⁓ in a in a time where it seems like a lot of the power is concentrated, you know, with a few. So with that, thank you, Andrew. Appreciate you, my man. we'll have you back for round two at a at a later point.

Always good to chat, Brandon. All right, take