Jason Shuman, Partner at Primary Venture Partners, Just Go Grind Interview

Jason, welcome to the show.

Thanks for having me, man.

Yeah, appreciate, appreciate taking the time to come on. And for people who aren't familiar with your venture firm, tell us a little bit more about what you guys are focused on.

Yeah, so Primary Venture Partners, we're the largest seed fund exclusively focused on New York City, trying to partner with the best founders here at pre-seed and seed and add value in unrivaled ways at the end of the day.

And then for you, so what is your individual focus then at the venture firm?

Yeah, so I joined about 2 and a half years ago to lead our new consumer investments. So mainly consumer tech, fintech, digital healthcare, stuff like that, marketplaces, and then proptech as well.

Nice. And so I want to take a step back. I love the context first to start off with. But for you then, how did you get into venture? I know it's a number of years ago already.

Oh, man. It's crazy. It's been about 7 years now. I started my career honestly, when I was a kid, I was like obsessed with startups. And in middle school, I was like writing business plans. And my mom would like shuttle me into the city to meet with founders. And, you know, high school, I got lucky enough to work in identity theft protection and under a former VC there at the time and started to learn more about it. But my career really started when I launched a direct-to-consumer footwear company in undergrad, bootstrapped with my best friends. Made every mistake in the book. I think it was good timing back in 2011. I think the other small companies in the D2C space back then were like Warby Parker and Glossier, and you know somebody else executed a little bit better than me. With that said, you know ran that company for about a year in school and a year out. Ultimately hit this 23-year-old life crisis where I was like, man, I don't want to do this for the next ten years. So. Decided to wind the business down, and then looked in the mirror and decided you know venture seemed really interesting to me. It was like for four reasons: one, I could learn about different industries really quickly; two, I could meet a great team to start another company with; three, I could raise capital much much easier; and then four, which is really like the biggest reason why I'm actually still in the game, is because it just aligns with my mission in life. You know, like I'm all about empowering other people. to live a more successful, fulfilling life and helping provide them with the tools and skillset to do that. So, in order to figure out a way to get into VC as a failed entrepreneur at 23 who went to the University of Miami, I literally started driving for Uber at night and during the day, sourcing deals in Boston for venture firms in New York and trying to give them feet on the ground there. And I was sending deals. for quite a while to New York and finally got a job offer to move to the city and to work for Corrigin Ventures.

I love it. So from that experience then, Jason, so you knew that you were sourcing deals already for other companies. In that, like, how are you going about that process of sourcing? Because you mentioned you're driving for Uber, you're hustling, right, at that time. Like, what were you doing to source deals at that time?

Yeah, I mean, I was lucky, you know, being a founder in Boston prior, I had a network of founders that happened to be either raising capital or knowing other founders who were raising capital. So, you know, for somebody to, you know, walk into a room to meet someone, a founder that was just getting going on the fundraising process, oftentimes, you know, first-time founders, not, you know, serial entrepreneurs that have raised venture before. And for this kid to walk in and be like, hey, I've got a big network of VCs in New York, and I'd just love to learn about your company and help you get in touch with them. I think it was a pretty easy yes for a lot of them. And, you know, on the flip side, it then added value to the people on the other side of the equation, the VC firms as well, which opened up doors and referrals lead to referrals, you know.

Yeah, that's something where I look at doing the podcast the last number of years and meeting so many founders and VCs that led the way to where I'm at now, another venture firm. But like for other people trying to break into VC, it's always a huge thing. If you can bring deals in, if you can have that deal flow, if you can know other VCs, you can know other founders, such a leg up in terms of then your career, and even just more fun anyways, to know more founders and everything. And it helps you as you want to, whether you want to get into VC or have your own VC firm as well. From that experience, and so going from that, then being at Corrigin. At Corrigin, what was your focus on in terms of investing when you're there for the 4 years or so?

Yeah, so I got brought in there, you know, as the first hire below David Goldberg and And I was on a 90-day trial. And I think David was the only person there full-time on the venture side then. And it was like, okay, what do you want to look at? What's interesting to you? Where does your intellectual curiosity take you? And having been at a real estate firm, I mean, it was a single LP real estate family office at the time, I felt like we had an advantage, you know, going after proptech deals. So, you know, going out looking at those companies like Latch and Morty and LoftSmart, you know, had the opportunity to meet with them. At the same time, I think there's a little— there was a lot of scar tissue in terms of direct-to-consumer businesses. So you'll notice my track record has some spotted misses on the DTC side of things. But with that said, I then started to look at a lot of marketplace businesses, you know, they were super complex. I love digging into them, supply-side dynamics, demand-side dynamics. So I started to look a lot at that. And then fintech was just really, really interesting to me. So I started to look around that as well.

With the marketplace side of things, I know I saw that before when I was doing my little research on this. And I think I find them fascinating as well, because they are so complex. What are some things you were looking for at the time, at least? Or what have you learned from that the last number of years, what to look for in terms of marketplace businesses? What are some of the key maybe metrics that help to figure out, okay, this could be Great in terms of potential. I'd love to hear more about that.

Yeah, for sure. So oftentimes, I mean, it's definitely a case-by-case basis, but, you know, what you want to look for is promiscuity. So between like the supply side and the demand side. So, you know, you look at the best marketplaces that exist out there, you know, Uber, Lyft, DoorDash, you know, you're not ordering from the same person or the same place as the demand side every single time. And on the supply side, you know, you're not providing that service to the same person every single time. And by doing that, you know, you're avoiding what we call leakage in the industry, which is when you take, you know, the transaction off of the platform. And so that's, you know, one of the biggest issues at the end of the day. So when you're looking for, you know, the best marketplace businesses, one actually good blog post to check out, Bill Gurley has a good scorecard up there. And the guys over at NFX, you know, are super, super talented marketplace investors. They've written a lot of good stuff. But the other thing I start to look for, especially, you know, when you're looking at consumer businesses as a whole, repeat rate and the velocity of that repeat is so important. So, you know, you're studying how often are people buying from that marketplace, how quickly are they buying from that marketplace, and then, you know, what percentage of the customers are. Because even if it's not a subscription business, you know, I mean, SaaS multiples are beautiful things these days. You do want it to look like a subscription business.

So now then, so from that experience today, I know you mentioned some of the things you're kind of focused on looking at today. What are you, what are you most excited about in terms of different areas, different types of companies, anything around that, like you're like, this industry or this market or these types of companies, we definitely want to invest in, or we're looking in these areas? I'd be curious to know more today what you're looking at.

One thing that really like underlies almost all the investments I make these days is all about democratizing access. You know, I didn't join the venture world to make a bunch of money. You know, it's one of those things that I think is really important to make a positive impact on the world that we live in. So democratizing access to the tools and the services that have historically been available to the wealthy or the large corporations is something that I think is really powerful, the personal mission of mine. So a few things. One, on the digital health side of things, how can we find tools that improve outcomes? You know, increase access. I think like those 2 things and dramatically reducing costs and helping provide the high-quality care that we get in the cities, you know, to people in what I'll call care deserts where they don't have the specialists. I think that's one thing that's super, super important for the next, you know, has been for the last couple of years, but it really will be even more important over the next 5 to 10 years as our population starts to age. You know, the second one is really in the financial services. I mean, I think we're both seeing this crazy fintech boom. It's been pretty fascinating to watch. There's a lot of companies that are loading up even more debt on Americans, which is slightly intimidating in a lot of ways. With that said, I think, you know, how can we increase access to the tools that the wealthy have? I mean, you know, we backed a company called Lily that is improving access for freelancers to the tools that big businesses have had in regards to accounting and, you know, lending and all of the software for taxes. So I think that's another thing that we're going to continue to focus on from Yeah, and there are more and more companies you've seen that are attacking these problems, they're attacking these different angles from—

I've interviewed a number of them and have Ethan Block from Digit coming up, so fintech company. It's interesting to see how people are taking a different approach to it. And it's just, it's something that's so obvious, like, why is this not a thing yet, where everyone having kind of an equal playing field of sorts? And so companies in the blockchain space, VCs obviously investing in those areas. Love that because it's helping obviously fuel the companies grow, but also other founders seeing how there are opportunities and there are ways you can get involved. And whether it be fintech, whether it be health, as you mentioned, I think I've interviewed like, it seems like dozens of health companies that are finding a different way to go about it. Whether it be a company, I think it was Wealth, there's a couple different ones that are out there that have done some kind of unique angles for kind of democratizing access in terms of health, especially digital health. Which we'll see how that evolves over time as well. And for you, I know you've also led, I think, diligence and kind of other aspects of venture. What does that prospect— like, how does that process look like for you in terms of the diligence process after you kind of get that first look at a company? Take me through for you what that looks like. I know every venture firm is a little bit different.

Totally. So the first thing I'm analyzing before anything else is the person, you know, who is the founder. And, you know, when we're digging into that person, I like to say, you know, my mom's a therapist, my dad's an entrepreneur, you know, I try to dive into the psychology of that person and a little bit more of the story behind them. So how resilient are they? How resourceful are they? And then what's their sense of urgency and their speed of learning? Like, those things are absolutely critical, you know, pillars to a successful founder in my book. And then the last boxes that we're really looking to check are regarding, you know, can they sell? Can they sell stock? Can they sell their product? And can they sell people? And if they can do those 3 things, we think they're in a really, really good position to succeed. The next thing is we're gonna do diligence on the market. So the product can oftentimes change. The market changes far less. So even when you're pivoting a product, you're usually staying in the same market. So how big is that market? And really, what are the gotta believes regarding that market in order for this company to be worth, you know, over $1 billion. I mean, we have a $150 million fund now, we need to have some pretty large returns in there. So even if the market isn't, you know, $10 billion, $20 billion today, do we think that there is the potential for it to 2x, 3x? What are the macro tailwinds there? And then is this a 10x product in that market that can ultimately build moats, you know, barriers to entry for other companies to get in? The last thing I'll just mention is on the product side, we're gonna play with it. We're gonna go out, we're gonna talk to customers. So there's all sorts of things, you know, from a diligence perspective, we're also going to talk to people that that founder has worked with, to just reassure and give us the confidence that they're gonna be able to go out there and figure things out.

Just to double-click on the people side, because that is the first thing you're looking at. That's, I mean, everyone's evaluating people, especially early stages, and looking at seed and everything with that. What are you doing? You mentioned kind of the speed of learning, you mentioned their ability to sell, how do you Analyze that? How do you— what kind of questions do you ask to think about that? Or how do you figure out that side of it? Because they're important for sure, but I'm curious. I would love to dive deeper into how you kind of go about that.

So there's a few different questions, I think, within that in regards to like sense of urgency, for instance.

Yeah.

How quickly are they responding to your emails? Like at what, at what time of night are they responding to your emails? Or at what time in the morning are they responding to your emails? I mean, when somebody is in a fundraising process, you know, making that a real, real priority and showing the ability to prioritize is something that's absolutely critical because there's going to be so many things that pop up throughout the course of the company that you're going to have to say no to that during a fundraising process. I think it needs to be a top priority for you. In terms of speed of learning, you know, and resourcefulness, oftentimes I'm going to ask the founder about, to walk me through the process. How did you get to this point where you sit in front of me today?

Yeah.

today with this company? What did you do with customer development? Okay. How did you learn about the industry? What people did you talk to? How did you get in touch with those people? You know, as they start to like walk you through those very nitty-gritty tactical details, it starts to come to light, you know, how resourceful they actually are. And then if you ask them about the learnings between 12 months ago, when they first came up with the idea, And now there should be a real wealth of learnings and the self-awareness to be able to explain to you what it was that they had from a takeaways perspective.

And then for you as well, so with that process, obviously there's 2 sides to it. So there's you looking at and evaluating these founders and then the founders evaluating you. Why do you think it is that founders end up wanting to work with you in primary? Because every venture firm, especially the best deals, They're all trying to get access to the best deals. How do you think that goes or why companies end up working with you?

I don't know, man. Pure luck. Jason seems nice.

Yeah, I'll work with him.

Yeah, I think, you know, we're super lucky at Primary. You know, I'm blessed to be able to work with an incredible team here. And Brad and Ben, who co-founded the firm back in 2015, ever since day one have really put forth a priority to invest in portfolio impact. So I'm not talking about platform, like platform teams are a completely other thing. I mean, and there's a lot of good platform teams out there. It's a dirty word here internally at Primary. You know, we have, we have incredibly successful, incredibly smart and hardworking portfolio impact operating partners, folks like Cassie Young, who is the Chief Revenue Officer over at Sailthru, you know, led a 9-figure ARR business on the revenue side of things. We have Rebecca Price, who's been a Chief People Officer at multiple places now and really impressive can go in day to day. You know, we have recruiters, market development people, we have CFOs that go in and help you out with things, really getting from seed to A. And, you know, because of the fact that we've been pretty lucky in the past to partner with incredibly talented founders, we've now got a track record on the fundraising side and a very tight playbook in order to go out and raise funds. And, you know, being able to use the portfolio impact team to get everything tight and really help you in the hardest days at the earliest stages when you have the least amount of resources And then being able to partner with, you know, hopefully people that you really enjoy working with. And whether it's myself or Ben or Brian or Sam or Leah or Brad, like, it's, it's, it's one of those things where the human connection at the end of the day certainly goes a very long way as well.

Yeah, absolutely. And for you then, with sourcing deals, I know we kind of talked a little bit early days especially. Has it evolved today? Like, what does it look like today for you in terms of sourcing deals, in terms of finding Finding those gems when everyone's after them. I'm curious if it's changed or what that looks like maybe today for you.

It is night and day compared to 6 years ago. Oh man, you look at the market back then, it's like 5, 6 years ago.

Yep.

There was a bunch of sheep in venture capital. We all followed each other. We wrote like $100K, $250K checks. Like, maybe you had a lead that was putting in $500K or a million bucks, but the amount of firms that led with a check that was that size was like, I could fit on one or two hands.

Yeah.

So, you know, you're getting deal flow from your friends that were other investors, and maybe you got deal flow from other founders, and that certainly helped. But like, I'd say 30 to 50% of the deals we were doing came through that channel. Now it's like maybe 10%.

Wow.

Wow.

Quite the change.

You got to get on your horse and you got to grind. And like, you know, what we do at the end of the day, there's a few things, some of which are proprietary. I mean, we built some technology to help us go out and find the best deals. We certainly do content marketing, you know, the whole like Twitter game and blog post thing. Like, that's certainly one thing. But we actually, we've built different microsites like the New York City Founders Guide, which I definitely recommend people check out to go find the top funders in New York City. We have our Future Founders program that just got launched by Brian and Tobias that's helping founders equity-free, really to help in the early days, very Y Combinator-like. I think that's going to be another one for us. And then the last thing is we just try to bring a prepared mind to different markets. So whether that be coming up with a thesis about a certain market and a macro tailwind, and then finding the best operators, the best angel investors, and surrounding ourselves with those people, it enables us to become far more Yeah.

And for me, I'm definitely very interested in hearing more about this. I want to double-click on this because I'm leading the way on the content and kind of the community side of what we're doing at Vitalyze. For you guys then thinking about whether it be creating a different site, whether it be looking at how we look at our Twitter strategy, what are those discussions like for you internally around how you're using content or marketing or other things like that to help you grow? To help the firm? What does that look like for you guys? You touched on some of those areas, but I'd love to dive deeper into how you think through that because there's only so much time in a day and you guys are busy looking at companies. I would love to hear more about how you think about that for you guys.

Yeah, so we're actually on day 3, I think, or day 2 right now of a new marketing hire that we brought over from Kickstarter and Catherine, and she blew us away during the interview process and how she thinks about things. But historically, the way we've gone about it is like a startup. We're not afraid to like launch something that's not perfect and to test it and to shut it down if it's not working. We've done that multiple times. And, you know, we're in an industry right now that unfortunately can be too transactional at times and too buttoned up where people are like, don't want to express their failures and things need to look super pretty, you know, from day one. Internally, we're like, all right, we're all pretty entrepreneurial, like, go figure things out. And, you know, for us, what that— the way that that looks from a content perspective is trying to think about our customer. Who's our customer? And really, we actually have like a couple different segments of customers internally. We do have founders, so we try to think about what type of content will add value to the early-stage founders that are thinking about starting a company from day one. But because of our large portfolio impact team, we also have operators, you know, the chief revenue officers, the young salespeople, the growth marketers, the engineers, you know, how can we add value to them? And then how can we repurpose the content from the events that we're doing to then try to share it out into the world and create a bit more of a flywheel that will enable more access to better quality people to create even higher quality content?

Yeah, it's an important thing you mentioned there. The purpose of the content in the first place, think about who it's actually reaching and who you're trying to target. Like, for us, in terms of what we're doing, it's like looking at, obviously, the founders are going to be one, one side of that. But you're also looking at, we've had an angel group historically with Irish Angels since 2012. And then you're looking at angel investors as well. And then what we're trying to do, and you mentioned kind of democratizing access, like we want to increase access to more and more, for more people to essentially invest in startups. And so obviously, crowdfunding is doing some interesting things.

New regulations is opening things up.

It's got people thinking. You can see like Backstage Capital raised through Republic. You look at Sahil from Gumroad raised through Republic as well. Different things are kind of happening there on those things. So it's like you're also looking at like making content for other like aspiring investors, because if there's more money there, then they can obviously feel other people who normally historically aren't getting investments. So like we're trying to think through that as well. So I love asking people about how they're going through that process of thinking about the content side of it as well, cuz It is tough because there's, you're busy with other things, but obviously you can hire out for that to kind of make up for what you can't do or don't have time to do, but it's still important for the firm. And with, with what you've done in the last like 6 years or so here, you've been in New York City this, this whole time. How have you seen the whole idea of location not mattering as much? Or, you know, with everything going digital, with everything with COVID the last year, how has that changed how you find deals, how you access deals, everything with that?

So I think the how we find deals piece has actually probably improved in a bit of a way because there was a lot of wasting time going to coffee meetings and drinks events and doing all sorts of activities that probably did not add value. And as an extrovert that has run probably 150 miles an hour since getting a job in VC, it enabled me to look in the mirror and ask myself, myself, like, what's really important and where am I actually getting value out of these events. And for the most part, we actually looked at our deal flow data the other day, and we're up like 40% year over year. So I don't think that we're having any trouble there. But I did mention, you know, we are New York City focused, we're essentially New York City only, although we will back, you know, remote teams. But I think New York's coming back, man. Like, I know New York's coming back. Like, the energy here, it's crazy right now. And I'm sitting in my office right now. I can't wait for the 16 other people that I work with to come back. I can't wait, you know, to go to visit the portfolio companies here in the city and feel the energy in the room. And, you know, certainly remote work has its benefits. benefits. And I think remote work will be more, you know, common these days than it was previously because we've broken that cultural mold. But nothing will ever be working in person.

Yeah, I mean, yeah, it's difficult to imagine not having that at some capacity. And for you guys, I mean, how do you think it'll change, I guess, with Now these meetings can be done virtually, they can be done on Zoom, but that's a, that's a more efficient process. But you're, you know, it's not the same as meeting in person. What do you think that mix will be as we kind of move forward? I'm just curious on your perspective.

It's a good question. I, I think that at the end of the day, we'll try to meet with as many founders in person as possible. And this is at least my personal, like, opinion and how I'd like to approach it. I have trouble in the Zoom world. You know, I'm fully in my own head when I'm in the Zoom world because not seeing you in person and not feeling your energy as like a human being, it doesn't give me the same like fulfillment and the same energy as like when we're actually like meeting face to face and sitting on a couch and talking about your ideas. So I completely understand and respect the way that a number of investors are going to go about it. I'm doing mainly Zoom meetings and That's great. I just don't think that anything's gonna beat the connection, one. And two, it's just not gonna do it for me. Yeah.

And if that, that doesn't do it for you, then it's like you can find your own way to do it. And it's one of those things too, I talked to someone else about this where like you can't smell anything, you don't hear any other noises out there, you don't know how tall the person is. Like there's so many different details. Like I have no idea. I've interviewed since the pandemic probably over 150 people. And I, I have no idea like how tall they're, how like what they look like, anything aside from like, I, most of 'em are just audio interviews too. So like I have no idea, which it's great that you can get the access to people all over the world that I wouldn't like be able to meet up with in person anyways for some of those. But for others it's like, yeah, it would've been amazing to have that experience. If you remember what the room was like, you remember, you know, whatever your first impression of them, all these different things that you don't, you don't get in the virtual world. So it's gonna, we're gonna see what the mix is gonna be. I'm excited to get back to in-person. Even people in Los Angeles I've interviewed who like, we're in the same city, so we should definitely hang out in person at some point. It just is weird that we haven't yet. But we will soon, hopefully with the pandemic coming to a close, knock on wood. But we'll see.

I mean, that LA traffic, I don't know if you wanna be dealing with that to hang out with people though.

Yeah, I'm on the west side, so I hopefully can avoid, avoid as much as possible and make people come to the West Side because it's nice, but we'll see how that goes as time progresses. But it'll be interesting to see the evolution as well. And one thing I'm always curious about with anyone, whether it be a startup founder, whether it be an investor, how do you kind of invest in your own learning, your own lessons, trying to become a better VC, but also on top of that, just becoming a better person overall? How do you invest in that?

I'm curious. Every Friday, I have a 2-hour chunk of time that I call my weekly review time. And so the week prior, I have like a calendar block of like what my optimal schedule looks like, you know, how many pitch meetings do I want to take? How much time do I want to, you know, read and put together research for an investment thesis? And then part of that monthly routine is I want to be reaching out to people that I can learn a lot from on the investor side of things and on the personal side of things. And I have goals that are related to that in terms of the amount of conversations. So if I haven't hit, or let's say I'm lagging behind a goal for like, okay, I want to talk to 2 of the top investors in the world. And I have like a list of folks that I'm trying to track down or get in touch with. I'm going to use that 2-hour block. to get in touch with those people and to catch back up to the things that I'm missing and not prioritizing. So that block of time is really personal to me. And then, you know, I try to listen to good podcasts like yours and a number of other folks in order to learn because I don't really watch a lot of TV these days. So I think podcasts, when I'm walking around and trying to clear my head, is just this incredible democratization of access, you know, going back to that again. To information that, man, I wish I had back when you and I were in college between '09 and '13.

What does that calendar then look like in terms of some of the other things? I would love to know, you know, more on the details. I talked to— I always love asking people this. I talked to like Marlon Nichols from, uh, from MacVenture Capital, went through his schedule, went through some other people's in terms of their, their blocks, because I find that it's helpful to— it's definitely helpful to block things off, otherwise it's not real. If it's not— if it's in your calendar, it's not real.

How do you go about that in terms of how you structure kind of your I have a codified system, by the way, that like I share with my EA to help like color block everything. But Mondays, Wednesdays, Fridays, I have 2-hour blocks in the morning for like deep reading, deep learning, deep research. And that has to mainly do with thesis development and what we just discussed, which is getting caught back up on my goals.

Love it.

The other stuff that I tend to focus on, so pitch meetings is certainly one of them. Work time, portfolio support, portfolio impact is like a really, really important thing, not only for, you know, our firm, but me personally, and a big reason why, you know, I'm at Primary and why I do venture. We only do, you know, 3 to 4 deals per investor per year. So that type of, you know, concentration makes it so you're going to want to work with the companies. Personal development time certainly put aside. I do spend about an hour and a half every week on calls with other VCs. I try to limit that just because I think it's great for learning, but unless it's like a focused call that's less to do deal flow, but more like, okay, I'm looking at this space and you're looking at this space, I try to think about that. And then future founder networking. So I want to invest time in like the next generation of founders, and I try to spend a few hours every week Meeting with folks that are still working at companies, but have been identified by folks that have worked with them in the past as potential great founders in the future. And I want to help them think through you know their career path and what they might want to do in the future.

Yeah, it's like playing playing that long game. You have to seeding the future investments before they even become companies.

I'll tell you, like talk about the long game. I I met this founder Tony Alokko back when he was seventeen years old. So like. Like, this was 8 years ago, 9 years ago. I'm 30 now. So, yeah, this was 8, 9 years ago now, right when I moved back to Boston. And 8, 9 years later, got a chance to back him. And man, is his company cranking now.

Really?

And there's nothing more fun than getting to bet on people that, you know, you've seen grow up because that evolution is just incredible. And to be a part of that ride and that journey, you know, I'm grateful Yeah, and building those relationships for that long of a time period.

I look at so many of the people I've talked to on the show or I've met in the last number of years, it's like, yeah, you're playing the long game and just like understanding that you never know when someone could start something later or like they might eventually bring someone else in. I know talking to Yuri Engstrom from Yes VC, and they have a pretty small fund, I think it's maybe $5 or $10 million, but they're like seeding ideas into people. They're like, hey, you should probably start this company, I have this idea. And then they'll like seed it into people. for you. And they're like helping them start the company, and then they'll invest in them. So it's like, that's like, I mean, at the earliest of stages, that's what people are doing.

We do the exact same thing. We, you know, we help give ideas to folks who we think are incredible operators who might not have an idea, but they say they want to start a company just because we really believe in them. And I'll give you one quick funny story that just happened right before this, which was Somebody I was interviewing for an MBA associate position asked me a question at the end and she goes, you know, what's one thing you would change about venture capital today? And I said, I'd get rid of all of the transactional people in the industry. And, you know, when I look at early-stage venture and we're talking about future founders who might not start a company for 2, 6, 10 years, you know, it's transactional people that aren't going to take those meetings or they're not going to treat those people really well in those meetings. So I think, You really need to pay attention to every interaction you have and really bring your genuine, curious self into those meetings and figure out how you can add value. Because there's just too many people that are just not good actors in this world.

Yeah, it's unfortunate. But I think the ones who are the good actors, who again are playing kind of more of a long game, I think will win in the end. Because yeah, there are so many people that will start companies, there are people I Like, you think of how someone got access to a deal from, you know, this person they may have known for a decade or something. Like, that happens all the time where it's like, how'd you get access? It's like, well, I've known them and kind of put the time in for a long time. I've helped them. You know, it's like giving without anything, expecting anything in return. And eventually good things happen from that. I think over time that more people do that, it's a better way of going about it.

Um, overall. My, my, my mom used to tell me good guys don't finish last, so I'm, I'm gonna believe it.

Thank you, mom, for the wise words. Wise words. I want to ask about your decision-making process, because any VC especially, you're making decisions constantly. And whether it be saying yes or no to a quick deal you see, I know from talking to, I think it was Rick Smith at Crosscut mentioned like, yeah, we see, we get like 5,000 or so requests, we were looking at maybe 500, and then we'll maybe invest in like 15 to 20. So there's obviously a lot of decisions that go into that type of process of saying no and everything with that. Give me like a high level. I would love to hear like how you look at making decisions, what goes into that process for you with a company.

So in order to have us take a meeting with a company, it needs to really match the criteria that we're most interested in on the consumer side of things. One, we're trying to understand like, does this company jump on a major macro tailwind? You know, is it the digitization of healthcare? Is it Gen Z and their shifting, you know, consumption behavior regarding how they like to look at, you know, user interfaces? What are the colors of the brands? So on and so forth. So like, does it match a macro tailwind? 2, we ask ourselves, is this a 10x better product? You know, does the original product they're bringing to the table, is it going to be much, much better than that that exists today, because that's an important thing. And then the last thing is, you know, is this founder well-suited to, you know, create this company? Do they have a unique insight? Do they have experience? So on and so forth. And that's a big thing that we're really evaluating. And then as we get into the weeds with the company, starting to understand the moats that they can ultimately build is really important to us. And we went through some of the ways we evaluate founders, but—

Yep.

I don't mean to overcomplicate things, but if you end up looking at like those 3 things, I just mentioned, and they check all the boxes, and then you isolate what are the gotta believes for an investment, and you personally believe in those gotta believes, pull the trigger, you know, do everything you can to win that frickin deal.

For you, then, what is it? I mean, there's a lot of saying no in venture. How have you gotten better? Or what does that look like for you in terms of saying no, whether it be saying no to a You're saying no to a founder who obviously wants to get your investment. Like, how has that gone? That's one of the crappier sides of venture, you saying no. How have you gone about that?

It's both personal and professional, honestly. I mean, I'm like a middle child that loves to try to make everybody happy. So saying no is not easy. It goes back to the calendar. And that's why I'm doing my Friday sessions and then looking ahead at the next week. Because if it doesn't match things that, you know, I've already outlined my optimal calendar and I know what energizes me, so I just got to say no. And I say like, you know, unfortunately it's not a priority for me right now, or unfortunately I'm really tied up in the following things, but, you know, would love to reconnect down the line, or if I can be helpful, let me know. Or if I can leverage the team, I mean, you know, Leah is incredible. You know, she works with me mainly on the consumer side of things. Like, she's been able to take certain things off my plate and really make me feel a lot more comfortable in going out and prioritizing other things.

Yeah. And it's one of those things too, I think, to your point of what you're looking for at primary, it makes it easier to say no on the investment side when it's like, hey, we have these criteria, these things, like, it's obviously business. On the meetings as well, it's like, you know, you have your calendar, your priorities. Because I get a lot of inbound requests now for the podcast, people wanting to come on the show, are there things that happen with that? And like, eventually it's like you go from like, oh my God, someone wants to come on the show to like, oh, this doesn't like fit what I want to have for the show. And I'm also out doing outreach to your point, like to people I want to have on the show. And so like you mentioned, you know, reaching out to other VCs you want to talk to. It's like I have this whole list of people I want to talk to, plus inbound to look at. And then like you're saying no to a lot of those people that like might be okay, but not also like what you are reaching for right now. And so. It has been evolution of like learning how to say no. And like, I'm the same way of like wanting to say yes to everything, wanting to like make everyone happy in some ways, but it's like, you can't. So you have to find a way to like prioritize. And once you make it clear, like, hey, I'm looking for XYZ right now, these are my priorities. Sorry, I have to pass because you're not fitting these priorities. Best of luck. But it's so hard to do, like mentally, it's so hard to get through that, to be able to do that.

I don't know.

It's a challenge. But yeah, you work on it.

You hit the nail on the head though. Write down the criteria of the people that you want on, and I'd put a sticky note up right next to your computer, and it's like that subtle reminder every day as your accountability partner. I mean, that's the one thing I think I've missed when being nomadic, living out of a suitcase for the last 8 months, is my sticky notes keep getting lost.

Damn it.

I need a space to say, No, Jason, don't take that meeting or, you know, whatnot.

Yeah. And you said now you have— so you have an assistant helping you. You have— I think you said you had a coach as well. Like, how has that helped you along the way, especially the coach side of things?

Yeah, the coach, therapist, assistant, you know, all 3 of them, I think, play a really, really important role for me. You know, I am, as I mentioned, I think a lot of folks in venture, like, especially at seed, because the sourcing is not the same in terms of being able to just do outbound. It's a bit more sporadic. And, you know, my mind is jumping in 8 different places in a given day.

Yeah.

Unfortunately, you know, you've got to find time to sit back and reflect. I say unfortunately, it's really fortunately, you know, I got to take some time to do that. So, you know, between like meditating and journaling in the morning, and then, you know, the coach really helping me figure out like, What energizes me, as I mentioned, but then what drains me? And when you write down that list of what drains you, it actually becomes much clearer as to how to address those things.

Yeah.

Because some of those things you can completely cut out of your life by saying no. Others of those things you can't completely cut out, but maybe you can go out and say, okay, this one thing, like meeting with these types of people, I want somebody else on my team to do. And you can start delegating. And that alone, you know, has become a lot more freeing, you know, to me. Uh, so I think that's a big thing. And then just identifying like what it is that you value and the coach to give you not only the headspace and the reflection time to like write those things down, but then to work with you on the tactics to execute that plan and then to keep you accountable on that plan, I think are the things that have been the most important to me day to day with them.

Yeah. That reminds me of the Tim Ferriss not-to-do list, having a not-to-do list every day or every week or every month, whatever it is. Like the things you're not going to do because it's so often like if you can just cut out those things, then you make so much more space for what matters and what, again, what gives you energy. And I think I posted on Twitter relatively recently around like really optimizing, not necessarily for time, time, time, yes, but like energy. It's like what things are gonna give you the most energy, what things drain you. I think that once you get to that thinking, it changes how you kind of operate day to day and like what tasks you do. Cuz you realize if you do certain things, Like, I can go all day. Like, yesterday was one of those really good days where I had podcast interviews and meetings with certain people that gave me energy and like felt like I could go all day. Whereas other times you kind of don't have that— those same feelings and you feel like, why am I drained today? Like, what did I do today? If you look back on it, you probably find that like, oh, this is why I'm doing things that I didn't care about as much. They weren't, you know, energizing for me and it drained me by the end. So like, yeah, trying to adjust those are something that's challenging, but it's definitely important. And one of the things I wanna just take a look deeper on. You mentioned the meditation journaling type of thing. What does that look like for you? What are some of the things you're doing there?

So I wake up usually at 6:00 AM and the first thing I'll do is I'll meditate. So I use the Waking Up app by Sam Harris. I used Headspace for 5 years and I think I hit a meditation wall and I was like, all right, I kind of wanna switch it up. And, you know, Sam Harris's way of meditation is certainly different from the way Calm and Headspace go about it. And, uh, it's been great. It's been super powerful to me, you know, 10 minutes sometimes with your eyes open and looking in the world and just realizing, you know, the difference between the thinker and the observer and, and so on and so forth. Uh, in terms of, you know, journaling, journaling is an activity that originally I started at the beginning of the pandemic. It started out with using the The Daily Stoic journal, which was good, but it was like, I don't know, 6, 8 lines. It didn't feel like enough to me. And so I bought a new journal and I'll just start in the morning with whatever's on my mind.

Yeah.

And it could be personal, it could be professional, it could be reflections on meetings the day before, it could be how I'm feeling about something, a goal. I mean, I just got back to New York as you and I were talking about.

Yep.

I wrote down my list this morning of like the things I'm most excited to do now that I'm back in the city. And, you know, I don't have a billion things coming into my mind at 6:10 in the morning. So it's much easier to dig into the parts of your mind that have to do with those other pieces. And so it's a, it's a very like important and therapeutic time for me that I try This is a subtlety I'm gonna ask about, but I'm gonna ask anyways.

Paper journaling, writing physically versus digital, thoughts on that? Talk to me, Jason.

Paper.

Paper.

I love Jour, and Maxime at Jour, by the way, is one of the smartest founders I've ever met from product perspective.

Yeah.

With that said, an app just doesn't do it for me. I'm like, get it. And by the way, my handwriting is horrible. So, you know, I'm grabbing a pen, I'm writing it down, I feel like there's going to be a good story where like 10 years from now, probably more than like 30, I'm going to look back at these journals and be like, what the heck was I writing? Like, I wish I could see, but like I can't even read it.

Well, it's definitely therapeutic and for you only, uh, in the, in, in the moment, which is what it's for. Like, like I, I've had a journal, I've journaled for years and like I've had the, um, I think Tim Ferriss had the 5-Minute Journal or something it's called. Yeah, the 5 Minute Journal I've used for a little bit, but then I shifted to, I have this one line a day journal I use every night. It's just, it's literally just like a couple lines, like you mentioned, not nothing too much, but I have a daily reflection of that. But then I also use a combination of like a Moleskine journal for longer thoughts when I'm writing. But then I also recently have fallen in love with Notion. So I've played, I've dabbled with Notion for journaling. I don't like it as much as a physical journal writing. But I do find that like, it's nice to have quick notes in Notion and then organize it. And like, I don't know, it's a mix of things, but I think journaling in general, the takeaway is super helpful for anyone to like get all of the junk that's in your head organized or out on paper so you can like actually operate and function in your day, which is important. But with that as well, then as we're coming to a close here, uh, any parting thoughts for, for founders? I know you have been a founder. You've then also been on the VC side of things for last number of years. Anything else for founders growing their businesses, thinking about starting businesses, anything else you want to leave them with as we wrap things up here?

When it comes to starting a company, make sure your heart is really, really in it for the right reasons. Ask yourself why, because 8 years ago, 10 years ago, when I first started out in tech, it wasn't that cool to start a company. And now the amount of entrepreneurship that's going on is great in a lot of ways, but failing fast should not be about shutting down a company really quickly. It should be, you know, all companies are going to have times where you need to jump over, you know, certain hurdles and run through certain walls. And that doesn't— not just for starting a company, by the way, that's life in And where you take that strength from, that's the place I think that will tell you whether or not you're doing something for the right reasons.

Appreciate that. And where can people go to learn more about what you're doing, connect with you as well, Jason? What's the best places?

You can follow me on Twitter @JasonRSchuman, that's S-H-U-M-A-N, and follow us @PrimaryVC on Twitter as well.

Perfect. I'll be sure to link that up in the show notes, justgo grind.com/podcast. Jason, thanks for the time today. I really appreciate it.

Thanks, man. I appreciate you having me. Have a good one.