My guest today is Jeff Veen who is a deisgn partner and head of platform at True Ventures. Interview Video: https://youtu.be/CeRkpEOrhWU In this episode, we discuss the following: - 00:00 Jeff Veen Bio - 02:19 How to deal with career burnouts? - 06:09 Why startup founders must learn to delegate - 09:29 Why join True Ventures as a Design Partner - 14:34 Taking a job opportunity on your terms - 19:44 Should you make friends at work? - 22:10 Having difficult conversations with cofounders early on - 26:47 A Day in the Life of a Design Partner at True Ventures - 33:58 Introverts vs Extroverts - 35:53 Challenge of keeping in touch with people - 40:15 How to Become a Design Partner at a VC firm? - 45:25 Importance of Trust Between Cofounders, Investors - 50:45 Does a Design Partner at VC firm need to be a Figma expert? - 54:30 Use Cases for AI Design Tools - 58:06 Power of Assuming Positive Intent For show notes, guest bio, and more, please visit: www.designmba.show
Jeff Veen is design partner and head of platform at True Ventures. He brings his design and product experience, management skills of large-scale programs, and common sense knowledge of being a founder to the mission and initiatives of True’s Founder Platform. Jeff was the vice president of design at Adobe after the company acquired Typekit, the startup he co-founded and ran as CEO. Jeff was one of the founding partners of the user experience consulting group Adaptive Path. While there, he led Measure Map, which was acquired by Google.
INTERVIEW VIDEO:
https://youtu.be/CeRkpEOrhWU
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Namaste and welcome. I am Jayneil Dalal and you are listening to the design MBA which is a real-life MBA program for designers. You will learn how to launch a side hustle and level up your design careers from the interviews rock star designers.
Jayneil Dalal: Today's amazing guest is Jeff Veen who's based in London. So, who's Jeff? Jeff is a design partner and head of platform in True Ventures where he spends most of his time helping founders create better products. He also worked as an advisor as well for companies about.me, Medium, and WordPress. Previously, he was a VP of Design at Adobe after they acquired Typekit, the company he co-founded and ran as CEO.
Jeff, welcome to the show.
Jeff Veen: Oh, thank you. It's so good to be here.
Jayneil: It's so finale to finally interview another podcaster.
Jeff: Former podcaster. I retired the Presentable Podcast about six months ago.
Jayneil: I heard your last episode and I was actually sad because I'm “He could have easily kept it going forever.”
Jeff: “Easily” is the key word there. I could’ve kept going. There are so many stories to tell and everything but at some point, looking for another creative outlet. what I mean?
Jayneil: I think it's different where for me podcasting is a platform to build meaningful connections with people. It's kind of like people talk about deal flow. So, for me, podcasting is deal flow but for you, given that you're a VC, you don't basically need the podcast for deal flow.
Jeff: Yeah, good point, good point. Yeah but it was a great run, did like 120 episodes, it's still all up online at Relay.fm. So, it's fun.
Jayneil: I am following your footsteps. My goal is to not stop until I release 101 episodes. So …
Jeff: There you go.
Jayneil: That's 64 episodes and kind of like halfway there.
Jeff: Godspeed.
Jayneil: So, one of the things that really inspires me about your journey, Jeff, is that you have just been hustling for long periods of time, decades, and I was like … I mean, you're superhuman but you're also a human like me. So, how do you manage burnout or just in between just continuing to do this for a long time,
Jeff: For decades and decades I've been doing this. It's true though. My first job on the web was working on the first ad-supported website ever at Wired Magazine. That was in 1994 which is coming up on 30 years, man. That's a long time.
Jayneil: Oh my god!
Jeff: But it's interesting you use the word “hustle” as like … that I've been hustling for this the whole time but that's not how I would frame it. And it's interesting now in retrospect looking back over so many years, so many different things that I've worked on. There is … I would define my entire career trajectory as a little bit like short attention span, right? When … I love the beginning of things, I love the zero to one in that kind of jargon of the startup world but the idea … taking a tiny little idea and nurturing into something that “Okay, we can see how it grows and is sustainable and it can go” and handing that off to people who are expert at systems and reliability and security and things like that, right? So … and I do get pretty obsessive when it comes to “Here's the idea and we have it. We have momentum and we're going to build on that.” And when I look back over all the things that we've done, it's almost like I would visualize it as a sawtooth, right?
Jayneil: I see.
Jeff: Like work, work, work, work, work, kind of a crash. When you say how do you manage burnout, historically I would crash. I would take a sabbatical. I'd be like “I'm done. I'm done.” I would wait too long, to be perfectly honest. I would have, now looking back, preferred less of a sawtooth and more of the sine wave.
Jayneil: Yes.
Jeff: That, to me, would have been a sustainable way to do the career rather than throw everything at it, work as hard as we can and fall apart. So, I have these periods of … and I can also … I could spin it and say sabbaticals are very important, I could, but the reality was I took a sabbatical when I couldn't work anymore, when I had spent everything and …
Jayneil: But looking back …
Jeff: Yeah, go ahead.
Jayneil: Given the nature of work you were doing with startups and things that could just … anything could go wrong, do you even think now looking back, it's possible for you when you look back at those times to kind of work in a way that didn't cause like crash and burn kind of effect, achieve those sine wave so to speak?
Jeff: Yeah, sure, sure. I don't know if I could have it in my 20s and early 30s. I didn't possess that kind of self-awareness yet around the connection between ambition and … not capabilities but stamina … ambition and stamina really like “Oh, I see I'm getting close to the edge. It's time now to start turning some of this raw effort into like sustainable systems,” right?
Jayneil: I see.
Jeff: But one of the things … I spent a lot of time, we'll talk about this more I'm sure here, but I spent a lot of time with startup founders now, right? That's a big part of my job is kind of a role of coach for a specific aspect of it but one of the most important things a startup founder can learn is that at a given point that comes sooner than you think, you have to let go of the parts of the job you love. It's really hard. I am deep down right at that the Buddha nature a product guy. I love, I love that part of it, understanding what people need and being able to translate that into the current capabilities of technology. That to me … I've done that over and over again. I love it but as a CEO of a company, when we did Typekit, there came a point where I couldn't do that part. I couldn't also be the head of the product. Somebody else is …
Jayneil: You delegate.
Jeff: Yeah, you call it … yeah, you say delegate. I am more than happy to delegate biz dev and sales. That's fine, right? That's not my … I don't get any energy out of that. I don't get any satisfaction. It’s not … it's not sustaining for me. A product is and working with designers and working with engineers, I love that, but the task becomes make the company, not make the product, right? And it almost entirely depends on like building culture and doing good hiring and making sure we never run out of money and all of those tasks while still kind of like pointing at the horizon and say “The product should end up here.” Anyway, that's a long-winded question of saying “How do you know when do you have to start to look for leverage and stop using just the pure sprint that you need at the very, very beginning?”
Jayneil: And just … kind of going on a side track … you have an amazing sense of humor because I was like anyone would be lucky to have you as a coach but now, it’s like you're so funny, joking jovial kind of person but I'd be like “Oh man, it probably wouldn't be on the conversation where Jeff is like “Jayneil, you've seen the quarterly earnings projections. You're not up to the mark.”” I don't even know what that looks like.
Jeff: Yeah. I mean, those conversations are inevitable, right? Those conversations are inevitable but they don't have to be … you don't have to Jekyll and Hyde that stuff, right? You can very much understand the systems that people are working in and saying “There's not alignment here. What's going on, right?” But anyway, that also comes with, I think, practice and leadership and stuff like that.
Jayneil: Absolutely. I'm kind of wondering after you sold Typekit to Adobe, you're there and given a successful exit, there are so many different paths that are available to a successful entrepreneur like you. You could have started your own VC fund. You could have decided like “You know what? I'm just going to LP into these fonts that I care about or I can just join an existing VC firm as a venture partner or just a VC guy” but then you decided to join True Ventures as a design partner. So, I was just kind of wondering how you were evaluating these different opportunities and why settled on this one.
Jeff: Sure, sure. The way in which you frame that question sounds all of those opportunities were lying on the table for me to look at, right? What I would say is I feel I probably could have generated a lot of opportunities that but that wasn't my goal at the time necessarily. Like I said before, my goal … it's attention span driven, my goal is what really is the most interesting thing right now and, frankly, put a filter on that of relationships. To me, especially as I got further along in my career, I realized that content is not as interesting as the people with whom I'm working, right? So …
Jayneil: What do you mean by that?
Jeff: I mean, what do I work on is less interesting than who I work on it with. I really do want to find the opportunities to work with the people I care very much about, right? And that's one of the things that happens when you do something for 30 years is you filter through the thousands of people you've come across and find … at least for me, this is very personal take on it, I find just a few people that I have the mind meld with like I really have aligned values, there's close friendship, there's the very sort of … very quick ability to step into vulnerability with each other. That's huge. I feel safe and try and trust people that I've spent time with in that capacity. And I want to work with those people. It's a lot more fun and a lot more productive and the outcomes tend to be more successful when you have that environment. So, when you ask why didn't I start a VC fund or why didn't I do X, Y, and Z, it’s because I looked at like “Well, if the number one goal is to work with the following group … small group of people that I've collected around me over these years, what's the most likely way to be successful with all of them?” And when I left Adobe, I certainly had ambition to potentially do another startup but I was also in the midst of things like changing … moving to another country and going through some … I'll put it euphemistically … going through some dynamics with my family that necessitated that change. And so, the idea of going from zero to one in another capacity concurrently, that seemed too much. So, I was like “There always will be opportunities to start a new company. Maybe there's something a little more grounded right around me that I could do at that time.” And likewise, I had never started a VC fund. I'm sure my list of people that I can call has and … there's enough people that could be a LP and something that but that would have been an all new experience for me. I knew at the time nothing about fund management and SEC filings and the whole thing. That would have been again a zero to one. So, looking for a transition to something more grounded. And True Ventures had been the lead investor in Typekit. So, I knew everybody on the team very well. I had been very involved in the founder community when I was a founder. And we started having a conversation about “Hey, what are you going to do next?” because they were like “If you're starting a company, we want to support that.” And I said “Not right now.” And they were like “Here's an idea.” We tried it for a little while. At the time, my good friend and former boss at Google Irene Ow had just taken a position at Coastal Adventures and took the title of Design Partner and I was lie like “Ooh! I've never heard of that. That sounds cool. What does that mean?” I spent some time talking to her about it, kind of crafted a different version of that inspired by what she was doing and decided to do that at True. And that was seven years ago. And so, I'm still doing that.
Jayneil: There's a couple of things I caught on to as you were narrating your story. One of the things you said that, after the acquisition, you could have generated those opportunities. So, this is like a question for me because for me, I kind of … I'm startled to hear the word ‘generated’. I get to put an effort to create those different opportunities, right? Because to me it's like once the headlines hit the TechCrunch or something like “Jeff Veen sells the startup,” I thought they would just come knocking on your door like “Hey, Jeff, do you want to do this? Do you want to do this?”
Jeff: I mean, yeah, but that's on somebody else's terms like “We would love to have you involved in this.” When I left Adobe, I also did a whole round of like going to all the big tech companies and talking about being ahead of product at Pinterest, Airbnb, Twitter, stuff like that. Just with that momentum in the career, there's enormous privilege of opportunity to at least take the first step in but when I say generate the opportunity, I mean like really get traction like “This is really what I want to do. Let me put a bunch of effort into making sure it's right, that I can define it in a way that I know I can be successful,” all of those things. It's a lot different than a recruiter reaching out and saying “We have this role” and being like “Great. I'll take it.” Those are opportunities and they're not equally or evenly distributed around but it's not … at some point, if you've had a couple of notable successes in your career, those things can start to happen a little more but for me, that's just a signal. That's not like “Oh, that's the path I have to take.” That's just like “Ah, all right. If these things are happening, what can I create out of it that I really want to do?”
Jayneil: It just blew me away when you said like … you just casually said it’s not on your terms and I immediately started thinking about it like “Wow! I didn't even think about it” like someone could be obsessed about, let's say, working for a brand name but then to think about are those on your terms or their terms, right? I mean, sure you're getting this prestige but who is really controlling the terms. And I really that you're focusing on those things “What are the terms that matter to me?” One of the things you mentioned is working with people that you care about, that you see eye to eye on.
Jeff: One of the ways that I kind of frame that up is to think about these kind of three levels in what I do. One is the job, one is my work, and one is this idea of vocation, right? So, when I think about my job like “What am I doing right now? I’m design partner at True Ventures or VP of design at Adobe,” right? That was the job that I was doing. And it had a set of responsibilities and a set of milestones and goals, achievements, whatever. I try to take the string of the opportunity I'm doing at the moment, the jobs that I'm doing over the course of time and have them … have a continuity through them that represents my work, what do I do. Like I said before, I love doing product, I love getting that team together to start from basic principles, user research, follow it through into ideation and testing and all of that stuff. That's the work, right? But then over the top of it is this idea of vocation. It comes from the word ‘calling’, what do we … what's the purpose in what we're doing all and how does all of … how does the work point to a bigger purpose, right? And so, all of that sounds like some abstract Medium essay that somebody would write but the reality is it's been really grounding for me to say like I have a general sense of purpose of what I think we are doing in this big transition from industrial to digital or whatever, in that, how that should work, who should benefit. I have a bunch of values around that stuff. So, is my work pointing at it and are all the jobs … are the jobs that I have done and will do in the future, are they all supporting that work to get to those values? So, that's how I think.
Jayneil: Yeah, sure. And I think, I can … it's just … it's coming back to me again and again what you said about working with people that you kind of see to eye or you care about working with and you said developing deep friendships. And in my mind, when I think about these things, some of the things that come to mind is do I have to work with people that I can become best friends with because I've got friends outside of work that we talk about Bollywood movies and stuff and whatever.
Jeff: Sure.
Jayneil: We just hang out. It's a very different vibe. Now, am I supposed to replicate that kind of vibe with these people that I want to work long term with or is it more of just we see eye to eye on the product or the features because you could be working with founders or people that have weird personalities … it's just like eccentric personalities. They may not be as funny or as charismatic or joking as you just made me laugh. So, I'm just wondering what do you mean by that. Is it like you're trying to make best friends there or you're just trying to work with people that you just sort of respect product wise and their active advice? That is a loaded question.
Jeff: No, I know. It's the latter. It is people that I respect. And then it is also the former that I have worked with him for so long that they turn into best friends over time. And I think that is because for a relationship to be really meaningful and valuable, you have to go through some really hard stuff to get there, right? The concern is what I hear underlying what you're saying is you have a bunch of friends that you really care about and maybe there's a little trepidation like “If I worked with them and something went wrong, I'd lose my friend,” right? And I value the friendship more than I might value the next work opportunity. And that's smart, that's important and that's a valid concern. And at the same time, really bad stuff happens in friendships anyway. It can certainly, right? Like “Oh, my God” And it is the same muscle that you exercise in both of those instances to get better at having deeper, more stronger relationships regardless of whether you're working together or arguing over Bollywood movies, right? So, for me, it doesn't necessarily … it's not too big of a concern. That said, all of those people who I consider like those trusted friends with whom I work, all of them, we started working together first and developed relationships at the professional level and then on the personal level. So … like I didn't start a company with my buddy from high school.
Jayneil: I see.
Jeff: That was … it was a different way of framing that up.
Jayneil: I think … aside from the fear you mentioned, I think, the way it's worked for me so far is with friends outside of work, it would be hard to have some difficult money-related conversations but then with business relationships, where we started off from the get-go about a partnership collaboration, it makes having those difficult conversations, money-related for example in this case, much easier because you didn't start out as friends. You started out as co-workers. You started out as partners in a venture, so to speak.
Jeff: Yeah. And there's the lessons to learn in those conversations that you're just talking about. There are so many co-founders of companies that I have met in the past that didn't get to the difficult conversations until a bit too late like they're just really, really tricky conversations to have around how you split equity … like how you split equity, like how about this like “We have agreed that I'll be CEO and you'll be CTO.” And then three years later, after you've written all the code for the initial project and then hired that first round of developers, it's very clear that we have to scale this massively and we need … from the 15 developers that you have hired, we need 150. And it turns out the board agrees you're not the one to actually build that level of an engineering department because you're an expert at the vision and the code but not the organization building. And we are really good friends and we are co-founders and I have to say I got to hire a new CTO.
Jayneil: Oh my God!
Jeff: Right. So, it's hard … right, it's hard but it's a lot easier if, when you're sitting in the pub and you're like “We should start this company. Yeah, I want to be CEO” and you're like “Yeah, I want to be CTO,” like “Great, let's do that. Hey, by the way, there's going to come time when either one of us is going to have to fire the other one. What are we going to do? Oh my god! Let's have that conversation before the first line of code, before we file the papers to incorporate in Delaware” like “What do we … how do we handle that?” Oh my god! Wow! And how do we handle when an investor comes in and says “You guys shouldn't raise 2 million. You should raise 50. Is that good news?” like “How do we handle those things?”
Jayneil: Wow!
Jeff: So, have those … and what I mean is try to figure out what the minefield is before. And the Minefield has terrible, terrible things that could happen in the first few years of a startup and amazing things that could happen. And both of those can be equally difficult conversations that you haven't anticipated yet.
Jayneil: In a recent business collaboration, I was sitting with this person and we were just having pizza and I used to just … think of orange flags … I just said casually as we were eating pizza “Okay, these are the orange flags to me.” And you talk about minefield. I said “Let's talk about it because now is the time. I mean, let's just see what we think about it.” And we openly laid those things from my side, from that person's side and then … I'm surprised that it was not that crazy as much as I feared. We were just able to have an open dialogue about it and understand how each person sees those things and actually just created more respect, I would say.
Jeff: Yeah, for sure, for sure. I like how during lockdown and everybody rethought their jobs and “Oh, my careers would be different” and everyone went and got a coach, right? Which is great. It's really, really good talking through with somebody that doesn't work at the company you work for, right? It's really important to do. And that is my recommendation for startup … like you want to start a company? The first thing you should invest in is a couples’ counselor for you and your co-founder like go get counseling, go sit down and say what are your values. And there are tons of amazing coaches that can kind of take people through like “Oh, you don't know all the questions yet but I've seen a lot. So, let me help you with that,” right? And talk them through especially when you have a neutral third party just sitting there who can pick up on dynamics between the two and stuff like that. So, that's a way … you want to work with your friends, you want to work with people you care about? Go sit down and figure it out right up front. Get some help to do it.
Jayneil: I love that. It kind of makes me wonder what does your day-to-day typically look like as a design partner? Is it more of these coaching connotations? Is it talking about growth? Is it talking about product or design? How might it be different from when someone traditionally thinks about a VC or maybe it's the same?
Jeff: No, I don't think so. I don't think it's the same. So, there was … for a while, I really did split my time with kind of the before and after, before the check and after the check, where I was spending a lot of time on the investment side, on the deal flow side and things like that and realized if I look at where the creative energy comes from for me, that it was very much on the after side than on the before because, I think, part of it is because I so hated saying no to so many people, right? Like “Oh my God! That's a great idea but it's not a venture-backed business. So, I'm sorry we can't do the deal.” And if you think you might do one deal for every 100-150 pitches you hear, that's probably how it plays out.
Jayneil: Crushing so many dreams.
Jeff: Right, right, but that is also … I think, to be successful at that on the sourcing investment side of it like what people think of when they think VC, out here in pitches, making decisions, a Shark Tank nonsense, right? That stuff. I think to really be successful at that, one of your primary focuses has to be on your network and growing your network on having very broad set of looser connections. And that is kind of antithesis to what I've just been talking about with a small set of deeper connections. And I don't have judgment for either one of those things. I just … again, where my energy comes from is not in the networking side of things. It's not … always reaching out. I find it really emotionally expensive, to be honest, it may seem you and I are having a very natural flowing conversation here but it's all I'll be able to do today because I'll be just exhausted after this. Anyway.
Jayneil: … opposite to that.
Jeff: I got a sense of that when we were talking before that for you … and the co-founder of my company of Typekit, my good friend Brian Mason, thrives on that. He’s just “More people, more people like more experiences.” And that's where he finds it restorative to go talk to people. And I, classic intro-extrovert, right? I get all my energy from contemplation, processing quieter moments and then expressing all of that in deep conversations with a small number of people. So, anyway, that's all to say … that's my network into the Freud territory in our conversation but that's all to say that I much prefer it like once we've written a check and funded somebody to work with them and to support them and things like that. I have since then more recently in the last couple years kind of grown that like what you would call a design partner practice into more of an overarching “How do we do everything post check for our founders? What are all the range of services?” We've got a team of nine people now that works on all of that that I lead. And we do everything … we're doing software development for them in basically like a sort of private portfolio LinkedIn connections service and community space and stuff like that. We do lots of this kind of consultative services, right? I've got somebody on my team who's great at culture and organizational scaling, somebody else that's great at like first revenue, ramp up to first revenue and build systems around that and stuff like that. So, that's what the job looks like. What a typical day looks is kind of … I just feel so grateful because. For example, I live in London, the most of the team … we're getting more and more distributed … most of them are on the west coast in America. And so, nobody comes online till 4 o'clock my time so that … when I say I get a lot of energy from processing and synthesizing and abstract …
Jayneil: Deep contemplation in the morning.
Jeff: That's how … right. So, I do get to spend my mornings with … I start with mindfulness and Yoga and then move into a triage of all the inboxes and chats and then a few big work tasks and then conversations in the late afternoon and evening. It's great. I love it.
Jayneil: Oh my God! There's so many going through my head. Oh my God! One of the things for me has been … I mean … and this is again just a mental model. So, maybe for me just where I grew up in India, in Ahmedabad, Gujarat, and some things I saw early on was that growing up there, it was all about who you knew that could alter your destiny. And maybe this is what are things where you're living in a … not a first world country, things are different, right? So, from an early age, I kind of saw that if you knew the right people, then number one, they could give you the right advice, they could open doors for you that were not possible. So, that's one reason why I love to connect but even more than that, to me, on a philosophical level, I look at it as like I don't have all the time in the world to figure everything out. Now, in this life, I don't even know if I'm going to be on your footsteps or not. I have no idea. I have no way to know what that looks in 25 years’ timeframe but what I do know is there will be some elements of our conversation that'll stick with me like the fact that we talked about having tough conversations. So, if I find myself in a similar situation, I just know that my brain is going to do some real-time pattern matching. It'd be like “Oh yeah, I remember a while back this funny guy who made me laugh, Jeff. He said this thing about this thing. Oh yeah!” And then somehow in that moment I'll have some data point or some reference point rather than figuring out on the spot and doing it myself. So, that's where I feel my fascination for books and reading and I feel talking to people is real-time books or just like books that are in the making rather than …
Jeff: Yeah, yeah, for sure.
Jayneil: It’s kind of like reading books.
Jeff: Yeah, yeah. No … yeah, I agree. I agree. There is a tension, maybe a little friction for somebody who is self-aware about a sense of being introverted and this idea of needing to find momentum in my career through connection. And it's not as dire as I kind of might be making it out to be but I do think much like in all the ways, especially in the tech sector, certainly in the design profession, we have learned in the last 10 years at least an increasing urgency around the necessity and value of diversity in our teams. I think one of the vectors of that is also a neurodiversity that people are genuinely wired differently and that we don't all have to be an extroverted influencer that goes to every networking event in order to be successful. I really kind of reject that premise that in fact the quiet introvert thinky people who never want to stand up and have the attention put on them, we do need to find a fair way for everybody to have that same kind of opportunity, right?
Jayneil: Yes.
Jeff: And I don't … and I think we're getting better at that, right? I think we understand that many people have had “traditionally” been on the spectrum actually have a superpower when it comes to aspects of product development for sure, right? So, could the same be true at the professional layer, not just the technical layer, right? I don't know. It's something I'm really interested in based on my own experience through my life.
Jayneil: It's definitely challenging at times. When I think of the notion that yes, I like to connect with people, but then also the challenge I face from being an extrovert is trying to find some non-intrusive way to keep in touch with all these connections.
Jeff: Right.
Jayneil: For example, like I met you, right? So, obviously, I mean, you've got so many things going. I don't want to go bothering you like “Hey, just sign up for Jayneil’s Updates newsletter and what is he up to,” right? And it's not we're soccer buddies and we just run into each other at a pub because we're going to an Arsenal match. I don't know. So, the point is that's also a challenge for me to figure out some meaningful way to say that “Oh, you know, I learned a lot from Jeff and maybe is there a way I can keep in touch with him.” I don't know but this is the same thing I've kind of faced with a lot of the connections that I make. It's like “How do I find this right balance between not being annoying and then being “Hey, just wanted to check up and say hi or this is an update.””
Jeff: No, I have the same anxiety as well, especially in the other side of that where there's some like “Ooh, I have found some need that I really have, some gap in knowledge or something like that. And who would be good here, right? Who would be good … who could I turn to for help? And of the thousands of people I've met, how do I …” I don't have good systems for that, right? I feel like I have very broad connections in social media but should I be doing more work in LinkedIn to make sure that's all like up to date and I know where everybody is and … God, the number of times I try to solve the problem by searching 20 years of Gmail archives like … it works but I don't know, right? It's one of the things that we are like … currently, we have a project going with the team at True, just around deeper … I hate the term CRM … there's that like relationships that need to be managed is almost as bad as ….
Jayneil: Put all your contacts in a CRM …
Jeff: Right. It's almost as bad as Human Resources like “Oh my God! That's awful” but there's a sense of like “Hey, I need a couple of people that can go kind of deep on robotics and it'd be great if they were on the East Coast.” And we know 10,000 people. There are so many products to solve that problem, of course, but it turns out it ends up … like everything, whether it's content management or source code version control, whatever, at the end of the day, it's social, not technical problem. And so … so, people should have some kind of personal CRM strategy for all the people that they meet in the world and be able to hold on and maintain those contacts and relationships but I have it, I've been pretty successful, I don't know.
Jayneil: I don't think I have one either. I think I tried it, to be honest, like this whole … I spun up an air table and then I was like “Let me just put all these people I'm connecting” with but then it felt from the inside very transactional and …
Jeff: Right.
Jayneil: What is working now is when I think of something like … you said robotics, right? So, then I just think about who is the person that comes top of my head. And I know it's not the most efficient system but at this point in my life, I guess it seems to be somewhat working. So, I'm just sticking to that.
Jeff: Well, the system gets less effective as the hardware ages. So, let me give you a little warning.
Jayneil: Wow! So, turning back some gears, for folks who want to become design partners and maybe they've had significant experience in the design field and they want to get into venture similar to what you have, I kind of wonder how much necessary is it to have a successful exit? Because I mean, you've had that. So, I wonder if …
Jeff: Yeah, that might not be necessarily the only pathway but it's certainly like … I don't know. at the end of the day, venture capital is a profit-loss like … it's right on the edge of capitalism, man? It's right there. And how do you … like … I started a consulting company so long ago. We were one of the first people doing user experience as a business, right? 1999-2000, that period.
Jayneil: Wow!
Jeff: And what we learned very quickly was that we couldn't go into … and we wanted to do like Fortune 50 like the high-end stuff and we did because they were … there was the dot-com bust back then and everybody was scrambling with like “The strategy didn't work. What do we do?” and we were like “We have the answer. You go talk to users and you do it in a systematic way, you take their needs and you build on top of it.” Anyway, we couldn't go do user experience stuff in those big companies at the board room, right? You couldn't sit down with a CEO and a CTO and a CFO and talk about user needs and interaction design and information architecture. You couldn't do that. you had to go speak the language of MBA. You had to go talk business, right? So, how do you become a design partner? You do the same thing. You learn the language of venture capital and you learn where … like you got to speak that language. You can't go in necessarily saying like “Design Sprints and …’
Jayneil: Yes.
Jeff: Right? Lean iteration and usability testing and everybody would be like “Yeah. Could we just hire an agency?” And the answer is “Of course.” And probably you should do that and not hire somebody internally to do it. You should … anyway. So, that's the way in is to say like “What is the core problem we're trying to solve here?” And for me, it has been that in the … so, first of all, to back up, True Ventures only does early stage, right? First, check. So, one, two, four people. That's who we're funding. We have some exceptions to that but that's the model. And our collective experience has shown us that the first 24 months which is kind of what your seed stages financing, right? The check is completely ambiguous. You'll have a plan but that plan will be pointless six weeks from now. Everybody knows that, right? So, your deck should be great, “Here are the 12 slides but at the end of the day, we believe in you. And so, we're going to give you this money to fund 24 months of creativity to see if this area that you want to explore is going to work and then leverage that to try to get you the series A from some other firm.” Those 24 months are filled with pitfalls, absolutely, right? It is tenuous and most don't make it. That's, again, the venture capital world, right? You hope for, out of the entire fund, a couple, two or three companies that return all the money and make the profit and then another 10% that do all right and then everything else fails. That's because it's, like I said, right at the cutting edge of the capitalist system. So, anyway, that's a long-winded way of saying I have a hypothesis that is shared amongst my partners at True that the application of all that stuff we learned about user experience can get you to product-market fit more quickly with less risk. Therefore, fewer of those companies fail and we get more returns on the investment.
Jayneil: I see.
Jeff: We have similar hypothesis around the culture of the company that the application of not just good user experience principles but also emotional intelligence, right? So, if we can help cultivate emotional intelligence in the relationship between the investor and the founder and the founder and their leadership teams and broader out to their community of users, you can nurture emotional intelligence, EQ, you're also less likely to fail. You have a higher probability of producing returns for the fund. So … that doesn't answer your question “How do I become a design partner?” but I'm telling you the process that I went through to kind of get there. you
Jayneil: So, you talked about emotional empathy, just cultivating the culture and maybe use of impression but being a venture partner, a successful VC, and when I look at you, I was, maybe in my mind, thinking of you and the Shark Tank stuff as a cutthroat VC or just that vibe the more I talk to you here, you're very laid back and kind of like … you just made me feel so comfortable even though I'm not pitching anything new. So, I can see that.
Jeff: Yeah, yeah, that's … I think that is also just sort of a point of differentiation for True. I think … look, one of the fundamental principles of culture, especially in something as creative as entrepreneurial effort, is the idea of psychological safety, right? Our business is innovation, right? We want to create things that have never existed before. We want to do them in ways that nobody has ever thought of before. That is incredibly powerful. It's the engine, frankly, of the entire economy, if you think about it, ultimately, the solving of new problems. It's going to be a big component of our pathway through the collapse of our climate, for example, will be this idea of we now need to retool everything and we have to invent it and it needs to come from a place of deep creativity. So, how do you get to that place, right? The way that I have found that consistently works is to get a group of incredibly talented people that primarily trust each other first. That's it. Not that they are … they should be very, very good at their craft but their craft should come second to things like empathy, understanding, deep listening to each other. Trust, right? Because when you're in a group of people that you fundamentally trust, you can say dangerous things. And in the dangerous things will be kernels of ideas that come out, right? For example, I’m completely off of all the social media now because it became a space where the slightest hint of danger in the thing that you put into the cloud, into the … all of that can be the end, it can go viral, can be like “No, no, no …”
Jayneil: Canceled, yeah.
Jeff: That's it, right? Across the political spectrum, it's just … it is … right, it's like tinder in a wildfire. It's terrifying, for me, anyway. So, that said, I want a group of people to solve this incredibly hard problem on a very limited budget in an insane timeframe. How are we going to do that? We're going to get together and trust each other and always assume positive intent and we are going to get everything out that we … every possible idea. 99 of them will be terrible, five of them will be deeply insulting, and “I'm sorry. Let me take that back. I went the wrong direction.” That's all right. We trust each other. We care about it. It's okay. And then one of those ideas is like “Oh shit! That's it. That's the thing.” And that's what you have to try to create. So, can you start that process in between the investor and the founder as opposed to what you were expecting like the Sandhill Road VC that turns up in the super fancy Tesla and it's like “I thought you said the number” like “You got to hit the numbers,” right? And you're inside a nightmare scenario where instead of generating deep creative solutions to incredibly hard problems, you're terrified that they're going to throw … the board's going to fire you and you'll be out, you'll lose everything and you've risked everything to do this, your reputation will be shot.
Jayneil: Oh my God!
Jeff: Which is going to work better, right?
Jayneil: I'd rather prefer working with you.
Jeff: That's right. That's what … that's I think … that's the point is that … right? And EQ doesn't mean we're just going to ignore the numbers, “Oh, it's all right. You'll make it next quarter.” No, you got to … we have to get to the plan. That's true but I'm not going to scream at you, I'm not going to humiliate you, I'm not going to spread rumors around town like “Don't fund this guy. He doesn't know what he's doing.” And that is kind of the tone and tenor of venture capital has been in the past. So, is there a way to use emotional intelligence as a fundamental part of the process to help our founders get to product-market fit, scalable culture, all the things you need to do to really then to … terminal velocity …
Jayneil: I think in an alternate universe, I can also see you being a very successful stand-up comic that just shared some funny things in … world. It’s just like some of the things made me just laugh. I was not expecting that, to be honest with you. I thought it was going to be very deep serious conversation but you made me crack up a lot … of all the … I think you cracked me up the most, I would say.
Jeff: Good, good.
Jayneil: Kind of one things that I was curious about, as a design partner, is the expectation that you know all the latest tips and tricks in Figma or is it more of like you have a team that follows your creative direction to help the early-state startup?
Jeff: Yeah, yeah, that's good. Can I just pause for a second and say 20 billion dollars Adobe paid for Figma? Yes, are you kidding me! That's … and I'm already in the camp of “They better not mess it up.”
Jayneil: Yes.
Jeff: And this is me, a product designer … VP of product design at Adobe 10 years ago or whatever. I'm like “Oh my God! That was like the begin when we were doing the Creative Cloud. That was our drumbeat of “The model is changing” like “Look at Google Docs and think of Photoshop at Google Docs. We got to bring these together.” And there's so much momentum and inertia and everything, it takes time to turn a ship that or you just write a check for 20 billion dollars and you turn it on a dime. I couldn't believe that. I was like “Oh my God!” I many ways, I'm like “Oh no” and in other ways, I'm like “Thank God.” So, good for them. I love Figma. I think it's great but your question was do I spend time in it. There's a … if you take a career that has a trajectory more towards leadership and less towards deep practitioner, I do think that you tend … the tools get more abstract over time but … and what I mean by that is I didn't design a single pixel of Typekit. I had Jason Santa Maria. No, I had Jason Santa Maria. He's like the best designer in the world at the time and with deep, deep knowledge of type of typography and everything. And I would spend hours, days with him and a couple other people like this absolutely insanely talented frontend developer. Our architect and CTO, Ryan Carver, would be there. And we would just thinktank it, right? And get in the room. And my tool that I would use for this was the whiteboard marker. And we would just … we would do all the work together and then one person would go work in JavaScript and one person would go work in data structures and databases and one person would go work in Photoshop but the work happened in real time at the whiteboard. So, that said, I love that stuff. I love the tooling, I always have and it was a thrill to work at Adobe and to see behind the scenes of like “We're going to make the next version of Photoshop? Oh my God! That's so exciting.” And so, I keep up with all of that stuff but I don't have to … I don't have to do it to make a living. I don't have to be good at Figma to get all the mocks out in time for the engineering meeting. I don’t don any of that. The only exception, I guess, is I still feel I continue to try to master keynote because a lot of my work is in imparting vision or ideas or whatever in public speaking. And I can get into flow, that true sense of like the balance between challenge and mastery with really tight feedback loops and just lose hours of doing pure work in Keynote, of all things, as a way of expressing “This is the direction we should all go.” So, love the deck.
Jayneil: Love it.
Jeff: Yeah but I'll tell you … can I ask you one more, if we have …
Jayneil: Yes.
Jeff: One more tool question is using … I’ve just now … I've just now been in a design process with one of our designers using those image-generating AI systems we've been using. Now I can't remember, of course, which one it is.
Jayneil: …
Jeff: No, the one that you do via Discord but anyway, it doesn't matter. They're all relatively … they have strengths and weaknesses but this is interesting. He and I are approaching it like the AI is an illustrator that we've hired and we are coaxing out of them iteratively over time how we want … I'll give you a great example. We do a set of events every year for our founders at True Ventures. Each year we kind of give it a visual theme stylistically so that it's very clear like the materials that we are giving them and the registration and all of that like “Oh, this is all new. It doesn't look like the last time I was here. So, …” and it's good and we do that on an annual basis. And this year we're doing it with an artificial intelligence to give us the theme and to execute out all of the backdrops and things like that and we'll take all of those assets that have been generated by the mind out there in the cloud and use that as the basis for all the deliverables we have to make. Absolutely fascinating.
Jayneil: It is mind-blowing. It is mind-blowing. I think some people will see that as a threat. Some people see that as a way to focus on more creative pursuits like rather than just focusing on those things, they can focus on other more interesting pursuits. So, I feel the … is divided on both sides.
Jeff: No … well, yes, yes. And this is kind of getting into a different territory than before. There's the old argument ATMs are better than having human bank tellers for the most part and it really does allow bank tellers to be more customer focused if they don't have to be so transactional. That was an argument 40 years ago but this feels a little different. It's so good at doing what we thought were deeply creative human tasks of creation and expression of emotion in the visual form.
Jayneil: Wow! But then going back to the bank example, recently I had to do some bigger wire transfer and I had to go into the bank and talk to an associate there and confirm my identities, talk about it and then did the whole thing. And I couldn't do that online or via the ATM.
Jeff: Yeah, yeah. No, there's still … there'll always be a way. I agree. I just feel there's a slight nuance to this what we're doing with AI that seems … I don't know. Ah, maybe it's just generational and I should let the kids run free and just chill out a little bit but …
Jayneil: Just one last question to wrap up just based on our conversation, I don't want to use the word advice, but are there any relevant things that come to your mind that I should keep in mind as I go forward on this journey? I'm deliberately trying to not use the word advice because then it just puts the person “Oh, what should I say?” but anything that just randomly comes to your mind unfiltered like “Oh, I noticed this” or “I noticed this,” just …
Jeff: Oh God! Just take care of yourself, man. Just … right now, I'm serious, take care of yourself. Everybody needs to take care of themselves. I even still get twisted around the axle worried with anxiety about work, about the work and wait “What did she really mean when she said that in that meeting and what was he …”
Jayneil: Like “Are you really successful? What … would not worry about that? I mean …
Jeff: No, you don't stop being human just because you made a few bucks. God! That's what I was thinking. Here's the way … here's the path that I have been trying to follow and that is … you know when I said earlier to assume positive intent?
Jayneil: Yes.
Jeff: That seems to be the key to all of this which is like I have to assume that everybody else is operating from the same fears and the same insecurities and the same damage that they got in childhood that they haven't been able to fix in therapy yet. We all are carrying that and it is working at an automatic level and we can use mindfulness to help cure ourselves of that to put a gap in between the trigger that comes at us and the response that comes out of us. And in that gap is freedom but everybody is doing that. And so, when I'm on the Zoom call and that person says that comment and I was like “Wait. What's that passive aggressive? Were they really … is that?” … assume the positive intent, find the gap between that trigger and the response that I'm going to have, the reaction, and try to find a skillful way to interpret it positively. And then verify and validate and go to the person and say “Can I just check?” because that lifts all the anxiety and I'm not like lying in bed not able to sleep because somebody said something in a Zoom call. And I'm sorry, it doesn't change as you get older. It just goes on and on. That's how we're wired. We're wired for survival, not happiness. It's how it is. So, take care of yourself. Be good to everybody. That's it like that's it.
Jayneil: The kay thing I took away is a Zoom-positive intent unless proven otherwise. It's kind of the default mode just thinking that way.
Jeff: Yeah, yeah. Again, it’s the EQ stuff. An important part of intelligence is also boundaries, right? I don't want to be all sitting here in some hippy-dippy happy world of like “No, it's all good. We all care about each other.” You also have to be like “Hey, that wasn't all right. When you said that, that wasn't all right. I'm assuming we're still good, positive intent, but don't do that anymore.” It's …
Jayneil: Gotcha.
Jeff: Right, right. So, anyway …
Jayneil: Jeff, thank you so much for just taking the time to chat with me.
Jeff: That was great. Absolutely a pleasure. I really enjoyed it. You really … I think we … I think we sort of created the safe space here.
Jayneil: Yeah, that’s true.
Jeff: Thank you very much.
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