#6: Jeff Wald, WorkMarket

Welcome to From Startup to Grown up, the podcast. My name is Alyssa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grown Up. Each week I talk to founders, creators, advisors, investors and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number six and it's an absolute joy to have Jeff Wald on the podcast. Jeff is so many things. He's a serial entrepreneur, a board member, a best selling author and an investor. Jeff's most recent company was WorkMarket, an enterprise software platform that enables companies to manage freelancers. WorkMarket was acquired by ADP in 2018. Now, Jeff is a longtime friend, so it was amazing to be able to talk with him about all his experiences on the podcast. And one thing I love about Jeff is that he's so super honest. We cover co founder drama, his and other people's, his depression when his first startup failed and what he said to his investors when they told him to get a coach. We talk about all sorts of frameworks about what he now looks for as an investor and more, more, more. This discussion is packed with so much hard earned wisdom that you're going to want to listen to it more than once. So please enjoy my conversation with Jeff Wald. Jeff, welcome to the show. You have the distinction of being my first guest who I've actually met in real life. I'm so happy you're here.

There are so many reasons I am happy to be here. It's great to be here with you. Having been your friend for many, many.

Years, I know it's so nice to do this together. And actually for me, we met probably 10 years ago. I think that's about right at Renaissance Weekend. And we became friends slowly, I would say slowly over time. And, and I woke up one day, maybe two or three years ago, I'm like, oh, Jeff's kind of a big deal. I didn't realize.

Well, you've held, you've held many flights for me as I raced to airports and tried to make flights. And you're like, where are you? I'm like, I'm not even at the airport yet. I've already boarded.

That is true. Jeff and I attend a regular event over New Year's. It's called Renaissance Weekend. And it's true that we have traveled from New York to Charleston many times together. And it is true that I've held the plane for Jeff on more than one occasion. So you're welcome, Jeff, you're welcome.

Always, always. Thank you.

But I Want to start today. I want to talk about your life as a serial entrepreneur. That sounds so exciting and exotic. And I want to start with. Actually with your background, specifically. You know, I believe in the adage, show me the boy and I'll show you the man. And I'm curious, were there signs of your entrepreneurial life, early days?

Well, look, there were certainly the selling of lemonade and various other stands, if you will. I remember starting a newspaper with some friends, and we had subscribers and we'd have to produce content once a week. It was. It was a sports paper. Yeah, yeah, yeah.

Before that was like. Before Internet.

Like, we're stapling this together in a friend's basement and riding our bikes around town, delivering the paper, the sporting news, I believe. Don't think we trademarked, copyrighted that. And I'm pretty sure we were violating all kinds of content rules with the stuff we distributed. But those were some of the early. The early instances. And even when I started my career as an investment banker with JP Morgan, I was working with a group called Lab Morgan on ways we could innovate our business. And I helped them lead an investment in a company called Capital iq. And there was just always this entrepreneurial bent to my career, which didn't take its full form as a startup founder until 2016. So deep into my career, about 16 years into it. But there had always been undercurrents. 2006, I was going to say.

That doesn't. Yeah, okay, that makes more sense. The math on that wasn't quite good. There's four companies in four years, right?

2006.

2006.

Yeah. It all feels so long ago.

Yes, I can imagine. I can imagine. Well, Work Market was your fourth company. Fourth company. And Spinback was your first company. And it didn't go so well. So tell us. Tell us the story of Spinback.

Well, there, you know, I had spent a couple years as a venture capitalist, and I had backed a number of entrepreneurs. And there was this one guy named Jeff Leventhal who I had cold called and said, you know, look, I read about what you're building, and I love it. What we would do at Glenrock sometimes is do some whiteboarding sessions. We'd spend a week and just say, let's think about an industry or a trend that we are very bullish on, and let's find a space in there. Let's double click on the competitive environment, let's double click on the value chain, and let's find companies to invest in. I mean, this was back in 2003, 2004. And we talked about the repair of information technology. And we found this guy, Jeff Leventhal, who had built a company called Onforce that allowed for and it was the repair of information technology utilizing a marketplace of freelancers. This was. He was the first labor marketplace. I mean, way, way, way, way, way in advance of the e desks and olances of the world. And so he and I got to know each other and he wasn't looking to raise money, but a year later, he was looking to raise money. We got outbid by General Catalyst and a few others. And about a year later, he got pushed out of the company because he wanted to sell it. They didn't, and, you know, they paid him a lot of money. He did great. But he came to me and he said, you know, I should have gone with you. You would have been a better venture partner. He and I had become very close at that point. He said, here's my next idea. My next idea is this company. And he'd already called it Spinback. And he and I spent about a year iterating on that. And he eventually said, all right, I'm going to start it. And he looks at me, he's like, aren't you coming with me? Because I had always thought, you know, I'm going to fund it. He's like, no, no, no, you're going to co found it with me. And that was my first real leap. There was a third partner who has to, because of court documents, remain nameless. And Jeff was introduced to her through actually through General Catalyst. And as the company evolved, the two of them just couldn't get along. And so while the idea and the idea was a content sharing platform, the idea was sound like we were doing well. We had a bunch of beta customers like we were about to launch, but the two of them just could not trust each other. And I spent the entire time trying to fix their relationship, trying to bridge their gaps. I mean, at some points they wouldn't talk to each other, they would only talk through me. And by the time I realized that this was irreconcilable, which I should have realized a long time before I and that one of them had to go. They both had dug their heels in and one of them had lawyered up. And then once somebody sued somebody, somebody countersued the other and we had to shut the company down. It was heartbreaking. I relive those last few months over and over again in my head, like, what should I have done differently? How could I have done this and saved this company. And I should have realized it earlier, and I beat myself up about it, but this content sharing platform called Spinback, we did eventually restart. That was company number two, and it was successful. And while I'm happy about the success, I do lament. If we had gotten this right years earlier in the first iteration, how much bigger could it have been?

It's heartbreaking. And I do understand what it's like to relive something over and over and that. So even I think people don't quite understand that sometimes even like, oh, it was sort of a good outcome, but actually there was a moment of trauma or moments of trauma for you inside of that.

There were deep moments of trauma. I mean, when I actually went in and shut the company down, told, you know, we had 10, 15 employees, and I was like, guys, that's it. It's over. Everybody go home. We don't have any money anymore. I can't pay you. The whole company shut. I went home that day and I didn't leave my apartment for a month, which I appreciate right now, given the trauma we've all been through collectively as society. Doesn't seem like that big a deal not leaving your apartment for a month.

That's right. We just did that for 18 months. Whatever.

Yeah, at the time, that was a lot. I mean, I didn't get out of bed for a couple days. I mean, I was deep in depression, quite frankly.

Were you in depression or were you beating yourself up? And I should have known. And second guessing, like. Like, what was that really like?

I mean, are they mutually exclusive? You know, a little from column A, a little from column B? Yeah, I mean, all the feelings, all the feelings of shame, of, you know, of doubt, of, you know, facades, and all of them came rushing to the fore. And I just. I mean, and I was personally wiped out because I had been funding this company and that was it. Like, I, you know, got the call from my mom, do you need to move back home? And this whole notion of, how did it come to this? But, you know, as with any failure, at some point in that failure in that grief, you get to acceptance and you pick yourself up and you dust yourself off and you keep going. Yeah, hopefully, I should say, hopefully.

Right? Not everybody does that.

Yeah.

Right. But I respect that you do that. I definitely want to get into that sort of dusting yourself off and also, you know, your openness now about those feelings. But before we get into that, I first want to. I want to do a little sidebar on. On co founders, because as soon as you say I can't say her name because of court documents. Right. We already know there was like a foreshadow of an issue, of course. But I'm just curious from that experience, I guess. First of all, what do you mean they didn't get along? And big picture, what did you learn about co founders and how has that formed your experiences going forward?

Well, I'll tell you this. I have nothing bad to say about this particular person. I think she was wonderful and I think he's wonderful. I thought they both were wonderful and had a lot of things to add. Why it is they didn't get along. You know, I really wouldn't be able to answer that question, but I should have realized that they weren't getting along and that it was irreconcilable. I'll tell you this, whenever I as an angel investor go to back some co founders and especially people that don't have a history together, I will ask them. Tell me about some disagreements you've had because you never know who you have until bad stuff's going down. You never know who you have until somebody wants to do X and somebody else wants to do I. And you have to find a solution. You have to compromise. You have to figure out what's the best. Maybe not compromises in a little bit X and a little bit of Y, but somebody able to convince the other that X is the right path. And saying, you know what, you gave me new information. I didn't know that. Yes, I'm all in on X. We are.

Yeah, yeah. Or I don't agree, but I'm willing to do it your way because that's the way things are sometimes.

Completely right. Completely. And unless you've had that dragged down, unless you've really had a blow up, you don't know how you're going to react. Do you have the kind of partner that's going to stand with you and figure things out or you have the kind of partner that's going to go to their corner and be like, whoa, whoa, what's mine? And I got to look out for me. And that's, that's, that's what anyone should do. You know, we're a capitalist society. All right. Yeah. But you know, are we a team or are we not a team? And so I will ask that co founder group, tell me about some dust ups you've had and if they're not real desktops, that's a risk to me in the U.S. i'm not saying I'm not going to make it. It's a risk.

Yeah, Yeah, I totally see that. I actually have a co founder prenup, I call it. And it's not really like a signed document as much as a set of questions about how do you handle conflict? How did conflict show up at your house, Right. When you were growing up? How do you. What are your values? How are you seeing sort of success in this venture? Right. Because I think people don't talk about that necessarily in advance. And I think even if you can't really get to the heart of the matter, like as in have the conflict, at least you're gonna have a conversation about how I handle conflict in general.

It's brilliant. I love it. Right. And I would love. And I would add a question, maybe, and maybe this is one of your questions, but how do you see it failing? How is this thing going to fail? And what will you do?

Yeah.

Because when I make an investment, and especially when I bring friends along for investments, I make sure I'm super clear with everybody. The most likely outcome here is we're gonna lose our money and this isn't gonna work.

Yeah.

Everybody's got to go into it knowing that that is the most likely outcome.

Right.

And that's okay. We're. We're all adults. We can take risks, and if they pay off, we're gonna make money.

Right.

But most likely they're not, and you're gonna dust yourself off and keep going. And it's important that every member of that team, including the co founders, understands that if there's a co founder, it's like, no, no, no, there's no chance we're going to. We're going to fail. I'm like.

Another red flag.

That's not good.

Yeah.

I mean, I appreciate the enthusiasm, I appreciate the confidence, but let's operate in the realm of the real and the possible.

Right? Right, right, right. Well, you're very open about failure now, but I don't think it was always that way. You know, you were sort of in your apartment for a month, probably, you know, sheets up to your. To your. Over your head. And so what changed for you that allowed you to be more open about your feelings about failure now?

I mean, how much time do you have we could spend here? Yeah, I mean, you know, I'd have to bring in a bunch of therapists and coaches and things like that and friends and family. I'll tell you this, you know, we all go through life thinking we have to be strong enough and we have to power through it, and we don't and we think that asking for help is a sign of weakness. And so the first area that I kind of learned that asking for help is not a sign of weakness was actually my time as an officer in the nypd. I was a reserve officer and they, if you ask any cop anywhere in the world, I mean certainly I've spent a lot of time with the officers at the full time officers in the nypd. If you ask them what is their most powerful weapon, they will tell you without hesitation my radio because they will call for help the second something is happening. And if these, some of the bravest men and women out there are willing to call for help that quickly, why was I not willing to? I can point to my meditation practice and my wellness practice which is entirely built in me from my older brother and his wife. They have a wellness company and they provide coaching services and wellness services to a lot of very high powered individuals. And you know, it was my brother that finally came to my apartment and dragged me out like, what are you doing man? Let's go dust it off. And so, and then I think about vulnerability and you know, Brene Brown's work and a few other people and watching those videos and my work with my coach, which has been so impactful for me in terms of going from startup to grownup for me.

Well, there's a lot there actually. I'll double click a little bit on the coach. You can imagine I have a lot of interest in your experience with your coach. I've met your coach. I've heard from you about your coach Jonathan. Right. And pretty much, let's just be honest, I think you're in love with him. I think you're like in love. You have a bro crush on Jonathan.

Tell us. Not embarrassed to say it. Not embarrassed that he's going to hear this and be like, what? He's going to be like. Yeah, no, he tells me that all the time.

That's amazing. I'm again so happy. I'm so pro coaching. Yes, everyone should have a great coach. So I met Jonathan once. He seemed fantastic. But like, tell us how you met Jonathan and what that was like and tell us what he's sort of brought into your life.

Well, I met Jonathan kind of kicking and screaming, which is my series. My board came to me and said, all right, look, we're going to do the Series C at work market. At work market. This was an internally led round at Series C. We were going to put another 25 million into the company. But they felt like I needed a Coach. And we could spend hours talking about why it is I needed a coach and the. My suboptimalities as a manager and as a leader.

Well, I wouldn't mind hearing what symptoms were they seeing? What were they seeing that said, hey, you should find a coach?

I don't know that I really was a grownup. I mean, I was very immature in a lot of ways. And look, a lot of those were just insecurities that I needed to be proved right, that I was more, you know, concerned with whether I was right as to whether I was effective. I wasn't very goal oriented. I was all right. They were like, jeff, you might be super smart and you might have a very clear vision of how this company's going to go about, and you might actually have engendered a lot of loyalty from the team because you work really hard and they know that you care about them, but you're not as effective as you need to be as you can be. Right? And so it wasn't a, hey, we need to replace you. It was, hey, how much better can this company be if you were better? But that being said, I didn't really feel like I needed a coach. And so one of our investors is one of the most famous investors in the world and one of the considered one of the best investors in the history of venture capital. And he said to me, hey, you know, I think you need a coach. And, you know, my response was, I don't need a coach. You need a coach.

Wow.

Just looks at me, he's like, do you see what I mean? I was like, oh, all right, fine. He said, look, we're not suggesting it. We're telling you, we're not going to put the money in unless you get one. I was like, okay, well, then clearly I'm going to get one. This is not the hill I'm dying on.

Right?

And so I interviewed a bunch of coaches. And look, for me, given my hesitancy in doing it, my lack of understanding at the time of the benefits of coaching, of the science behind it, of the study of the. Of the. Of everything behind it, I felt like I needed somebody that had sat in my chair.

Ah, yep.

And so the reason I went with Jonathan is that Jonathan had been much more successful than I may ever be in startup world. He was the president of DoubleClick and had done a number of other things. And then he said, you know what? I want to go and help people and help other people be their best selves. And so he went back to school and got his master's, and then he started a coaching practice. And so when I met him first meeting, we walked in and, you know, I had already selected him because I had already thought, all right, this guy's sat in my chair and he's done. He understands what my day to day is. He understands the pressures I'm under. We went for our first meeting, and he walks in, he goes, all right, so we're going to spend this whole time talking about your goals, because my job as a coach is to make you effective at achieving your goals. So let's lay out their goals. I was like, I don't know what my goals are. He's like, what do you mean you don't know what your goals are? I was like, I don't know. Just to sell the company for a lot of money. He's like, you don't know what your personal goals are, what your development goals are, what your goals are for the company in a specific basis from a quarter, yearly, five year? I was like, no. He packed up his stuff. He said, all right, I'm not going to charge you for this session. You have homework. When I come next week, I expect you to be able to articulate what your goals are, and we can continue to refine them, but I can't help you if you don't know where you want to go.

Wow. Strong move. Packed up his stuff.

Packed up his stuff, walked out the door. He's like, I'll see you next week, buddy.

Yeah. So what did you think?

I thought, I like this guy. I like it because, look, I don't like when people waste my time. Every meeting at work market cannot be longer than a half hour. And there are a whole host of other reason, meeting reasons. And everyone that comes in my office needs an agenda and a goal and a host of other things, which are all tips that he taught me, by the way. He helped me refine this notion of don't waste my time into more actionable ways of making sure my time was effective. But he. I just thought, wow, this guy is not wasting his time. He's not charging me. And that's. He. Yeah. I mean, I've always thought you're more likely to get to where you want to go if you know where you're going. And he just was saying, how do you not know where you're going? He's right. I need to articulate that to myself, if not to anybody else.

So then what are some of the other things that you got out of the experience of working with Jonathan? Like I'm sure that you got frameworks and thoughts about it, but also, you probably had an inner experience. Right. Like, you probably had interchange with him.

Well, I will say this. I think he not only made me a better manager, a better leader. I think he made me help me become a better person. And so, you know, look, there are frameworks after frameworks after frameworks. And if I were still in my office, you would see all of them up on the whiteboard. I always kept them on the top row of the whiteboard. I'd stand on the chair and I'd write all these frameworks, and that way I'd look at them every day. Because there was a broad framework of moving from consciously incompetent to or unconsciously incompetent to consciously incompetent to consciously competent to unconsciously competent.

Oh, very good.

Well, there were a lot of things that I just was not even aware that I was incompetent of.

Yeah.

And so he helped me to think about that and really to stand on the balcony and see myself and see my performance and how I was doing. And it created an ability to be introspective. And that ability, more than anything else, has been helpful.

It sounds like it was also a pause in a way.

Yeah.

Yeah.

I think that combined with everything now is goal oriented. Right. What do I need to accomplish? And when I say everything else, I don't mean everything in my life. Right. There are just relationship talks and just time that you're hanging out and whatever. But every time I start a call now in a business context, I'll say, all right, before we start, I want to make sure I'm clear. What are your goals? People sometimes are taken aback. What do you mean? I said, well, we only have a half hour. I want to make sure when this half hour ends, we've accomplished what you wanted to accomplish. And people, they get thankful. They're like, wow. Yeah, thank. All right, look, I wanted to ask you to be an advisor to my company. That's actually what we're on the phone here today. I'm like, okay, great. Well, let's talk about it and see if there's an overlap and see if I can do that for you.

Yeah.

Or they'll say, I wanted to get some intros. Great. Let's talk about how I can help you.

Yeah.

Or whatever it is. As long as everyone's clear about what the goal is, we can work towards achieving. I may not agree with your goal, in which case we'll debate and discuss. It's not A shared goal. But if I'm able to identify what that goal is in a conversation with somebody in my actions, whether they're in regards to my wellness and their regards to my personal professional development, my personal development, what I want to do with the rest of my career, I feel a lot more focused. And so that I think combined with this framework of being able to take a pause and be introspective were the biggest gifts that he, he gave me.

That's beautiful. That's so lovely. I just want to, I want to maybe re articulate the learning model that you just articulated, because I think it's so powerful for people to really hear it. So it starts with being unconsciously incompetent.

Yes.

Right.

You are bad at something and you don't even know you're bad. You say things like, I don't need a coach. You need a coach. One of the richest, most well thought of investors on the planet.

Exactly. Great example of unconsciously incompetent. And then you move from there into consciously incompetent.

So that is the wow. What, just what did I just do in that meeting? So to me, I always think about this as the reflection time of wow, I just didn't. I just wasn't effective as I could have been. What could I have done differently? I'm aware of it. Right. And then we will move to the third phase, which is consciously competent, which is I'm actively taking a role and kind of in real time thinking to myself, all right, you got to be careful here. This is a trigger. Don't overreact. Think through it. What's your goal? And I'm constantly reminding myself, what's your goal here? All you're here to do is achieve what you want to achieve. So it's an active mental process. But as with a lot of things, you got to develop that habit. You got to build the muscle to get to that fourth phase of unconsciously competent. You're not even thinking about it, and you already have developed those habits and those behavior patterns.

That's well, well, well said. That's so beautifully said. And specifically the consciously competent. Sorry, Conscious competence burns a lot of calories. It's just exhausting, right? Until finally you are doing the muscle memory. You get the reps in that then helps you be unconsciously competent, which is like probably the way you drive a car, brush your teeth, just like it just happens around you.

Well, for those of us that live in New York City, maybe driving a car is not best example, because I really don't know how to drive a car that much anymore. But this, though, this is why I had everything written up on my whiteboards. I had them written up again. I stood on a chair on my tiptoes and wrote them on the tip top of the. There was a whiteboard wall. It was a whole wall. And so at the top of the wall, where the wall met the ceiling, were all of Jonathan's frameworks around what types of conversations I want to have, what are my goals, what are the shared goals, what are blockers internal, what are blocker external. And I needed to see those on a daily basis during this period, which I would still say I'm in for a lot of these skills. Consciousness, competence. In a lot of ways, I'm actually consciously incompetent. Some. I'm still unconsciously incompetent, but we'll leave those aside for now.

Right.

But for me, just seeing everything up on that whiteboard was super, super, super important.

Yeah.

It reminded me constantly. And I would help me catch myself as I was starting to get emotional or starting to maybe do some things that were suboptimal.

Yeah. Having them in front of your face is so. Is like the best thing, actually, when I go through something with someone I'm working with. We'll get to a place like, okay, good. So you're going to start, like reflecting more often before this kind of meeting or whatever it is they're going to do. And they say, how am I going to remember? So as a coach, I say, how do you think you should remember? And they say, the only thing I can think of is put a sticky note on my computer. Perfect. There's only three ways to remember. The whiteboard, the sticky note, or a calendar reminder. That's it.

I was just going to say calendar reminder is. That's what I do.

Right.

If there is a big meeting, I will put in a half hour before I will sit down and I'll think about, what are my goals in this meeting? Am I going to get to what. What am I going to do to be effective at achieving my goals? And then importantly, what is everyone else's goals? Right. And to me, that's the ultimate level of effectiveness is when you are so in control of yourself that you can be then outwardly focused. And how am I helping everyone else achieve their goals? Because we spend way too much time thinking about ourselves. And if we're nothing, if we're so inwardly focused and we're burning all those calories, we're not picking up on all the cues that other people are giving us that are going to help us in achieving not only our goals, but theirs as well.

Yep, totally. I love that. So I think you also, at some point in this goals conversation with Jonathan, you talked about identity a little bit. You sort of began to realize that your identity, Jeff Wald, was kind of fused with the identity of work market. And you maybe thought, maybe that's not ideal. So what did you come to think about in terms of your identity as compared to work market?

You know, this is a conversation I have with a lot of startup founders that at some point there's a bifurcation of interests. And whether that bifurcation is between you and the company, it usually manifests itself as you and the investors. Right. And the most common example of that is that the investors have made 50 different bets, and so they're pushing you to roll the dice and go for the highest outcome, because that's the only thing that changes their life. Whereas you selling the company for just a little bit of money might substantively change yours, even though it's a not meaningful return to them. And so I, look, I was all in on work market. I was there 18 hours a day, seven days a week. And, you know, in the early days, I was there 48 hours straight. Right. I would sleep there. I would sometimes not sleep at all. And I had turned my life over to the company and that it wasn't fair to me. And in a lot of ways, it's not fair to the company. And this is something I'll talk a lot about with people I've invested in to say, look, the biggest value you have as the founder is your perspective and how much you care. But if you're so fried because you're doing a bunch of mundane things that you don't need to be doing, you're not going to be able to take that step back and have that aha moment. The biggest value you're going to create is not because you were on the phone with another customer or this or that. The biggest value you're going to have is when you're going for a run or you're meditating or doing something else. You're going to be like, oh, my God, I got it. I know how we're going to just tweak the product. That's going to blow everything up. That's how you're going to change things. Should you be on the phone with customers? Of course you should. Should be on the phone with the team. Of course. Course, of course. Of course. But if you're Doing it at the expense of you getting the space mentally and physically to be in the best position you can be to have that aha moment, you're doing yourself a disservice. And so while this isn't really answering your question on the individuality, that's how it manifested itself for me was just time. I was spending so much time there and I wasn't giving any time to myself. You know, look, it's a choice I made and it leaves me, you know, where I am in life and I'm a very happy person. But you know, maybe there are different parts of life that I would have optimized for if I hadn't made everything about that startup.

Mm hmm. Well, I think life is trade offs.

Very well said.

Yeah, yeah, yeah. I think that's very interesting. Your point about it's that when you as a founder throw yourself into the company, on the one hand you're giving a lot, on the other hand you're not leaving room for that creativity.

Yeah.

And I think that's important. And then you also talk about your investors. I mean, you know, this is maybe a good time to talk about boards in general. How do you think about when your board tells you something, gives you an opinion, maybe even tells you what to do, gives you some advice, maybe says, get a coach, otherwise you're not investing. But actually other has other business advice. How do you distinguish when you should listen to them and when you should realize I'm the one that knows here because they have a lot of experience.

They do. They do. I will tell you, if your board has taken the time to have the context in which to give advice, then you should listen. If you're spending time at your board meeting explaining yet again what it is you do, then you really can't listen to their advice because they don't really understand if they are sharing experiences as opposed to advice. And there's a big difference between those two. Right. Advice is you should do this and experiences. Hey, the last time I was in a company kind of like this, it went down like that. And obviously it's an analogy. So therefore there are a thousand ways in which analogies break down. But there might be something in that story.

Yeah.

That sparks something in you that maybe helps you think about it. So I would say unless they have a lot of context, unless they're experience sharing or unless they're willing to open up their networks, they're for customers or people. Their networks are. And no disrespect to our venture capital friends out there, that's their big value add to us in the startup world. They know more people certainly on the financing side and all that, but customers, you know, care about who they are. Potential employees, team members are going to go, you're backed by XYZ or. Oh, you know, I heard XYZ talk about your company. So. And so either through their patina or through their network, they can help you with customers or they can help you with team members that you always listen to. But experience shares, I'd always listen to Experian shares. But advice that's given without understanding the full context, I am almost completely discounting and not spending any time thinking about.

But how about when you were the first? Because I work with first time founders sometimes and they're young and they sort of have this impression and they're not wrong. The board has been there and done that before and so I need to take their advice. In my book I talk about board members and one of the kinds of board members is the general fighting the last war. If you can relate to that. Right. And so what, how did, how has it changed the way you thought about your board and how did you relate to them when you were sort of a first time founder?

Well, as a first time founder, I was more enamored by their experience. Right, right. You know, they had been there and done it and they had backed tons of companies that had been there and done it. But look, the people that are there with you every day, I value their advice and their experience shares more than I will the people that kind of swing in once a quarter.

Yeah.

If again, if your board members taking the time to really understand the context in which they are giving advice, then I'm more comfortable. But I'm very conscious of this notion of the general fighting the last war. Look, they're not there with you every single day. 90% of the things that people will say to you, you're going to look at them be like, yeah, I thought of that because I'm here 18 hours a day, I'm thinking about this company every waking hour of my life and I've talked to every single customer, every single user. Why would you think that you would. The blindingly obvious thing is something I didn't think about or yeah, I appreciate that's how people did it three years ago, but that's not what's going on in the world today. To your point about fighting the last war. And so if they don't, I'm going to just beat that drum. Right. If they don't have that Context, if they're not there with you more than once a quarter, it's really tough to listen.

Yeah.

But it is your job to make sure that they're informed.

Yeah, yeah. That's a good distinction.

And that includes informing them about things that aren't going right. As a young founder, I was hesitant to share bad information. And I'd always want to paint this good picture. Everything's great, we're crushing. Everything's amazing. Not in any way, shape or form lying. I mean, that is fraud and that is illegal.

Literally.

Do not do that.

Just be very clear.

Jeff is not advocating fraud. But, you know, do you need to have radical transparency and candor with them? Maybe. But as a, as a kid, as a. I shouldn't say kid because it has a pejorative context, but as a younger founder, you know, you might not be comfortable doing it. And you should. You really, really should. And I was actually at an all day board meeting yesterday. It was the first time that a lot of people in the company met each other in person. Wonderful, wonderful experience. And so we spent the whole day together with all the team leaders and a lot of members of the team. And I asked the CEO because it was such an upbeat meeting and everything was amazing. I was like, you have built an amazing culture. Everybody here is so collabor collaborative. But are they sharing their failures? And he said, actually we do a weekly retrospective of what went wrong this week and anyone can present. And we've actually had people leave because they don't like that kind of candor. That's great.

That was music to your ears, I'm sure.

Oh, my gosh. Completely music to my ears. Look, as a board member, as a team member, I can't provide the best advice. I can't provide the best context because the failures and where things are going wrong, that's. That's the meaty stuff. That's where you're learning, whether it's from a customer standpoint, an architecture standpoint, a personal development standpoint. You know, life is lived outside those comfort zones and things are learned outside of normal processes. And so that being able to talk to your board about that and sharing your information will give your board the right context to be effective for you. You.

Who else have you gone to? So we have Jonathan, we have your board, and you sort of matured into your board. Who else do you go to for support, advice, mentorship in your life?

I am fortunate enough to belong to an organization called ypo. The Young Presidents Organization.

Yep.

And it is another one of those Places that without it along my journey, I simply would not have been able to get to where I am today emotionally. Mm. And so YPO is a thing called forum, where once a month for five hours, you get together with the same eight people and you go deep. I mean, deep, deep, deep. Like, this is where people come in and be like, look, I'm cheating on my wife and I don't know what to do.

Whoa.

Oh, yeah. I mean, I've been in other. I've heard of other forums. I shouldn't mention my own or anything going on there.

Not Jeff's forum, not Jeff's forum.

All. They're all very faithful to their spouses, but. Which is actually true, by the way. But, you know, I've heard of other forums. People will come in and say, look, I've been cheating on my taxes and I feel like the IRS is about to find me. Like, you tell. Because everything's in a forum confidential context. So these people have got your back and there's total trust, which YPO does an amazing job of building that.

How do they build that trust?

They build that trust through a host of things, the most important of which is called a lifeline, where you, when you join that forum because some forums form and everyone joins at the same time and other forms exist and a new person joins it because someone else, you know, moved away or dropped out or whatever, you do the lifeline and everyone else shares the lifeline. And the lifeline is about an hour long look at your life where you go through all of the things that you are vulnerable about, ashamed about, all of your insecurities and fears, all of your accomplishments as well. Well, it's not just a, you know, a bummer hour, but being able to share that vulnerability is one of the most powerful ways to build trust. One of the reasons that I hope, or at least I was told many times, and the surveys would show that the people at work market trusted me, is I would tell them the things that I was afraid of and how I was, you know, sitting there with some imposter syndrome and sitting there not sure about what ideas were going to make or sitting there, very concerned because these customers had left us. And, you know, maybe that's a trend and maybe we didn't figure something out. This was radical candor on my part to that team about what was going on in my head and what I was scared of. And then they felt comfortable to share. They knew that, you know what, Jeff's being authentic.

Lots to say there. So let me back up. I Want to talk about authenticity in a minute. But backing up to ypo, sounds like YPO has kind of created structures, systems, if you will, to build trust very quickly if a new member comes in. It reminds me of the Blue Angels I met at a. It was a speaker at a leadership seminar I was helping to. I was also a speaker at. And the Blue Angels, this, you know, stunt flight team, they have six members and they have three new members every year, if you can imagine that. 50% turnover in the team every year. And as he said, the stakes are high. The stakes are high. So there's no sulking. You said you were going to be there and you weren't there. No, no, no. If you're not there, when you say you're going to be there, it's like, that's a. It's a crash in midair.

Yeah.

And he talked about all the different ways they built trust and how important that was in order to integrate new members of the team. And it sounds like. I'm not saying that's exactly what YPO does, but it sounds like it's really very determined and intentional about building trust.

100%. Look, in any study of effective teams, trust is the foundation.

Yeah.

If you don't have it, you will not have an effective team. Just stop. End of conversation.

Yeah.

And one of the most powerful ways to build trust is to show people that you're willing to be vulnerable. Because in that state, that step of being vulnerable, you are inherently saying, I trust you with my secrets, with my shame, with my vulnerability. Trust that you're not going to be like, oh, yeah, well, way to go there, baldy. And like, you know, the fact that I was very insecure about when I started losing my hair, like, that was something that was very important for me. And I wouldn't talk about it, and I was very ashamed of it. And yet it's a tough thing to be ashamed of that much or keep that much of a secret, given that I have to walk around like this. But our listeners.

Our listeners should realize that Jeff is actually bald, but on him. On him, it looks good.

Well, you know, that's what they say. You and my mom agree upon that.

Well, I don't mean to make fun, though, because that was actually something that was, like, really serious for you as it was happening. And the YPO people helped you. Is. It is accurate to say they helped you kind of open up about things which are really uncomfortable for you.

100%. Those are. Those seven people in my forum know more about me than anybody. In the world.

Yeah.

Right. Like, they know everything there is to know about Jeff Wald. The good, the bad, the ugly.

Yeah. So then at any given moment, you can reach out to them and actually tell the truth, what's going on with you, and then get great advice because.

They actually know back to this thing. Right. They have all the context.

Right.

And so if something's going on in a relationship and I bring it to them, they're like, well, Jeff, this is something you've talked about before. And like, maybe that has relevance to this issue or that issue. They, they. They have all the receipts. Right. They know where all the bodies are buried. And so they are able to give me advice.

Yeah.

Because they understand everything.

So now I want to. I want to follow up on what you said about authenticity, because that's, to me, in some ways, a loaded concept.

Right.

You're supposed to be authentic. But what does that really mean? Because people don't really want your grumpy self. And if you're falling apart as a. As a leader, as a CEO, as a founder in a company, let me tell you something. Actually falling apart at all hands is not recommended. So how do you think about that? And also be authentic and build trust.

That's a very fair point. Look, there is a fine line between showing your vulnerabilities and being somebody that people want to follow. Nobody wants to follow the grumpy person. And the person that's completely insecure and doesn't want to, you know, is afraid to do X, Y or Z. You can show. Share that. That you have some insecurities about it. You can share, you have some fear about it, but then you need to make a decision and you need to lead that team. And so, you know, look, there are no common traits of all leaders. Well, let me take it back. There's one common trait that every single leader has, and it's that they have followers. So you can lead in any way you want, but if people aren't willing to follow you, then you're not a leader. And maybe this isn't the right role for you. But yeah, look, I would not advocate having a breakdown in the team meeting, at least not too often, you know, once. Maybe you can recover from that, if that's happening. But yeah, look, you do need to show strength and you need to show those attributes that people want to follow. You need to show that vision and be able to paint the path and do to your team as to how you're going to get there. And if you're not capable of of leading them there. Find someone who is. You can be the founder, but not the day to day leader. That's okay.

Yeah.

And knowing your strengths, knowing your zone of greatness, to borrow other people's phrases, what you're good at and what you want to be doing every single day, for some people, that's not leading in that context, managing people, that's not necessarily the best thing for them.

Yeah.

You know, I didn't love it. I happen to love it now. But my initial approach was, I'm smarter than everybody. Get out of my way. I'll just do it. And you know what? A. That first statement is not true. I was not smarter than everybody, certainly not than my developers because I don't know how to write code. So they. I couldn't tell them, get out of the way. But that, that was not productive for anybody. It wasn't true and it wasn't effective. And so me evolving into the person that helps the team find the answers, as opposed to where I started, which was I thought I was the leader because I had all the answers. And if anyone could show that I didn't have the answers, that I wasn't the smartest person, well, then that questioned why I was the leader. No, no, no. I'm the leader. For whatever reason, I'm the leader. And now my job is to be effective at leading that team to help this group of diverse people with all these amazing perspectives and skills to collectively find the answer to help this team get to where I am leading them. And so that, that. That's kind of where I've evolved to.

That is very well said. And I'm sure that your coach helped you evolve in that direction, but what else were contributing? What else contributed to that evolution?

Well, honestly, listen, the. The fact that I had had earlier success contributed to it. And so look, it would be a better journey for me if I come to these things through a lot of hard work and therapy and group discussions and forum and coaching and introspection. But, you know, I was able to shortcut a bunch of them because, you know, the second startup and third startup, they got sold, but they weren't monetized. And then those companies got sold and it actually produced cash to me. And all of a sudden, I went from very little to almost nothing in my bank account to a lot.

Mm.

And all of a sudden, I then felt comfortable again, just to be clear with every one of the listeners, I wasn't. I'm not proud of this part of the journey, but it is what happened. Yeah, that I felt comfortable talking about the past failures because now I was already successful. And so this, to me, was a big distinction that I've talked a lot about between vulnerability and talking about failure. Because I started talking about failure then, but I wasn't being vulnerable. Me talking about something that had failed that subsequently was successful, and it made me a ton of money. That's not. That's not being vulnerable and sharing about failure. But it was my first step in saying, wow, if I'm able to talk about that failure, maybe I should talk about things that I'm really vulnerable about, that I'm still scared about, that still I have shame about, and that is vulnerability.

Sounds like your path to vulnerability is more confidence.

For me, I needed some external validation points. I needed those to push me along on my journey.

Right. Actually, what I tell people all the time is that the confident can or the strong can afford to be vulnerable and the confident can afford to be vulnerable.

Yes. And they in some ways have an obligation to do it because it helps other people on their own journey to see that vulnerability. And they'll say, wow, if Jeff's comfortable doing it and sharing those things, then hopefully they think to themselves, well, then I should be. I'm comfortable too.

Right, Right. So it's like a role model. And something else you just talked about is your imposter syndrome, which is so common with founders, and people just don't talk about it. So thank you for sharing that. Can you share a little bit about how that showed up for you and how that still shows up for you? Maybe.

Well, I'll start with how it still shows up as I think about my fifth startup, and I think, what if this one doesn't work? Are people going to think the others are just a fluke? Maybe. You know, what? If that's what they want to think? That's what they want to think. And you know what? There was a lot of luck with all of them. So, you know. And you know what? I'll take it. I'll take it every day of the week. I am super lucky. I have started on third base, given where I was born and how I was born. And you know what? It doesn't mean I don't work hard, but I'll take the luck and I will take the advantages and the privilege I've been given. That said, you know, in the back of my mind. Because that's where it is now, right? It's in the back of my mind. Before, it was at the front of my mind. Like, are people looking at Me, do they think that I'm not capable? Like, I don't. What's happening? I don't know. And then when you get that slight little data point on, someone says something like, oh, my. Are they judging me right now? No, no. That I don't experience anymore.

Right, but that was present for you. That was present for you in the earlier days.

It was. And you know, let's borrow on another one of our favorite positive psychologists, Dweck, and this whole notion of mindset, because I was coming with a very fixed mindset, this idea that anything that happened was either a validation of my fixed mindset that I was super smart and I was going to be very successful and something was a validation of that, or it was an indictment on it and therefore. Oh, no, no. And then if that happened, then none of this is true. That's just a hard way to go through life versus the growth mindset of every single thing that happens allows me to just build and get stronger. And our good friend Jonathan Shapiro, my former coach, would say that he is a. What was the exact words? He was a reformed or former fixed mindset.

That's great. Recovering.

Recovering. Recovering fixed mindset guy. Because we're all recovering from that. We all. For some reason, or I shouldn't say all. A lot of people start out that way, and I certainly was there. And that was, to me, kind of the manifestation of an imposter syndrome, this fixed mindset that anything that might happen is going to tear away this facade. And therefore I got to keep everyone at bay and make sure nobody knows anything. And. And everyone's going to think I'm super smart. And if I'm not, then why am I the leader and blah, blah, blah. Versus, yeah, you know what? I'm not the smartest person in the room, and that's great. I want to hire people much smarter than me. And you know what? I'm going to make mistakes, and that's okay. I'm going to learn from them. And when I sit with my direct reports and they'll say, hey, I'm going to go give a speech. It's the first time I'm like, great. You know what's going to happen? You're going to totally screw it up, and that's okay. I want you to go out there, I want you to have fun. I want you to learn and just know 99% you're going to screw it up. That's okay. And the next one you're due, Maybe only an 80% chance you'll screw it up. And by the time you've done your 10th, you're gonna be pretty darn good at it. But don't go out there and think you're going to be great. You won't, and that's okay. I got your back. I'm going to be there. I'm a cheer for you no matter what happens.

Yeah, that's. I think it's so important to sometimes level set and take the pressure off people to be perfect all the time. And it sounds like that's what you bring to the table with your direct reports. And actually, I want to talk a little bit about that. When you think about having difficult conversations with your direct reports or complicated topics, you have to address what shows up for you time and time again that you either have a regular script for or that you wish you had a script for.

Well, there are a few things to come to mind. One is the idea that nobody will care how much you know unless they know how much you care. One of my favorite quotes. And so what comes up for me a lot is I want them to know that I do care about their outcomes. And for me, the way that showed up a lot was, look, let's talk about your professional development, including when it might be time for you to leave. Because if you want to go, I will help you find a job someplace else. Like, if you want to become the, you know, head of product. Well, look, we just hired head of product, so that's not going to happen for you here. But when you're ready, I'm gonna help you find a job as head of product somewhere else. And being able to demonstrate in real time, because, by the way, those stories propagate, you know, they go tell, hey, you know, Jeff is gonna help me find a job someplace else because he really cares about me and not the fact that I might leave and no longer be a part of this team. He wants what's best for me. People go, wow, that's awesome. And then they want to come in and have a conversation. But what shows up a lot is making sure that they understand that I care about them and care about them in the context of their life, not in the context of their time at that company. For me, right, because so many people are like, well, once you leave here, like, you're not doing anything for me. So what should I care? No, you should care. You should care a lot.

Yeah.

So that comes up a lot for me. And the other thing comes up a lot is what are their goals and what are our shared goals? And those are the kinds of things that I thought that I wish that I had a playbook on or I had done more of when I was younger. Because certainly when I was a young banker, I wasn't sitting there thinking of the analysts that worked for me, hey, you know, maybe, you know, do you want to work at a different bank? I'll help you get a job. No, no. I was like, build this model for me or get out of my way.

Right.

Like, I didn't care about them at all. And that wasn't effective.

Huh. So when you became a founder and then over time with different companies, it was still, was it awkward to talk with about their, about their goals and shared goals and you had to grow that. Like what, what was it about personal goals, the goals that you're talking about or about business goals or what do.

You mean by that?

Both.

Both. So what we started to do is we had quarterly plans of record. Some people will say okrs.

Yeah.

But for me and for my direct reports, and I insisted on everybody doing it throughout work Marketplace for all their direct reports, part of that plan of record. What you want to accomplish this quarter with smart goals, specific, measurable, action oriented, relevant, time based, where your professional development goals and your personal development goals. And so people come in, they'd say, well, I want to be a public speaker. I would say, okay, I can't do anything with that. That's not a smart goal. The smart goal is you want to join Toastmasters and you want to give two talks to groups greater than 10 people. Because at the end of the quarter, I can either put a check. You either did them or you didn't. Like, I can't judge. Did you become a better public speaker by the end of the quarter? I can't do that. I can judge. Did you take these actions that will lead to that objective? Did you get those key results? And so that might be a part of their professional development and their personal development might be books they want to read or a trip they want to take or a vacation that they need to schedule. Because if you're not helping people on their personal and their professional journeys, I'm not sure that you're showing them. You're not. You maybe aren't showing them as much as you could how much you care about them.

Yeah.

Because helping them on those journeys really, really should. There are other ways to do it, but that really illustrates them that you're helping them and that you care that you're helping them on those journeys.

Right. And that really unlocks performance and loyalty and Discretionary effort and all the things that you want as a leader.

That's been my experience. I'm sure there are tons of other ways to do it. This is what's worked well for me.

This is your way. I love that. I love that.

Well, it's Jonathan Shapiro's way.

We'll take it you've adopted it. So, okay, you sold work market to ADP, your most recent company in 2018.

Yep.

What that was, was that your biggest acquisition? Just from a dollar's perspective. Okay, so what was that like for you? I guess what I mean is on the one hand, that is sort of the what we're hoping for, right? As a founder, you're looking for that so called exit. And at the same, or, you know, whatever that is. And at the same time, that is your baby. You've been giving 18 hours a day, seven days a week too. So tell us about that, that experience.

Well, I will tell you this. One of the things that I will coach founders on is you should always be thinking about what your goal is and how you're going to make that goal happen. And for most of us, that goal is a sale of the company. For some might be a public offering or whatever. And if your goal is a sale, who are the potential buyers? And if you are not on their radar, if you don't org your way in to the head of corp Dev and Strat at those different companies, you know, you're just not increasing the probabilities of your success. Not saying it won't happen, it's just you increase the probability. When you get to know those people. If they come to town and you're not sitting with them and having coffee and just talking about what's going on in the world, you may be doing yourself a disservice. ADP was not on my list. I had 15 companies that I thought were the logical buyers of Work Market. ADP was not on that list. But ADP came knocking and you know, we had a dance for a couple months and then the president of ADP and the head of corp, Devon Strat took me out to dinner and they did one of the. They slid the little piece of paper across the table.

They did not.

They did. I am telling you right here, hand to God, they did it. I know exactly what table, I know exactly what restaurant. I mean, I'll remember for the rest of my life. Wow. And too many movies. Yeah. I looked at the number and I looked at them. I said, all right, I'll get back to you. They're like, that's it. Don't you have reaction? I mean, I wanted to like get up and start dancing, like, yes, but, you know, you keep your composure. And I said, look, I am the largest shareholder, but I am only one person on a five person board of directors. I have a fiduciary response, responsibility to all the director, to all the shareholders. And so I will convene with the board and we'll get back to you asap. And so, you know, look, we had, we were at this crossroads of we were going to run out of money. We had investors that were willing to put in more and so we hired a banker and we went through a process and ADP up their bid and you know, other people put in bids and it was, it was really cool. And we came down to that last board meeting of are we going to put 25 million more in or are we going to sell the company at adp? Because they've won the auction, but we don't, we're under no obligation to sell the company. And there were two things that go on in my mind. One is if I take 25 million more, I get diluted down. How much do I need to grow the company? Expected value, probability, outcomes, time value of money, and what's the math? And do I think that I can grow the company enough that I'll have a bigger exit in 18 months to 24 months that I'm going to have now? And for me, that math said, no, I did not think that was the case. And we could go into it, but that's very detailed as to work market stuff. The other thing is, what do I want? What does Jeff Wald want? And so we had that board meeting and I didn't really talk a lot, which was very unusual for me at this point. And Fred Wilson, who was on our board as our lead outside investor, he and I took a walk. He's like, you know, we took a break and he's like, you know, you're not really talking much. And I just said, fred, I'm done. Like, I am just exhausted. And if you guys want to put 25 million more in, I've already given you my reasons why I don't think that's the best expected value outcome. But I can't do it. I'll stay as long as necessary and transition to somebody and I'll always be there to help because work market is my baby and I'll do everything I can to help, but I'm just exhausted. And he looked at me, he's like, well, we're not going to put more money in if you're not staying. I was like, oh. And I didn't think about that.

That didn't cross your mind?

It didn't occur to me. Yeah. Didn't occur to me.

Yeah.

And he's like, well, we could have just saved two hours of time. We didn't need to have the conversation. And so it was just where I was mentally, because when you go that hard for that long, it's just not sustainable. And so I needed the break. And the irony, of course, being once ADP bought it, I then felt a little re energized because I now had new owners that I needed to prove things to. Right. They just spent a lot of money to buy this company. And much like I delivered a return for my venture investors, I wanted to deliver a return for adp. And so I spent the next year going at pretty much the same intensity. Yeah, not the exact same intensity, full disclosure, pretty much the same intensity. And what helped me a lot, a few days before the acquisition, I sat down with the CEO of adp. While it was a big acquisition, ADP is a hundred billion dollar public company. It was not that significant for them. So I hadn't met the CEO yet. And I finally had a chance to meet Carlos Rodriguez. Who a nicer person and a more effective CEO I will never meet. I mean, he is amazing. Just a wonderful, wonderful human. And he said, look, Jeff, we need you to give me. I need you to give me three years.

Three years.

Like I can't do three years. Like I'll give you two.

Yeah.

He said, can you give me two and a half? I was like, okay, I'll give you two and a half. And I put in my hand and he shook hands. He said, all right, I'll tell the lawyers. I said, you don't, you don't need to tell the lawyers anything. I just shook your hand. That's it. That's it, baby. Like, I will be here come hell or high water for two and a half years. And so given that period of time where the agreement was, for a year, I'd run it as if they didn't buy it. And then for the next year, someone from ADP was going to run it and I would be at their side helping them. And for the final six months, there'd be whatever transition those final six months, by the way, ended up being. Covid. But that aside, by the time I got to those final six months, it really wasn't my baby anymore. Right. Like, I spent A year running it for somebody else where I had no economic upside for it. So that kind of starts to loosen the baby threads because off doing its thing, then I hear when I. A year, when I wasn't running it, I no longer had penile responsibility. I no longer had any direct reports. And then those final six months, I mean, it was Covid. So, you know, the whole thing was just a little bit of a mess on, on, on every front. And I felt relief because if we had not sold the company we're going into Covid, I mean, my heart goes out to everyone that we're running companies. A year ago, yeah. Because I was unbelievably grateful as I had been for many, many moons, because I no longer had to worry was I going to be able to make payroll.

Yes.

We now were part of one of the largest companies on the planet.

Yeah. Who also could make payroll for you. Literally.

Literally could make payroll. They are the largest provider of payroll on the planet.

That is very interesting. I love your sort of taper down model. That's kind of what it feels like.

If I had left the day after the acquisition.

Yeah.

I would have, I would, I don't know what kind of mental state I would be in. This was fair to them because all my knowledge was transitioned, all the relationships, everything got institutionalized. And I remain an advisor to ADP on the future of work and, and I talk to work market people all the time. I still talk to customers. I still do sales pitches every now and again. And so whatever I can do to help that team, I will always do.

Yeah. Yeah. I spoke to SV Band, who is the founder, one of the co founders of Contactually and they sold their company to Compass. And he talked about kind of that, the depression that kind of set in after that sale. And I wouldn't. No, actually I wouldn't say that he felt the depression, but he knew that he needed to take his identity away from the company before that would, before, during and after that sale. And he knew that he needed to kind of mentally steel himself because this was going to be a transition and there was going to be a feeling of grief and loss. And he talked about how it is natural and maybe surprising for other people, but not surprising for founders to. To have those experiences of grief and mourning after they have a good outcome.

Yeah. So you can understand that I want that company to be successful no matter what. And anytime I hear, oh well, this customer actually may leave, it still hits me in my gut. Does it keep me up at night anymore? No. But does it still hit me in my gut a little bit. Will it? Will it? Maybe. Always, maybe.

Yep. Yeah, I can relate to that. So while you're at adp, you also wrote a book.

I did.

You wrote the End of Jobs.

It's true.

Why did you write that book?

Honest answer. Frustration and annoyance. Frustration and annoyance. Look, as the founder of this piece of enterprise software that was helping companies transform their labor model, I had, over the intervening years, been invited to many conferences and given speeches and heard other speeches and been on panels. And people have a tendency in the world of work, and I'm sure in other areas, it's just these are the only conferences I go to or future work conferences. People have a tendency to just say things that have a high probability of getting heard, but a low probability of being right. They want to make some outlandish statement like, oh, in the next 10 years, 50% of the labor force is going to be this or 50% is going to be that. And you're like, no, it's not like, like a zero percent chance of that occurring. And I find that very frustrating because you have companies, you have families, you have communities that are planning how they're going to think about the future and choices they're going to make based on what some experts. You're quoting here for our listeners. Experts have to say. And it's just when I think you have an obligation, if you're talking in the public square, to have a logical, reasonable, defensible point of view. And so I started challenging people on panels. People would say, oh, I think this and this. I would say, okay, great. What data do you have to support that? And they'd get flummoxed, like, well, I mean, I don't. I don't have any data. I'm like, well, then maybe you should shut up. Maybe you should.

Diplomatic, Jeff. Yeah.

No, I was not diplomatic. Yeah, I was on a panel the other day, by the way, and this guy said, I think 50% of the workforce is going to work remotely post pandemic. I said, oh, that's interesting. How do you juxtapose that with the fact that only 42% of the workforce can work remotely? Because clearly people in manufacturing, logistics, and other places can't.

Right?

He said, oh, I didn't. I didn't know that. I was like, shouldn't you know that, though? Shouldn't you know that if you're going to make a prediction? So anyway, I felt that what people needed to do. If you're going to make a prediction on the Future of work, and probably the future of anything is you need to look at history, you need to look at data, you need to look at how companies actually engage workers. And if you're looking through those lenses, it doesn't create a crystal ball. You're not going to be 100% correct, but you have a high probability of putting forward a thought, a projection, a statistic, whatever it is, that has a reasonable chance of being correct. And so when we think about the fourth industrial revolution, which we're in the early innings of, not the beginning, we're kind of, you know, a little deep in it, probably the third and a half, fourth inning as we think about that. How do we not look at the first three industrial revolutions and how companies, workers and societies reacted? As we think about the robots and AI, how are we not looking at the pace of automation, technological automation, computers and all these other things, how those things impacted the workforce? How are we not looking at how companies actually adopted those changes over the long term and over the most recent history? Because when we look at those things, it paints a very different picture than the common narrative of oh my God, the robots are going to take all our jobs. And so I appreciate that. I called the book the End of Jobs. What I was talking about is the end of that nine to five, one office, one manager job. That job is ending. And I talk about in the book, obviously written pre Covid about these flexible team based work from anywhere, always on job. And that's the job of construct of the future. And Covid certainly has sped that up. But I also talk about the fact that we will see no net job losses to robots and AI. And I spell out why I take that position. And so that, that is why I wrote the book is because of frustration and annoyance.

Good answer, honest answer. Well, Jeff, I just have one last question for you, which is, what do you wish you had known before you started this journey of entrepreneurship?

That is, that's a tough one. There are a lot of times that I wish I could go to my past self. And the number one thing I'd want to say is just, it's going to be okay, you know, because that, that little guy, he was wracked with insecurities and racked with the burden of expectations. You know, I'd gone to all these wonderful schools and I worked at these amazing firms and I was about to start my first company and when it failed, I just want to, I want to go and just sit with that guy and be like, it's going to be okay. Like. And so the things that I wish I knew when I started out, my journey is it's okay to fail. And that failure won't define you as long as you pick yourself up, you dust yourself off, and you keep going. And that the key to success is just keep putting one foot in front of the other. And so perseverance is something that has been a hallmark in a lot of things that I've done because I will just work as hard as I need to work and I will bring everything I have. But understanding that it's okay, that if you fail, you pick yourself up, you dust yourself off, and you keep going.

That's so beautiful. Is there anything else you'd like to tell us today?

I just want to tell you how much fun this was to have this conversation with you specifically, given your amazing background and this amazing book that you've written. And I am so excited and so honored that I got a chance to talk with you in this form on your podcast.

Oh, thank you, Jeff, for saying that. I really appreciate that. And what a pleasure to have you, my friend. Jeff Wald. Thanks for so much for joining us today.

Thank you.

Thanks for listening to From Startup to Grown Up. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alyssacon.com.