Jeff Wald is the Founder of WorkMarket, an enterprise software platform that enables companies to efficiently and compliantly organize, manage and pay freelancers. Jeff built WorkMarket from the ground up and sold the company to ADP for $400million. Along the way he learned some incredibly valuable lessons, some of which came during the exit process.

Jeff shares his journey, what it’s like to take on investors as a company grows, his thoughts on the future of work and Universal Basic Income, and why retraining will be key to a successful economy.

What lessons have you learned along the way as you’ve started and grown your business?

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Mark Peter Davis: Jeff. Thanks for being here today. 

Jeff Wald: Mark is always a pleasure to be anywhere with you. I 

Mark Peter Davis: appreciate that even digitally. All right, let's start off. Uh, I'd love for the folks listening to get a sense of your entrepreneurial journey. Would you mind giving a background, um, feel free to start kinda early on, do the, do the life story.

Jeff Wald: Wow. Um, let's [00:02:00] see. I started my entrepreneurial journey as an investor and an Israeli venture firm. And after being there for a few years, met an entrepreneur who I was so enamored with. And I tried to back the company, he was building, it was called enforced at the time and I got outbid, but he and I became friends.

And when he came back a year later, having exited that company, uh, he said, look, you know, I should have done that deal with you. We had a good exit, a good outcome, but it wasn't as good as it could have been. And so he and I started working on a company together called spin back. Uh, and I eventually left the firm and founded that company with him and it failed miserably and bankrupted me.

That was, you know, I put everything I had into it. You put an equal amount and it's just, he had a lot more, so he was not bankrupted. I was, 

Mark Peter Davis: did you officially go bankrupt or you just ran out of money? 

Jeff Wald: It's a very, very good statement because I should be more careful with my words. I did not declare bankruptcy.

I just was out of money. He got the call from my mom. Do you need to [00:03:00] move back home? And, uh, you know, it's lucky to be able to have that kind of safety net. And I am grateful that I was able to get that phone call. Does it make it any less horrifying to get. And so, you know, I was able to not do that, but, uh, you know, after a few months of depression, having never had failed at something at that level before and been wiped out before you eventually picked yourself up and you dust yourself off and you get back in and we ended up re forming that same entity and ended up having a successful outcome with two new partners.

Uh, and then I founded with this same man, uh, A company called work market. We were lucky to raise 61 million in total from union square ventures, spark capital, and a few others. And we took that through to its conclusion, a sale to ADP in January of 2018. I had the pleasure of being on [00:04:00] the executive team that ADP for about two and a half years of running the work market division.

Uh, but in September of 2020 is when my obligation ended and. I remained an advisor to our friends at ADP, but now I am thinking about what my next entrepreneurial journey will be. Ooh, you're going to have to share. 

Mark Peter Davis: Okay. Before we get to that. Now, when I look at your background before the entrepreneurial part started, you were a bit of a finance guy, right?

You did investment banking and that's not an uncommon story in the New York 

Jeff Wald: tech 

Mark Peter Davis: startup ecosystem. Um, 

Jeff Wald: How 

Mark Peter Davis: did you know when you think about being a founder, did that feel like something you had always thought about doing, but what was the mindset going from kind of traditional, safe institutional finance world to entrepreneurship?

Jeff Wald: Well, I will tell you, it was certainly not the plan. When I left JP Morgan, where I had been for about seven years as an M and a [00:05:00] banker that includes time at business school. Uh, I, in no way, shape or form thought I would become an entrepreneur. I, you know, maybe did some things as a kid that were entrepreneurial, but I always thought of myself as like a big company guy.

And there were actually a lot of people in JP Morgan that kept saying, you're going to run this place one day. And I thought, yeah, I am going to run that place one day. Um, but when I got, I went to business school and I finally got a chance to see other people doing other things and hearing about other career paths because, you know, I came out from undergrad and went.

Well, actually I did a combined undergrad and grad program, but I came right out from school right into investment banking. And then I didn't leave the office like 18 hours a day, seven days a week for five years before I left to go to business school. And in business school I saw, wow, everybody else doesn't do this.

This is crazy. And I got back, JP Morgan was nice enough to pay for business school and. I [00:06:00] remember being back for a few months and thinking, this is the worst job ever. Why does anybody do this? And knowing and meeting entrepreneurs of business school, that there was a different way. So I went to an investment firm, but market, I called a venture capital firm.

They wouldn't call it that they would say they're an investment firm. And I just started gravitating towards the early stage investing because as you sit with entrepreneurs, if you sit with an entrepreneur and you don't get fired up, There is something wrong with you because entrepreneurs are the most engaging, exciting people in the world.

They may not know exactly what they're doing. They may be dead wrong and what they're trying to do, but they are so darn sure that they're going to change the world that it's infectious. And I remember my boss at the investment firm saying to me, you have to stop fawning over these entrepreneurs during meetings.

Because I would say, there'd be like, Oh my God, you guys are so great. Oh, this is so cool. Oh my gosh. That's so interesting. Oh my God, you're amazing. And he would [00:07:00] pull me aside and say, you have to stop that because we have to negotiate with these people. And all you do on meeting is tell them how great they are.

And at one point he said to me, if you think they're so great, you should go do it. And about a year later, I left to go do it. 

Mark Peter Davis: Do you think you'll ever go back? I mean, you've got this big corporate experience. I know you're on a bunch of boards. Um, and you've been a successful entrepreneur now, so you have options and 

Jeff Wald: it's possible.

Um, will I go back to working at a big company, no. I mean, I will tell you, ADP is as good, a big company as you're going to find. These are some of the nicest people I've ever met. There's some of the smartest people I've ever met. Everybody there stays there for 20 years and I couldn't wait to get the heck out of there.

And if I was going to stay anywhere, it would be an ADP area. Great, great company that are doing great things. But gosh, even at a company that I love and ADP, it was so slow. And so bureaucratic, you have to be, you just [00:08:00] have to be, when you have 800,000 customers, you have 15 billion in revenue. So will I go back in that context?

No. Did I say to them, when they said, is there anything you would consider doing to stay? I said, sure, give me a few hundred million dollars and a corporate venture fund, and I'll build you the best corporate venture fund you got. And they said, well, we don't think the corporation should run venture funds.

And I said, that's actually a very good point of view. I don't disagree with that. So, you know, outside of an entrepreneurial context, within a company, it is highly unlikely that I would go back to a, to a big. 

Mark Peter Davis: Okay. Now this is a little bit of a different note here. I've known you for a little bit. Uh, I gather, 

Jeff Wald:

Mark Peter Davis: think you got a few years on me that you're in the back half of your forties.

That is true. I know that you're single, not married. 

Jeff Wald: That is also true. 

Mark Peter Davis: You don't have a family, a nuclear family 

Jeff Wald: that is also true. 

Mark Peter Davis: How do you think that affected, helped or hurt your entrepreneurial journey? We [00:09:00] had a guest on recently who made a. 

Jeff Wald: Strong 

Mark Peter Davis: case for the importance of spousal support. What's 

Jeff Wald: your take?

I often think about my co-founder through work market, who married at two young children and the sacrifices he had to make to be there 18 hours a day, seven days a week. And without spousal support, it would have been impossible. I mean, just impossible. I think about the. Relationships that I didn't nurture because I was spending so much time nurturing the company.

And I have some regret in that regard. I'm not sure that those were the best decisions for me as a person, but I made the decisions I made and I am where I am. So when I think about doing another one Mark, and then potentially putting life on hold again. Yeah. That scares me in a lot of ways. And I'm not sure that I'm ready for it.

And. [00:10:00] This is an opportunity to really focus on a lot of the things that I delayed doing. You 

Mark Peter Davis: mean the moment now 

Jeff Wald: where you've 

Mark Peter Davis: exited ADP and you're evaluating your, 

Jeff Wald: your life. 

Mark Peter Davis: Yeah. Interesting. Well, we'll, I'll be watching. Uh, can you tell us a little bit about work market, right. To shift over? Maybe you can just give us the high level what the business did.


Jeff Wald: for folks. Work market is enterprise software that enables companies to organize, manage and pay their freelancers. So as companies continue to transform their labor forces and freelance becomes an increasingly important part of the labor landscape companies need the enterprise software to efficiently and compliantly manage that part of the labor force and the systems to integrate that part of the labor force into the rest of their labor force.

Mark Peter Davis: So is that, you know, when did you start work market? How long ago was it 

Jeff Wald: 2010. Okay. 

Mark Peter Davis: So it's we're 10 years later. [00:11:00] And the goal then was for, to help big companies manage their freelancers through technology. Is that still relevant today? Is the need greater or lesser? How do 

Jeff Wald: you, how do you view, 

Mark Peter Davis: uh, the relevance of the mission?


Jeff Wald: years later? I think the mission was important, then I think it's important. Now, there are certainly still an untapped market opportunity. There work market is not taken a hundred percent of that market yet. Uh, there are, I think two or three other companies in this space at this point as specifically enterprise software to manage freelancers.

Um, and it is a. It's an area of opportunity because there are still a lot of transformation of labor forces to be done, but I don't think it's as big of opportunity as some people think it is. Or as people thought it was in 2010. I see. 

Mark Peter Davis: Okay. Why is that so hard? When we, when I hear the managing [00:12:00] freelancers narrative, you know, companies have a lot of HR technology and solutions these days, why do they need something specialized for freelancers?

Jeff Wald: The way you engage with freelancers is just different than you engage any other employee. The freelancer has a very different workflow that requires a different profile and structure requires different data flows requires different approval flows. They don't get paid through payroll. They get paid through accounts payable.

They have a host of different regulations in terms of how they're managed. And it is something that legal and procurement and HR gets very, very involved in. Uh, and so it requires very, very specific, special and specific systems that you can't use for temps and that you can't use for your full-time employees, but at the same time, the way every person engaged as a freelancer is very different just because you have KPMG as a client.

And they're a huge accounting firm. If you go into [00:13:00] PricewaterhouseCoopers or Ian yeah. Big accounting firms of Deloitte, you are starting from square one again. You have no learnings from that to add to that new cycle and the entire integration and configuration and implementation phase will be entirely, entirely different because even though those companies do the same thing, they evolved very differently in how they engage freelancers.

Mark Peter Davis: So this is enterprise tech. Did you have a big services operation to onboard the client? We 

Jeff Wald: did. We had an entire implementation team. We had an entire onboarding team. We had an entire scoping team. And it, they were invaluable because as a salesperson going in and trying to sell that product, you wouldn't get into the nitty gritty.

And the nitty gritty is where things are we'll kind of succeed or fail. 

Mark Peter Davis: Got it. How big was the team when you guys sold? 

Jeff Wald: About 200. Okay. 

Mark Peter Davis: So you went from a couple of founders to a 200 person operation working with some of the biggest name VCs in the country had a [00:14:00] big exit. What was the hardest part? 

Jeff Wald: What was the hardest part of that journey?

Uh, I would say the hardest part of that journey, or was probably the, uh, I mean, look, I can kind of list out the mistakes we made enough. I would call those the hardest part. The hardest part may have been selling the company because look, we had a big exit. We generated returns for our shareholders. All of our employees made money.

Some of them made a lot of money. But you're left with the realization that you didn't achieve, what you set out to achieve. Right? Whenever that exit comes, that is the exit, unless it's an IPO, right? If that, if a sale comes, you are done, whatever you set out to do from a value creation standpoint or from a conquering, the world standpoint, you either did it, or you didn't.

And so, as we were selling the company, as excited as I was a part of me was [00:15:00] incredibly sad. And it was very, very difficult because I knew we had made so many mistakes and we had left so much on the table, but we didn't leave anything on the field. Right. We gave it our all, but because of all the mistakes that were made, and I knew at the end of the day, Mark, that they were my mistakes because of me.

Right. I was very conscious that because of me, we got to that exit, right. There was nobody more important than me and getting to the exit. And I say that with all the appropriate humility, like those are facts. But it is also 100% true that because of me, the exit was a smaller exit than it could have been.

And so I carried that burden as 

Mark Peter Davis: well. You know, it's interesting when I've coached founders and worked with founders in the past, who are evaluating the exit, they're often weighing the idea of cutting short, against achieving a mission relative to the payout, the financial return that the investors are seeking.

Any advice for folks on how to weigh the [00:16:00] importance of the mission relative to the financial objective? 

Jeff Wald: That is a really good question. I would say that it depends on how much money you've raised, because we had raised so much that I ceased being the founder of the business as my primary role. And I started becoming a fiduciary to the people that I had taken money from.

And so look, they offer me another 25 million to keep going. They said, look, we'll put 25 million more in the business. You keep going for another, another two years. And I had to sit back and think about it and say, this is the best expected value outcome. If we take that 25 million, there are certainly some chances that we can build something bigger and have a bigger exit, but they're very low.

And the smartest thing to do to return to generate the biggest returns for all shareholders is to sell this company today. And I, I stand by that decision given, you know, the hindsight that I can now look back on, it was the right decision, [00:17:00] but I couldn't sit there and say, look, when that was 25 million, I could go and maybe I could build this thing and nothing that I've always wanted to build.

I couldn't do that at that point. And so it depends on how much money you've taken and whether you become a fiduciary, what 

Mark Peter Davis: was the mission statement of the company? But do you remember it. 

Jeff Wald: So here in lies, one of the biggest mistakes that we made, not only did we not really have a mission statement, not only could I not tell you the purpose of the company.

So I draw a distinction between mission meeting my North star, and then my purpose, that kind of why we're there, but also during diligence, our friends at ADP said, you know, we asked every single employee what work market does, and here are 72 different 

Mark Peter Davis: answers. Huh? Wow, 

Jeff Wald: dude, it was like a punch in the gut.

I was like, ah, 

Mark Peter Davis: how did that happen? 

Jeff Wald: Cause I thought they would all say work market is enterprise software that helps that enables companies to organize the medicine and pay their freelancers. Right. It didn't they do now, they do now, [00:18:00] but we did not have a defined culture document. And I put that very high in the list of mistakes that I made.

Mark Peter Davis: Why do you think that matters other than the acquirer going around and getting different answers? How does that hurt a company to not have that culture document and that alignment? 

Jeff Wald: I will tell you this, everyone that founds the company is super smart and they're super engaging and blah, blah, blah, blah, blah.

They are massively fallible. And if they are not harnessing the power of their team, they are decreasing their probabilities to success. If you have a group of people. That are all aligned and they understand why they're there, where they're going, who they are. Right. That one sentence of the company, that purpose of the company, that North star mission of the company, then you have all of these people rowing in the same direction and you can get away with not doing that when everybody's in one room.

Not one zoom room, mind you both, [00:19:00] just one room because everybody will just APR behaviors. They'll just look at what the founder does and they'll repeat what the founder says, but the second you start losing line of sight to everybody. You've hired really smart people that are really creative, and they're not just going to be robots.

And just repeat what you said and did outside of your presence. They're going to start thinking for themselves as you want them to. So how much higher probability do you have of getting to where you want to go? If you've got everybody rowing in the same direction, if you've got everybody bringing their authentic selves to work, because they know that they're valued, everybody bringing their ideas, but all remembering what they're doing, why they're there and where they're going.

I think you've massively increase your probabilities of success. And it's something we just didn't do. 

Mark Peter Davis: We had another person on. Recently who talked about minimum viable process, the idea of having fewer [00:20:00] meetings, less all hands kind of breaking down communication internally at some 

Jeff Wald: level. I think you can certainly do that.

If everybody understands who they are, why they're there and where they're going. I think you can get away with a lot of things. I think you can get away with a more distributed company where people aren't together all the time, but I will say that. I am a huge fan of learning and transparency. And I think those all hands are incredibly valuable for people to really understand everything that's going on in their company.

And you don't get another chance to do it. One of the reasons Mark that I did our all hands and I would always, the all hands would be right after our board meeting. And I would take the board deck and I'd take out things that were, you know, that has to do with people's salary, because I would always tell everybody at work market, you could know everything that's going on here except what other people make that's between me and them.

And I would present the information that I would present to Fred Wilson and to the other board members. And I would present it to that team [00:21:00] because they had every right as shareholders in that company to know what was going on. But the reason I really did it was not because I wanted them to learn, which was a huge reason.

And I do, and didn't want them to learn. Because it helped me sleep at night because I was so consumed with, wow. If I miss this up, I'm going to mess up like 200 people's lives and their careers and things like that. But if I told them everything that was going on with the company warts and all customers, we lost dev cycles that broke, you know, errors.

We were having people that were leaving how much, how close we were to running out of cash. If I told them that. On a regular basis and they all made the decision to stay and there are super smart adults that I've given them all the information. And if I mess everything up, it's on them. They made the decision to stay and I gave them all the information off.

I hid information from them, very different, but I didn't. And I thought that was a core reason that that team stayed. And it was [00:22:00] a core tenant of work. marcus' values was transparency. And that was one of the many ways in which. We, uh, live that value. 

Mark Peter Davis: So the American model is the shareholder model. Where, when you talked about making, uh, the decision to sell you are focused on representing the investors.

He said he became a fiduciary, not a founder. 

Jeff Wald: Yes. 

Mark Peter Davis: And other countries have a stakeholder model where you have to think about everybody, including the staff. You said you might've lost sleep over the welfare of your team. How much did they factor in your, to your decision to sell the company? 

Jeff Wald: The fact that a lot, because they were all shareholders, every single person at that company owned stock, that was very important to me that, you know, hired a new secretary.

She got shares, we hired a new receptionist. He got shares. Everybody on that team got shares in that company now in a transparency [00:23:00] model. You know, I was very clear with them about the price per share that we raise money yeah. About what their options were priced at. But that being said, you know, you can only teach so much.

I remember the day after the acquisition, he walked in and said, you know, I just, why did we sell now? I said, well, I felt that this was the highest price per share we were going to get. He said, well, I just, I really hoped we sell for 20, $20 a share why. You said, well, then, you know, I would have been able to pay off my student loans, so, okay.

But I just, I got to make sure I'm clear about something. You were aware that we sold stock 12 months ago at a dollar a share. He said, yes. You were very clear about that. And you're aware that we just sold the company for a dollar 70 a share it's a 70% increase over a 12 month period. Yes. So what metric did you think was going to yield 20.

It's like, well, I don't know. It's just what I wanted. It's like, okay, get out, get out. I can't, I don't know what to do there. [00:24:00] Right. Um, and so I felt bad about that, but there is no world in which more than a dollar, 70 cents a year, no reasonable world would have been paid. And look, he couldn't pay off the student loans, but he was able to put a down payment on a house.

Right. And so that was something like, I felt good about that. 

Mark Peter Davis: Trying to make everybody happy in these situations, 

Jeff Wald: we do our best. 

Mark Peter Davis: Um, what do you wish you had done differently? 

Jeff Wald: I mean, I don't know if we've got time for that, what I could have done differently. So I heard once I really thought about it. Um, and I will say that the, there were three decisions that really decreased value in the company.

One was chasing two very big clients. There were two very, very large corporations that came to us and said, we love what you're doing, but we just need this just a little bit to the side, 

Mark Peter Davis: a little customization to the product, 

[00:25:00] Jeff Wald: a little customization, and that customization cost us because we were chasing that customization for a year with this company.

And we derailed our process. And any time you start changing your roadmap and your product, people are working on new specs and you're throwing everything off. It costs you twice the amount of time you think it does. And it was, it was a disaster. It was an unmitigated disaster. And look at the time we were doing 4 million in revenue.

This company offered us a $4 million contract. And so it was hard to say no, but we should have said, no, we knew we should have said no. But despite our better judgment, 

Mark Peter Davis: this is a classic enterprise problem. 

Jeff Wald: A hundred percent 

Mark Peter Davis: people get asked for the custom solution. Everyone entrepreneurs are sitting there thinking, well, I can avoid dilution.

This is a great source of revenue, but we're building bespoke 

Jeff Wald: work. 

Mark Peter Davis: That may not be relevant to your other [00:26:00] clients and derails, the scalability 

Jeff Wald: you convince yourself to think it's going to be relevant to other coins. 

Mark Peter Davis: Is, is there a time or a framework you use to know when that's a good thing to do? Like when shuns, should someone take that deal?

Jeff Wald: Well, I'll tell you, you could take that deal. If they are willing to sign on the dotted line and start paying you. If it is, Hey, we would sign this deal. If you guys did X, Y, and Z, and you think, Oh, we could just spend a few months and get to X, Y, and Z, then a hundred percent do not do that. I shouldn't say a hundred percent, very high probability do not do that, but it is like, I don't pretend it's an easy decision Mark, but I know that it was the wrong decision for us.

And I think our board could have been more vocal in kind of their pattern recognition and, and their statements to us. Uh, not that it's not important fault. It's my fault. I am the one that the end of the, I said, all right, let's do it. Let's go. 

Mark Peter Davis: Did the client eventually sign? Or was it a bait and switch? 

Jeff Wald: I wouldn't say it was a bait and switch.

It was just what they wanted was [00:27:00] super difficult. And we convinced ourselves we could do it. We had a few preliminary meetings with other people in their space and they were like, Oh my gosh, if you did that, we would do it. And so we convinced ourselves that there were many more clients behind them. And it was, it was born poor judgment and in inexcusable.

Um, the second thing was the refactoring of the code when, and this is, I think, a problem that every company faces, you know, as founders, you have a responsibility to get an, a minimum viable product out as quickly as possible. Because as smart as everybody is in our world, we don't know a darn thing. You think you got, you think, you know it, you know, it, when a thousand people have used it and interacted with it, And so you need to get something out there and let them interact with it.

And then you need to stop cogitate and then break out the monolith of code that you wrote to get it out really quickly into a series of services. And we avoided this for so long [00:28:00] because it was going to be painful and it meant growth was going to slow. But the cost that we faced to go through this in a piecemeal way is immeasurable just in measurable.

It still takes. Months for developer to get up to speed, because there's still parts of monoliths and everybody's enterprise software. And you need to bite this bullet probably at your series. A maybe your series B in my, you know, obviously very broad heuristics here and you need to just, and your venture capitalists need to encourage you to do it.

And you can hope that you'll sell the company before. 

Mark Peter Davis: How much time do you think people use when they shift? Is it, are they losing a year of development or six months or. I'm sure varies. 

Jeff Wald: It depends obviously how long you're there. Uh, for us, it was going to be a year and we should have taken a year and we didn't, and it meant that we lost way more than a year in terms of the kinds of things that we could bring out.

And then the stuff's off that we brought out was riddled with errors [00:29:00] and our bug rate was still high because you have all kinds of regression issues. And so it was just a huge, huge, huge, huge mistake. The challenge. 

Mark Peter Davis: I think people face when they face that decision is they realize, well, I have to hit all these milestones to raise our next round of capital.

And if we lose a year in development, just to get back to where we 

Jeff Wald: are, 

Mark Peter Davis: how do we stay on the course? How do we stay 

Jeff Wald: on track? I would say this has to really be driven by that, that series a or series B investor. That they have to say, guys, we understand, and we're in this to build a company that is going to persist.

It is going to be able to do something great. And if they're not in for it, okay. Maybe not. And then you hope you sell the company and it's the acquirer's problem to rip it all apart and fix it. Um, but if you start getting into year four and five, you made a mistake by not doing it. If you can sell before, then God bless [00:30:00] God.

Bless. That's great. But if you start getting into your four and five, you have made a very, very big mistake. And again, I'm making generalizations and they're not fair because every company is different. I should say this more specifically at work market. When we got into year four and five and we haven't done it, we made a big mistake.

Right? That's the way I should say it. And then yeah, the last big mistake would be that culture document that I stood up in front of the company, our first town hall, after the acquisition. And just said, I'm sorry, like I let you all down. I didn't do this. I just assumed that you all knew why I was here and why I thought all of you were here.

I assumed you all knew what I thought we are. I assumed you all knew where I thought we were going. And not only did you all not know, but you all had different ideas and you know what, maybe some of your ideas are better. And so I spent six months going office to office and listening. And saying, what do you think we are?

Where do you think we're going? Why are you all here? [00:31:00] What are our behaviors and policies that support the things that we believe and which ones do you want to call bullshit on? Maybe we shouldn't be doing certain things and it was incredibly illuminating and it was very reassuring because there weren't too many things people call bullshit on.

Uh, but there were certainly some, and we certainly changed some processes. And I thought it was a powerful exercise and now every single I shouldn't say now, cause I'm not there anymore. So I don't really know what happens now. Um, but for a long time, every single company gathering we'd started off with who we are, why we're here and where we're going.

And as soon as people start to complain that you're doing it too much, I would say you're probably halfway there. 

Mark Peter Davis: Got it. Very helpful. And you are the founder and president, correct 

Jeff Wald: of work market, 

Mark Peter Davis: not the CEO. Can, can you tell us a little bit of how that functions internally? The president definition seems to mean a lot of different [00:32:00] things in different companies, any pros and cons.

When does it work? Well, when does it not? 

Jeff Wald: So my co-founder was CEO and then upon his departure, I did become CEO for a little while. And the board. Felt the need to bring in a kind of, you know, very seasoned industry executive with, uh, with some gray hair. And, you know, I, as the largest shareholder in the company was supportive of that.

And so sure there's somebody that can grow the value of the company bigger than me. Great. Um, and so, and I learned a huge amount from him. Uh, both one of my co-founder did it. And when industry executive did it, it really becomes a question of who reports to who. And so I always owned everything in the company except for engineering and product engineering and product always ended up reporting either to my co-founder or then later to a CTO.

Um, and so from my perspective, the CEO role, it worked market was [00:33:00] always vision helping to build the team, especially at the executive level and making sure there was enough money in the bank. I spent very little time with our investors in both contexts, both with my co-founder and with the hired gun, but the day-to-day making sure the trains run on time.

The rest of the team that isn't the executive team. Those, I all view it as my responsibility. And 

Mark Peter Davis: typically that's the COO. Did you have a COO as well? 

Jeff Wald: Uh, I had a COO title. Oh, I 

Mark Peter Davis: see. So you were, you were president and COO got it. 

Jeff Wald: And CFO and head of HR and head of legal. 

Mark Peter Davis: Got it. 

Jeff Wald: Okay. I'm 

Mark Peter Davis: gonna shift gears a little bit.

Um, look, you're, you're an innovator in the workforce and labor space. Uh, and I know over the last couple of years you've been busy and you wrote a book. 

Jeff Wald: I did write a book. 

Mark Peter Davis: The book is called the end of jobs. Can you tell us a little bit about the [00:34:00] book? 

Jeff Wald: So I will tell you this writing a book is really hard, did not.

It did not, uh, go as quickly as I thought it was going to go. Uh, Margaret wrote the book because I get very frustrated when people basically, actually, I get very frustrated when people speak without evidence, without backing their statements up based on data or some other body of evidence in the world of work.

There are three important bodies of evidence. One is the history of work. The second is the data and the numbers and how they've changed in where they are today. And the third is how companies actually engage workers and people that make predictions without understanding those three in the world of work and get very frustrated because those predictions have a very low probability of coming true.

And when you talk about making predictions about the future of work, those are things that companies start to think about as they're doing their labor planning. Those are the things that families think about. As they do their own planning for the future. Those are things that individuals [00:35:00] think about.

And so I think it's incumbent upon people in the world of work. And again, anybody in the public square to be thoughtful about making predictions about the future of anything, or even again, speaking without evidence. So the book takes a very hard look at the history of work, takes a very hard look on the data patterns and trends.

And it takes a very hard look about how companies actually engage workers. And we try to make all that very clear so that as we think about the robots and AI, as we think about a host of other changes coming to the world of work, we can at least have a basis for the predictions that we make. So I read your book, 

Mark Peter Davis: uh, and it's very thoughtful and smart as expected.

Uh, I took away one of the major headlines to be that we're increasingly moving towards an atomized workforce. Where atomized, meaning people are not full-time employees. Part of the larger machine, [00:36:00] um, a company will be increasingly defined as a web connecting a lot of disparate pieces. Uh, and so that includes the on-demand workforce, the freelancers you've talked about, and that does square with the pattern that I'm seeing personally for the, my own ventures and the things I'm involved with.

What does it mean for the wealth gap in America? This pattern. 

Jeff Wald: So there are a lot of issues that we have and a lot of gaps in society and the wealth gap is, is certainly one. Uh, I don't know that it necessarily has to have that much of an impact when we look at things that drive the wealth gap in society.

Tax policy is usually the number one driver of the wealth gap and changes to tax policy. I would say that as you think about the relative power of companies versus workers, That is something that also drives the relative gap in wealth, in society. As companies accumulate more power, the people that are capital owners [00:37:00] and company managers accumulate more wealth.

And the biggest counter to that is regulation. Regulation can include things like an increase in minimum wage or overtime rules or a host of other things. So I'm not concerned about the atomization of work. I'm not concerned about robots and AI and their inherent ability to exacerbate those gaps in society.

I get concerned around retraining because if we do retraining correctly, you will see. A much smoother transition to a world with ever higher standard of living and more jobs and people working fewer hours. And if we do training incorrectly or we ignore it as most societies tend to do, uh, then I think we're in for a pretty rough ride because those gaps will continue to get exacerbated.

And eventually [00:38:00] people start voting for populism and nationalism, which history has shown. Are short-term solutions or short-term hosts that end up creating many more longterm issues. 

Mark Peter Davis: So as you know, I'm also friendly with Andrew Yang who wrote a book on the topic. His book is called the war on normal people.

And in it, he makes a case for universal basic income. Part of his narrative is that retraining programs have historically not worked. What's your view on UBI universal basic income, the efficacy of training programs. 

Jeff Wald: I think there are more effective ways than universal basic income to achieve a relatively similar outcome.

I'm a big proponent of expanding the earned income tax credit personally, but we don't need to kind of geek out on the. Different aspects of tax policy and social safety net policy. I would prefer [00:39:00] to zero in on the retraining aspect. I don't know that I'm prepared to say retraining doesn't work so much as I'm happy to agree that retraining hasn't worked and the reasons it hasn't worked need to be fully explored.

And I would argue some of those reasons are that it has been difficult and costly. And other parts of the reason are it's never clear who owns the retraining to does the company that does the layoffs, do they own retraining? Are the companies that are hiring, should they be doing all the training of workers?

Does the education system on it? Is it an individual responsibility as more and more things increasingly seem to be unknown. And as you think about new technologies that are coming on stream specifically VR training tools, I get very optimistic about the prospect of the ability to retrain workers into the high growth, high demand jobs that are being created.

[00:40:00] Are 

Mark Peter Davis: there particular social policies you think are important for the world to be thinking about as we're entering into this evolving labor 

Jeff Wald: market to be thinking about yes. Well, I would not in any way, shape or form work, say that I would offer any prescriptions here. These are incredibly complex issues.

I will offer one prescription at the end. Actually, I think UBI is an important conversation. I'm not sure that it's the best policy, but it's an important conversation to have, I think expanding the earned income tax credit is an important conversation to have. I think the government mandating how retraining occurs for companies is an important conversation to have.

I think they're important conversations around the education system and this push that we've had as a society to bring people to four year colleges when most people don't need that educational experience. So I think there are a bunch of very interesting conversations to be had, and it's [00:41:00] important that we have them because society is going to evolve and we need to have this marketplace of ideas and the best ideas need to be moved forward and, and be put into place.

I think they're important conversations around the minimum wage and making sure the right parts of the economic pie are being relatively equally distributed and certainly around tax policy and what kind of obligations we have to our society as a whole and to future generations as we continue to accumulate debt.

But I think the most important conversation to have is one around our election process. Because we clearly are not putting the right people into the room to have these conversations because they're very difficult. They require a lot of back and forth and a lot of compromise. And right now we are electing people and putting them into the room with the wrong system, the wrong incentives in place for them to have intelligent conversations and come up with these solutions.

And so when I think [00:42:00] about things around term limits, And mandatory voting and open primaries or non-partisan primaries are ranked choice voting things that really make every politician beholden to 50% plus one vote of their electorate. Not the 2% that vote in a primary. That to me is a fundamental policy prescription that I will put forward as necessary in order to attack these very important issues and the myriad other issues that we face as a society.

Mark Peter Davis: For everyone listening. What is the earned income tax credit you referenced to it? 

Jeff Wald: The earned income tax credit is a basic topping up of your salary based on what you've earned, such that we are increasing and giving you a tax rebate, if you didn't hit certain levels. And so it creates the incentive to work and ends up topping up some income for those that weren't able to hit certain thresholds.


Mark Peter Davis: it. Subsidy of sorts. Yeah. Okay. Um, what should entrepreneurs be [00:43:00] thinking about? How can they help improve the labor market? This is something you've done. You've been staring at it for a long time. You've written a book on this space when entrepreneurs who are out there picking their next venture, but things to do, we need help with, uh, 

Jeff Wald: well, I'll say this.

First you should go and buy this book. You should read this book. That's the most important thing you should do right now is read this book and really understand it. Um, okay. Maybe, um, I will tell you, Mark, I thought about, about this question. Um, the, the labor markets are really tough and you know, when I thought about this question, my gut answer was don't, don't go into this space.

This space is really, really difficult. Whenever you're involved in a market that involves the regulatory, uh, where range is, I should say, it's definitely with the regulation and the regulatory overhang is a huge variable in your outcome and [00:44:00] your success be very hesitant because you have literally no control over that variable.

And it is a more challenging variable than I anticipated. If I had known how many of my sales processes would get hung up on a, I'm not even sure we should be using freelancers, but you are using freelancers and I'm, I'm helping you like yeah, but maybe we shouldn't. I'm like, okay, shouldn't you guys have decided that before I showed up, like what, why are we having this conversation?

Mark Peter Davis: And that was for regulatory reasons, there were, yes, there was some sort of. Liability. They were incurring 

Jeff Wald: worker misclassification claims. I will tell you every single time, Uber ended up in a courtroom, every single sales cycle that we had going, came to a dead stop. 

Mark Peter Davis: And 

Jeff Wald: so it's, it's a huge challenge. Now, if you want to go to live mergers because the labor markets are huge, should've been $15 trillion in labor spend that occurs in the United States, right?

It is it's real big. It is real big. I think [00:45:00] about. Retraining as an area, shocking. Nobody that's been listening have incredible opportunity because we are going to lose a number of jobs to robots and AI. It's not going to be as big as people saying, it's not going to happen as quickly as people think, but we will lose millions and millions and millions of jobs.

And those people need to be retrained. We don't do that to our detriment as a society. So I am unbelievably hopeful that new technologies help companies, help individuals, help communities to retrain those workers for the jobs that are going to be displaced. I think about efficiency and the ability. Once we have HR ecosystems that start opening up via API, via app ecosystems, the efficiencies that can be brought into the day-to-day processes.

And one of the things I always focus on are our meetings. And the just tremendous waste of time in meetings, I've never found a single executive that said, no, I love meetings. I think [00:46:00] meetings are very efficient and effective. No, no one's ever said that everybody complains about meetings because they mostly are a waste of time.

And there are a lot of interesting companies I've seen just over the last few weeks that are doing interesting things on meetings. So there are a lot of efficiencies to be had in the way we are working. Uh, but to get a deeply involved into temp, labor, or freelance labor, one very, very complicated, two huge regulatory overhang, three, not as big a market as people think and not growing as quickly as they think.

And so I would certainly offer that caution while certainly saying labor force transformation is real and the way we work is rapidly changing and certainly remote work is a very important part of the future of work and flexible work arrangements. Uh, but be very mindful of the areas that you are tackling in the future of work.

Are there particular 

Mark Peter Davis: industries where you think people should be trained to be prepared for those new jobs? What jobs should people learn to be able to do? [00:47:00] So I 

Jeff Wald: generally tell people three things. One is. There's a phrase out there that some people think is overused. And I would argue that is completely underused and that is you need to be a lifelong learner.

So whatever industry you're in, you need to constantly be reinventing and up-skilling, and re-skilling, it used to take 30 years for a skill to a bait, to no longer be monetized. Now it's four to six years. So constantly be updating that's thing. Number one thing, number two and three involve the general phrase of go hard.

Hard tech in one context, the idea that you are going to see tremendous growth, as we've seen over the last 10 years, we will see for the next 10 in robotics and AI and data and software programming and cybersecurity, blockchain, blah, blah, blah, blah, blah. All of the hard tech industries and STEM industries.

We've heard it for 10 plus years. The data is all completely clear on this and those jobs will continue to grow the other less well [00:48:00] known. Is to go hard human people have a very clear understanding of what robots and AI systems can really do. And when you think about empathy, when you think about customer service, we think about design and creativity.

There are jobs in sales, in marketing, in customer service and support in HR, in healthcare that there is zero prospect. Of those jobs being displaced by a robot or an AI system in the near term and the longterm everything's off the table, but in the near term, the next 20 years, the idea that you're really going to have a customer service interaction with a AI system that you're going to enjoy, and the companies will completely rely upon.

It's not going to happen in the near term. Where 

Mark Peter Davis: do you see yourself in 10 years? 

Jeff Wald: I hopefully at that point had moved into fully serving my country in some capacity. And whether that is serving in somebody's administration, uh, or running myself [00:49:00] for something or forming a nonprofit focused on electoral reform, which to me is a.

Primary cause or root cause of some of the societal issues we have. Uh, that's, that's a role I'd love to play. 

Mark Peter Davis: Fantastic. I hope you do that last question for you. What's the most important thing that you've learned as an entrepreneur. If you had one parting gift of knowledge to everyone listening 

Jeff Wald: well, Mark, have you ever heard the phrase that gets tossed around in our world?

The key to success in startup is being knocked down seven times and picking yourself up eight. It is one of those phrases. I've seen it on bracelets. I've seen it on t-shirts and I love it. I love it for two really great reasons. One is it's so true, right? You're going to get knocked down again and again and again, and the phrase is pick yourself up because there isn't going to be necessarily somebody there holding their hand out to pick you up out of the [00:50:00] dust.

You gotta to pick yourself up. You've got to dust yourself off. You got to go forward knowing. That you're going to get knocked down again, and there's something so evocative about it. And I remember hearing it and just loving it for those reasons. But the second reason I love it is that it actually doesn't make any sense because if I got knocked down seven times, wouldn't I get up seven times.

Why am I getting up eight times? Did I start down on the dirt? It doesn't make any sense. It should be knocked down. Sometimes get up eight times, but t-shirts have been made. The other way. So I just, I always love it. It always makes me laugh and I always think that's as true as it gets. Man. You have got to persist the outcome of your company, the biggest variable in the equation as to whether it's going to be successful.

It's you. And if you don't find a way, it won't happen, you're not the only variable, but you are the biggest variable in that equation and you have to persist and you have to find a way to make it work or, well, Jeff, 

Mark Peter Davis: this was absolutely great. Thanks for making 

Jeff Wald: time. [00:51:00] Thank you for having me always a pleasure to speak with you.

Great. I'm 

Mark Peter Davis: very grateful to Jeff for taking the time to share his experiences with us today. I felt that his insights were very valuable, especially for founders who are building companies that service the enterprise market. 

Jeff Wald: If you like what you heard, 

Mark Peter Davis: please look us up at the five star review, wherever you consume 

Jeff Wald: your podcasts 

Mark Peter Davis: and feel free to share with a friend.

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