Leap Academy with Ilana Golan - What It Takes to Scale a Company Without Breaking It | Mike Seckler, Justworks CEO | E151

Episode Date: March 24, 2026

In the late 1990s, Mike Seckler started a company with little experience, plenty of curiosity, and no idea what was coming. Then the dot-com bubble burst. Almost overnight, capital disappeared. Companies collapsed. And Mike faced one of the hardest decisions of his career: laying off a third of his team to keep the company alive. That moment changed how he builds companies and leads today as CEO of Justworks. In this episode, Mike joins Ilana to share the real lessons behind building and scaling through uncertainty and how founders can avoid the leadership mistakes that derail most companies. Mike Seckler is the President and CEO of Justworks, an HR platform helping over 14,000 small businesses manage payroll, benefits, compliance, and workforce management. In this episode, Ilana and Mike will discuss: (00:00) Introduction  (02:42) From History and Geology Student to Entrepreneur (07:05) The Early Days of Founding Employease (09:08) Navigating the Dot Com Crash as a Founder (14:53) Selling to ADP and Starting a New Venture (17:23) Joining Justworks: From Board Member to COO (24:37) Lessons from Transitioning to Justworks’ CEO (26:00) The Biggest Blindspots for Small Businesses (31:58) How to Beat Founder Loneliness (36:34) Adapting to a Rapidly Evolving Market (42:03) Justworks: Empowering Small Businesses for Growth (44:49) Review and Q&A: BREAD Productivity Framework Mike Seckler is a serial entrepreneur who has built and scaled multiple companies over the past two decades. Before joining Justworks, he co-founded Employease, an HR outsourcing firm that was eventually acquired by ADP, and later co-founded Euclidean Technologies, a company applying machine learning to public market investing. Today, as CEO of Justworks, Mike leads a platform serving thousands of small businesses and helping founders navigate the complexities of building and scaling their teams. Connect with Mike: Mike’s LinkedIn: linkedin.com/in/mikeseckler  Resources Mentioned: Justworks Website: https://www.justworks.com  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

We felt like we were on top of the world because everyone was telling us we were on top of the world and all the numbers said so. But we couldn't see that right in front of us were these massive risks and how everything was going to get super hard. So we felt best right before things were about to be at their worst. Mike Zecler, president and CEO of Just Works, an all-in-one HR platform for small businesses. And before Just Works, Mike co-founded two other companies and will drill into what it actually take to start and scale companies. The world is changing super fast, and I've been through some of these dislocations before. I think this one may be bigger than anything that's been in my career with AI. This is a time to lean into the change, be the change manifested, and not to like hold on tightly to the way things used to be.

If you're sitting in front of a room of small business owners, what would you say are some of the biggest blind spots or things that they need to like really acknowledge? Well, just two statements. I mean, one is... Welcome to the Leap Academy with Ilana Golan. I'm so glad you're here. In the Leap Academy podcast, I get to speak to the biggest leaders of our time about their career, how they got where they are today, the challenges, the failures, and countless lessons. So lean in. This episode is going to be amazing. I'm in a mission to help millions reinvent their career and leap into their full potential, land their dream roles, fast-track to leadership, jump to entrepreneurship, or build portfolio careers. This is what we do in our Leap Academy programs for individuals and teams. And with this podcast, we can give this career blueprint for free to tens of millions. So please help my mission by sharing this with every single person you know because this show has the power to change countess of lives. Deal?

Okay, so let's dive in. Mike Zekler, president and CEO of JustWorks, an all-in-one HR platform for small businesses. And before Just Works, Mike co-founded two other companies. We'll talk more about them. And we'll drill into what it actually take to start and scale companies, the cost of isolation for founders, the leadership in hard times. And what you also will love about Mike is not only that you're going to hear about his own companies, but he brings lessons from 14,000 startups, the patterns in scaling, the hiring, the market shifts,

when it separates top performers. So really get ready for an incredible episode. Let's dive in. Mike, I'm so glad to have you here. Yeah, Alana, thanks so much for having me. You're going to have to take me back in time because I remember when I looked at what you studied in college, I was just like I needed to read it again and again.

It's like geology and history or theoretically they're not connected, but maybe they are. History of the Earth, history of humanity, maybe they're connected that way. But yeah, I wasn't going to school for like a vocational reason. I was in college and just taking classes that interested me. I didn't really know where it was going to take me. I thought for a while I might go to graduate.

School in the Sciences and then had some experiences that made me think maybe that wasn't for me. And then I just got a first job and took steps, you know. But what I studied and what I ended up doing don't seem directly connected. But I think there were some connections just in terms of learning how to think about problems, learning how to analyze things, learning how to communicate. How did that shape you? Overall, do you think of a situation as a child or early teens that shaped you? to the person that you are today or the entrepreneur that you are today?

I don't know. I mean, I grew up in a kind of a wonderful way in some ways. I never saw my parents fight. I don't know that they ever fought. And I grew up thinking I was probably like six foot four and graded everything. And so there's pluses to that and that you develop a sense of confidence when you raise that way. But there's some downsides, too, around some of the things I'm sure we'll discuss, which is life isn't easy.

and there wasn't a lot of talking about emotions and they're growing up and then going through hard things. I didn't necessarily have all the language to process those things as I was going through those things. But I don't know that there was anything in my growing up that made me like always knew I was going to be an entrepreneur, always knew I wanted to build companies. I just was moved to wherever the energy felt real at the time. And it's kind of hard to connect all the dots in terms of what I ended up doing, I think. So did you know when you finished college? Did you know where this is going to take you?

What were the first jobs? And how did that become employees, basically? There were a couple things that happened. One, I mean, I have and continue to have incredibly close friendships with a number of people I went to college with. And I was in college from 1990 to 1994. We were using the Internet. We were using email, yet the world wasn't yet using it.

It's like someone who might have been using things. AI over the last couple years before this recent boom. So this was all pre the dot-com boom. Yet we were pretty excited about what was going on. I had a friend who started a company in college, and so I saw this entrepreneurial journey up close, and that was quite inspiring. The idea of, like, to start a company, I grew up in a family. Mom was a nurse, dad was a doctor, that led to some of like the stable living that I grew up. You know, they went to work at the same minute every day, came home the same. So the idea that someone would start a company and entrepreneurial journey was kind of exotic. And then, you know, I thought I might go to grad school in the sciences.

I wrote a master's level honors thesis as an undergrad and then got to present it at meetings and began to sense that there was a politics to science that I didn't really like. The idea that you might have to work really hard for a long time before you're able to do your own science, wasn't as exciting. So I just got a job as a research analyst at a management consulting firm. I guess they figured because I had crunched a lot of numbers and processed a lot of data and the sciences that that might be a value to them. But I had another friend from college who was like the beautiful mind of school. He was, you know, create his own major between math and computer science. And we were always talking about how the future was going to evolve and imagine business ideas.

And so that conversation carried forward post-graduation to, you know, it was like a year. after we graduated, we got together at a friend's house for a Fourth of July celebration. And we ended up talking all night about, you know, Netscape was talking about going public. We had both had our first jobs for a year. Like all my summer jobs up to that point were like working on the Appalachian Trail. So I worked in a company for a year and I was like, wow, there's a lot of things that don't make sense to me, like why they do things this way. And so we started having these conversations and it led to us starting a company about a year

and a half after we graduated from school. and that was that first business employees. Talk to me about those early, early days because you don't have a lot of experience with different companies, et cetera. And you're starting a company, employees. It's in 1996, I believe, right? Correct, yeah.

And eventually a decade later, it's acquired by ADP, so everybody wants to listen. But how did you maneuver, especially the early days, which there's this plateau of possibilities and nobody really knows where to go and market fit and all of that stuff. Well, you know, it's crazy because that business is now like the largest part of ADP, this $100 billion market cap company.

And so it was quite successful. And yet those early days, we were naive enough to like do the thing, to think we could do it. But boy, we were naive on a lot of ways. And so we made a lot of mistakes. We were fortunate, though, to find some good people that were a little bit more, you know, further in their career that had come from the world of HR software that brought some of the domain expertise we were missing and some of the patterns that had worked or not worked in the past. We weren't figuring out everything from scratch. But sure, we made mistakes.

Is there one in particular that sits there that you're like, gosh, how did you do that? We had like a couple other people around the business when we got started, almost like another founder. And we took steps and then realized like there were some foundational misalignments. And so breaking up, that was hard, lawyers and stuff. And so that was challenging, raising money for the first time. It was hard, but it just, I don't know, we just solved that. We had all those things, but the thing that was important, I think, that gave us an edge was that John Oliver and I, as co-founders, we had very shared values and shared respect,

but very different skill sets. John was a technologist, and I think my skills ended up being more around just the company building, finding people, finding space, finding capital. figuring out how to go to market, although we had some failed, you know, experiments there for sure, as we eventually found things that worked. And that's incredible. And you also needed to go through the dot-com bust or whatever, right? How did you maneuver around that 2000-ish where a lot of companies actually lost their footing altogether? You know, it was really interesting because the first chapter of that business really coincided with the start of the dot-com boom. And so that first

chapter, those first three years, really rewarded a certain kind of entrepreneurship, bold, aggressive, storytelling, be a magnet for capital, a magnet for talent, manifest the future, right? And that was challenging but fun. And certainly it was easy to get full of ourselves and somewhat arrogant at that time because things were coming relatively easily. But with the dot-com bust, it was a really difficult period because the message up to that point was gross fast as you can capital. I mean, everyone wanted to invest more. It was easy to raise capital relatively so. And then it changed overnight.

If capital was like oxygen, imagine the room you're in right now, all the oxygen was getting sucked out of the room. Like you wouldn't be thinking about anything other than how are you going to get another breath when the air is gone. That's what happened at that period. It felt like that. The capital was no longer available. all these businesses, including ours, were running at big deficits and burn rates.

The clock was ticking, and you had to get to cash-generative. You had to extend your runway and eventually generate cash. And how we decided to do this and how we knew to do this is unclear, I would say, in retrospect. But we were very early and aggressive at accepting reality and making decisions to change the trajectory of our business. These were hard things. We let go of a third of our team. We took a little bit of very dilute of financing, and we got to the other side.

And businesses that thought it would just get better or hoped it would just get better, they just ran into walls. The companies were exploding left and right. There was these websites that would track, like all these business failures. It was such a different time from like 99 to 2001 and two. Do you remember that day that you're starting to realize

that this is like you as a leader? Because again, I do believe that there's a difference between number two and almost anything else in the company, right? Or one and two, right? Like there's a big difference between being at the helm and needing to have all of this weight on your shoulders. Do you remember that, Dave? Yeah. It felt terrible going into it.

It felt like, you know, when you feel viscerally sick to yourself. But the day itself went a lot better than I had been playing it out in my mind because we were just super transparent. We just communicated all the facts. These are the lines crossed. We got a lot of customers that depend on us. we're going to have to let go of a number of people, but it's to preserve the opportunity for this business to employ the two-thirds that are going to remain

and then hopefully get stronger and hire more people in the future. And we did it early enough where, despite being a small company at the time, we took care of people the extent that we could. It wasn't like Ford Motor severance packages, but it wasn't like you lost your job and sorry. And that's what happened to a lot of these BC back companies that went out of business at that time.

They just ran into walls. We took care of folks. And what was interesting was the people that were let go were obviously sad and disappointed, but they understood. And the people that remained had enough information to process it and felt good enough about how their friends that had just departed were treated, that they were able to get back to work. And that was like a really interesting lesson about making a hard decision the right way and what it feels to get the other side of it. And we did get to the other side of it. And it was fascinating because we ended up proving to ourselves, we could do basically

everything we were doing, but with fewer people, which obviously raised some questions about how we were operating prior to that moment. And the other thing I'll say about that is a big lesson. And I think there's a generalizable message here around when you go through hard times, which is that period from 2000, end of 2001 to 2003 was brutally challenging and not fun. And there were lots of moments of thinking about quitting or why me kind of thing. But in retrospect, this crazy thing that messes with one's mind became apparent, which was that in 99, we felt like we were on top of the world because everyone was telling us we were on top of the world and all the numbers said so. But we couldn't see that right in front of us were these massive risks and how everything was

going to get super hard. So we felt best right before things were about to be at their worst. And then in 2003, when you're just walking through mud through three years, you're just trying to survive, get to the other side, growth is slow. Is this ever going to be worth anything? All these questions. what we couldn't see at that moment was that we had all these competitors in like 99, but they were all gone by 2003.

Like it was only upside. And from 2003 to 2006, we like grew super fast and had a great exit. But we felt worse at the moment when it was like the best was in front of us. And we felt the best when only the worst was in front of us. And so what I took away from that is it's kind of like one, often hard to like predict the future. And like we spent a lot of time, attack. to like imagine futures. And so that seems like a big waste of energy.

And then the second is that as bad as that period was, and I wouldn't want to go through that again, I wouldn't wish it on myself or anyone, there's a lot of good things that came from that, strength and confidence around actually how to run a business and get a business to where it can live on its own cash generation, right, which is the name of the game. And I feel very fortunate I had that forced opportunity

to figure that out for John and I. Yeah. And that's incredible. And eventually I do want to tie it to just works. But right before we hop there, you had one more company. So you're selling it to ADP. Territically, now you can cruise. But you decide for some ungodly reason to start another company.

Take me there for a second. Why? So when we sold that business, I actually stayed at ADP for a little bit to get it settled there. And that was a good experience, better than I expected and also meaningful in a set of ways. But John left with the acquisition and began working on some new ideas. And that first experience, entrepreneurial experience with John was everything. It was like hard and great and formative and brought us super close. And the idea of building a company with John again was all I could think about doing.

And it led to us starting a company. It was really different than the first one. Company is named Euclidean Technologies. And starting to 2008, we were applying artificial intelligence and machine learning to questions of public market investing and raise some funds and put them to work. And it was really interesting. It was interesting because after spending 10 or 12 years really trying to make one company work, it was an opportunity to think about the data footprints on how what the data can tell you about the operating models of every company and how to make assessments around why one company

ought to be worth more than another and why one business might be a better business than another. And so it was a good learning opportunity, but that was a different business. You know, when you're making investment decisions using algorithms and data science, you don't need to have big teams of people. And that can be a feature, not a bug, because you can make money and you can pocket more money as an owner. But I started to really miss, and this goes beyond your question, but just to state it, because it leads to some of the things I started to explore after. I needed a break from it, but I started to really miss the meaning.

that came from leading large teams. And so that was something I had to reconcile with and eventually made some decisions around. Right before that, and I don't know if that, I was trying to piece it together, but it sounds like you started it before the housing crisis or right around the housing crisis. Did that impact anything?

Well, it was a great time to be deploying capital. And so we raised initial funds when there was some nervousness in the air, but before the big crisis. And so to be able to invest into that was quite fruitful and enabled Euclidean to get off to a really good start. So in some ways, it ended up being a fortunate time to get started. We need to pause for a super brief break.

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That's leapacademy.com slash training. Okay, so take me through that journey from that moment of, but I actually kind of missed the big organization, the leading of big things. And then you actually got into JustWorks a little bit in a different way from a typical career standpoint. Like you got in as a board and then there's a CEO and then there's a president and CEO in 2022.

Take us a little bit to that journey. So John and I, I mean, we remain super close and we were building Euclidean. And it was a great first couple years of that. But then I started to feel a little bit, I don't know what the adjective would be, but maybe itchy, where after like 12 years of exhaustion

and learning how to lead from scratch, not having worked in company before just having to learn it, I needed a break from it. But after I had a bit of a break and we're building Euclidean, I started to miss it. And so the first step was I ended up, we had three daughters, my wife and I, and she's got big family around New York City. So we wanted to raise family here, and John Alberg wanted to get back to Seattle where he was from.

So we ended up building Euclidean, New York, and Seattle. And I wanted to get networked into the technology community here. And so I reached out to some people. And the most important person I connected with here was a guy named Fred Wilson, who runs Union Square Ventures. And he was generous to introduce me, around to some folks. And I had known some other venture capitalists here and they introduced me around. And I was just wanted to be around other builders for energy. Like I wasn't looking

to do something different. And through that work, I ended up on a number of boards. I was on the board of Shopkeep, which we sold the Lightspeed and that was a very interesting experience and a couple other boards. But one was Just Works. I was introduced by Fred, Wilson to Isaac Oates. He was a founder of JustWorks. When he had like 20 employees and three years, $300,000 in revenue. And Isaac just, I found him to be a super interesting person. He grew up, military intelligence officer, Amazon engineer, small company that Etsy bought. And then he built the payments infrastructure there.

And he was innovating in this HR space. I was like, well, that's pretty different background to be innovating here. And I think he was interested in talking to me because I had built a business that had some employees, yeah, had some similarities to what JustWorks was aspiring to do. But there was no commercial interest. I wasn't looking for angel investments. I certainly wasn't looking for board seats. I just wanted to be in the flow of things. And we got energy from each other. And we probably hung out like six times or so. And six months in, he said, you know, I've gotten advice. Because at the time, it was just Thrive Capital, a guy named Will Gaborick, who's now at Stripe.

So Will was on the board. And Isaac, you know, obviously as the founder was on the board. And they wanted a third board member. And they thought it should be an independent board member. And so they invited me. And that was, I thought, an honor and would be fun way to like stretch my skills and contribute to the community. So join the board and I put a lot of effort into being a great board member and helping Isaac grow and that was a great chapter in our relationship. And then four and a half years goes by and we're still building Euclidean and JustWorks goes from 20 people to like four or five hundred people. And there were two things that were happening at the time. One is I was starting to really We've reconciled with this set of facts that I felt like I needed to be in a leadership role again,

but John loves and continues to love and run Euclidean. So the idea of building another more traditional software company with John was not on the table. And the idea of starting something without John was like a little intimidating. But I also had a mental block around the idea that I could work in anyone else's company. It had been like 20 years of working out of my own companies with John. I mean, that year in a period, I was at ADP. But I still kind of view that as working on my own thing in a transition period. So that was going on.

And then Isaac calls me, again, four and a half years. I'm on the board. And he's, like, not enjoying leading the company as much anymore. It's getting harder, the things that he enjoyed spending time on. He's having a harder time spending time on. And he just says, I think I need to find, like, a chief operating officer or something. And I'm like, well, Isaac, as your lead director, I'll do my best to find you the best chief operating officer. And then there's, like, this pause.

And then I'm like, if you think it might be me, we can talk about it. that's weird, you know, and he's like, would you? And it was like this funny interaction. And we both left the call and he called me the next day and said, hey, listen, if you would be interested, I would be very interested in talking about that. And then there were like a set of things. I was like, well, I am kind of interested, but boy, how do I talk to John about this? How I talked to my wife? And so there were a series of conversations that I went through that all felt a little bit scary as well as like a lot of people that had invested in and were involved with Euclidean. But the first call was to John, and it was a great phone call.

I think he knew that I needed something a little different, and he supported that and just expressed some anxiety about what it was going to mean for Euclidean, and we talked through that, and we talked through a plan, and we were successful in transitioning that and getting other people to buy into Euclion's next chapter without me there. And there were some other conversations as well with my family, but ultimately led to me coming inside the company as chief operant officer, which led to the second chapter of my relationship with Isaac, because I went from being his board member, working for him, and then we did another.

So let's go there for a second. Just a set. Before we jump, because, again, a lot of our listeners are like, I want to reinvent myself. I'm trying to figure out what's next. And for you, that is a big move. And it's actually a really interesting hierarchy move on your end. How was it? It was intimidating in the sense that, like, I essentially had never worked for anybody.

I've been an entrepreneur since before I turned 20, And I did the ADP thing, but again, that felt like a period where I was representing our company, and I definitely reported into someone there. So I kind of had some experience with it. But not only was I reporting into Isaac initially, which was new, but I also have a big founder bias. I know that it's like a lot that he's carrying. I've been in his shoes. How do I manifest in a way where this is positive for everybody?

And how do I make this great for the team and for myself, but also for Isaac? And so, you know, that was just something I hadn't had to do before. And I thought hard about it. I think it was successful in a lot of ways, although it became clear about a year in that Isaac had like a two-step transition in his mind because he would bring up things like maybe you ought to do the CEO thing. And I was like, whoa, that wasn't the initial plan. It wasn't like, hey, I'll come do this.

But I needed to know this route to CEO. In fact, my mind was like companies tend to go further when their founders are in seat. I like building the company stuff. I don't need to do all that external stuff. I was kind of fine with that. But it became clear that he was really thinking of a two-step thing. And navigating that with him was like a year-long process. And I think the board was nervous a little bit.

But ultimately, it all was really well handled and a beautiful transition for the company. Because to Isaac's credit, he put a lot of thought into making it that way. And to me, that's incredible because it probably made you such a better president, CEO, because you've seen the different angles. But how did you see it? How do you see the different lessons? And especially in JustWorks? I mean, everyone has their own path. And my path includes founding a couple of businesses, being a board member for a couple of businesses where I was like the only independent director. Well, in some cases, it JustWorks. We actually built a nice slate of independent directors. And then to come into a company and,

and be an executive and then and now a CEO in a company I didn't start. So those are like four different things that are all like around in any given company. You might have board members and a founder and a CEO ultimately who wasn't the founder. And so for sure, they all give me different perspectives. But at the end of the day, building these things, it's about taking great care of customers and create an environment for incredible people to do their best work. And so in each seat and in each phase of the business, you're just trying to do those two things, obviously the way to do them and what it means in different product category.

Like the specifics are different, but be the best for customers and create the best environment for incredible people to come and do their best work. It is that simple. But it's complicated. Yeah, yeah. If you can do those two things right, you're going to have a great company, the details on how to do that for sure. It's like there's a lot to it. But it all does come together at that level.

So let's go deeper there. As a company just works sees. I mean, I have the number of 14,000 business owners. I'm sure there's fluctuation. But I think when you see big data, like we see a lot of like people in transition in their careers. So when you see big data, you start seeing patterns. And I'm sure you guys see a lot of patterns and really important lessons for small

business owners. What would be some of the things? If you're sitting in front of a room of a small business. business owners, because you have a lot of people listening to this, what would you say are some of the biggest things that either they're blind spots or things that they need to, like, really acknowledge? What are you guys seeing? Well, just two statements. I mean, one is there is a lot of data on the 14,000 businesses that we're currently serving and businesses, you can say fluctuating where it's just going up. But like a lot of like, I think the insight here is less than the data

because like the psychological journey that people go through and getting the fundamentals right or wrong, It doesn't always show up in the data. But where I get to see that is, you know, I spend a lot of time with our customers. I spent a lot of time when invited to, like, founder and CEO forums. And I learn a lot in those environments because a lot of these people are our customers, and a lot of them should be our customers. But because I founded these businesses my own before, I know that behind, like, the surface, everyone shows up at these founder, CEO gatherings with, like, their chest puffed out.

And I'm killing it. I'm doing this. I just, you know, but once everyone settles in a little bit, realizes they're with people. There's a lot of peddling. And the armor comes off and you get a little bit more like the real deal and the vulnerability. You realize everyone's on these incredible emotional roller coasters and these incredible journeys. And you began to see patterns there around the folks that get the furthest with the least drama and the folks that are stuck in the washing machine of how hard these things are.

And I think that what I've observed is that founders and people that start small businesses and growing businesses, whether technology companies or not, there's always like some amount of self-inflicted wounds in retrospect. And the best ones have a low self-inflicted wound quotient, right? Tell me more about that. Well, these self-inflicted wounds, where they show up, right? Co-founder relationships. Good co-founder relationship could be like a great marriage, bad one could be like a bad marriage

and debilitating like a bad marriage. And by the way, breaking up is like a divorce, right? So the co-founded relationship, the first investor that puts money in, did they bought in to what you want to do or not? Did you take a little bit higher valuation, but you sacrificed on alignment? If you sacrificed online meant, you might have 10 years every time that you've got to interact with your investors,

it sucks your energy out. Whereas if you get a great aligned investor, and if you gave up a little bit more of the company to get the right investor in, every time that you talk to them, you get new energy, you know, they're a good foil for you, like, you're going to go so much further, right? And building these businesses is hard.

And so if you have this accumulation of self-inflicted wounds, and I think it's pretty common where several years in, you realize like 20, 30 percent of your energy is just paying down these debts all the time, your chance of building something great is low versus someone who has mitigated those things. You've got an opportunity to go a lot further, right? And so first customers, customer feedback can be great, but an early customer can also take you off your product strategy if you want it too bad. I think that founders that put a lot of thought into their foundational, like culture, mission, vision, values stuff. Some companies do that and it's just stuff on a wall.

Other companies, like, breathe it. Just works. People breathe it. I talked to a new hire today. He's been here for like two months. And he's like, yeah, everyone talked about the values in the hiring process. But now that I'm here, it's like, whoa, everyone like lives. And I believe that's true, but I love hearing that.

And I think companies that do that, it's like you have a better foundation on which to scale. Because if your values and your mission and vision are like lived, then when someone is making a decision two levels away from you or making a hiring decision to bring someone in the company, what you would want as the founder, the CEO, is more likely to be done if you were in the room. But if you don't have that shared understanding, then it's going to go all over the place, going to have a mess. And so those are just some of the areas where I feel like folks are super intentional about those things that get those early decisions right or take the time to make them right and don't optimize the transaction, but optimize to get the foundation right. That's what I think the pattern is for the best outcomes and where you see a lot of people having trouble, it's because they miss those early things or rush through them.

That's incredibly valuable. But tell me for a second, as a founder, if you're trying to run a thousand mile per hour, acquire. the first clients, market fit, right? And you're trying to do everything relatively alone. And then on the other hand, you're trying to build that foundation to not make these mistakes that you mentioned because you're right.

Every single one of these can take you down. What do you focus on? How do you balance? How do you do this right? I'm going to make a statement, and this could be misused, okay? But it is go slow to go fast. It's like no, when you not go slow

to make certain of these decisions right, and then other times when you just, and speed's going to win. And I think there is judgment and art required to know which modality to optimize for. But if you're thinking about teaming up with someone as a co-founder, or you're thinking about your first investor,

or you're thinking about what product feedback to take out of the gate or to not take, maybe you go a little slow. But once you have a plan and you're like, we want to get to a thousand customers in this market, and we have a sense of what product market fit is for us and our ideal customer profile, well, then you just go as fast as you can. You're going to break down walls.

And so going slow to go fast later, I think, is a way to balance those two things. So what do you say to founders that they feel like they're carrying all their weight on their shoulders and it feels like a lonely path? Or maybe it shouldn't? Well, I would say it is a lonely path. And for me, I think there were times that it felt lonely in that first couple years. but boy, like in that dot-com bus, I felt super alone. And it was tough because I was feeling all this pressure.

I was making decisions that were impacting people's lives. Nothing was working the way I'd envisioned it should be working. I couldn't talk to my co-founder about it because he felt the same thing. I didn't want to be a burden on him. Couldn't talk to my investors because for them, I had to keep their confidence up. So they didn't just, like, give away our company or like suggest that we sell for parts, as a lot of companies did in that period of time. And so what I invested in then that is,

been an essential part of my personal foundation going forward is I found a group of entrepreneurs that I started to spend time with, all of whom, and these are not all technology founders, but people building serious builders that were all alone. And we found each other and we helped each other and built enough trust so that we could be truly vulnerable about the things that were on our minds and we helped each other. And so that group, there were a couple of people that came and left from like 2001 to 2005, but since 2005, the group's been the same. And so for 15 years or so, we met every month. And I could tell you the format of those meetings. And then once a year, we'd go on a retreat together. And we're actually all going to be together

in like two weeks or something out in Montana. So we still get together. And it's been essential to have a bunch of entrepreneurs who all know how lonely these journeys are. But we've all been through multiple ventures together, ups and downs, failure, success. is multiple exits, to then be able to go to this group, be like, here's what I'm thinking about, and to be able to benefit from their experience has been prices. So I guess the takeaway is, you don't need to do it alone. There are other people out there that would love to connect with you, and they also feel alone. And if you can make that connection, it can be really valuable. I do want to hear more about this, because I think one of the things that maybe struck me in Leap Academy

is, first of all, I needed my own network of founders. You're right. Otherwise, it was lonely as but also what I realized, and I don't think that initially was by design, like I didn't mean to build a movement in a community. I thought I'm teaching content. And what eventually was created is this community of people mentoring and peer groups and things that they call it movement. We call them leapers. And I don't think that that was a design. But I think we kind of stumbled on it. But I would love to hear a little bit about what are those meetings look like. How do you create something that is so consistent? Because 15 years is a long time.

Like, this is really consistent. I mean, when we all met, we didn't have that depth of understanding and trust. And so it was a little bit more professionalized, right? You'd start off. Everyone go around the room and share updates. So like good, bad, personal and business, three minutes each, timekeeper. And it was like rigorous. Like, if you missed more than one meeting a year, you had to get voted back in.

Like, you were default out. And if you showed up late, you know, you'd be. you're not in the meeting. So for a number of years, we ran it that way. And then over time, we got a little bit more flexible. But after that, someone would have prepared a presentation with a coach and a coach would be on the team, one of the other founders in the room. And they would prepare like something where they might present for 20 minutes. They would get 20 minutes of questions. But then this is the essential thing. Then we'd go around the room and everyone would share or something. But it wouldn't be like, Alana, this is what you should do.

wouldn't be that. It'd be like, okay, Alana, you just explain that you're hiring a CFO for the first time or you're thinking about buying a company and whatever. The closest experience I had was this. This is what I did. This is what I learned. So solely speaking from experience, not advice. And then you got to dinner after and then you could get the advice over the drinks, right? But you had the benefit of getting like 10 people's like best, like most analogous experience. And it would always be super helpful. But, you know, not. just to know that you're not alone, because you feel so alone with these crazy business challenges, but you're not alone. People have gone through similar things. Over time, you know, once a year,

we go on a retreat and we, you know, we all want to learn about something or we want to discover something about ourselves. We'd structure content like that. So that's how we did it. Oh, that's such a good specific example. So first of all, thank you for sharing that. And I want to take you to something because, again, you've been through a lot of turbulent times and you shared a little bit. And right now, I think we are seeing a really weird, fast, accelerated time that I think a lot of leaders are trying to grasp, like, what on earth? And sometimes they're founders,

and sometimes there's just leading big organizations. But still, this is moving faster than anybody can ask that you actually grasp. And I think a lot of us don't even know what's on the menu soon, right? So how do you navigate that in Just Works? And then, you know, I do want to hear a little bit of, like, like, you know, about JustWorks and like what you guys do and how do you help people with everything that they've done because you are kind of this all-encompassing solution. So take me there for a second.

So JustWorks is all about helping small businesses grow with confidence. And we do that by taking over and providing solutions around everything that one needs to have a workforce and to be compliant as you employ people over the place. So the world is changing super fast. And I've been through some of these dislocations before. I think this one may be bigger than anything that's been in my career, you know, with AI. I guess the most fundamental thing, and this is what we tell our people and our teams, is like, this is a time to like lean into the change, be the change manifested and not to, like,

hold on tightly to the way things used to be. And that decision that you have to make yourself may well be decisive about how relevant you will be and the skills that you will have going forward. And we're going to create a lot of, you know, opportunities and, training and forums and so forth to like deepen your understanding of how the world's changing, but it's up to you about how you lean into it. And so this is a time when resisting change could be really challenging for someone's career if they choose to do that because the world, I think, could just pass them by. So there's kind of that general message and then that general

like heavy investment in enabling the company to have the opportunity individuals to learn and to adjust. But then we think about AI here in like three areas. How is it going to impact the market we sell into? How is it going to impact customer expectations? And how is it going to impact how we operate? And, you know, there's, we have points of view on all three. You know, the companies that will be hiring in the future may well be different than the ones that were hiring in the past. What I've seen in other periods of time of dislocation is that industries and companies that and jobs that were relevant can become less relevant on the other side, but whole new industries and companies and job families get created, right? And so what are those new ones going to be

and how are we going to make sure it just works that we're like super relevant for like where the future is going to be? As well as to customer expectations, if you think about like B2B SaaS and so forth, like no one very soon, no one is going to log into an app, click around, pick a date range, select fields to get a report, you're going to like just talk to like. Right. It's going to give it to you. Yeah. Tell me about how my workforce is evolved. No, I want to see it by tenure. No, show it to me by location. Okay. But I don't know if that zone is going to be an area of sustainable advantage. Like I think our aspiration would be to be like 18 months in front of our competitors. But like everyone, I think will catch up to that, much like on internet apps today, like they're really differentiating

by your single sign on login or way reporting works. You might be ahead of a competitor behind, but you can kind of like overcome that. I think the real area of differentiation is going to be in how we operate and how other companies may operate. Because there, instead of like having these tools that I think everyone will have access to, it's like your unique context, right?

Your data, your knowledge of how these processes are to work, like your company's embedded knowledge, getting, you know, manifesting in whole new ways. And so that's what we're focused on. And we're taking processes that in our industry are done by others largely manually that we had in the past semi-automated. We're taking them a whole new levels. And looking at triple word scores, right, where you can take a job to be done and you can make it now that you're providing even better experience to customers because like something they had to wait for before, they can now get instantly. Number two, we're able to increase our margins by like doing things in more automated ways.

and then three, we're able to, like, focus our humans on, like, providing concierge-level care. So not, like, managing a manual process in the background, but freed up to do concierge-level care for customers when they're going through these key lifecycle moments, right? When you really want to talk to human, the first time you might be hiring in California or in Germany or the first time, like, you're terminating someone in a protected class, how are you going to do that? Or you're thinking about your benefit strategy so you can grow in a new market. You might want to talk to someone, even if, like, all the answers could be there.

and, you know, a chat interface. So focusing our humans there, which also then elevates their jobs, right? And so we've got a lot of things that we've done, a lot of things in motion, big plans there. That's the zone where I think we can create real lasting differentiation versus our industry. But for sure, we're all learning all the time. These tools are getting better all the time. There's examples in other industries emerging for us to learn from. And so you got to be open to that and willing to be the change, embrace the change,

and certainly not hope that it's going to stay. stop changing because that's not it's not something yeah for yourself right don't be the ostrich yeah it's not going to happen do not be the ostrich so tell me if i'm like a business owner if somebody's listening and they're a business owner how do they know if it's just works or maybe it's gusto or other things like i know there's like so many other options how did they decide to get to just works and who is an ideal audience for you way to think about it like if you had like two axes. One is people that focus on enterprise customers or people that focus on the people that you and I are talking about, like the entrepreneur and small business owner that has everything

on their back, but no one pays attention to them because smaller businesses, they're hard to reach. You don't make much money on. So like a lot of the companies you hear about in our space are really focused on enterprise customers or if they serve small businesses, they're kind of trying to use them as a stepping stone to go enterprise. We don't do that. We are focused on helping the underserved companies often will start with us. Definitely when they have under 100 employees. We have lots of customers start with us when they have like two employees. And a lot of our competitors won't even talk to companies when they're that small.

So we want to be great for the people that most need it. And then we want to be there for them as they grow into the hundreds of employees. That's one dimension. On another dimension, though, there's a lot of tools out there. There's folks that will just provide a tool for you to run payroll for your team. But you're kind of on the hook for everything, figuring it out, how to comply, what decisions to make around how to structure. your workforce, how to structure your benefits. JustWorks is there for you within our platform.

We're not just providing tools. We're providing insight. We're taking over responsibility for like compliance risk. We're doing everything necessary so that you can focus on what's really unique in your business. And that frees up entrepreneurs to do amazing things. It's another one of these energy questions, right? So we're talking about self-inflicted wounds, but then also like, how do you structure

your company? So you're able to put 100% of your energy on building your, your own product and serving your own customers, as opposed to figuring out how to terminate someone in California or how to put together a benefit plan that's going to allow you to recruit from much bigger companies. That's for JustWorks is the best. Ah, that's incredible explanation, by the way, and you're like, oh, I need to check them out. So thank you, Mike. Be an honor to have you as a customer. We can talk offline. So tell me, how do people reach you, Mike? And thank you for this incredible conversation.

www. www. justworks.com, one word. In terms of reaching me, I'm Mike Seckler at CEO of JustWorks and you see me on LinkedIn, but it's been really nice talking with you.

And I can't wait to our next conversation about getting Leap Academy as a JustWorks customer. Mike, thank you for being in the show. That was incredibly insightful. And thanks for sharing all these stories. And let's go. Let's grow.

Yeah, let's go. Whoa, I hope you got from this as much as I did. I learned so much, especially what to do with peer support. Like, how do not be alone on the journey? And yes, Leap Academy is part of that. And if you're listening to this after LeapCon, just make sure to check some of our free trainings. We have free trainings all the time.

We're going to have a lot of links in the show notes. So I want to read a review from you. Remember, every week, I choose a review from either Apple or Spotify or whatever it is that you sent your reviews. So make sure to review us. So maybe we'll choose you next. So right now we're going to read from writer forever. Thank you. Writer forever. I like that name. And he basically said, I'm not sure why I get out of the habit of listening to Ilana's podcast because every time I revisit her series, I get great information, helpful suggestions and positive encouragement from the interview that she does. Thank you, writer. I appreciate you so, so much. And seriously,

these reviews mean the world. So add yours. And what I want to do now is answer a question. So every week, we look at the YouTube, we look at your comments, and we choose a question to answer right here on the show. And right now, it's a question from Helena who asks, how do I become a more productive leader? And one of the ways that I like to remember it is use the acronyms bread, B-R-E-A-D. And the way you can want to look at it is B, you want to batch. You want to start batching things together because as much as we think that our brain is really good about multitasking, it actually takes capacity away. So batches many things together, batch your emails, batch your social media, batch things together. The next one is R, reduce. There's a lot of things

that you are busy doing that you could probably reduce. You'll answer maybe a few less comments on LinkedIn. You're going to answer a few or less emails. You're going to wait a little bit between answering emails, et cetera. So what are the things, for example, as a leader, I realize that if I don't rush to answer the emails, some of these things kind of solve themselves. There's a place for urgency and there's a place to actually give your team a little bit of an opportunity to step up and actually answer themselves. So kind of find where are you actually stepping in to help your ego versus where are you stepping in? Because it's really important. And I've probably done both. So reduce. And then E is for eliminate. There are things that you are doing today that should be

totally eliminated. And I want you to really think about where you're spending your cycles that probably are not serving you or they're not taking you closer to your goals. Sometimes it's about people that you need to eliminate because they're right now sucking your soul and sucking your energy. Sometimes it's about the Netflix that is taking you all the way to the middle of the night and then you're tired. So what is it that you need to eliminate altogether from your day? And then A is for automate. What are the things that you're doing again and again and again

that should actually be automated? Now is AI. It's so much easier. But overall, like, what are the things that you can start automating and creating flows around? Because it's just going to make your work so much easier and so much more productive. And the last one is D is delegate.

What are the things that you can actually delegate in a lot more helpful way? If you're going to send an email to info at leapacademy.com, tell us that you heard about delegation in the podcast. We have a really beautiful PDF or some of the tasks that I believe you can delegate. And it's going to give you a lot of ideas of how to structure the days and what are the things that you can actually start delegating ASAP and why is so much worth it. So maybe next podcast I will actually talk about how do you value your worth and how do you

decide what to delegate to. So stay tuned. Make sure to always check those at the last piece of the episode because there's always going to be a really fun Q&A at the end. So share your questions in the comments on YouTube because I check every single one and I pick one and I talk about it. So I would love to name you and give you credit. So share this with everybody you know because it really, really helps us bring amazing guests and have a beautiful rest of the week. I'll see you soon. Remember this episode. It's not just for you and me. You never know whose life you are meant to change by sharing this episode with them. And if you love today's episode, please click the subscribe or download button for the show and give it a five-star review. This really means

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