Better to Be Fast than to be Right - Jessica Lin - Work-Bench - Episode #102

Between meeting a founder for the first time and deciding you want to invest in them, how long does that take you? 5 minutes. What is that thing you're looking for?

Yeah, I think first principle is really around velocity. I really do believe it's better to be fast than to be right, because if you're fast, if you just have more at-bats, you'll at least be able to course correct.

Today's guest is Jess Lin, co-founder and general partner at Workbench. I met Jess over a decade ago in 2013 when her and her co-founder John started Workbench. Fast forward to today and they're investing out of their fourth and largest fund, $160 million fund. Over the years, they've invested in companies like Spring Health, SoCure, and Courier Health. In total, Jess has done over 20 investments herself. To me, it feels like an inevit— we're in a bubble. AI bubble. What do you think of that? Is that the case? Do you think that—

100,000%.

Today's guest is Jess Lin, co-founder and general partner at Workbench. I met Jess over a decade ago in 2013 when her and her co-founder John started Workbench. They were trailblazers. It was the early days of enterprise tech in New York City. There was very little infrastructure. There definitely wasn't a community. They were the ones who created it. I built some of my most important relationships at their events and at their office. Fast forward to today and they're investing out of their fourth and largest fund, $160 million fund. Over the years, they've invested in companies like Spring Health, SoCure, and Courier Health. In total, Jess has done over 20 investments herself. What really stands out to me about Jess is how she operates and how hard she works for her founders. She's in the trenches with them. She's hustling, pushing them to be their best selves, and will do the unglamorous work that many investors avoid. Jess Lin, welcome to Not Another CEO Podcast.

I mean, do those intros all day. It's like I need to like play that to have you hype me up every morning, just like the DP intro.

I'm excited.

Thanks so much.

I was on your podcast, now I'm— now you're on mine.

I know. I mean, this is such a long time coming, right? I mean, it's been incredible what you've built with Not Another CEO.

Thank you. Thank you. Okay, first question. Um, between meeting a founder for the first time and deciding you want to invest in them, how long does that take you?

5 minutes. Yeah, usually 5 minutes, right? Um, and what ends up happening is what, after the 5 minutes is you either dig in more or you find out more information that makes you lean out. But within the first 5 minutes you have, I would say, a vibe. Mm-hmm. Right? And at Workbench we have this joke of like, I mean, it's like a, it's almost like a relationship, like falling in love with someone, right? And you're like, the first 5 minutes you're like, I, I love this person. And like I said, you either get more information that makes you fall in love with even the more, or you're like, oh, actually, like once you dig under the hood a little bit more, you realize this is not a good fit. But it's truly a roller coaster, right?

Do you think that those first 5 minutes, do you, um, is it a subconscious thing or do you know exactly what you're looking for in those first 5 minutes?

Well, it's definitely subconscious. Like, I think for me it's definitely, I mean, the word vibe is very overused these days, right? But for me, it's, it's definitely like a feeling of sorts, right? And for better or for worse, I probably am much more of an emotional-driven founder versus a data-driven one. And at Seed, you know, at the end of the day, you only have so much data, right? And so, yeah, I would say honestly, within the first 5 minutes.

Do you, do you think founders understand that dynamic?

I think so. Yeah, I think so. You don't think so? You think they like assume you have all this time to bake and cook on it?

Interesting. That's, that is. In all the meetings I've had, so, and the interviews I've had with investors so far, almost everyone has given me the same answer. 5 minutes, 10 minutes, 15, whatever. But then I turn around and I have conversations with founders and I say that same thing to them and they're like, what do you mean? Like, I, yeah, I'm gonna do the pitch deck, I'm gonna do this, I'm gonna do that. And like, they're gonna make their decision. Like, I don't think they fully appreciate how fast. And my opinion, my opinion is the reason why is because You still continue the meeting. Every investor still continues the meeting. You finish the meeting. And then they say, oh, well, are you guys interested in investing? And the answer not is yes or no. It is some follow-up question or come back to me with more information or this or that. So they go away and they tell their co-founders, I think that went pretty well.

Totally. Totally. Yeah. Well, I'm going to ask you, I mean, when do you— the flip question I ask for founders is when do you decide on an investor?

Actually, no one. I haven't thought about that. That's a good question.

Like when? I mean, that's a great question, right? I mean, you've worked with incredible investors at this point. Did you know within 5 minutes of meeting?

I don't think so.

Right. It's such a different burn time.

Right. That's a really good— it's taken me— it actually, in most cases, pretty long. I'd say multiple meetings. I would say before— well, I think also because the dynamic in that meeting is you're doing usually the founder is doing most of the talking.

Yeah.

So you don't even know kind of the other side, you know. And, uh, so I'm curious, let's talk about— so when you're looking for— so you have this kind of subconscious thing happening. What are you looking for though, specifically, like, that you're gonna take and go back to your team and say, hey, I just met with this founder and these 3 things, this one thing, like, what is that thing you're looking for?

Yeah. Well, can I tell you what I used to look for and what I look for now? I would love that. Right. So for the longest time, probably for 10 solid years, I was a person on the team who said if a founder comes in with this massive, ambitious 10-year vision, like, that's me, that's me. I will lock them down. And a great example of that is actually April Koh of Spring Health based here in New York City. I met her in 20— it must have been 2016 or 2017. They, at the seed round. And we happened to sit next to each other at a conference. And then we ended up going to dinner. And at dinner she literally sat across from me and she goes, I'm going to change how mental health is done in this country. Like full stop. She said it way better than that. But like, it was like how she said it was so powerful. And I remember being like, you're totally gonna do that. I don't know how, right? And there's gonna be a lot of like stuff in between. But like, I genuinely believe that you believe this and you're going to do it and you're gonna do it with or without us. That is the key part. I believe, which is like, I'm gonna do this whether you wanna get on this train or not. Like, that's your choice as an investor. But like, I'm going to build this one way or another. And I just felt like she had such a clarity of vision and thought of saying like, this is how I'm going to do that. And again, like, this is early days of Spring. It's easy to say that now, right? Where they are, you know, valued over, you know, billions of dollars and so forth. But like, at the time it was still so early and she knew, she was like, this is the, a, a game plan and the attack plan of how we're going to do that. We're gonna start with employers, then we're gonna go into the different plants. And so forth and so forth and so forth. And the reality is she's actually done all of those things, right? When you look back over her initial seed plan to now, it's actually incredibly on point. Wow. Right? And, and so the team jokes, it's like, oh, Jess like loves a big 10-year vision, right? Because, and I think that's really important. I think if you don't have a 10-year vision, what ends up happening is you build for like, you know, these like foxholes, I like to say, you know what I mean? Instead of saying, hey, look, this is like the big place where we're gonna go. These foxholes are like how we're gonna get there. Mm-hmm. Right? But you need to understand where where we're going, just like a map, right? And we can talk more about it, but we talk a lot right now about this concept of a car, a plane, and a satellite, right? And like how founders need to be able to switch between those modes. So, I say all that because, again, historically, I love the big 10-year vision. I will say, like, in the last 3 months, right, I've been really— I think I have been forced to think about or recalibrate that question a little bit because who knows what's going to happen in 10 years, right?

Like, who even knows what's going gonna happen in like 3 years.

Mm-hmm. Um, I think we're all gonna be a little right, a little wrong, right? In some way, shape, or form. But it's just, it's really tough cuz then you start getting into like really like sci-fi stuff. You get into like these really like philosophical things. Like, is there even gonna be B2B sales? Is it just gonna be agents? Right. And, and I just find that like not to be that productive if I'm being honest. Like, you know, it just starts to like devolve into this like, oh, is anything even worth it?

Right.

Cuz like AI's gonna take over anything, everything. So the more recent, I think, you know, first principle is really around velocity. Right. And I, I really do believe it's better to be fast than to be right. Right. Because if you're fast, if you just have more at-bats, you'll at least be able to course correct than only, you know, shooting like, you know, one free throw and it being on, on, you know, being getting in. But like you just want as many at-bats as possible, assuming that you will course correct.

How do you figure out if someone— I agree with you actually, and I do think that that has changed. In the last year or 6 months or whatever. How do you assess if someone has that velocity? Yeah.

So I'll tell you what VCs are doing and then I'll tell you, like, how we're trying to do that. There's investors who are now sending out emails on Friday nights and seeing how fast a founder will apply, like, by Saturday morning. Really? There are, there are investors who just even—

I would do very well at that test.

I know you would. You'd be up at 2 AM. You'd be like, I got this. Yeah. There are investors who will score based on how fast a founder replies.

To them.

Wow. Like as part of like an AI scoring model, right? Wow. And it's like plus 2, minus 2, how long it took for them. And it's funny, I was talking about this with some of our, my founders. My founders were like, I am working with customers all day. I am prioritizing customer calls and meetings, right? I'm not prioritizing an investor email. But I was like, honestly, maybe you need to a little bit. Like I, which is unfortunate, but like that is the only, these proxies, you know, because these are such short lifespan of companies now at seed, you don't have, again, these data points to be like, well, how fast did they move, right? You have these like a very, very, you know, fast 2-week process, if even. Right. And so anyways, that's one example. I think other things are, of course, you see, okay, what have they shipped today? Who are their customers? I like to— the questions I ask the most in first meetings is actually what has changed in your initial hypothesis to now? And that might be even 3 months ago, right? But if they're like, oh, well, like everything's gone according to plan, I was like, I don't know, maybe you haven't like pushed it fast enough, right? Like I would like to think that you've gone out, you've talked to customers, you've changed this, you've changed that, you've tweaked this, right? And so for me, it's really about what are the experiments you've run today and what are your learnings? And I actually think like the really fun conversation founders like, I tried this, it didn't work, right? We then moved to this and then it turned out actually like this was the goldmine here.

Right. Um, I get that. It's interesting because you, you know, actually a company that you, um, I think you may invest in or maybe invested in, um, you know, when I met them over a year ago, they were trying something, building it, shipping it, shutting it down, shipping the next thing because they were getting the real feedback. And I— for me, that was my— that was actually my first experience of seeing someone do that in this new era where they're like literally shipped a product. Yeah. Gave it to the people that were their quote unquote design partners. They didn't really react well to it. They shut it down. Exactly. They built another one like 2 weeks later. It was crazy. Like production grade. Put it in people's hands, shut it down again. And then on the third one, it just took off. And they're like, okay, we found it. And I was like, wow, what a crazy— like, that pace is, is unbelievable.

It's —so wild.

You used to do it on like a, you know, Figma before Figma, you know, literally draw the wireframe and be like, what do you think? They're like, oh, it's interesting, let me get in my hands. That's going to be like 6 months' time. I know. Now you could do that in hours, you know, weeks. Like my kids this weekend, literally on, uh, over the weekend they went on, they got on Lovable. I, I pushed them to do it, but I left them at Lovable and the two of them coded, uh, an application they were like, well, let's think about— let's have it tell us what we should do based on our mood. And they, they told Loveable that they want— they found the Yelp API, they, they signed up, got a Yelp API key, plugged it in so it would give them real location. But I watched them do it. Yeah. And even they— one of them was like, no, but now there's too many things. We have to give people the choice on itineraries to put on multi-days. So now the last page is multi-day. Then the other one's like, yeah, but if they're going to make the reservation, we have to let them make it from. So they're doing this in a matter of 2 hours. Yeah. And very simple, obviously. But even watching them, I'm like, wow, this, this is a different— you can think about things in such a different way.

It totally is. And how people talk about like how AI-native companies are being built, you know, I think everyone thinks like, oh, you're just going to cloud code everything. But it's like, obviously the teams, how you think about go-to-market, right? And we can talk a little more. I mean, there's the pros and cons, right? The cons is just like it's competitive as all hell now. Right. And we talk about this all the time. Right. And so if anything, I actually think building on my, you know, okay, founder needs to have velocity. I think the other point really is a founder needs to have a contrarian take in some way, shape, or form to the rest of the market. Right. If there are a million customer success tools, why is your way like the way? Why do you even need another way? Right. Like, you know, and I think you need to have a contrarian take, because to play the same game as everyone else and think you're going to win is just—

it's going to be very hard. When you think about— so you've made a bunch of investments, a lot of different companies. I've met many of the CEOs, the founders. When you think about now kind of post-deal, what are the attributes in the founders that you've seen kind of really thrive and get to the A and B and kind of, you know, because it feels— it feels like it's harder than ever.— to raise pre-seed, seed, there's— you can do that. To get to A, B, like, it's feeling to me harder.

Yeah, that Death Valley is very real, right?

And a lot of people getting stuck, and a lot of— what those people who are breaking through that, what are the attributes that those people have?

I mean, I think honestly the thing that people— I don't find people talk about enough in founders. Everyone's like, they grind, they hustle, they're super smart. I just think you have to be really creative. Right. I think you have to be super creative. And going back to my point about the competitive landscape, be like, okay, if everyone is like, you know, zigging, like, how do I zag? Right. And I think the really, really elite founders are like, of course you want to work hard. Like everyone works hard. Everyone's working truly like, you know, whatever, 996, right? But it's, it's actually how do you do it in a smart way? And that's where I see the really, really smart founders be like, okay, like if we go to market like this, And we do direct sales, of course, right? Like that is the, the, the main motion. But we can also partner with so-and-so here, right? That can be like a backdoor into this relationship, right? This is how we can shortcut this. Or even when they think about, okay, well, um, you know, we have these dinners, but then actually I can connect this person with that person to help them with their next hire. And then that will place us really well for the next deal, right? Like you can just hear the wheels, you can literally spin. I can see the wheel spinning, right? And I think that creativity, AI is enabling a lot of it now and you can actually do really creative stuff. You and I have talked about some of the really creative shit people are doing. But I think that's the, that's, I see a slight difference in our founder and like great founders and then like exceptional founders who can kind of look at it like again at the satellite level and look down and say, okay, like where do the chess pieces need to go? Yeah.

What, what, uh, if you think about the top issues that companies— like, let's talk about this gap, this, this Series A gap, this, this Death Valley. What, um, why, why is that happening?

A few things. One is just everyone's growing really fast, right? And so you have to grow really fast. That's just almost like the baseline. Like, people are growing 0 to 2 million in a matter of months., right? And whether or not that's durable or not, we can talk about that separately. But like people are signing customers and getting them live really, really quickly. So that's just like the base case, which is like you almost just, you just have to grow. Um, I think the, the reality is investors also can appreciate or, or understand, hey, is this a customer that truly like depends on your product? Right? Mm-hmm. Um, and they are doing that type of diligence now when they're calling up their customers and saying, okay, if this cut, if this product shut down tomorrow, like what would happen? I think a lot of people would be like, nothing. We'd probably just sign up with another product, right? Like, how can you truly be mission critical, whatever the term is, right? Whatever the phrase is. But I think it's not just, hey, I grew really quickly, but you have to be indispensable to your customers, right? And I think that's, that's still like at the heart of what, you know, all of us are trying to do when we find product market fit, right? Is to be indispensable. And so, and so I actually think that's, that's actually not very easy to do that also in a very short amount of time.

It seems to me that the, that second part, maybe I'm wrong, but it does feel like more back-channeling is happening to do those customer references. Maybe then, then I've, then I've seen at least, I'll talk to a founder like, oh yeah, this person showed up for Series A with all this information about my customers and I didn't even talk to them yet. Yeah. Yeah. And that didn't maybe later stage that was happening, but I don't think that was happening.

Yeah, that's true. I mean, I think you're seeing Series A investors show up with like these full-on decks, right? And memos. And they've done a lot of the research already. And part of it, I think, is just like there's just more customers now to get to, right? In theory, like by the time you get to Series A, you have a lot more customers, whereas maybe before Series A you had like 10, you know what I mean? Like 20, 25. Now you're like, people have hundreds of customers already by the time they get to Series A. So I think in theory, that work of doing the customer references is a little bit easier. Maybe now it's all easier now with the TAGIS and so forth. Exactly, right. Right. But yeah, I mean, Series A investors, I think, are, you know, coming to the table like, you know, ready to jump. Yeah.

With really great customer feedback. What, what as a firm, you know, where do you— like I said in the intro, I mean, you definitely hustle for your companies more than I've seen most investors, especially at an early stage, which is amazing. How do you talk about that, like with founders, you know, do you, do you, do you, how do they buy into that? How do you convince them that that's something they need?

Like, yeah, well, that's something I know you've been very passionate about helping us on. Right. And I think if I'm being honest, right, we've been in business for 12 years like that continues to evolve or it can do. We have to continue to tighten and refresh the story. What has always been true, we believe, is that go-to-market is at the heart of building a, you know, world-class enterprise company, the hardest part, right? And if anything, nowadays it's easier in theory than ever to ship products, right? But the go-to-market and the distribution engine, you know, quite frankly, you know, is your only moat in some ways, right? It's like your only differentiator. And so we spend a lot of time on that. How that comes to be,, you know, brought out, I think, in companies. Um, you know, some of it might be, sure, we make some direct intros to potential customers, but a lot of it is a lot more strategic, right? It could be like, we help you land that first great hire. We help you think through, um, these customer dinners you're doing, right? A lot of this tactical stuff. What I will be very real with you about, and we talked about this, right, is we say all this stuff and hopefully it lands really well. And we believe it does land with a certain type of founder and with some founders it doesn't. And, that's okay too, right? The hardest part of the job is when you have founders come back after they, for whatever reason, have not taken our term sheet and say, I wish we had worked with you guys. Because like that, that to me is so hard as a seed fund. You know, you don't get another shot at working with them, at least in this current company. Maybe if they come back in the future. And so, yeah, in that way, I actually think that's like I said, like the hardest part is it's like, you know, what are you going to do with that? You're like, okay, well, we tried to convince you, right? And I think a lot of, a lot of founders have come back and said, yeah, like, I went with a firm because they gave me a higher term valuation. And I totally regret that. Yeah. You know, and, you know, we can only say these things so much. And so, look, you'll win some, you'll lose some. But like, I reflect on that a lot. Right. And look, maybe, yeah, maybe if founders are optimizing for really high valuations, like, they probably are not going to be a great fit for us. Right. And vice versa. So there's a lot to, like, unpack there. But. It is interesting to reflect back and say, okay, if we have not won deals, like, what's the reason why?

Right. I think your question you asked me, how long between meeting an investor and knowing that you want them to be your investor? I actually think as a first-time founder, the answer would be quite short and it would probably be whatever the highest valuation, you know. Yeah. And if you get to a second-time founder, which I've seen on my podcast as I interview people, the second-time founder is always like, well, what I'm looking for in an investor. And then they can list like 20 things because they've been through it. Tell Totally. And they know, you know, but if you're a first-time founder, you don't really know exactly what you're about to walk into. Yeah. And you're like, well, my self-worth is tied to the valuation of my company.

I know. And you know, I've talked about this so much, right? How to break that down. And I don't know, you've told me it's possible. I don't know. Well, here's my question to you. Is there an investor that you look back on, they're like, oh, I should have worked with them?

Um, I don't, you know, that's a great question. I don't think off the top of my head, I can't think of one, um, that I wished, that I wish I had worked with. I can probably think back to my earlier part of my career and think about people I wish I hadn't, knowing, knowing what I know today. But I do think by the time I got to BetterCloud, I had a lot more insights into, you know, who to work with. Yeah. Um, and probably my experience at BetterCloud, and I've talked a lot about this, is I think there was not my investor pool, but I was learning more about my— the concept of an advisor pool there. And I, I think I learned about people there. I probably had advisors that I wish I had worked with and advisors that I wish I hadn't worked with and that I wish I had done better diligence on. Yeah, yeah, yeah.

That's interesting. Yeah.

In terms of— so again, we're early stage, you know, we're talking about pre-seed, seed, seed rounds, seed stage companies. How do you think about engaging with the founder post-investment? Is that— is it the board meetings that you really kind of look to? Is it— do you have some regular check-ins? Like, is it ad hoc? Like, how do you do that?

You know, you have to figure out at any given point as an investor you know, the role you are. Sometimes you're the cheerleader, sometimes you're the coach, sometimes you're maybe the last one's like critic or something like that, right? Like you have to figure out who you are and, and different times in the journey you're different things, right? Like there could be times when things are going really well. You should just honestly be like that hype person and be like, let's go, let's keep it up. How can I help you hire? How can I help you do X, Y, Z? There's times when shit is really hard and you have to give them the real talk and it sucks, right? And you have to like sit them down and be like, you are burning way too much cash. Like you have to figure out a way to like cut back, run away, right? And yeah, and then there's other times, you know, you, you, you're, you know, connecting and so forth. So yeah, I think that's the part that knowing who you are at what point in the journey and, you know, I've talked about this, right? Like how you communicate with a founder truly. I mean, in some ways every founder is truly a snowflake, right? And like how you communicate with them, how they take in your feedback, right, is very different. Right. And so like I could be on an 11 a.m. call with a founder and share feedback one way and at 2 p.m. I have to like completely like, you know, turn on a new face, right? And be like, okay, this is how this founder is going to take this feedback. I will say, you know, immediately we get into Slack every day. I mean, we're, we're effectively slacking with our founders every day, every other day in some way, shape or form. Right. So I do think that's important to have that trust that builds up. Over like over a daily period versus just, hey, I see you once a quarter in this like big fancy, you know, conference room. Right. And so we have the daily Slacks, we have the monthly catch-ups, all of that. But I actually think the Slack interface is, is really critical because then you can jump on things much quicker. I mean, once a quarter is not enough time, right? I always say the board meeting is like the least important part of what we do. And I'm sure, you know, you probably agree in some ways. Oh, I couldn't agree.

That's why I don't do board seats because I, Yeah, I don't know what value that they— I mean, that sincerely, I really don't know what value most board meetings, at least early stage, deliver. Yeah. Yeah.

I think the one thing they do do is it forces the founder to sit down amidst like chaos. Right. And the daily battles and be like, okay, like, what have we actually done this quarter? What have— what do we say we were going to do? What do we not do? Right. And what do we want to do in the next quarter? And like, because genuinely, I think if we don't have that touchpoint, founders are just keep going like through a wall. Right. But it's very— and like to really pull out and say, okay, like, are we actually doing things we said we are? Right. Is not easy. In terms of what, what is a very valuable board meeting, I genuinely think the ones where there's an independent board member, it's like you can tell there's a night and day difference. Interesting. Between that and an only VC board. Because an only VC board is like, a VC echo chamber. And we, you know, obviously, right, an independent board member ideally has come, has built a company or, you know, has some sort of domain expertise. Truly, that conversation is like night and day difference. So, I can't say enough about getting an independent board member in that Series A who's actually gonna do the work.

Yeah. Yeah. What, what do you think is something that founders don't understand or maybe misunderstand about your job?

Well, I should have you answer this too, right? Because you've come in and you're like, yo, this is not what I thought. I think, well, I will speak to being an emerging manager or someone who has started their own fund. Right. I think there's a, there's a whole, there's, you know, investors who work at a fund that is a longstanding fund and there are investors who start their own funds. Right. And we're, of course, of the latter. And I used to joke that like, starting your own fund is almost the worst of these two worlds where like, if you're at like a blue chip tier one fund, everyone respects you. If you're a founder, to be honest, like people really respect founders, right? There's like a decent amount of founder glory. But if you're the founder of your own firm, you're like the worst. Like no one really wants to like talk to you, right? And a huge part of that I think is like, you know, the fundraising is really hard. Building a firm brand is really hard. It's more competitive than ever now on the venture front. So I think And I think founders actually appreciate that. I think founders understand, like, hey, if you're starting your own fund from scratch, like, you are much closer, I believe, to a founder than maybe like an Andreessen or Sequoia, right? Like, and if anything, like recently they've, they published the success rates or the death rates, right? It's actually like your chances of being a more founder and being successful is way higher than being an emerging manager. Really? It's very hard right now to be emerging manager. Yeah. To raise Fund 1 to Fund 2. And then even after that is like, I mean, the rates are just— wow. Yeah. So, you know, hats off to any and all emerging managers. You know, we give them obviously a lot of credit, but it's really hard. You're actually literally more likely to have success as a founder.

Yeah, it's, it's— I, again, I'm not sure founders actually do appreciate all of that. I don't— I did not understand the fundraising process for funds until way— like, I did not appreciate that motion. I actually didn't appreciate the— how competitive this market really is. I mean, when you, when you think about how many— I mean, how many venture funds are there in the U.S.? 3,000 or something? It's some number, right? 2,000? It's like a big, big number. And it's a crazy— like, when you, when you think about how you have to differentiate. You know, you, you just, you don't think about venture funds as companies a lot, you know, but, but especially at the stage you're at, like you said, it is a comp. I mean, it's a company like anything else. The branding, the marketing, the operations. Yeah, it's all the talent that you're building your own company.

Yeah, yeah, yeah. The question is the product, right? And this is like what a lot of, of course, investors talk about, like, what is your product? And you and I have talked about this, like, what is Workbenches product, right? And we continue honestly to evolve on that, right? I think it's always been go-to-market, but like I said, certain founders value parts of our product more than others, right? There's parts of our product that, you know, is more useful to certain founders, you know, at a certain stage than later. So it's an evolving, constantly evolving, as it should be, right? You should constantly be evolving and iterating and refreshing. The product, the brand, right? And that's, that's a huge part of the work is 12 years in, you know, it's actually, I think in some ways very similar to, I'm sure other later stage companies where you've built these habits over time that were really good habits at one point, right? And to unwind those habits when times change, market change, you know, like the best companies have to evolve and adapt, right? And unwinding habits is ironically, I think, actually quite hard, right? When you've gotten to somewhere and you've built a certain muscle and then to say, actually, no, You need to unwind that and build this muscle. It is not easy.

Let's talk about actually that change, because I think when you started, I know when you started Workbench, there really literally was nothing for enterprise tech. I mean, there really wasn't.

I know. Well, we started to go explain to people enterprise software. People used to be like, well, so what's enterprise software? And I had to be like, oh, it's B2B. You're selling to a certain type of company. Yeah, truly. But it's not.

It hasn't been that long. I mean, it's been long, but it hasn't been that long. And it's completely— I mean, yeah, people love B2B now.

Ones on the B2B chain, which I love.

So, like, can you talk about how you, how you've seen that evolution? You know, maybe just paint the picture for everyone of what it was like, you know, if you're a first-time founder right now building B2B software in New York, you don't know what it was, you know, 13, 12, 13 years ago.

I mean, we literally could get every B2B founder in one room, right? Quite literally, we would host these events. It would be like, that would be like, that's it. That's every B2B founder. That's here. And even then, like some of the B2B, you know, like you're like, is this really B2B? You're like, okay, close enough. So, you can get everyone in one room. I think again, like the reason why I love New York is, you know, obviously it's a lot bigger now. There's competition, but I still think of it as generally like a much more approachable place. Right. And people are like genuinely trying to help others. Like, that's what I've been so moved by our community over years. Like there's people and founders like you who truly are like, I am happy to share my learnings. Right. And give back to the community. Community, and we can't say that enough. Yeah, I think the big thing now actually is just thinking about, you know, there's just more and more obviously companies, the talent pool, right? I hope it's expanding, but it's very competitive to grow talent here. And expensive. And expensive, right? And so, The founders who are here, I really believe, understand that they are close to their customers in one way, shape, or form. Right. And that is, again, like so indispensable and so critical. And that was always the thesis actually 12 years ago, right? It was that customers, Fortune 500s in our backyard, right? They will be the magnet and the honey to attract founders. And that has largely played out. And you see actually incredible healthcare companies here in New York City. You see obviously companies selling to financial services, insurance, media. A lot of CPG brands and so forth. So I think all of that continues to hold true. And again, like as we talk about this like AI revolution, how it's changed go-to-market engines, people now are realizing, okay, cold calling, cold emails, like you're just going to a sea of spam just like everyone else. The only thing that actually seems to cut through the noise is in-person. It's back to the in-person dinners. It's back to conferences, right? Like it's truly like a pendulum swing. And obviously in our, in our career, right? Just like back and forth. And so I think now, again, it's more powerful and more critical than ever that you are getting face time with your customers because you're not getting through on their emails.

Someone said something to me, actually, in an episode that I just did with— they said the success— like, people are being successful with things that are unmistakably human. Mm. And I thought that that very simple description is perfect because that's exactly what I am seeing. Yeah, it cuts— it does cut through the noise. And when you're here, you are around. Yeah, those customers, you can do the unmistakably human things that otherwise would require you to get on a plane and go somewhere. And, you know, but I, I, I— yeah, I couldn't agree more on that. I, in terms of the way, like when you talked about the go-to-market stuff, I want to— I think one of the things you've been very good at is helping these customers, helping these portfolio companies get those customers, like, and do these unmistakably human kind of things. Can you just talk a little bit about that? Because I, I do think, and we've talked a lot about this, you know, in private, is that I do think it does separate Workbench from kind of many other seed investors. Can you talk about like specifically the tactics that you— Sure.

Yeah, I'll talk about two specific companies of ours, Courier Health, which is building a patient CRM for life sciences companies here in New York City. Another company of ours called GovWell, which is building an operating system for municipalities and local governments. Right. And what both of them did is they took their end user and customer and just swarmed them with love. Like, you know, they truly elevated these customers and said, hey, the work that you're doing is so important and it's underappreciated and underrecognized. And we are going to, again, like, just like completely cover you with like appreciation and respect and elevate you. Right. And time and again, and we can talk about obviously what you saw at BetterCloud, right? Like, I mean, this was your playbook obviously from day one too, which is like these end users are the ones who actually are doing truly incredible work, but not being recognized. And so we saw this with Currier Health. They've done incredible work, especially with their patient engagement teams who are working with patients with really rare diseases. I mean, truly like work that like make you cry. You hear these stories and they've done it in a way where they highlight them, they spotlight them, they talk about them in a way that has never been done before, right? And I think when you do that from a place of true genuine appreciation and love, like the end customer user, you know, feeds off of that. And like, obviously, like, you know, appreciates that. And so it's this like cycle of like, you know, elevating you and helping you be better at your job with our software. But like, at the end of the day, like we're making you better at what you do, which is helping patients with rare diseases, right? It's the same with GovWell. I think they've done an amazing job where every month now they spotlight like a government employee on LinkedIn. They're like, look at this, like, you know, You know, Tom from Louisiana, right, who works in City Hall, right, who's worked here for however many years and who, I don't know, has, have they ever been really recognized in this way? Right. And it's truly from a place where people are genuinely like so excited and happy. Right. And I just think that's the part that, again, to the part about being human, right? Like the more human you can be and you can attach names and faces and stories. Like I just think it also, I mean, from like a team perspective, who you hire, right? It's, it's a huge, very different type type of person, I think, who ends up like joining it. Yeah, kind of driven company like that. But I also just think like customers see— can see and tell the difference in some of these. Like, yeah, I think the marketing materials— I mean, it's still marketing materials, right? But if you're going to do it, do it from a place of like really authentic, like, love.

Yeah, yeah, I, I do. I— that is the thing, you know, I've been talking to, um, some of the companies I work with. I interview, um, people for them, you know, executives, salespeople, whatever. And I keep telling them the same thing, which is the people who are really successful, I think, at early-stage companies, growth stage even, are people who have the work ethic, who want and have the ability to learn. And the third one is who understand the customer and can put themselves in the shoes of that customer and champion that customer, have empathy for that customer. Because I think that really is, you know, you're calling some— as a CEO, as a salesperson, as a market— you're calling that person and you're just like, hey, buy my product. It's— but that's what most people do. Yeah. Versus, no, I see you. Yeah, I see you. I understand what's happening in your life. I understand what's happening in your career. I understand that actually, because most people, most, not all, you're selling to the CRO, that's different. But most people are not seen in their job. Yeah. Most people are, you know, they're doing this work and it's kind of thankless for the most part. And so anyway, I love those two examples because I do think And it's more fundamental to just the DNA of those companies than it is some tactic. It's kind of like, yeah, this is, this is how we're going to treat this customer. Yeah.

And this isn't even the case of SpringHill, right? Like every town hall, every team meeting that they always kicked off with some testimonial or story. Right. And when you can ground the team in that, right. And then they obviously share it publicly, but I think, I think it really is a big differentiator. I mean, you did amazing work like this with BetterCloud, right? Like, and you like really championed like the IT leader, not even the leader, but the end user, right? Which I actually thought was like, you know, there's a CIO, but then there's like the people who are actually doing the work.

Exactly. In terms of, let's talk about kind of, so now you work with these companies, you've been doing it long enough, you've had people kind of go through the stages of the business. How does your involvement change in a company over time?

Yeah, I mean, the early days as a seed company, you are talking to them truly like every day, every other day in some way, shape or form. Yeah. And then our companies like get older and they graduate, which is great. They have other investors who are also kind of putting time on their calendars. Right. And I think the key thing is understanding again, like where can we add value versus like we're a standing meeting on your calendar just because we want to be a standing meeting on your calendar. Right. I do think I think the part that a lot of founders maybe don't really recognize is your seed stage investor in some ways, hopefully, is a person like you're closest with, right? Just because you've known them longest. They took a bet on you when you had very little, right? And hopefully they're the person you can go to with like truly what I call like dumb questions, right? Like you should come to me and ask all these things that you just like are not sure that you might not ask your Series C investor, right? And I genuinely think like those relationships, like, again, evolve over time, right? Once you get to be a later stage company, the things you're thinking about, the questions you're asking are different than what they were at Seed. And that's part of the journey. But I think, yeah, we probably are not talking every other day, right? But I do think the conversations you have in some ways are deeper, right? Because they're less tactical, right? They generally are less tactical and they're much more, hey, like, these are the things, I'm thinking about, um, like at this, at this massive scale now versus, hey, like this is a white paper we're putting out, what do you think of like, you know, this like super interesting—

I think it's almost like, uh, when you gave that, when you said that, it's like it's almost they're your friends from, um, you know, middle school or high school or something where they know you in a different way. I really, I really think that that's a good way of thinking about it. Yeah, you know, that investor saw you when you had nothing and you had no customers and no revenue and you didn't take any secondary, you know, we're living in the like studio part. Literally. Yeah, exactly. It's like kind of that's, that's, that's where that relationship started. Yeah. Yeah. Versus, you know, further down the line, you're also much more aligned economically. Yes. Because you're both in from that very beginning.

Yeah. Stage. Yeah. Yeah. And I'd like to think that like we can hopefully share feedback in a way that might come differently than like a later-stage investor, right? I mean, I just think, yeah, the nature of the relationship evolves and it's a really fun thing, actually.

What, um, what deal— I've asked some of the investors I had on the show, but I'm gonna ask you, what, what did you miss? Like, what is that deal that you look back and say, man, that was— I missed that one?

Yeah, so I'll give you two examples because there's two— there's— when you say miss, right, like miss can mean a few things. Right? There can be a company. So there's a company in the video AI space that— sorry, video API space, I should say— that I met. It was at a time when I was looking at a bunch of other companies. They were not here in New York City, so I didn't get to meet them in person. And so we did a few calls, but, you know, these calls are just so superficial, right? Like, I really believe, like, I should have gone on a plane there, right? And met them in person if I truly wanted to, like, get to know them as people. And I just, like, didn't. I just quite frankly, like, did not dig deep enough. Like, like, and, and that's obviously like the miss there, which is like, I should have just like put more work into it. It was one of those like in the first 5 minutes, I didn't like get the feeling, right? And again, but that's again where like the spidey sense is, can be wrong, right? So you just gotta make sure like the spidey sense, you know, comes through. Again, it's really hard on Zoom, I will say. So like that is my preference of why I think for us doing New York City-based companies is very important, right? Then there's a company in which, um, here in New York City in the accounting AI space that has now done phenomenally well. We were at the finish line. We were really, we were like there. We were wanting to do investment and we couldn't come to terms on the price. And we ended up walking. And it's one of those things I look back now and I say to my team, like, should we have walked away because of the price? Right? Like we actually really wanted to do the investment. But then, you know, we just didn't think that the higher valuation was something we could get behind. And it's one of those things, well, if this company is not worth like X, you know, hundreds of millions of dollars, right? Like, should that matter? Right. And it's a very— I think it's just like a very important question that we as a firm need to constantly be asking ourselves. Right. Now, there's also the flip side of that for lots of deals that we've done where, like, it didn't have that outcome. Right. It wasn't like, you know, we end up— even if you give them the valuation they want, they don't end up becoming super successful. So I don't think it's necessarily like conditional in some ways, but it does make us think like, okay, these first principles by which we operate the firm, how, how tied should we be to them? Now, the flip side of that is it's a very slippery slope and you make exceptions for every other deal too, right? But I think about those two a lot, right? I think about the work that I should have done. And then I think about, okay, how, how closely tied do we have to be on these like principles we have around pricing?

So let's talk about that because right now the valuations are— to me, it feels like an inevitability. We're in a bubble, AI bubble for sure, which we've been through this. You know, I have— I'm of the opinion right now that this is like the SaaS bubble of 2020 and '21 where basically all demand for these products is being brought in like by 10 years. Yeah. And so, you know, I think it's worse than that. Maybe worse.

You know, I think it's worse than that.

But your Zoom of 2020 and you kind of get all customers customers in the world in 2 days, and now you're trying to keep up with that kind of growth, and that— which is impossible. You know, you're Peloton and you get all customers in the world in 6 months, and then— and so it feels like AI is the same, except for the difference feels to me is instead of buying one vendor, people are buying 6 vendors to do that thing. And so there's 6 people with a dollar of revenue that will become $2 for one person down the line. Yeah. So the question is, what happens to— like, it feels more bubbly than I've— than I've seen. And I wasn't around in the first dot-com boom, but it feels kind of in that bubble kind of way. How do you deal with that? What do you— first of all, what do you think of that? Is that the case?

Do you think that 100,000% we are in a bubble? But, you know, me running around all day saying we're in a bubble is apparently a downer. So I don't do that. But I 100% agree. I think it's even worse than 2020. And there's a lot of investors who, again, are not that price sensitive because they're like, well, this is going to be bigger than anything we've ever seen. I would like to hope that. That said, I think it's becoming very clear that, you know, we're not going to have 100 winners. We're going to actually have fewer companies who are going to be great. So I think instead of, again, like S&P 500, you're going to have like 10, you know, of the most generational companies that we or Ken Ortiz's name. Right, right, right. I don't think that pie is then, you know, like I said, like even 200 companies. Right. And again, lots of smart investors have already written about this. Right. Which is like, as much as we'd like to think everyone wins, I just don't believe that. Right. And so this is where I actually do think pricing still matters. Right. And it's very hard to think that, like, when you're in this frenzy and everything's like la la la, it's succeed. But I mean, we all saw what happened in 2021. Literally, we all saw it because it was only 4 years ago. Right. Right. And it's just, I think it's very, it's very risky to say, well, it's all different because of AI. Right. I mean, that said, right. The flip side is, yeah. I mean, does software even matter? Right. And it's becoming very clear people aren't even building software anymore. Right. You have these like multi-tenant, you know, agents effectively. Right. So, You know, I think a lot of this, like I said, we are thinking about in real time. It's forcing us to even like rewrite some of our own internal kind of rubrics, if you will, and say, okay, like, well, how do you assess a founder at seed? Right? When you can't really take into account their 10-year vision because who knows, right? I mean, I'd be so curious from you, like you asked me what I've seen in New York, obviously, and obviously founders now. Is the advice you're giving founders now different? Than even a year ago?

I think that the advice is not, to be honest, really actually not that different. I think it is. I really believe that execution, which goes to speed and the ability to kind of continue to evolve and change direction and do— I actually think that is what I'm seeing separating the best from the worst. I think that the people who are going to fail are the ones that they're moving fast but without purpose or deliberate motion. Yeah. And they're just like, well, let's vibe code this thing, then let's do this, then let's throw this out there. And it's like I told the founder the other day, it's like chickens with your head cut off just kind of running around trying to find something that sticks. Yeah, yeah. Versus we're going to try this now, we're going to align the team, we're going to take a step We're going to see if this works. If it does, great, we'll double down. If it doesn't, we'll move to the next thing. But in an organized fashion where the company, right, because what I'm hearing from employee, forget founders, like employees on the front lines, people are getting whipsawed.

I mean, the whiplash is unreal.

It's crazy. I talked to someone the other day and he said, literally, we released a product, the next day we shut down the product. We released, we then started working on another product because our competitor was doing this. But no one told us why. It was just being, you know, so I actually think there's so much thrash. There's so much thrashing that I actually think the execution and the creative, the creative pieces of it, the execution, the quick changes. But I don't think that that's different from before. And, and, and I think that I don't know, I am very— of course, AI is changing everything, but I sometimes I look at these applications that are getting delivered and I'm like, They're, they're good, but they're basically SaaS, just a little bit more automated and predictive. And yeah, yeah, you know, they're not really like, you know, yeah, people like, well, I have 73 agents and no employees. I'm like, that's not— so far I haven't— I've tried, I myself tried, and I'm like, I can't actually make that work. So either you're lying, yeah, or you're a technical genius, which is great, but you're probably going to suck at the go-to-market part.

Yeah, yeah, totally, totally.

So that's —That's what I feel like. We did this open call workshop the other day for this, for like a New York community of founders. I think it was 10 founders in the room. And after 2.5 hours of an open call workshop with an expert, only 3 got open call working. Yeah. And when I said to the instructor, I said, that sucks. You know, like we had all these— He said, oh no, that's what I was expecting. Yeah.

Like, it's hard. Yeah, it's really hard. It's really hard.

And to hear that, and you're just like, you read on LinkedIn like as if open claws, like running everyone's personal lives, work lives. It's like doing everything for them, and they're growing 5 trillion percent. But then you get in the weeds, you're like, I don't— I'm not seeing those. I am seeing pockets of cool use cases. Yeah, but that's not what I'm seeing.

I mean, we are in such a bubble too. I mean, LinkedIn— if you just lived in a LinkedIn world and you walk outside, you're like, well, these are— you know what I mean? And so I think that is what's interesting now, is we're seeing a lot of companies again tackling this, like, non-tech world, right? They're going and they're building vertical AI for pest control, landscaping, fleet management, like the whole kind of other, I would call the 99%, right? Because let's call us, if this is the 1% of like most pilled, you know, Claude pilled people, there's like the whole world, which is not. And I think the question, and you and I have talked about this, is when all of them, these are very sharp founders. They all have some revenue, some real revenue already. A live product, they all seem to be executing at extremely fast velocity. It's like, how do you pick? Like, truly, this was our question yesterday in IC yesterday. We just like, we're like, it's, it's just, I think, even harder than before, right? Where you saw some spread and now you're just like, oh, you're all honestly doing great. And so then the question goes to, and this is where again, you have the longevity and longitudinal view, which is, okay, you back a lot of companies. They all like, you know, are doing their thing and then like, you know, only a few break out. Right. And why do only a few break out? Right. Like that's why I'd be curious again with all these episodes of Not Another CEO. Yeah. Like if you, it's one thing to execute really well at seed, but like what makes a company truly like a generational lasting one? Mm-hmm. You know, and I would say when people ask me, I'm like, if I'm being very real, I, I actually think it's a, a decent amount of luck in there. 50%. 50%. I don't know.

A lot. A lot.

50%. Exactly. Yeah. I actually am like, it's probably more luck. I do think tailwinds is a huge part of it. And Spring Health, you know, and the COVID tailwinds truly elevated, I believe, to be this, again, truly world-class company. But, you know, I think they could have gone there just like the slope would have been much slower. Right. And we see this, quite frankly, with like a lot of our other companies too. So like, you know, the question of tailwinds is an interesting one, but I'm curious what you think.

No, I think, I think luck. Many of the people I've talked to, the exited ones, the ones who have time to reflect and who are being really honest, they'll say luck. They'll say, look, did I create some of my own luck? Yes. And I agree. In the beginning, I was like, I don't know. But I believe that. They put themselves in the right place at the right time. They were ready to jump on the wave when it was there. You know, I mean, we used Spring Health at BetterCloud during COVID It was a lifesaver, but they were ready to handle the volume that came with it. If they weren't, they probably would have gone out of business because they would have crushed under their own success. So like, there's some element, you know, there's luck, but there's also, you know, and I, I feel like the CEOs I've interviewed who have really like gone to massive scale, all of them have continued to reinvent themselves in all of those stages. And I think that is definitely one of the biggest indicators of success is themselves as a CEO or the company.

Okay.

Themselves as interesting. And you can see, especially some that I actually know personally from 10 years ago, and then I talk to them today and you're like, wow, you're— you really are a different leader. You know, you approach things differently. You've learned from this thing. You've got to— yeah, yeah, yeah. And so I think those people, like some of the people I've interviewed who were 20 when they started their companies and now they're 30 and they've been very successful. They are definitely a different person than they were at 20. Yeah, but to do that, they, they study. I mean, one person was telling me, like, I will literally consume books and podcasts, and I, I'm just consuming that content trying to push myself to be better. And the reality is that if you think about exec teams, most times, hopefully, the CEO sees that this person stopped growing, this person stopped, and they fire them and they replace them because that makes sense. And that's what we all have to go through. Through. But that doesn't usually happen with the CEO because usually venture firms, for good reason, don't want to replace the founder. And so you end up with the person who could hit a ceiling with no real, let's say, ramifications, like, you know, versus the leadership team who is being— every quarter, like, you know, up-leveled, which makes sense. Yeah, but that doesn't happen. So the best, in my view, the best— the people really scale they find the way to push themselves kind of to the next level.

So you believe people can fundamentally change?

Oh yeah, yeah. I, I don't think they fundamentally change who they are as a person. I think they can change who they are as a CEO. That's what I believe. Now they have to have a high— you know, we, we've all worked with those great people where you're just like, wow, they just keep rising to the next challenge.

Yeah, yeah.

They get— but, but they kind of keep finding that way. You know, I, I, I, I've— there's a number of the CEOs that I work with that, that, that we know that just in the matter of 2 years, they're the same person fundamentally, but as CEOs, they're— I mean, they're like different people. You know, it's like seeing 2 different people. Yeah. And especially if you saw them 2 years ago and today without anything in between, you'd be like, what the— this is like a completely different person. Yeah. So I believe— I actually think luck is a big part. I think that is a big part. I mean, the tailwinds. And then I think that the CEO kind of growth, because that comes with replacing your team because you realize that they can't do it. That comes with aligning your team around execution at scale versus when you were 10 people. That comes with all the hard stuff that you have to go through, you know?

Yeah, yeah. Well, I think about all these companies that really popped off in the heyday of 2021. And it's like what becomes of many of them, right? You and I talked about this, right? And I think a lot of them have evolved. Yeah. Yes. You know, yeah, they've evolved. I think some, you know, I think a lot of them raised out of places that are just going to be very hard to get out from under at this point. So, yeah, I don't know. It's like, it's a very, it's like there's, you know, like the very practical example, just like a whole some, some one investor I had, I'm trying to remember who was on the show.

They said, you know, when the sun is shining, that's when you want to make hay. That's when you want to actually start to, to take advantage. So his, his point was, I remember it was, but his point was basically these AI companies that are raising crazy money, crazy valuations, instead of being like some of the 2021 companies who thought this is never going to end, I'm going to keep raising, the Hoppins of the world, you know, like good platform, actually good product, but they burned through all that money versus saying, you know what, we may not win like this for the next 10 years. Let's take the time, the money, the, the freedom we have to start preparing for our second act now. And when he said that to me, I was like, that is a really, really good point. Like, if today you can raise money and you're raising it $5 billion and $7 billion, you're probably not worth even close to those numbers today.. But you have enough capital where you, you can probably navigate it. But if you're burning $500 million a year, which some of these people are, you're going to hit a wall before you have a chance to kind of do that. Yeah. Yeah. Which is an interesting—

that is interesting. Yeah. I mean, again, the only two things that matter as a founder, right? Hire great people and don't run out of cash. Exactly. Yeah. Yeah. Right. I think teams are more lean than ever. And so, I mean, your compute costs are going to be obviously what kills your runway, but like teams are more lean than ever. Definitely. So that part is cool. Cool. We've got to figure out all this, like, you know, the model costs because that is a big limiting factor. But yeah, I think it's just going to be very interesting to see if we have this conversation again in 5 years. Yeah, yeah. If you sit here in 5 years and it's not just bots, right? Like which of these companies have managed to 100% break out from the fray?

100%. Okay. Last question for you. Why did you start your own venture fund? What drove you to become an investor?

Yeah, I don't know if we've ever talked about this, right?

No, we haven't.

We haven't. So, there's two ways to answer this. One is, I don't know if people really know, but I am in some ways an accidental VC. I did not come into this role thinking I'm going to raise a fund, I'm going to be a GP, I'm going to raise four funds. I was introduced to John, my co-founder, by an old mentor of mine who's who said, hey, there's this guy in New York City, they're starting this thing called Workbench. It's gonna be a VC fund in a community. Like, go down and talk to them. And I remember that I was living in Boston at the time, this was 2014. I actually had wanted to move to SF, 'cause everyone went, all my friends were in SF at the time. And I came down, I met John, and I mean, like, I look back at some of the things we were talking, I'm like, wow, that was, some of it actually was directionally very correct, but some of it was just like so early. And I remember being like, I don't know about this. And I didn't even wanna live in New York City at the time, so I was like, I was like, okay, listen, worst comes to worst. I had been at Cisco for a number of years. I knew I wanted to start something. I knew I wanted to build something from the ground up. Right. And so I wanted to do something earlier stage. I didn't think it was a VC fund. Right. But I was like, look, I'll do this for 2 years and if it doesn't work out, I can always move to SF. And that was literally 12 years ago, you know? And so it's just one of those things. Like, it's so interesting, you know, I meet so many young people these days that come to me for career advice and they're so structured. They like are like, this is the game plan, this is what I'm gonna do, this is what I'm gonna do. And I really commend them because I was like, ah, you're way, you know, more put together than I was. But I think it doesn't account for some of the serendipity and like chance and opportunity that like might come up that again, you just like would never have guessed that it would happen, right? And so I joined Workbench. I actually led the community piece of the house for probably 3 years, and I started leading my own investments in 2017. But it was very— those first 3 years were like an apprenticeship to me, and I was learning alongside by John and the early venture team. And, you know, even to this day, like, I still admit, like, we make lots of mistakes. Like, I'm still learning on the job, right? I think that's the part that I feel like is a whole nother show, which is just about like, why did you become a VC and why have you stayed a VC? Yeah. Yeah. Right. Because there are so many times, you know, especially in the early years and even now still where you're just like, this isn't crazy. Like, it is a crazy job. Like, am I even good at this? Like, why am I doing this? Right. And This is, you know, why a lot of investors talk about imposter syndrome, right? Right. Right. You're— the returns on your work, I mean, it takes 10 plus, more than 10 years, right, to even somewhat know if you're good at this job, right? It's so crazy. And you're just like, I think I'm doing the right thing, but you just, you don't— honestly, for the first 5 years, you don't know, right? I mean, especially at seed stage, right? Because your company's just like, it just takes a while for them to kind of pop off, right? So I mean, every day for like, honestly, probably first 8 years even, I was just like, honestly, I don't even know if I should be doing this. Right? And so it's gotten to a point now where I genuinely feel like it's an intellectual pursuit, right? You need to have enough data points to be like, oh, like, I think this works and I think that works. And then you have to at times be like, don't even listen too much to pattern recognition because pattern recognition also is very dangerous, right? For a bunch of reasons, right? But it's like, on to a point now where I think it's fun. But for the first like 8, 10 years, like, it was not fun, right? And you're just like constantly just like riddled with self-doubt, honestly, right? And you have to push through that like every single day. Um, and, um, and that's like the part that, you know, I think is like a whole thing to talk about. Yeah. Which I don't think most investors are, are quite as open about. The other part of it is, again, my, my before Workbench, I actually was in the education space. I still care really deeply about education. I teach the adult GED and all that. And in some ways I actually think like the best investors, I don't want to say they're teachers per se because I'm not necessarily teaching my founders, but what I am obsessed with doing is being a sponge and just like learning from everyone. Like you said, like podcasts and CEOs and everyone and just sponging everything up and then to the right founders, like being like, have you considered this? Have you have you considered that? And especially now in this age, it's like, it's so important where things are changing so quickly, where I'm constantly just like, you should meet this person, you talk to that, this is something you might have to consider. Because I actually think like the creativity, experimentation, and just more at-bats, and if as an investor you can be another crank of the wheel for them, like that's the part that's so fun, right? Um, so anyway, so those accidental—

yeah, the accidental VC. Jess, thank you for doing this with me. I really enjoyed it.

Yeah, this is so fun.

Can't wait to get this in the— into the world. So thank you.

Yeah, we'll see you in 5 years. Yeah, see how this goes— all goes down. Awesome.

Thank you everyone. Hope you enjoyed. If you did, please share this out with your networks, and we'll see you for the next episode. Not Another CEO podcast. Okay, that was great. Hopefully that was great. Useful. That was perfect. Is there anything you guys want to punch in or take a second stab at?

Nope, we're good. Um, yeah, I did have to go back and look at that.

Yeah. We're good. Thank you. Yeah, I'll be cool.

And then you can, uh, just voice it. Yeah, yeah, it's Chance.

Chancey Coach. I like that though, the 3-seat. That's a good— it's really good.

And I want to give him a— give him credit because he's the one who really told me about it, and I think about that a lot. So thank you very much. Thank you so much. Of course. Um, appreciate it. Come on.