That Portfolio Life

0:04This week on Great Chat, we discuss living a portfolio life. What is it? Pros and cons and how to make the transition. I'm Helen. And this week I'm joined by Ashley, my fellow portfolio life person. Great chat is brought to you by Mercury, the fintech used by entrepreneurs through every stage of company building. We use Mercury to run this podcast and love recommending it to other founders and fund managers. Try it for yourself. Visit mercury.com to join over 200 ,000 entrepreneurs who use Mercury to make managing their money unbelievably simple. hello two person format this week i saw a photo and i don't know if it was ai generated or real of a tinder subway ad that said may i meet you and then like you know dash bill ackman so i know we were talking about how this was a very low tam initially um and maybe we should like back up and give some context in case in case the TAM is still moderately sized.

1:07Billionaire investor Bill Ackman decided to do his part to help the youth of America and specifically young men be better able to meet women in the real world. And he shared a story of meeting his second wife after splitting from his first. It was actually kind of a weird story. I don't know, Helen, if you read it. It was something about how, like, his friend wanted to introduce them, but she was, like, with someone else. Anyways, but the. He's very good at, like, really getting his, getting the$8 a month, like, the ROI on that by, like, just really taking up all of the characters. Oh, yeah, yeah.

1:47So Bill Ackman's also, he's famous for many things at this point, but he's also, you know, now famous for, like, writing really, really long tweets. I think that's like probably the only way he is known to younger generations. Yeah. Like he's just like a Twitter, a Twitter, uh, uh, poster, um, at this point. Because everyone has their own theory as to why, like, you know, marriage is less and less desirable for, for young people. Right. And, um, you can blame anything. And so at least he offered a solution, even if it is a silly one or, you know, whatever you might think of it. it's bill ackman scott galloway and joy jordan peterson who are the spiritual guides for young men aren't we lucky um yeah it's funny i think and it's not just marriage it's like dating and sex and uh all the things that all the things are in decline yeah and i think the hypothesis like most people agree tend to agree that um just being glued to our phones and addicted to you know, our digital life, um, you know, whether that's gaming or just spending too much time on the internet or YouTube or whatever, like is a contributing factor to this.

3:02So I think the, the may I meet you is this sort of like IRL, right? Like just sort of push towards meeting in real life. And I don't know, maybe sex will happen as a result at the line. We'll see how long the line is from may I meet you to, to that end state. All right. So Bill Adman's back. Jeff Bezos is also back. It's a good week for the billionaire men. Well, Ashley, did you get any questions from your LPs? Like, why didn't you see this deal? This is so funny because I saw a tweet along those lines. Like, I bet all the LPs are asking and like GPs are scrambling to figure out how to rebuild their sourcing.

3:43I'm like, man, my LPs would be if I invested. What were the terms of this? It was like$6 billion at who knows what valuation. This is not my entry level. Do you think that that's still considered a seed? Will Peter Walker at Carta be showing the average seed raises and valuations and account for this deal? Yeah. I mean, it feels like the stages are becoming a little bit, we need to rebrand. I saw people when the new funding round that is supposedly in process for Mira Mirati's Thinking Machines was announced to be valued at like 50 billion posts. People were like, 50 billion posts for a pre-seed.

4:38And so, yeah, that's absurd. She's raised a couple of rounds now. So maybe that would be. I know, but I think they meant more like company stage. Oh, 100%. We still don't know what the product is, but. Yeah, I just, I think people are just like pointing out the absurdity of like, what do you even call it? When we're using that, that amount of capital as like a blunt instrument to just, you know, have companies operate in a completely different playing field. So I don't know. I feel kind of relieved that it's like a small fund with a mandate to invest actual early stage. Like I just get to like sit these out and be a participant and, um, not try to chase down Jeff Bezos.

5:20Yeah. A hundred percent. I think, you know, I subscribe to this, like only the only alpha left in venture is conviction. And so like, you know, as you know, I invest super, super, super early and it's like, you can isolate the variables that you can control and everything else, like how hypey or buzzy or expensive something gets in a consensus, you know, sort of driven round. Like those are elements that like I really cannot control. And so it's just been like an interesting way to see it play out in the most extreme ways. Like I think I was telling you guys about this deal last week that apparently is oversubscribed now, or the founder was raising a billion on 5 billion post and raised the whole thing in five days and it's an AI it's another model company which is cool like I think people have hypotheses that either open AI has already won the race or that in the future or that maybe it's an incumbent like you know Google or somebody's gonna win the race there will be one winner and then other people have this thought that in the future there are going to be so many model companies right and so this was a nice sort of like nod to the people who believe that, you know, it's not a foregone conclusion on who the winners are.

6:30Um, but anyways, they, they went, set out to raise a billion and they did it, you know, oversubscribed in five days. Like that's okay. On a 5 billion posts. I was like, well, I don't know why I see standard safe. Like what? Oh my gosh. I want to see the first safe where the cap is above a billion. That will be, that will be a special moment in this industry when everything has broken. uh yes i'm sure we're close we're close um okay and then another fun one that we were talking about in the group chat so roe um is a fintech company rho for those of you rho not the glp1 serena williams rho yep yeah roe is a fintech company a new york-based one i believe um I feel like I'm very, yeah.

7:20So Ro, they first came on my radar. They actually acquired Capital, which was Jordi Hayes' company of TVPN fame. And then they acquired another company, Creative Juice, that we were investors in. And it seemed like they were doing this like fintech roll-up strategy. Cool. that that might be like the thing that they're going to do this like cool PE style roll up. But still like, you know, very New York based fintech. And then recently, like, I think past six months, it feels like they are everywhere in San Francisco. And so I used to call Ramp Rex of the East. And now Ramp is also everywhere as well.

8:08So it's just been interesting to see like these fintech wars, but particularly Roe, they have a promotion, which like if you move your banking, if you're a startup and you move your banking from, you know, another provider, I don't think it's clear whether it has to be from like another fintech or a traditional bank over to Roe, they'll give you an eight sleep. And that is wild. It's also so targeted and so niche. Yes. It's like, yes, they know their target customer. Yeah, yeah, yeah, exactly. Um, and I think the idea is that, you know, people will be so grateful and they share, you know, it's like a, like the, the marketing of it will be worth the cost of these very expensive, um, you know, mattresses.

8:57But like, if you actually look, or if you talk to somebody who works at a traditional bank and you ask them how much they spend on customer acquisition and how much they spend on retention, like it's astronomical. So like banking is a, is a great business and, you know, very quickly point to how much they're willing to spend to acquire a customer. I'm sure that these eight sleeps are like nothing, right. Especially business customers. Oh yeah. And they probably, yeah, they've, they've, they've baked that into the cap. They've decided that that is acceptable relative to like the incredible lifetime value.

9:30Cause like once you're on a bank, it's like pretty sticky. And yeah, like I, it's, it's a clever, it's a clever campaign. Cause if they're targeting, if they're targeting like longevity, bro founders, totally. It's like squarely in that wheelhouse to your point. It's like, they must be targeting extremely online founder, solo founders, because how do you split an eight sleep. Like, you know, there's like four co-founders. It's like, well, we only get one. About to make a very inappropriate joke. Exactly. Um, but like, yeah, very, very targeted and, and, and small tam, but, but maybe worth it. Um, well, we are very loyal to our, our favorite FinTech Mercury.

10:16So given us an eight sleep and so that really exactly, exactly. That's, um, I sleep well at night just knowing that my money is in Mercury. I don't need a special mattress. Okay. Let's move on to our big topic for this week. Um, especially because it's just Ashley and I, um, so we joke that we are living, uh, a portfolio life and we're trying to like make this phrase a thing. Like I think I like mention it, uh, every opportunity, uh, that I can, but yesterday somebody actually said it to me. So I don't think that we're going to be attributed to the originals. Unfortunately, it was a, my former boss from Dropbox days.

10:56And she was saying, telling me how her week looks. And then she's like, and that's the portfolio. And I was like, portfolio life. So, you know, I think we want to talk about like, what is portfolio life? You know, why have this conversation now? Is it something where we're seeing more and more of? And I don't know what your experience is, Ashley, but I do think more people are in transition between jobs. And that number will increase, you know, whether it's layoffs, whether it's, you know, whatever, also life stage. I think we're kind of at the stage of life where people are kind of think about like, can I create a more, um, flexible schedule sort of around the other parts of life?

11:35Um, and what does that mean in terms of, you know, weighing the options between having a full-time traditional job, right? Where you're sitting at desk all day versus something a little different. Um, so I just, you know, I'm getting more questions about it. I think you are too. And then, you know, what are the pros and cons for you and me, you know, we've been living this for a couple of years now and sort of how have we managed it? Yeah. So just very honestly looking at like what's been hard, what's worked for us. Yeah. And maybe just like to be super crisp on the definition, there's like, you know, and we'll narrow this to tech because of course there are ways to do like a portfolio life across any fields, but like specifically within sort of the tech world, you can have your full-time operating role where you're all in one company, you have like a function.

12:25And that is where you not only have your income and your equity, but like, you know, make sense of your identity, camaraderie, like structure to your life, et cetera. Like it's kind of like built in for you. And then there's deciding to not do that or to do that and other things, I guess we should say. There's kind of like a sort of hybrid, which I did for a while. I was a glossier. I started angel investing, advising. Helen, I know you did something similar when you were an angel list where you have your full-time job. So you have all of that, but then you decide I'm going to have like a side hustle.

13:02And the portfolio piece, especially for being, looking at this through like an economic lens, is like you have exposure to equity and to, you know, or potential income streams beyond just your full-time job. And then there's like full portfolio, which is no full-time job, a bunch of different things that you're working on. They might satisfy different elements of what you want from work. One may be about cash flow. One might be about equity exposure. One might be about brand building. But it's really just sort of unbundling the full-time job. I feel like I'm actually still in that, even though I have a portfolio as a VC, I'm still very much like 110 % of my energy goes to coalition.

13:52And now I have a little bit that goes to great chat as well. So I feel like I don't know that I'm like the poster child of like true portfolio life, but I have done it in between Glossier and raising our first fund. So I'm excited. Well, I think that's a good point that portfolio life can often just be a transition into something more full time. So like my experience with portfolio life, I currently live it. I'd say very much so. But I also tried it and hated it and ran away the first time. So my first time was I left Plaid in September of 2019 with the intention of like, you know, sort of exploring and finding a new career.

14:40And what that looked like for me was like, oh, I'll do more angel investing. You know, I'll take on some consulting gigs. And one of the companies that I was working with, what happened to be AngelList? AngelList. And later on, I think pandemic, and I think the pandemic actually accelerated the number of people who sought portfolio life for one reason or another. But I sort of, I struggled with the, just having so many different, you know, projects and I didn't love it, which is why, you know, eventually I just joined AngelList full time. So I was, you know, I was like a consultant Angelist from like September to I think like April.

15:20Um, but then I just joined full time and, uh, because I was, and I was a little bit like, okay, phew, cause that was a mess. And then like wound down all the, you know, sort of open consulting picks that I had. Um, and now I'm, I'm, I'm living it, uh, again, I think when I decided to start a fund leaving Angelist, like, you know, the, the mechanics of starting a fund, like you don't raise that full fund on the first day you decide to go out and start a fund, it's like, there's a long period where you're fundraising and, you know, you don't have management fees to collect. So you don't have any money.

15:53And so I think oftentimes, and Ashley, I think this is what you do too. You pick up some side hustles to be able to sort of like even out cashflow. And so I started to do that again. I started to work with startups and because I feel very comfortable with how much exposure I have to early stage venture in terms of just like equity. Um, you know, I, I would, I would do like a cash base compensation for, for a lot of these consulting gigs. And then you sort of figure out the upper bounds of like how many companies you can work with at a, at any given time. And then, you know, you, you figure out how to make it work.

16:25Oh yeah. I found that out the hard way. I way overshot. Yeah. And like, you'll, you'll, it'll be very obvious, right? You're like, okay, I think a little too much or, or, okay. Then you scale back and you're like, oh, I could probably take on one more. And so it's not, you know, it's, it's fluid, but I think the, the most common question that I get are from people who are thinking about that, but are currently, you know, very much in a full time, you know, W2 salary and benefits sort of role. And they're just kind of like asking and curious, like, what's it like, how do you manage? Do you put structure around it?

16:59Like, well, I do this on this day. And then I only do this on this day, or I, you know, go into the office and they know that when I'm physically in the office is when they get my time dedicated this outside, you know, I'm not available. So it's, you know, the questions that I get are usually from people who are in a full-time thing. Right. And asking themselves, like, could I make this work? Not just from like a, you know, stitching together, like different sources of income, but like, can I make this work just from like a, time management or lifestyle standpoint. Yeah. And I think the challenge is there's no blueprint, right?

17:38Like, I mean, individual people have figured out what works for them, but you know, what worked for me might not work for you. I am a big advocate for trying this at some point in your career. Like you, Helen, I actually didn't love it when I did it. Like I, I, I love collaborating. It felt transactional. I hated pricing my time and expertise. I mean, venture is amazing because I can just give away my time. Incentives are so aligned, but it was so empowering because the thing that it taught me is that I do not need a full-time job to support myself. There are interesting projects to work on. I learned a lot about how I would structure things differently if I ever did this again.

18:27And it actually allowed me to be much more risk on in my career and decide to raise a fund and take that leap. And take that leap even knowing, you know, like if I couldn't continue on that path and I needed some transition time down the road, I could always go back to doing this sort of more like portfolio approach. I think it's incredibly empowering. It's funny, I have a friend who just left a job and she sort of like took that leap ahead of having anything lined up. And I was the one being like, you are going to have no problem finding people who want your time and expertise. I think if you are, maybe this is a really important qualifier.

19:11If you have a great reputation as an operator and you have some sexy company names on your resume, I think it's actually like pretty easy to find people who like want your time and expertise I do think there's a question of like what is the right point in your career to take this leap because you you want to do it at a point where you have a bit of a reputation where you're not going out and like having to like look for opportunities where you have like a network and word of mouth or for me when I announced I was leaving Glossier and I had no I really did not know I was going to raise a fund like a couple months later I just tweeted it and I had my entire you know I said yes to the things that came my way that I wanted to do and I had my I more than filled out um my my uh capacity and so um that's not to say that's like what everyone needs to do but as as an example um you know if I had done that 10 years prior there would it would have been crickets another like empowering thing about portfolio life is unlike a job where let's say you take it and then you're like oh no what have I done and then you have to start thinking about the story if you leave or you know it looks like a short tenure another blip on your resume it's like I think one of the most empowering things about um you know doing fractional work or a consulting project is like you can decide whether you extend it and you continue to keep them on.

20:42Um, or if you're like, yeah, when this project is done, like I'm going to move on to other projects. And, you know, like, I think for me, AngelList ended up turning into a full-time job, but I did not go into it with that intention. It just like was a fit on both sides. Um, and you hear of a lot of people who are just sort of like, you know, consulting or doing fractional things with different companies. And then, you know, they end up finding their like forever job that way too so i don't think that there's downside in in thinking of like portfolio life is almost like this sampling of different companies and opportunities um especially if it's like maybe a little bit different of an industry just feel like oh you know do i like working in crypto yeah well a good you know you could go join full-time at a crypto company or you could just like do a little bit of fractional work for for a crypto startup and then you know sort of immerse yourself in that world and like that, that gives you some data.

21:35And so, you know, I think that there are, uh, really, really, uh, useful parts of, of doing it as well. Let's talk about some of the hard things, because I think one thing that I mentioned to you and Sally, cause I think we all live portfolio lives just to some degree is like the hard parts in my experience have been around identity. And there is less of a blueprint on how to navigate some of these things, especially if you are somebody whose identity is so closely coupled to this place that you work. And that's no judgment. I think, especially living in San Francisco, it's literally, you meet someone at a coffee shop.

22:14You're like, hi, what do you do? It's like, that's just like a, you know, it's like an unfortunate thing, but it's, it's a real thing. And so, you know, the equivalent of that is like, you get invited to go to a cool conference, you know, and they send you the link to register and you, it says like title and company and you sort of like freeze up and you're like, do I put my consulting LLC? Do I put the company where I'm spending the most time? Like, will I get rejected? If this is on my badge, will people take me seriously? I think that that is a, a, an experience that, um, you know, is sort of the thing that nobody prepares you for.

22:54and also like the farthest you have to fall, especially if you have been, you know, a company person for, you know, a very long period of time, if that makes sense. That resonates a lot. And I'm actually been like reflecting on maybe this is a key difference with San Francisco and New York, because when I actually, I was going to say when I left Glossier was in New York, but that's not even true. I was like literally on a road trip during the pandemic. So everything felt up in the year, but I did ultimately come back to New York. I think that's real. I think it's another reason why it's helpful to do it a little bit later in your career when maybe that piece matters a little bit less to you when you feel like you have a sense of yourself and the place of the ecosystem separate from your latest role.

23:46I think the piece that I struggled with the most like far and away was just like loneliness. I really love like collaborating with people, working with people. I get so much energy from that. And I found that like the client relationship didn't quite satisfy that need. And so, um, it's funny. I went back and I like found a tweet and from September of 2011. So like a month after I'd left Glossier where I was like musing on like 2021 if you want 2021 what did I say 2011 no I'm not I'm not that old um 2021 where I was musing on like like if you unbundle a full-time role like what are all the things you have to find elsewhere and like a big part of it was like camaraderie and purpose and like where does your sense of like motivation and drive come from and and you know I got some of that at the individual project level, but it did feel like a little bit more transactional to me.

24:48And so that was the piece. And actually, I got to experiment with like doing some projects with other people. I did a really big, fun, like comms project with like two other people. I probably can't name the company, but like a big tech company. And that was so fun because it felt like we were a team and we were doing it together. But yeah, but that piece, and I know a lot of other people struggle with that piece as well. Um, if you are a team player and a team person, suddenly you are like, you know, the, the CEO of your own tiny, tiny little kingdom. And, um, and you're going to have to do some sort of unnatural things to rebuild, um, that part of your work.

25:30Yeah. So my, my experience is a little different because I think the way that I engaged companies was pretty consistent. So I would be like offering to set up the scaffolding for like the marketing and comms function, meaning like, okay, here's what I think the structure should look like, right. And here are the first few roles. And then I will help hire that team. Right. And then I would be like this, you know, sort of fractional interim person. And then we would eventually hire like my replacement. And so, because I did that pretty consistently, I did that with four companies. Um, I, I was naturally sort of like growing a team around me.

26:06Sometimes we'd bring people from other parts of the org. So I always like the, I had a team, but it's, it's different to not be, you know, like a real part of the team and sort of like just be fractional. So I definitely, the, the loneliness thing definitely resonates. Um, even if, you know, you, you're sort of like dropped into sort of more of a team function. You know, I think that as an emerging manager too, like it can get quite lonely. Even if you have partners, you know, I've experienced it both ways. It's just this kind of like, like you have to set your goals, you know, and then you have to work towards those goals and then also hold yourself accountable on your progress towards those goals, right?

26:50Like you talk about the freedom of not having a boss or a dashboard at work where they're tracking your progress or needing to like share status updates or reporting. If that's the environment that you have been used to. And, you know, I think that this is where operators and investors, we talk a lot about like, you know, how, how their lives are different and their modes of operations are so different. I think if you're a long time operator, you're just very used to these like structures in place where there are goals and then there's accountability to the goals, Right. In portfolio life, you know, it's like you have to say this month I need to bring in this much money.

27:28Right. Therefore, I need to have this many projects or bring on a new client or something like that. You know, similar to raising a fund, it's like I need to have this much money. So I need to raise this much money as all all of those things. But it's like no one's no one's holding you accountable, but you. And that is that is, I think, a very unique portfolio life experience, you know, where it's not so much in the bucket of loneliness, but it's just like, well, I have to play many roles. yeah it's like no one is coming to save you but even more than that like no one really cares that much like you know no one else is like in the trenches with you except for your poor spouse who has to hear about it all the time and and so yeah I think that's it's interesting when I say loneliness too it's like the the key like I don't know the thing that I have found matters the most to me is like energy.

28:17Like how am I spending it? Where am I getting it? And, you know, like I think when you're part of a team or when you have like a founder who's super inspiring, like there's a lot of transfer of energy that enables you to like run at things. And when you are doing, you know, whether it's portfolio life or, you know, a solo GP at a fund, you have to generate that for yourself. And that's like a very different equation as someone, I mean, coalition has unique structure, as you know, I'm the only full-time GP and then I have three amazing partners, but they're running companies full-time and investing part-time.

28:52And so I do spend like, you know, a lot of time with my own, with my own energy levels. And so I have had to invest in like finding ways to like really build my network and ecosystem around me and figure out like, how do I structure my days so that I do things that give me energy and ideas that I can then spend over here on the things that don't. And, you know, now I'm, I'm almost four years in to this phase of my career. And I think I've like figured it out, but it was a really big, it was a really big adjustment for me that, that piece specifically. Yeah. And you just said four years in, and I feel like post COVID time has just strange things because I mean, when you, when you would say, Oh, I've, I've spent four years at a company, right.

29:45You're like, wow, full vesting. You know, it's like, that's, that's, that's like a good tour of duty. And I think that when you are living portfolio life, like in many ways, four years just goes by so quickly because you're just busy, busy, busy, busy, busy. And, um, you know, there are new projects coming in and out and sort of like, there's just activity in a way that is different. I'm not suggesting at all that there is an activity when you work at a company. Um, but yeah, it's just, it's, it's just, it's just different. Uh, the time scale, there's plenty of activity at company, but I think the thing that I found with operating was, it was always obvious to me what I should be working on.

30:24Like it was kind of like built into the role and the company's goals. And, um, I think when you have, whether, whether it's as like a fund manager or if you're doing like full portfolio life like you have a lot of autonomy and there's a lot of room for creativity and you know you could spend a day doing any number of things you can focus on the near term you can focus on the long term you can focus on specific projects you can focus on like investing and building your brand or right like there's so many so many different ways to spend your time which is both exciting and also like you know very challenging when you're used to like the cocoon of company structure okay well good luck with portfolio life I think everyone should experience it and especially women if I'm being totally honest um I do get comments about like oh how do you do that and how do you do this and it's like well sometimes you know I get to create big holes in my calendar around certain things and it's funny I like work a lot more than I did when I was in a company and I've always been a hard worker, but I have full autonomy and I will always take like autonomy and hard work over like more rigidity.