Spencer Rascoff — 75 & Sunny

Wednesday, September 28, 2022
Spencer shares all about 75 & Sunny–how he is trying to avoid putting dot.LA behind a paywall, how Pacaso is not at all like a timeshare, and how he’s reinvesting back into startups in LA and beyond.


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Spencer Rascoff is with me today. Spencer is the co-founder of Pacaso and DotLA. He’s a serial entrepreneur who also co-founded Zillow and Hotwire, and was the CEO of Zillow for a decade. We probably can not cover it all today, but we will definitely talk about his fund, 75 & Sunny. 

Spencer- Thank you so much for coming on the podcast.

Minnie. I super excited to be here. 

Let’s start with 75 & Sunny because I do think it’s the best name ever.  I live in Pasadena where it’s like 85 and sunny, but.

Yeah, I live closer to the ocean where it’s 75 degrees. I mean, 15 years in Seattle and I love Seattle I, you know, made a lot of great friends there and, grew a lot personally and professionally there. But when I moved back home to LA a couple of years ago and started investing more intentionally, I decided to pay an ode to the weather in LA and named it 75 and sunny.

I love it. so you are at 75 and sunny. you’re incubating companies. You’re also investing in companies. I’m fascinated by, by both, but I thought maybe we’d start with the, the companies are.

Sure. Yeah. I mean, this is what I get most excited about, I mean, I’m at the stage of my career where I’m trying to be a coach and a mentor and an advisor. I I’m, longer can be CEO of something of a specialist startup, which takes such singular focus and time and attention to energy. So I have a lot of ideas.

And what I’m doing is I’m finding great partners to work with, to co-found these companies. And I’ve got five underway so far and more on the way. And what my studio does is it comes up with these ideas. It finds great co-founders it puts in seed capital it iterates and innovate, surround that early product market fit

And then we typically raise capital with the co-founders and start these companies. So the first one that I did was. Which was sort of foundational for, for what I’m trying to accomplish. Like when I’m focused on in this stage of my career is, is to a large extent trying to help LA tech achieve its full potential.

 so.la, we raised a $4 million seed round from the LA tech community launched I guess, two years ago.

And it’s got great traffic. It’s got great brand awareness. It’s fulfilling its mission of telling people what’s happening here in LA tech and putting on events and bringing the community together. And I’m really excited about it and proud of it. anything about the LA tech community that surprised you or that you’ve learned doing.la?

So, yeah, there were a couple of things I was unsure of. when we started the first was would anybody care? And we’ve proven that people do care. And we have hundreds of thousands of monthly unique visitors, So, you know, that question has been answered. I think the other thing I would point out is just how collaborative and friendly.

Amiable the LA tech community has been,It’s sunny.


I mean, I think we all have a sense that sort of what’s good for one is good for all It feels very much like we’re all trying to lift each other up and, and that’s fun. that’s great. I mean, that’s a, a more fun environment to be operating in.

I guess the other surprise was just how many venture capitalists there are here. And I mean, you, you know, this, this podcast is a perfect example. I think you told me you’ve been doing it weekly for a couple of years. Right?

So most. Most people think maybe they’re two or three venture firms in LA and that is just not true at all.

Yeah, anything else? I know you’ve got a, sort of a journalism background. and do you think about sort of the future of news and what business models are gonna survive?

I do I think about it a lot you know, the original thinking for.la was that if we built a large enough audience and an important enough brand covering LA tech, that the business model could be focused on events and events are totally on mission because it brings people together.

And they also monetize pretty well. And, and then COVID happened. but to answer your question about business models, we are trying like hack at.la to not have a paywall. You know, most of these new services have put their content behind a paywall And. That’s pretty counter to the mission of.la. The mission of.la has tried to get everybody that’s interested in LA tech to read it. Like I hope that we can build a business based on events and sponsorships that still allows for editorial independence.

And not having to charge readers for content, but, you know, that’s an open question and meanwhile, we’re swimming upstream a little bit at.la where every other new service seems to be moving towards putting their content behind a paywall or moving towards a pay sub stack, email subscription product, which also we’ve shied away from.

It’s a challenge. Uh, do you want to talk about Picasso? Sure. Yeah. I mean, one of the other companies that I incubated and worked on and started a company called Picasso, it is a platform for letting you buy a portion of a second home. I started this with an amazing co-founder named Austin, Alison, who did another startup called dot loop, which is a low acquired.

And, Austin and I were both lucky. And fortunate enough to have second homes. And it has had a huge impact on my life and my family’s life and my friend’s life. And we started talking about utilization and the sharing economy.

And. Democratization of things that wealthy people have access to. And most other people don’t. And we hit upon this idea of co-ownership. And so Picasso allows one to democratize ownership of second home through co-ownership. So you own a portion of, of a Picasso with others. we’re now growing very, very quickly.

We raised our series C recently from SoftBank, and there are a lot of great LA investors. Sarah, is I on a, from global founders, capital Brett brewer from cross-cut Dana settle from Greycroft. let’s see Kelly for moonshots. Um, I fear I might be forgetting others, and that actually you’ll appreciate this many when we started the.

What else? And I started the company and we were discussing, where should we put the company? and we decided to make it an intentionally distributed workforce. This was pre COVID. And I said, you know, that’s, that’s fine. But, when we go to. I have to have LA venture be well-represented on this cap table. Like if I’m positioning myself as like, one of the leaders in LA tech, I got to have LA tech, front and center.

And so, that is How it played out.

and how did Sarah and that bleeding that first round?

Yeah. so through.la, I met Sarah and her husband Christian, and then got to know GFC. And then Brett brewer from cross-cut actually, Brett was my daughter’s, T-ball coach, And so that’s where I first met Brett was with socially on the softball field and, uh, Dana I’ve settled at Greycroft.

I’ve known for a very long time. So the, the series a was led by. And by Maveron cross cut and GFC. And then the series B was led by Dennis settle at Greycroft, and then the series C was led by SoftBank.

Yeah. And it’s the fastest unicorn ever, I think.

Yeah. I mean it, yes, it’s a little eye-rolling

Oh, but come on. It’s

and boastful, but yes, Proven that we can raise money. But yes, it, we, raised a lot at a high price


Hopefully it won’t look like a high price.

I liked, liked that you can be, I, I think most of us in the founder position would love to be the fastest unicorns ever. So, and you know, I think that it’s quite different than a timeshare, but maybe you could just explain tic, which is

something I know coming from San Francisco.


So, so timeshare, you know, we try like heck at epic also to not use the word timeshare. Cause it’s like the verboten word in, in the industry for good reason. timeshares have a well-deserved bad reputation because it’s very hard to get out from them and because the. It is just not that great for consumers.

I mean, a timeshare is basically you’re paying a lot of money up front and then an annual liability going forward for the right to stay at a hotel at a certain price is basically what a timeshare is and what Picasso is, is very different. You’re actually buying a portion of an exact, a specific second home.

So it’s a, single family home. It’s not a hotel type product. the way I think about Picasso is it’s much more like the, do it yourself kind of hacky way of two or three families getting together and buying that place in Tahoe together which has always happened.

And it’s actually a, good kind of framework for startup ideas. I think which. Things that people have found a DIY way to do, but haven’t been productized. because it’s doing the same sort of thing.

People at families have always gotten together and bought homes on their own. Mortgage finance, like how do you actually get a mortgage if you own a quarter of a house? scheduling is almost impossible to do. If you’re doing it on your own, cap ex taxes, how do you maintain the home? how do you govern the co-ownership of the home?

These are things that families struggle with and when friends buy homes together, it usually ends friendships. okay. So first off it’s like an asset versus a liability, I


interesting point. Um, and I can, I could sell my one-eighth.

you can. Yeah. I mean, here’s a good thought experiment to think about how we’re not a timeshare is if Picasso were to go out of business. Yeah. Knock on wood. That it doesn’t happen. But you’d be fine. You would still own that eighth of a house in Napa or Tahoe or a quarter of a house in Aspen is like, we don’t have to exist.

Whereas you know, if you own the Marriott vacation club, timeshare in Orlando and Marriott goes out of business, you’re done. Like you don’t own anything because that thing doesn’t exist anymore.

so yeah, you can resell your Picasso. We’ve had lots of resales already. Usually people upgrading to some other home, you know, you can resell it to the other owners or just is on the open market, and it gets listed in the MLS, Picasso makes money through the fractionalization.

So the way it works is we’ll find a home in, let’s say Aspen for $6 million. We’ll buy that whole home. We’ll fractionalize it into say, or recorders, and we’ll mark it up 10 to 20% on the resale. And then we do the property management going forward, and it’s pretty turnkey for.

No, it’s very appealing. except, okay. Touch a little bit. There’s been some pushback. Do you think that’s because people always have pushed back or.

Yeah. So, so there has been some pushback, you know, in some communities, really a very, very small number of people, but smaller people can make can, can look loud, And, you know, the, pushback mostly comes from people that don’t understand the model and they can fuse or.


Picasso with Airbnb, with short-term rental people. Don’t like having short term rental properties next door because they sometimes become party houses and transient people are coming and going. and they treat it like a rental because those are not like that because those are treated like an owned home because they are And so most of the pushback has come from people that just don’t understand it and part of the pushback is just because innovation is hard and people aren’t used to it, you know, nobody was sure what to make of the scooter companies initially, or the ride sharing companies initially, or some of these other sharing economy companies.

And as time passes and everybody realizes that the world hasn’t come to an end because there are a couple of scooters parked here or there, and yeah, maybe they. Parked in, you know, a dedicated area and maybe people should wear helmets, et cetera. But like it’s okay.

Like the world is going to still spin. I think that is generally what happens when innovations come, especially into local communities,

I mean, it was a question I was going to ask you later, but how do you of go through being a very CEO and having a thick skin when people criticize you?

It’s hard. I actually hate it. Um, to be honest, it’s like the, one of the, it happens a lot less today than it used to when I was running Zilla and I was running Zillow. I’d get, you?

know, angry tweets all the time from real estate agents or people unhappy with there’s estimates. Nasty emails and, some difficult situations, somebody, you know, lost their home for a reason, some reason other than they were blaming Zillow for it or what I mean tough stuff.

And it would really weigh on me a lot and it still happens a little bit, actually just the other day on Twitter, for example, somebody tweeted to me that, they bought their vacation on Hotwire, which was a startup that I, I started hot or 20, 23 years ago. And we sold it 19 years ago. So I have not worked at this company in 19 years.

And this person was complaining to me that, you know how our stole $400 from them. And can I do anything about it? And it totally ruined my day. I can’t do anything about it. I replied to the tweet, I copied it at Hotwire. I’m like, I’m so Sorry.

I haven’t worked here for 20 years. I am sure how are, will do their best, you know, CC at Hotwire or whatever.

So, so yeah, it does actually weigh on me quite a bit. and, it’s, you know, but it comes with the territory.

and you’re quite public. I mean, you’re still out there, right? Like you’re


a lot. You’re on my podcast, Spencer thing.

I, Yeah.

I am public. and I’m very engaged in social media and very accessible to people. And, you know, that, that makes you a bit of a target.


um, know, even on this, on the Picasso community pushback, you know, some of those people reach out to me on social media and express their displeasure with Picasa one way or another.

And again, it, it, Personally, it does weigh on me. Like I internalize it. A lot of people don’t care. A lot of people are like, ah, whatever, who cares, you know?


Yeah, Um, people are going to say nasty stuff. Who cares? I, uh, I do care. I, I like to be liked and that’s hard for me

Yeah, me too. but okay. So let me bring out one more and then we’re going to definitely talk about investing, but recon food. I got kind of into that,

I saw you. I saw you on it. Yeah. Yeah. so reconn food is another company that’s 75 and sunny labs incubated. I’m super passionate about it. recon food is essentially Instagram for food. And so my, thinking is that. Food is a big enough category, both home cooking and food at restaurants. And it’s a very, very social category that it deserves a dedicated social network just for food.

And I started this with my 16 year old daughter during COVID because during quarantine, we were cooking a lot as a family and she was using social media all the time as the teenagers do. And as all people do really. It was bumming her out. I mean, all the Facebook disclosures that we’ve been reading about the last couple of weeks, like she was living that real time, like every teenager does, she said to me yesterday, she’s like, I mean, are we really like surprised that there was data at Facebook that said like, it. makes teenage girls feel like crap, like any teenage girl can tell you that, like, that’s not news to anybody.

 Like, duh. And so that was kind of her reaction during COVID was social media has got me down. Cooking has built me up. Like, let’s try to turn this into a thing. And so idea is to reconnect with friends and family over food.

So recon food and

It pulls photos out of your camera roll using computer vision to identify food photos. And so you can relive your food memories and say like, oh, I forgot about that great meal. I had three years ago in New York or wherever because We plot your photos on a map. So you can see, you know, all the meals that I’ve eaten and where I’ve eaten them. So it’s a really fun.

And, um, it’s been, uh, a ton of fun to do it with my daughter

Well, this is what I was going to social media, bringing us all down. are you friends with Mike Jones?

uh, we, I mean, yes. Uh, we don’t like hang out all the time, but yes, of course everyone knows Mike Jones?

he was just one of, he was one of,

my guests who talked a lot about social media. I mean,


of my space


do you have kind of thoughts on how we can on just social networks and what works and how you can


empathy in them.

Yeah, well, I mean, there are a lot of product decisions. I should, I tweeted about one the other day that we made at recon that are trying to keep it a healthier place. Like for example, we don’t show the number of likes. So I’ll post a meal that I cooked and it’ll say, You know, this person, this person and this person and others liked it and I can click on it and it lists all the people, but it doesn’t count them.

And that’s a tiny little product decision, which, you know, it’s like, if it, if it counted and it said six people like it, I would feel bad. I’d be like, why only six? Why not 12? My last thing I cooked, 12 people liked it. And so removing counts for likes is a dumb little product thing, which you probably don’t think very much about as a feature, but it matters.

I think the verticalization or the unbundling of social media. We’ll be able to play a large part in solving some of these issues because in these dedicated communities, they tend to be more positive environments focused on just that vertical. What do I mean, I mean, all trails for hiking or, Peloton for cycling.

I mean, Peloton is a social network essentially, right? It’s it has gamification, it has leaderboards and league tables. and of course it’s connected to the hardware, but you don’t even need the hardware anymore. It’s basically an athletic social network, but it’s all about, lifting you up and, connecting with other people over the shared interest in cycling and exercise.

That’s what recons trying to do, shared interest in food. And so I think these dedicated vertical, specific communities tend to skew more positive and full of affirmation. And also the feature sets that they build can be more focused on that vertical, like Strava, allowing you to post an actual map of your run.

Like Instagram’s never going to do that because of course, some people say on Instagram, like Iran and here’s a photo of my room. But it’s a vertical specific feature that a vertical specific social network and built the horizontal social networks have become kind of cesspools of humanity, where everyone’s yelling and screaming about everything.

There’s all this misinformation, The algorithms are sending us down. These black holes, the vertical specific social networks, I think. there’s hope there and, um, personally investing in a bunch of them for that reason.

what about Facebook becoming a metaverse company?

It’s a big news today, Metta. fascinating. Right? I mean, totally fascinating. I’m not quite sure what to make of it. I personally, I’m kind of ambivalent about it. nobody asked me to vote, but if I were voting, I’m not sure I would vote in favor of this future where we’re all kind of living virtually in these online kind of 3d AR communities.

Like, someone told me the other day, I need that they’re totally convinced the 20 years from now, most people will never meet in person at all that like, they’re going to have all of these friendships, like in these games and on zoom or whatever.

And like the idea of actually meeting somebody in person, shaking their hand, looking them in the eye and real life is like going to be so quaint. And I fear they might be right.


And that’s also super creepy and I don’t really know how I feel about it, We’re investing in all these companies where


meet with them every week for a year. And then I meet them in person for the first time. I’m like, oh,

Isn’t that interesting.

I mean, Picasso is a good example of a 150 employees. We’re all remote. We just got together in person for our first ever all company, IRL meeting and you know what surprised me most. I couldn’t even remember who I had met in person and who I had. I just like, like you and I’ve met in person, I think what once. right.

But whenever we see each other in person next I w like our brains will remember this conversation almost as an in-person interaction, even though it’s not a, it’s all very strange. can see the future. I’m not trying to like it.

well, but these vertical ones are an interesting response. I mean, the ones you all named are all these physical ones. Tell me about what you’re investing in. let me

Yeah. Okay. So, so, so I’m invested, I pulled some stats for you. So, so 75 and sunny, which to be clear is not really a venture fund. It’s just my own capital. you know, a small team that’s just, investing ourselves. we’ve done 42 investments year to date. 30% of them. So 16 have been in.

So it’s usually pre-seed seed or series a, Heavily over-indexing on LA. the categories are about a third or PropTech where I have a lot of deal flow from my Zillow experience about a third or consumer.

and then about 20% are FinTech. And then future of work also is an area that I’m super passionate about. there’s some kind of off the wall stuff like universal hydrogen. That’s trying to convert airplanes fuel you know, from gasoline to hydrogen.

Relativity space is one of my bigger investments. That’s an LA company that you probably know about, which is 3d printing rockets. The nice thing about being a solo GP with no LPs is it’s kind of whatever I want. It’s like, whatever I am interested in, or, you know, there’s you know, me and one other investment professional will Chockley And we invest in what we think is good.

And when’s the right time to come you. And should entrepreneurs have a term sheet in hand? yeah, the most typical situation would be, like somebody has, is, is raising a seed round, Uh, couple of other angels are involved. Maybe there’s a seed stage fund. Like you guys like 10, 1 10 And 75 and sunny would look to do like a 100,000 to $500,000.

A lot of my deal flow comes from the venture firms themselves. I’m an LP about 50 venture funds. And um, you know, spencer@seventyfiveandsunday.vc, or you can tweet at me or whatever. if you want to talk to us about.

And how about will is well also a good person to, again,

We’ll as the, the right person, that pretty much everything gets bumped to, well, you can start with them or you can go to me and then you get to him.

Um, do you want to talk about any of the themes?

Sure. Yeah.

there, I mean, there’s so many, things I’m excited about, the untethering of people from their offices.

And it has huge implications on everything. And by the way, once self-driving cars entered the mainstream, then it’s like, holy cow, all of a sudden, I don’t need to pay a crazy price to live in Santa Monica, if I only need to go to my office in century city, or maybe I don’t even have an office, you know, once a month therefore I can live in Calabasas or Santa Barbara or wherever.

And if it’s a self-driving car that drives me from Santa Barbara to Santa Monica, you know, once a week, then really who cares where I am. I know it doesn’t bother me if it’s a two hour drive So implications, obviously on real estate, software for, employee engagement.

So I mean, I see it on the bigger companies that I’m involved in. They’re saving tons of money by reducing their commercial real estate footprint. You know, Zillow, for example, when I was there, we had a 15 floors of Zillow tower, which was a 40 story, high rise in downtown Seattle.

We had thousands of employees in this one building. They have basically abandoned that building. They switched to entirely remote 5,000 employees and, you know, they’re dramatically reducing that footprint. So a company like Zillow now is going to be saving tens of millions, maybe a hundred million. On office space.

But what they’re going to do is they’re going to turn around and buy software to drive employee engagement. So, one of my companies in LA company from Techstars LA actually, you mentioned Anna Barber, before we started this podcast and as a friend of mine and, and accompany that she introduced me to you, that she was mentoring and Techstars LA is called Kona or psych insights is the parent company.

But Kona is a great example, LA. That’s trying to create a software for employee empathy through slack and other communication channels. So the insight here is that when we worked in an office in person, I would walk by your desk and I could see you were having a crappy day because your body language was just sort of emoting it.But we’re all at home nowAnd so, cone is trying to solve that problem by basically coaching you on communication real time.Anyway, the point is. Companies are going to invest a lot in this type of stuff.

So there’s going to be a lot of software around employee engagement and play retention, which I think the wallets are wide open from companies for that type of software, because they’re saving so much money on reduced off.

Um, picking up on Kona and you talked about executive coach and you’ve done all this work thought around leadership. Like I’m curious, are there certain ways you approach coaching, leadership questions? You ask anything like that?

Yeah. I mean, my management style is this servant leadership concept where the manager works for the direct report, not the other way around and where that came from was being a manager at a very young age. When we started hot wire, I was 23. And I had people in their forties and fifties, which at the time seemed impossibly old.

You know, now I’m 46. It doesn’t seem so old anymore. But at the time I remember they thought, oh, this person’s ancient. Um, and I remember thinking to myself, how can I possibly manage this 45 year old I’m 23? Like, what do I know that could possibly help them, you know, teach them anything

And. The answer is you don’t tell them what to do. You help them succeed at their job. You clear their roadblocks. The role of the manager is to make their direct report more successful. It’s to say to the direct port, what can I do to help you be successful? What can I do to, you know, to, to help you do your job?

I work for you. A great one-on-one is one where the manager walks out with it to do lists.

So that’s my management philosophy. That’s How, I coach others to manage.

How about anything that stands out for you around scaling an organization and leading as you scale?

Yeah. So the, one of the hardest things to do. In a scaling company is to change the way that you communicate as the company scales. So, it’s two employees, it’s 10 employees, 20 employees, a hundred, like everything changes at each of those stages and you have to change to, you know, it, was totally appropriate early on. Of course you should attend. Product review, you should attend. you know, when the head of customer care provides customer insights, like, of course you need to be there.

As the company scales, you need to clear those things off your calendar and start changing everything about your communication style and your time. And that’s hard to do that requires real intentionality. and it’s hard because there’s a lot of inertia on your calendar

And so I always tried to force myself and I always suggest to people that I mentor to try to do that every three to six months to say okay, what job. Do I have for the next six or 12 months? Like, okay, I’m running 80 person or that closed at series a and needs to accomplish these three things for the next year. If I started my job today from a blank slate and I walked into that role, what would I do? How would I organize my time? My schedule, my direct reports, my org chart, my communication channels,

Yeah, no, there’s a lot of meetings or whatever that are legacy. I like that exercise a lot.

declare calendar bankruptcy every six or 12 months, and just like cancel every recurring meeting and then start over. because chances are, you’re attending a lot of things that you shouldn’t actually be attending anymore.

I think I do that with my inbox every night. Um, how about really? you have this amazing podcast. You’ve had amazing guests on your podcasts. I mean, this is a hard one. I get asked this, which is like, what have you learned from your guests? you know, are there guests and lessons that certain people have the, just have changed your mind?

 I mean, I think I started my podcast for similar reason to why you started yours, which was. I want it to meet a lot of cool people.

And I was like, you know, how do I get 15 minutes with Sheryl Sandberg? Like, I know I’ll have run a podcast. And it grew into something which was again, sort of like this conversation, like, how do I let people be a fly on the wall when two founders or two investors are just chatting about stuff?

And I think the common theme across a lot of these people that I’ve talked to, whether it was a four-star general or a CEO of a big company or, whatever is, creating a mission orientation where people feel that their work is part of something bigger than themselves. And, you know, give you a quick story, from an LA company. Um, oh gosh, I think it was Workpop Yeah.

And I remember I was talking to the founder of worktop and work pop was a. software platform to help. kind of lower wage workers with scheduling. So like if you work at burger king, like how do you know which shift is yours? the point is it’s not a particularly sexy software. It’s not like, crazy cool consumer type stuff. And I remember. when I was talking with the CEO about it. I kind of gave him that reaction, like, yeah, this is kind of like boring stuff. And he’s like, no, you don’t understand, like, this is world changing because know, if you’re like a single person.

And you’re trying to figure out like how to balance your life and pick this kid up from school and take your sick mom to the doctor. And you got to know, you know, what time am I supposed to show up at that? , or McDonald’s or whatever, like, this is, it is really, really impactful in their lives.

And he was just describing this with such passion. And I was like, wow. Okay, there you go. Like, ding, ding, ding. A-plus like here’s somebody who. You know, convinced himself and probably convinced his employees that their work is like God’s work so whether, you know, you’re trying to 3d print rockets and send cool stuff to space like relativity space or you’re making, scheduling software Kind of doesn’t matter. You just ideally want to try to create a mission orientation and then you can get people to do their best work because they feel connected to something bigger than themselves.

 I love it. you made me think there was a question that came from our listeners, Christian Guzman, Spencer what his mission is, or like, where is he going? Like, you’ve got multiple specs. We’re not covering everything you’re doing. are you going with your life? Spencer.

Well, where am I going with my life? Let’s see. That’s a good question. I don’t know. I’m not sure I can answer that. I’m still trying to figure it out. I guess I’ll say a couple of things. Number one, I’m at the stage of my career where I’m trying to mentor and coach I’m like I, as I said, I don’t want to be on the field anymore.

That’s a younger person’s thing because it just requires such intensity. When it’s 75 and sunny ventures, that’s putting a couple hundred thousand dollars into an early stage startup.

I’m excited to coach and mentor that founder. If it’s my speck, that’s taking public a big company. I’m involved in that way and I’m coaching and mentoring that founder that way. Or it’s a company I’m incubating. I like Picasso and I’m an active chairperson and co-founder, it doesn’t really matter.

It’s all kind of the same. It’s all coaching and training or a class. Like I teach a course at Harvard on entrepreneurship, where we talk about all these, these topics. in terms of like the unifying theme of most of my investing and, stuff, I would say it’s democratization. It’s like take something that was previously pretty inaccessible to most people. And make it accessible to a lot more people. So Hotwire was like, travel discounts were kind of like hard to find and they were sort of in the shadows and bring them online and make them widely available.

Zillow was information about real estate was in county courthouses in the MLS, which only agents had access to in these secret industry databases. Let’s try to democratize access to real estate information, Picasso. Let’s take something that really only small portion of people can have, which is a second home.

It’s life enriching though. So let’s try to democratize access to it and I could go on and on, but like generally that’s, that’s a theme I, I get fired up about. I think that’s cool.

especially with like the stratification of society. I feel like there’s such an opportunity to democratize things that the bottom half of society really is not getting access to.

Yeah, it’s it’s, uh, I hadn’t actually thought about that. That’s a great point. It’s like, it’s another approach to fairness, I guess like one approach is, to just like spread wealth, equally or nearly equally another is to try democratize access to the things that, rich folks have that others don’t.

or it’s not just rich, always. It’s it’s. In the know, you know, a lot of this stuff is actually information. It’s not even, goodies per se. It’s just like, content data, information, even like.la is kind of in this. It’s really, how do you democratize access to that information? So that like a huge swath of people interested in that topic, know the things that you and I already know. you know, like I was just reading the article about what you were quoted in about, is LA in a venture bubble, right.

Evaluation mobile. And you know, you’re recording that article and I was reading it, thinking like, Yeah, I get this, I get this, like, I think this, I agree with this. I disagree that whatever, but like, but like that’s a good example of an article that’s trying to democratize access to those insights.

Yeah, I read it every night. Um, eh, let’s talk about your Harvard course. So that’s kind of an interesting, like let’s democratize that information.

what are the points you’re trying to get

So I taught, a course at Harvard business school to MBAs pre COVID. So it was a 12 week course called managing tech ventures, which was basically how to run a big tech company. And it was a great course, super fun to teach MBAs, but I’ve always wanted to teach undergrads because, I wanted to go upstream from that and try to convince more younger people to enter the field of entrepreneurial-ism and like take more risks with their life and their career.

So I’m super excited. This winter, I’m going to be teaching a course at Harvard college. Is going to, I, I’m not even sure what’s called data. It’s going to be like from idea to exit or something like that. But it’s basically like, how do you start with an idea? How do you do a startup? And then how do you take it to where it needs to go?

So the first class will be, how do you brainstorm an idea? Like what makes a good idea? How do you assess market size? How do you figure out if this is a feature or a company? The next class will be. How do you get it started? How do you hire the original team?

How do you actually launch the product? How do you raise a seed round

So from an idea to an exit, like that’s what I’m trying to teach, and it’s going to be a bit of an inch deep and a mile wide. I mean, I’m not going to obviously teach everything you need to know about. And I certainly don’t know everything there is know about these topics anyway, but the idea is to try.

Teach it, 18 year old, like some of the basic skills and knowledge base, that they’re enticed to, to hopefully enter this field. you know, I went to Harvard, undergrad, and I wish they had this course when I was there.

Um, you know, in the absence of this course or courses like this, lot of really smart people end up with kind of Monday.

Career choices. You know, they, they go, they don’t end up going into fields of innovation and entrepreneurship because they don’t know what else to do. So they kind of fall into wherever, whoever recruits on campus.

Totally one of my questions. Okay. My main two questions for you, Spencer, we’re going to be essentially, how does someone get in your orbit? Because I think people wanna know that and you’ve given your email address. So that’s, that, that has been answered. The second was like how to become you. Like to Harvard Westlake.

A lot of kids here went to Harvard Westlake. but they don’t all become you. Right. And like, so the question is, is it, they need to take more risks. Is that what, one of the, like.

Um, I, I mean, yeah, I, I will say this. I think people, especially high achieving like.

high schoolers or college students, they tend to. shy away from risk because they overstate the amount of risk associated with something. And this is the whole, I mean, growth mindset is a great book. It’s like I encourage people to read it.

It’s a, it’s really a parenting book about making sure that your high achieving kids don’t, become so addicted to straight A’s that they fail to take risks. and so I think people tend to overstate risk and that holds them back in terms of, you know, You know how to be me sounds so arrogant.

I can’t even answer it that way, but I’ll say this, like, I’ve been very lucky, very fortunate to surround myself with great people, like all along the way. That’s the most important thing is surrounding yourself with people. that You learn from that you are motivated by, that bring out the best in you that complement your skills.

Like that’s, that’s everything. don’t optimize for compensation early in your career optimized for, development and for learning and mentorship and find ways to put yourself in situations that you’re gonna learn.

And you’ve done that well, and I sometimes think about why don’t I do that? Like, why don’t I call Cheryl Sandberg and ask her on my podcast or something?you know, and I sometimes wonder what holds people back from putting themselves in those situations. I think there’s fear, I guess.

Yeah. I mean, I see it now as a parent, I guess.

with three kids. I think a lot of the, like a culture of positive reinforcement is around conforming. And it’s like, you know, learn, acts, prove, you know, X, get this pat on the head, get a cookie, basically. But, um, I think that’s where some of it comes from is people overstating risk because they just, are used to achievement. And I mean, was. Harvard-Westlake Harvard college and then went to Goldman Sachs and it’s like, I’m like, oh, I’m done. Like, I made it like, everything is great. Like if I just get my head down, I’ll end up like a rich investment banker, which I would have, but I also would have been miserable. And, so for me personally, what helped with every big career decision along the way was my wife was who I’ve been with since we were 17 And every time I switched jobs or switch directions, it was because she told me I was unhappy. She’s like, yeah, you’re a Goldman Sachs, but like, you’re not doing what you want to do.

You should move to something else. And I went into private equity and do that. Less than a year. And she’s like, you’re super unhappy. Now, actually you should do a startup. and that to me has made all the difference.

Okay. One more question. Your wife or your friends, how would they describe you?

Um, I think they would say I’m pretty intense. but I’m, empathetic. I’m really organized efficient. Um, I don’t think that’s very funny. I wish That I’d like, I wish I were fun here. I don’t think I’m That funny

That was a funny comment, at least.

well, I’m self-aware um, I guess, but I don’t think I’m funny. uh, you know, good coach, a great parent and, um, yeah, person.

well, nice person. Great


it. Nice person. be called worse things.

Yeah. Well, sends a thank you so much for coming on the podcast. it’s really inspiring what you’ve, what you’ve achieved.

You were very, very, kind many thank you for the chat and thank you for doing what you do for the other tech community and beyond.