Transcript

Mike Seckler: How to Build a Business That Thrives When Others Fail

From Young and Profiting · Episode page · Watch on YouTube

· 1 h 10 min · 13,930 words · 171 timestamped sections

This is the full, timestamped transcript of "Mike Seckler: How to Build a Business That Thrives When Others Fail", an episode of Young and Profiting published February 3, 2026 (1 h 10 min, about 13,930 words). It mentions 10 people, works and ideas, including Just Works, Mike Seckler, ADP, Workforce Now, Anne Winblad.

What this episode is about

Mike Seckler, CEO of Just Works, discusses the importance of resilience and adaptability for entrepreneurs and small business owners in a rapidly changing environment. He emphasizes the value of genuine company culture, customer loyalty, and strategic decision-making, drawing on his extensive experience navigating various business cycles to offer advice to young entrepreneurs facing challenges.

Key takeaways

  • Entrepreneurs face chaos, but those like Mike Seckler thrive, proving resilience turns adversity into opportunity.
  • Liberal arts grads can excel in tech—communication and problem-solving trump formal business training for many founders.
  • Customer loyalty isn't just a buzzword; it's the heartbeat of enduring businesses that prioritize genuine connection.
  • In your 20s, the downside of entrepreneurship is minor compared to the colossal upside of chasing your dreams.
  • Naivety can spark innovation; sometimes the unprepared visionaries reshape industries without knowing the rules they’re breaking.

Who speaks in this episode?

What is discussed, and when

  1. – 10:00: Just Works, Mike Seckler, ADP, Workforce Now
  2. – 20:00: Anne Winblad, Bill Gates, Steve Jobs
  3. – 30:00: Just Works
  4. – 40:00: Just Works, South by Southwest
  5. – 50:00: Just Works
  6. – 1:00:00: Just Works
  7. – 1:09:44: Just Works, Mike Seckler

Notable quotes from "Mike Seckler: How to Build a Business That Thrives When Others Fail"

  • I'm so excited to interview you. I don't know if you know this, but Yap Media is a customer of Just Works, and so we use Just Works all the time, and all my employees get their…
    about Yap Media · at
  • And people that we that came over from our company number of them are still there including like ADP's current chief product officer is someone that joined us soon after…
    about ADP · at
  • Yeah. speaking of that, I know that you have a mentor, an early mentor. It was a legendary VC Anne Winblad who taught you about intellectual stamina.
    about Anne Winblad · at
  • Bill Gates, Steve Jobs, she knew all these folks. And then she joined with John Humber to start Hummer Woodlad Venture Partners where Bill Gurley was a young venture capitalist at the time.
    about Bill Gates · at
  • Can't wait. but before we do that, let's let's talk about how you got involved with Just Works. So, you started as a board member, then you were COO and became CEO. Talk to us…
    about Mike Seckler · at
  • Get out in the market, and when we're hosting an event, we do a lot around South by Southwest. I went this past year, probably talked to [clears throat] a hundred of our…
    about South by Southwest · at
  • So Just Works exists to help small businesses grow with confidence and you know we are a very missiondriven company. The way to think about our kind of architecture is we have a purpose, a.
    about Just Works · at

Who and what is mentioned in this episode?

People

  • Mike Seckler — Person · Main guest · 4 mentions · first at
    Primary interview subject; discusses entrepreneurship lessons from the dot-com era, leadership energy management, customer obsession, and scaling Justworks as CEO.
  • Anne Winblad — Person · Referenced expert / mentor figure · 1 mention · first at
    Cited as an early mentor and legendary VC who influenced Seckler’s thinking on repeated pivots and resilience (“intellectual stamina”).
  • Bill Gates — Person · Referenced industry figure · 1 mention · first at
    Mentioned as one of the tech “legends” in Anne Winblad’s network, used to establish her credibility and proximity to major tech founders.
  • Steve Jobs — Person · Referenced industry figure · 1 mention · first at
    Mentioned alongside Bill Gates as a tech legend known by Anne Winblad, reinforcing the historical context of Silicon Valley leadership.
    Bill Gates, Steve Jobs, she knew all these folks. And then she joined with John Humber to start Hummer Woodlad Venture Partners where Bill Gurley was a young venture capitalist at the time.

Companies & orgs

  • Just Works — Company · Business focus · 17 mentions · first at
    Primary company discussed, providing HR tech solutions for small businesses
  • ADP — Company · Case study · 2 mentions · first at
    Mentioned as the company that acquired Mike Seckler's previous venture
  • Yap Media — Company · Referenced company · 1 mention · first at
    Mentioned as a customer of Just Works
  • HP Inc. — Company · Referenced company · 1 mention · first at
    Mentioned as a previous employer of the host
    So cool. I had no idea that turned into Workforce Now. I remember I used to work at HP and Disney and we used to use those platforms. So really cool. So you had mentioned briefly that you were able to navigate the dot crisis when 80.

Products & tech

  • Workforce Now — Product · Referenced product · 2 mentions · first at
    Mentioned as the platform at ADP that evolved from Mike Seckler's previous company
    It was a different kind of leadership challenge and it was really successful in the end and the legacy of our business now lives on at ADP and a platform there called Workforce Now which is the largest part of ADP.

Places & events

  • South by Southwest — Event · Referenced event · 1 mention · first at
    Mentioned as an event where Just Works engages with customers

Full transcript with timestamps

We very much believe that entrepreneurs and small business owners deserve the best and we feel that our industry has not historically provided them with the best and so we exist to change that.

If you're a founder, leader or dreamer navigating today's fastchanging world, this episode with Just Works CEO Mike Seckler is packed with insights on resilience, adaptability, and building a business that lasts.

There's a lot of companies that have posters on their walls with value statements that everyone in the company knows don't mean a thing. No one refers to when making decisions. Just Works is not one of those companies. A lot of people who when they question whether they should be entrepreneurs overestimate the risk of taking the leap. If you're in your 20s and you go start something, the upside is massive. The downside is

what is so meaningful to you about customer loyalty? Why do you take it so seriously?

If the people with the biggest decision-m power are the ones that have the least understanding of what customers want and need, that's going to lead to a terrible outcome. You've lived through multiple business cycles. Any advice to young entrepreneurs who might be facing their first downturn?

The thing to remember is that these Yeah, fam. The business world never stops changing, but some leaders don't just survive the chaos, they grow stronger because of it. Just Works CEO Mike Seckler is one of those leaders. Over the last three decades, he's lived through the dotcom crash, massive pivots, and hyperrowth, and he still built a $300 million HR tech powerhouse that puts people first. In this episode, Mike opens up about all things entrepreneurship. We talk about company culture. We talk about values, energy management as a leader, and customer loyalty, which he takes really seriously. But before we get into today's episode, if you're a new listener, don't forget to follow Young and Profiting on your favorite podcast platform and join us every week to listen, learn, and profit. Mike, welcome to Young and Profiting podcast.

Yeah, thanks for having me. I'm so excited to interview you. You know, I don't know if you know this, but Yap Media is a customer of Just Works, and so we use Just Works all the time, and all my employees get their benefits and payroll through Just Works. So really excited to chat with you and have you on today.

Yeah, thanks for being a customer. I'm very aware that you all are customers. I'm happy that uh hopefully you're having a great experience and

Oh yeah, look forward to chatting for sure. Yeah, we are having a great experience. But you're not on here because I'm a customer or even, you know, you're not one of my sponsors. You're just on here because you're an incredible entrepreneur. Um and when I was studying you today, I realized that you don't have a business background. you actually went to school, I think, for geology and history. Uh, so talk to us about this liberal arts background and how that either helped or hurt you as an entrepreneur.

It's a great question. I think when I was uh in college, I didn't really have a great sense of what I wanted to do with my life. I was attracted to the sciences and being able to apply the sciences to the outdoors. Geology in some ways is applying biology, chemistry, physics to understanding the world around you. and I like that a lot. Um, I thought I might go into a career there and then did some, you know, more sophisticated like level research and then began to get disenchanted with the sciences and so just went and got a job after college. I done a lot of quantitative analysis. I knew how to use Excel that apparently made me employable

but you know I think and then you know how I became an entrepreneur from there is a story in itself. I think a liberal arts education though in terms of preparing me to be an entrepreneur. I got really good schooling on how to communicate, how to write, um how to, you know, work through complex problems and that probably was helpful, but there was certainly nothing about the specific subject matter that was all that relevant to, you know, engaging in starting software companies and the like.

So, there's probably a lot of people tuning in who are in similar positions as you once were. maybe they didn't get an MBA or they have no business background but they want to be an entrepreneur. So how did you prepare yourself for entrepreneurship and how did you become an entrepreneur eventually?

So the story of becoming an entrepreneur was you know I graduated at a time that might resemble this current time in some ways. So I graduated from college in 1994 and we were using the internet in college. um it was like we were net native and we graduated into a workforce that wasn't yet even using things like email and that gave us in a way a little bit of a superpower to kind of already be operating within the future. I think folks who are graduating recently might have a similar advantage with AI for example,

but my co-founder and I, we went to college together and when we graduated, we had our first jobs and we began to feel like a lot of what we were experiencing felt archaic, like filling out forms. There were, believe it or not, like envelopes for inter office mail that you would put them in and someone would get them to someone else.

And, you know, we had grown up using the internet. And so we began to believe that there might be a way to use the internet to rethink the way companies employed people and the employee experience. And that was

both kind of correct, but what was going to be required to manifest that in a business, I think we were quite naive about

and we were fortunate just to step into it and figure it out along the way. Um,

I'm not sure we were prepared because I'm not sure we really knew what we were committing to when we started that first company.

Yeah. Yeah. And that was called employee employees right? That's right. Employees. Yeah. Employee. E A S E.

Yeah. And you were acquired by ADP, which is absolutely amazing. That's every entrepreneur's dream. And uh from my understanding, you got acquired and then you ended up being a VP at ADP after they acquired you. So what was that transition like or and did I did I get that right or was that

Yeah, more or less. I mean we started that company and we built it for 10 years and we navigated the dot boom and bust

and got a lot of very formative business experiences and then in 2006 in the context of us having a partnership with ADP where they were distributing our product to their customers that was going far better than than anyone's expectations we started to become a little bit too important to each other and it led to a very clean acquisition discussion

um in terms of like me working at ADP after that wasn't in the plan. I always thought if I ever we ever got that business to the point where we could sell it, I would then take a break and go learn how to do something fun like learn how to ski or play guitar or something like that. But, you know, we sold that company in October of 2006 and our first daughter, my wife Karen and I, our first daughter was born in November of ' 06 and my wife had a big career as well. And so, it was pretty clear that not working at that moment wasn't going to involve living on the slopes. was going to, you know, be changing a lot of diapers. I mean, that was one bit of reality. And and then the other thing was, uh, our people were very nervous about the acquisition and like how their lives were going to change. And I was concerned that ADP was going to mess up our company. And so

when ADP asked me if I would run not just our business, but there was a part of ADP that was supporting our product because we had had this partnership. And then there was another part of their business where they wanted to migrate legacy customers onto our product. So there were three teams and they asked me to put these teams together and I took it on and I had no earnout so there wasn't a financial reason to stay. It was more of like felt like the right thing to do at the moment and it was a very enriching about 2-year period that I got allowed out of actually. It was um it was a different kind of leadership challenge and it was really successful in the end and the legacy of our business now lives on at ADP and a platform there called Workforce Now which is the largest part of ADP.

Oh wow. And people that we that came over from our company number of them are still there including like ADP's current chief product officer is someone that joined us soon after college at employees grew up there was the number two in our technology organization and decided to build his career there. And there's a number of other people who did that. So I'm very proud that we built something that continues to have a big legacy and impact in the world.

So cool. I had no idea that that turned into Workforce Now. I remember I used to work at HP and Disney and we used to use those platforms. So uh really cool. So you had mentioned briefly that you were able to navigate the dot crisis when 80 to 90% of other companies disappeared at that time that were uh similar platforms. You were software as service platform. How did you navigate that situation?

In the moment, it felt like we were just flying by the seat of our pants, making the best decisions that we could. I mean, John Alberg and I, my co-founder and I, we were in our mid20s. And the first couple years of that business in the dotcom boom, I mean, we were rewarded for evangelism, moving fast, you know, raising capital, accessing talent, and and then all a sudden, the world changed almost overnight. uh capital disappeared and we all had these big burn rates. All these companies that had gotten venture dollars in 97,98 99 entered 2000 and capital evaporated and it required really really fast decision-m to accept that the world was changing. And a lot of people were slow in in accepting that just hoping at some point it would turn or maybe reducing their burn rates by a little to extend runway but they didn't extend it for by enough. And through a combination of very hard decisions, having to reduce

the size of our team by about a third, taking on some diluted financing and making other decisions, we were successful in navigating that extinction event and it was brutal. The thing I will say though is that um in retrospect like the lesson was quite profound in that in 1999 we felt like we're on top of the world, right? were getting put on magazines and everyone wants to invest in our company, everyone wants to join our company, but we were blind to all the risks that were right in front of us.

Like it just felt great and and yet we had like 15 wellunded competitors and the world was about to change and we were blind to it. And then by about 2003 after we had navigated all these very difficult things, it felt like we were walking through mud. Growth was hard to come by and there were a lot of moments of maybe we should just do something else. those those questions. We woke up one day and realized like all those 15 competitors were gone. They had all either gone out of business or got boughten for parts and now we were the last one standing and we were able to then dominate our market niche simply by surviving that extinction event. And so things felt best when there was only risk in front of us and things felt worse at the moment that there were only actually there was only upside in front of us. And that was a searing lesson. Um because my ability to to correctly perceive like what was in front of me

was was off. Like I was misunderstood what was right in front of me. That was fascinating.

It kind of reminds me of like what's happening with AI right now? Like I think AI is going to disrupt so many businesses. So can you give us advice on how us entrepreneurs should navigate something like AI or things that we should look out for or how we can best prepare? I mean I don't know what advice I would give. I mean you know to the extent that this AI cycle plays out like other technology cycles you might imagine that it will get even hotter and hotter beyond what people can imagine and then there will be some uh you know reckoning that'll happen and some companies that raise too much money will go away. I mean that's what has happened in prior cycles. But that doesn't diminish the fact that internet or that AI much like I think the internet did is going to change a lot of industries forever and a lot of jobs that have been good jobs in the past may no longer exist in the future. At the same time,

some jobs that don't exist today, like new ones will be created and and so I think the biggest advice would be to just lean into that fact and to not hold on too tightly to the way things used to be because it's going to change big time.

Yeah. Uh speaking of that, I know that you have a mentor, an early mentor. It was a legendary VC Anne Winblad who taught you about intellectual stamina. Uh can you tell us about what she taught you and um how you use that throughout your journey?

Intellectual stamina, I don't think it was really it wasn't her term. It was what John Alberg and I put on as a label of a story that she told us. And so Ann Windland was quite a legend um and still is although she's perhaps less known because she's less active as an investor now but she was a entrepreneur much like you um and was was I mean you know women founders at scale who had great exits in the technology world are still it's still you know a minority and she had success doing that in the 70s built a company sold it was a whole owner and had this great outcome and you know was close with all the legends at that time.

Bill Gates, Steve Jobs, she knew all these folks. And then she joined with John Humber to start Hummer Woodlad Venture Partners where Bill Gurley was a young venture capitalist at the time. And so Bill Gurley and and Woodlad and John Alberg and I were at a table after they had given us a term sheet and they wanted us to accept their term sheet. And so the tables in a sense had turned where we were done pitching our company and Bill and Anne were hoping to get us to take their term sheet and not shop it up and down Sand Hill Road. And so we took advantage of that opportunity to ask Anne a bunch of questions and you know I said you've seen all these successful entrepreneurs what does it take to be successful and she gave a really interesting answer.

She said well there's really a spectrum. There's different ways to approach this. You have folks like Larry Ellison who you know are can be tough to deal with and if you don't agree with them he may choose not to talk to you again. And then you have folks like Michael Dell who are super good at bringing people together, even people with very divergent views and building, you know, teams in a very different way. He said, but what they all have in common is this ability to have a clear vision of the world and then to take a couple steps forward and realize that a lot of their vision was not accurate,

but to take the 10 to 20% of the vision that remained and recast it a new based on what they had learned and to do that over and over again. And an at that dinner said and you know her parting comment was and what I have seen is that to be a truly successful entrepreneur you have to be ready to go through that process 10 to 15 times over the course of a venture

and it felt like a very wise thing when we heard it but it was something we always reflected back on when things were in fact felt near impossible. It felt like so much of what we had bet on was not panning out the way we wanted and we had to pivot over and over and that concept that we dubbed and winlad's concept of intellectual stamina is still something that I reflect on as we go through these journeys. I remember when I first heard you tell this story, you had mentioned, you know, you've got to pivot and pivot without like a lot of drama. Like it's just part of the process. And to me that really stuck with me because when I think about my company, like there's certain things that I pivot all the time and it's not really like something I contemplate over. It's kind of like, oh, this is how it's like, you know, this is how we have to move so that we can, you know, keep getting customers and not really hold on

to the past so so closely. um even though it's the way that we've done things forever, we need to change. Um and and I like the fact that you had mentioned like do it without like a lot of drama.

Yeah. I think that uh it's all about moving fast and learning and then you know adjusting and anything that I think impedes that that makes you go more slowly or that causes you to miss a moment when you get a key insight that cause that that would suggest maybe you change your approach. Anything that stands in the way of going quickly through those things is going to diminish one's chance of success in any new venture for sure.

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The thing to remember kind of like I said, is that these cycles, I think, persist across time. It's hard to time exactly when they will turn, but cycles will always be with us. And so,

it's useful to keep that in mind because when things feel really good, as they did for me originally, my first time through these in 99,

it's important not to attach too much to that and to not make decisions that assume it's going to be easy times forever. Likewise, in 2003, it would have been a disaster if we gave up right at the at the bottom. Um and and so when things are bad to also realize that you know these cycles uh will change even though it feels like an excruciatingly you know long time can persist as you as you sit in these moments. So I think that would be one bit of advice. Um I think being resilient to these downturns um requires an acknowledgement that they always can occur. And so you know we use a fourbox framework a lot.

you think about like making a decision yes or no and then the world gets worse or gets better. There's there's often decisions there's often a quadrant that's super clear that if you don't make a certain decision and the world evolves a certain way that you'll have a chance of being out of business.

And so I think a good way to make decisions is to always make the decision that puts you in the row where you can't get sunk. That may mean that in the best case outcome, you may give up a little bit in terms of how great it could be. For example,

yeah, like if you have debt and one option, you know, you could raise some money and you could pay off the debt. But you say, well, geez, you know, if we kill it from here, like paying off the debt, that might require me to take some equity, so I'm going to get diluted. But if the world evolves bad in a bad way and you haven't paid off that debt, it can sink you. And so the same kind of decision that leads to the best case outcome in the best circumstances also leads to the one that could be fatal in the worst circumstances. And so I think often the right decision is the one that you give up a little bit of upside in the best case. But what it does is it preserves your ability to be a going concern when things get bad. And it's important to keep that in mind because after four or five good years it's natural for people to forget that can in fact get bad.

Yeah. We're going to play a game later um about that about exactly that. So, I can't wait. Uh but before we do that, let's um let's talk about how you got involved with Just Works. So, you started as a board member, then you were COO and became CEO. Talk to us about your journey and what made you want to get um operationally involved with the company.

So, I had done two startups with John Alberg. The second one was a very different one from the first. Um, it's named Uklidian Technologies. We started in 2008. It uses machine learning and artificial intelligence to invest in the public markets. And it's it's a great business. Um, but after a couple years, you know, there's it's just a very different kind of business than what employees was and what Just Works is. You don't need huge teams when you're making investment decisions algorithmically. And while I needed a few years of of a break from leadership after the employees to ADP transition, I started to really miss it after a couple years

and I didn't know to how to how to get it back in my life. Um cuz John still runs Uklitian, loves Uklitian. And the idea of starting a company without John, a more traditional startup felt kind of intimidating. So the way I started to get energy was just to be around builders again. And I just started to get re back reimmers in the startup ecosystem. I ended up, you know, sometimes very informally working with some founders and then I ended up on a couple boards and one of them was with Just Works. You know, I met the founder of Just Works uh 11 years ago. Company had 20 employees, like $300,000 in revenue. And I really liked how the the founder of Just Works thought about things and thought about company building and we just started enjoying being together on that. I wasn't looking for angel investments. I wasn't looking for board seats. I was just looking for energy and we got to know each other for

about 6-month period and then he asked me to join the board. So I was the company's first independent board member.

Well [clears throat] 4 and a half years went by and I worked closely with with Isaac to to make you know the decisions you know to to support him and making the right decisions and growing the business. And I got a phone call from him where he felt like he wanted help running the company. It had gotten larger 400 employees.

Wow. Um, and I was missing leading at scale. And so that conversation, it's kind of a funny one how it played out, but it resulted in um, you know, being invited to come in and help run the company. And that's how I got involved.

And once the transition to CEO actually occurred, how did you make sure that it was a smooth transition with the company, with the employees, and how was it to actually lead a company that you didn't found? Yeah, I had had a mental block on that idea. I kind of thought after 20 years of working on my own companies, I actually couldn't work in anyone else's company.

But when Isaac asked for help that time now 6 years ago, six and a half years ago, it was a unique thing in that I'd worked with this founder for half a decade. I knew the business. I knew the investors. And when he asked for help, like something in my brain quickly said, "Whoa, okay, if you don't lean into this conversation, you are definitively saying you'll never be able to work in anyone else's company,

cuz it's never going to be teed up like this this one is." And when I came in, um, it was a little bit like of an adjustment for sure. It was Isaac's company. He was still CEO. And I tried to be really thoughtful about how I approached it. And I enjoyed it. You know, when I came in, to be clear, it was the expectation was I was going to be, you know, the chief operating officer. Wasn't it wasn't um intended that there was necessarily going to be a two-step process where I would ultimately become CEO

to me. What became clear though soon after I joined is that Isaac did in his mind have

his mind on a two-step process. and we talked about it reasonably soon after I came in once and then another year later um it became clear that it was something he ultimately wanted to to do and so the the CEO transition was smooth largely because it was on Isaac's initiative and he worked closely with the board and with me to make it very smooth for the company and and when we announced it to the company it felt like like a wonderful graduation from Isaac through running it for a chapter to me and I think it was incredibly well done and and unusually so. I think these transitions typically don't don't feel as as smooth as this one did.

How did you guys structure the board um and leadership in general because I think Isaac is still involved in the company right?

Yeah. Yeah, he's uh he's on the board. Um how do we structure the board? Well, I mean, there's a couple I mean, there's how we built the board over time and and there's how it works now. But Isaac is he's a close friend and confidant. Uh we've worked together now for a decade. We've had three chapters. You know, I was in a way like I would I don't know mentored him maybe a little bit. I was had previously been a successful founder and then I was his first board member. He was CEO. Then I came in and I reported to Isaac as his chief operating officer. that was a change and now I'm CEO and he's on the board and so we're really in our third chapter of our relationship but it's been I think very much mutually enriching at each step even if the nature of it has changed.

Yeah, I want to dig deeper on the concept of boards. Um I think a lot of entrepreneurs that tune in to the show are bootstrapped. Um and I feel like bootstrapped companies especially don't often have a board. Um, one of the reasons why you bootstrap is you don't want to report to anybody else. But uh, talk to us about uh, some of the pros of having a board and how to set one up efficiently um, so that it gives you the best outcome as a leader.

Yeah, I do think in different settings the right answer would surely be different. I mean, Just Works is a company where

like no investor owns more than maybe 15% of the business or largest investor and and so it it's a distributed shareholder base. it makes sense to have a board. Um, you know, if you have a CEO that has a control position or so forth, the right answer might be something different. But I would just say in the ab, you know, abstracting away from that consideration, the benefit of having a board is to have a bunch of smart people that bring diverse perspectives to questions about the board, the way the company is governed and the company's strategy. you know, the management team should be managing the business. But in terms of big questions like should we go buy a big company, raise a ton of money, take on debt, should we sell the business, should we go public, like those are things that when you have a diverse shareholder base, a a board is I think essential to making good decisions. I think a board also can play a big role

in governance uh to help ensure that the practices aren't in place that customers interests will be protected that shareholders will be protected that you know bad things aren't happening in the company you know like anyone in the company can send a note anonymously to the chairman of the chairperson of our audit committee happens to be a woman named Chris Leslie and if there's a concern inside the company like she'll want to talk to me about it now I can imagine a lot of founders Well, why would I want that? Well, if you want to create a great workspace

for your people, and ultimately, I mean, Just Works, we have about 1500 people. It's a big company, so things definitely happen.

Yeah. You want to have mechanisms for people to raise their hand if they see something that they're concerned about, and maybe it's something that they would feel insecure about sharing with their manager. And so, how would that information even get to me, let alone to the board? And so I think having some of these structures are actually really wise if you want to build a company that can withstand the test of time. Now if you're a bootstrap founder, you have 10 employees. I don't know if what I just described makes any sense at all, but certainly having some people that

have an interest in the company's success that you can um engage with on big questions in whatever form. board of directors, board of adviserss, folks who who might invest, but also like kind of part of the agreement of them investing is maybe you'll get an hour of their time once a quarter,

I think is essential. Um, yeah, you know, I certainly had moments in my entrepreneurial journey where I felt very alone,

that I had no one I could talk to about big decisions. And that's a pretty shitty place to be. And over time, I've learned how to build those structures. I mean, the board is one, but other structures outside of that that I think have been both enriching and have helped me like stay in the game and um made better decisions.

Even just having like a support group of other entrepreneurs I feel like can be really helpful in your entrepreneurship journey. Um I I bootstrap my company so I own like only one of my business partners has 5%. I own 95% of my company. So, I never like really considered a board, but I definitely have a lot of entrepreneur friends who know a lot about my business and I get to pick their brain from time to time.

Yeah, I have one too. In the year 2000, when I was feeling alone and overwhelmed with those decisions with the.com bust through EO, sister organization of YPO, I found a group of 10 entrepreneurs, um, nine guys, one woman. The woman, by the way, is by far the most successful of all of us in the end. Um we started getting together monthly and helping each other and then and once a year we'd go on a trip together and then as we got to know each other not only we help each other with our businesses but we became like very very deep I mean friends [clears throat] even understates it. I mean like cousins siblings in a way of the amount of understanding we have of what each other have gone through both professionally and personally. And that group we got we did that for 15 years.

In the past 10 years, we still get together from time to time. We were in fact together just a week and a half to half ago. And uh it's been an essential part of the the support infrastructure that I was able to put in place that has both made life a lot more fun but also helped me as a leader.

I love that. Um so something else that you're known for in regards to your leadership is customer loyalty and you're really big on that. I read that you actually meet with 10 uh CEOs every single month. Um what is so meaningful to you about customer loyalty? Why do you take it so seriously?

You know, there's so many ways to answer that question. I'll just share one example that kind of crystallized something for me about what the need to be intentional on this. So when we sold that company to ADP, I was one of two people under 40 in like the top leadership group. Maybe there were like 60 or 70 of us. And I was meeting all these people that I was like at first a little intimidated by people that ran these like thousand person CS organizations, thousand person sales organizations, but then what I began to realize within that community is that none of them really talked to customers.

You know, they got their information through the chain. And growing up as an entrepreneur, I mean, I was talking to customers and prospects every day because that's how you get your business going. And that just become a habit. And I realized in that moment that I had a superpower that because I was talking to customers all the time, I knew better than anyone else in the room like where the market was, where it was going, and I could speak to it

with not only a confidence, but with like storytelling and specific examples that um could win people over. And what I began to reflect on is that, you know, when a company's small, if you think of it like a balloon, when a company's small, there's no one inside the balloon that's that far from the edge. And if the edge is where you meet the customer, but when a when a company grows, you get this balloon gets bigger and bigger, a higher percentage of the people are further away from the edge of where you meet the customers. And typically, the most senior people tend to be the ones at the center of that balloon, the ones furthest from customers. And that's a concern because if the people with the biggest decision-m power are the ones that have the least understanding of what customers want and need, that's going to lead to a terrible outcome over time for the company. And so because of that, culturally it just

works. Like we emphasize a key leadership principle here is that we obsess over customers. The expectation very much is that if you're going to be a leader here, you are

you're not just looking at customer data. Like you are talking to customers and prospects and you are in the market all the time and you should have your own primary perspective on where we're strong, where we're weak, where the opportunity is, where the puck is going. And if you don't have that, you can't be a leader here. So obviously in my role, I have to model that. Mhm.

Um, not just to model it, but also because, you know, when I go week and I'm not talking to a customer, I instinctively feel like out of touch. I start to feel nervous that something's happening that I don't understand. And so, you know, I talked to way more than 10 CEOs a month. Like, I I put that out there to start tracking it like two years ago and it was, you know, I do way more than that just as a matter of course. So, you know, tomorrow I'll be at a dinner with 30 customers and prospects. I will on a weekly basis I receive a lot of escalations and I make sure they get to the right place. But every week I'll take one all the way through and I'll talk directly to that customer who's having a difficult moment and make sure I understand why.

I think that is good to model for our team that like this is no one's above this. This is actually the work. And I think it does send a signal to our customers when our leadership team and CEO is getting involved in making sure that well one that we take their uh issues seriously and um and that we're we'll be involved start to finish to make sure that it's it's resolved to their satisfaction.

I don't think a lot of companies do that. Certainly not a lot of our competitors do that and I think that leads to u something pretty special in the market.

Yeah, I've been actually thinking about this so much. Um I my company I'm my own client and so I have a social media podcast agency, LinkedIn marketing company. I have a podcast network. So I have a team the same like you know a subset of our team runs my account and runs like client accounts and does the same thing for me for our clients. Same thing with sponsorships. I get sponsorships, we do it for our clients. And so I have this really unique position where I am the customer. So, I know everything that's going on and I can always make things better and and like I'm just like in that seat and I, you know, have a lot of entrepreneurship friends and sometimes I'm like, how do they even know what's going wrong?

Because they're not their own customer. Some of them have no experience even in the industry that they're in. Um, so talk to us about how like not everybody's in my seat where they're their own client. How do you actually get information from customers? you just mentioned a dinner, but what are what are some other things that you do to make sure you get that feedback?

You know, it's interesting. I mean, when JustWork started out, we looked a lot like our customers. And so, like we were getting that information just because like in the community, we would go out and, you know, our peer organizations were also our customers. And so, our sense of the market was it was naturally intuitive. But as we've grown, you know, 1500 employees, larger company, our average customer, I mean, we we start with customers when they're often really small, like less than 10 employees, just a few employees. And, you know, we work with customers till they have hundreds of employees, but but we're bigger than our largest customer right now. And so, we've needed to kind of put in more deliberate like mechanisms to stay in touch with the market.

As a company, we do that through customer advisory councils, by being out in market and hosting events. uh we have a research team. So we're always doing quantitative, you know, research and surveys and so forth. But again, for me, looking at my calendar, it's looking making sure that there's a good balance of my time that's going to obviously things that are inside the company, but making sure I'm never out of balance with that. And then I'm always creating space to do customer escalations

from time to time, to go out and meet with customers, to meet with prospects, to go join a salesperson on a call, to get out in the market, and when we're hosting an event, you know, we do a lot around South by Southwest. I went this past year, probably talked to [clears throat] a hundred of our customers and 500 people that are not yet our customers, but should be and learned a lot, right? you know, like um there's two venture capital events I go to every year where they invite their their founders and their CEOs together and inviting me to an event like that is a little bit like inviting the fox to the hen house because everyone I mean there's some truly scaled leaders there that maybe they're using something else because we're not Just Works isn't about helping large companies. are focused on small and growing businesses,

but 90% of the the founders and CEOs there should be our customer and often a lot of them are and I can hear from them, hey, how are we serving you today? How do you wish Just Works could serve you better? If we ever dropped the ball for you, give me feedback. And then others are using competitor platforms. What do why did you choose them? Why do you like them? What do you wish they did differently? And those anecdotal stories put me in a position to engage with our team way in a way more compelling way than it would be just if I had some data.

Mhm. You know what I mean? The data is good, but the data and the anecdote when they come together, that's where real conviction builds for me at least.

Yeah. And I love that you're like not letting your ego get in the way. You're the CEO of this huge company, but you'll get on a sales call uh and you'll talk directly to the customer. I feel like that's a really important part. Ego is such a weird thing. Can I just could we talk about that for a second?

You know, I was with my group of entrepreneurs. You talked about you have a group. I was with my group a week and a half ago and everyone in this room that room has had successful exits and done multiple things had a lot of success. We had this amazing conversation where each of us had a similar story where earlier in our career like it was clear that some of our initial success was very ego-driven and we were like you know your sense of self and your confidence and you just drive it. But all of us either through work challenges or personal challenges at some point started to get that ego be cracked a little bit and those moments when your ego gets cracked they are unpleasant.

And for me that do com bus period was for sure one of those. It was quite humbling. And while those periods are unpleasant and you never want to go through them again the benefit in our lives and all of us had you know stories that rhymed about this was that when you start able to live in a way that it that you just know you're more connected to the world around you not this closed off thing. It is a way better way to live. And by the way, I think it also has made each of us and certainly me a better leader because when you're leading from a place of deep connection and care as opposed to a place from ego, I think it's like it's it's better for all the humans around you.

And the idea that something anything and if it's ego would get in the way of a CEO or a founder spending time with their customers,

then gez like then that would be a statement that ego would be the biggest enemy to entrepreneurial success. And so overcome that first before you do anything else.

Yeah, I feel like this is a great place to pivot into like mission and and values. So what is uh the mission of Just Works?

So Just Works exists to help small businesses grow with confidence and you know we are a very missiondriven company. The way to think about our kind of architecture is we have a purpose, a mission, and a vision. And then we have values we can discuss. But our purpose is to help people realize their potential

and and there's a whole bunch of stories about how deeply authentic that is to the company's founding. There are internal manifestations to that like in terms of what we want just works to be for the people that work here. How we want this to be a place that more so than any other place they work can be a place where they can grow not only as a professional but also as a human being. Mhm.

The external manifestation isn't that mission statement which is in terms of helping people realize their potential. We want to help these small businesses realize their potential. You know what we believe at just works is that you know entrepreneurship, small business ownership like this is like the hardest most honorable work out there. Like you're out there, you're trying to manifest your dream despite all the odds and you know you got the whole world conspiring to make your life difficult. And yet when these entrepreneurs persevere through that period, this magical thing happens which is out of nothing, out of thin air, they create jobs for people

give meaning to their lives, right? That create the fabric for healthy communities and a great society. And so we very much believe that entrepreneurs and small business owners deserve the best. And we feel that our industry has not historically provided them with the best. And so we exist to change that. And the last thing I'll [clears throat] say about our vision is which is to make starting, running, and joining a small business a more accessible option for all.

And just to explain what that means, clearly this route to small business success is a hard road for anyone who goes on that road.

But it is an even harder and steeper road for folks in certain communities because access to capital, access to knowhow, access to mentors are not evenly distributed. And so just works the way we want the world, the way we envision the world being better from us having played a role in it

is is a world where we have in fact made those things change so that these things are more accessible to more people.

Yeah. And then when it comes to actually driving company goals forward, do you align that with your mission and purpose? Like how are those types of things structured?

Well, I mean 100%. I mean all those things need to be structured. and and align that way because to the extent that what we're focused on and what we're doing doesn't align to mission and vision and values then they disappear

right like it's these things come alive through action and through people seeing well seeing how I behave in certain settings seeing how our leaders behave in certain settings the way we make decisions there's a lot of companies that have posters on their walls with value statements that everyone in the company knows don't mean a and that no one refers to when making decisions. Just Works is not one of those companies. Um, and so I mean, how do you cascade those things through? I mean, our north star begins with our mission and our vision. We obviously have financial north stars and way points along the way around what it'll mean to realize this vision over time.

Like, you know, we serve less than 1 half of 1% of the small businesses who could help us today. So, we had a long way to go. And so we set these intermediate way points and then we cascade our goals around them

um so that everyone's working towards them. But but in it you know our values of camaraderie, openness, grit, integrity and simplicity. We reinforce them uh at company all hands. Our company awards are the camaraderie award, the openness award, the great like we do that around our values so that it's an opportunity for storytelling. It's not

these abstract things. to say here's what camaraderie looks like. You know, here is an example of someone who was confronted with a need to change and their openness to that need kind of created this breakthrough, you know, new initiative at just work. So, we celebrate individuals who are demonstrating things that are aligned with their values to make them kind of come to life and and to give people a very specific set of understandings around what they mean in practice.

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Sign up for your $1 per month trial period and start selling today at shopify.com/profiting. Go to shopify.com/profiting. That's shopify.com/profiting. So, when it comes to your values, um, sometimes values can get misconstrued. For example, you mentioned that one of your values is grit, right? But if you don't kind of define what that means, that could lead to people overworking or burnout and things like that. So, how do you how do you actually define your values and make sure that people understand exactly what those values are and at what point do you ever like reassess what your values are as a company?

Well, working backwards, our values have been consistent since the start of the company. So, we have talked about them, but we haven't changed them. But you ask such a great question both in terms of like how we make sure these values are correctly interpreted and you focus on the one that I think is has the opportunity to most um the most dangerous interpretations are around could be around grit.

Mhm. Because grit you can imagine could be weaponized to uh by a manager to push employees to levels that are beyond reasonable expectations. Right. Mhm.

And so when we talk about grit internally and we give out the grit award like we contextualize it. We explain hey listen like everyone needs to have some semblance of balance in their lives that's for sure true. At the same time we are in the business of helping small businesses these folks who are trying to overcome enormous odds with things that are essential to how they manage their companies how their people get paid the benefits that they provide to attract talent. The way they stay in compliance with all these things so that they can stay focused on what really matters in their companies.

Right. So, if there's something tough going on that's going to impact our customers ability to do those things, then sometimes that requires us to go the extra mile, even if it's not our job or even if it's after hours. Like, we will show up for our customers in their times of need and we'll have the grit to do so. But that certainly doesn't mean that people need to work 100 hour weeks here as a matter of course.

But that might mean sometimes people do need to do extraordinary things because extraordinary moments have called and

and the people that we celebrate I think and [snorts] the way that we celebrate them I think makes it clear about what grit means and what it does not mean.

Yeah. For us uh we had to recently reassess our values. So I started my company four and a half years ago and one of our values was scrappy right? we had to be scrappy. We had to be resourceful. We had to be fast. Just get it done no matter what. And as we grew and he had more resources, I realized that I needed to like redefine that like we're scrappy, but we're not sloppy, you know? And I had to add a new one right the first time. Like we've got to be right all the time. Um and and you know, take our time, not just run. So I do feel like especially for brand new companies there's a certain point where you can't operate like you did when you first started once you've you know gotten some success and some resources.

100% I agree with that. I think that that we have not changed our values since we started. However, I think it would be wrong to never inspect them and intentionally decide to maintain them. I do think it makes sense from time to time to evaluate them all and then decide whether they continue to support you or not. And I think it's that's a cool story that you just shared and that it makes sense to me that you would have made that decision.

Yeah. So, what are some other ways that you keep your employees engaged at Just Works? I think the the biggest [clears throat] gift to an employee and the biggest way to keep them engaged is to provide them with an extraordinary manager and extraordinary leaders that are skilled in helping them grow. Obviously, doing that at scale is non-trivial thing. Some of it is selection. Some of it is who you decide to promote. Some of it's how you train people. But all those things can be laded up to a set of leadership principles that are operationalized in training programs, in talent calibration processes, in promotion conversations so that the right people are getting in in the right places of influence so that a very high percentage of employees can have a very enriching um experience with the person that they're reporting into. Mhm. And what do you what do you do to guide your managers and your leaders to make sure

that your employees have a great experience? Like how do you think about leadership and energy management?

We have a set of leadership principles that we train against and that we measure people against. They include obsessing over customers and innovating fearlessly, building winning teams, fueling personal growth, acting like an owner. Mhm.

We also have engagement surveys um where and we do a lot of 360 reviews here. So you get a lot of information in different ways. So you know from the engagement surveys you get really specific on where people are feeling optimistic and where they're not and where they feel like they have clarity and where they don't and where they are supported and where they don't feel supported. Sometimes engagement will drop when a leader is driving an or through transformation and because change is hard for people and it's important to like be aware of the context to which these engagement scores come in. If you have a leader who's trying to elevate the talent in their part of an organization, you might expect engagement to drop for a while as the leader goes through that. But ultimately like you should expect an organization once it's like kind of at its desired state. You should see very high engagement scores that people feel

supported. They feel like they're an environment they can grow. They have clarity on um their future growth trajectory. They believe in the future of the company. They don't anticipate looking for another job in two years. They believe in you know like all those things like we measure all those things and you can do that down to the uh really to the team level certainly the the division level.

How do you make sure that you show up as the best leader possible? like what are the things that you do or pay attention to to make sure that you're showing up as the best leader you can?

Well, my understanding of what that question even means has evolved over time. You know, I um when I was a entrepreneur for the first time, I was super young. I didn't have a lot of management experience. I I was naive about what good management was and what it meant to show up well. Um, you know, I had this realization probably when I was 7 years into the into leading that, you know, the way I would describe it is that I would kind of notice sometimes the company I was unhappy with the company and I wasn't happy with the attitude of things. And what I came to realize was that when I was stressed out or visibly frustrated, the whole company would tend to be stressed out and visibly frustrated.

And when I was optimistic and high energy, the whole company would tend to be optimistic and high energy. And I began to see something that should be obvious or should have been obvious to me way sooner was that like there's this energy flow that goes in two directions. And it often started with me, but I was blind to that what I was feeling was actually just my own energy getting reflected right back in my face. And so

the first thing that I reflect on is how I am showing up and how are the conditions that I'm experiencing maybe just simply a reflection of my own energy. That's one lens. The second thing is I was naive when I was a young manager to the question you know people would say what's your management style or questions like that and I came to realize it's almost like a trick question because the best managers and what I aspire to be now as I'm further in my career realize that every person that works for you is a different human being who may need really different things to realize their full potential.

M some people want to get a lot of feedback. Some people need kind of to like stumble on their own before they'll learn things. Other people, you know, really care about like being able to get a drink with you after work. Other people it's like the last thing in the world they want to do is have a drink with their boss after work. and and and so like really trying to like learn about the team and realize that each one might require a little creativity each individual about how to coach them to their best is is something else that took me a little bit too long to learn.

But I put a lot of thought into that and and how I'm going to be a good partner to each person under my, you know, that reports directly to me um to help them be great.

I also learned that you're a very early riser. Is it true that you wake up at like 5:30 a.m.?

I don't know. I mean, yeah. I No, no, I don't know how early it is. Is that 5:30 early? Uh, yeah. No, I wake up early. Listen, I mean, my wife and I, we have three girls. Um,

so growing up with a full house and trying to do big professional things, the only time I could reliably have alone time is probably from 5:30 to 7, maybe 7:15. And so going back to your earlier question around like how I preserve my energy or how I show up, you know, getting getting time to exercise, getting time to think, getting time to meditate a little bit, get my mind right is essential. And so like, you know, when I was earlier in career, I wouldn't put as much intentional focus on that, maybe drink a little bit more, get by in less sleep because you could do it.

Mhm. Those things have costs beyond just my own health, right? They would have cost in my patience with people. They would have cost in my thoughtfulness, my ability to sit with other people's discomfort.

And what I've learned over time, both as a leader, but also as a father of three daughters, the ability to sit with people when they're going through wild emotions, um, when they're scared about something or excited about something and kind of be relatively even keel is a superpower that is a great gift to both the company and to a family. And for me to do that well, I realized that I needed to do a certain amount of intentional self-care on a regular basis by waking up early generally and and doing those other things to uh to show up the way I would be proud of.

[clears throat] Well, let's switch gears a little bit and head into our game. Okay. So, uh something that you were alluding to earlier is that smart leaders, they fix the roof when it's sunny. So, you don't just wait until things go wrong. You actually want to try to fix things while things are going really well. Um, and that's the best way that you can kind of make sure that your company doesn't get, you know, a storm when you're least expecting it. Uh, so we're going to play a game called uh, fix it before it breaks. I'm going to read a prompt and you tell me what could be the hidden risks that we're not paying attention to or like what should we think about even when things seem good, you know, what could be going wrong that we need to actually pay attention to. Does that make sense?

Yeah. Okay, let's do it. All right. Uh, let's start with the first one. Your NPS customer satisfaction score just hit an all-time high. Everybody is celebrating at the company. How do we make sure this sunny day doesn't turn into a storm? What might be the risk hidden in this perfect score?

Well, there's probably different ways of collecting net promoter score information that lead to better results or results that are suboptimal. So that might be one thing just to make sure that you're actually getting the right signal in that data. The other risk of course is that people might perceive that they're that you're better than you in fact are. Like it might be useful to compare that net promoter score to your competitor's net promoter score. Like a plus 30 or plus 40 might sound great, but if you're competing with folks that are at least as good, maybe that's not such an advantage and you're going to have to be even better to uh to get new business and retain your customers. H [clears throat] your exec team is aligned, calm, and there's zero friction.

What would you watch out for in a team that seems way too aligned? Yeah, that this is pretty easy. I mean, the team that isn't engaging in the hard conversations where there's a lot of things that people are feeling that they're not saying, that actually would be a a really big warning sign if the team was uh it felt overly aligned and overly cordial because if you're going to be growing something if you're going to be growing something great, it's going to be hard and smart people will see things differently. And so the only way forward is to like get those great ideas on the table, have the friction, have productive heat, and then have a means of, you know, deciding when there's been enough debate and then to align quickly on an answer even if some people disagree. Right.

Mhm. That's what I think. Yeah. You've got a a marquee customer who's your loudest advocate and your largest source of revenue. What's the risk of being loved by a customer too much?

I see this actually with a lot of startups where they have a vision of how they're gonna, you know, serve a certain segment and then they get a really big customer that gives them a lot of revenue and the customer loves them and the whole company pays a lot of attention to them. But that customer may not be representative of what it's going to really take to fulfill your vision and your mission. They may not be representative of the kinds of customers you're going to serve ongoing. And so if you over pivot your whole company to uh building product to meet that one customer's needs, you may find you have a really narrow market for what you're building. That's one risk. There's probably a couple others right behind it.

Okay. You've hit every revenue target for three years straight. Revenue targets are too low.

Love that. Okay, one more. You just landed a top company culture award. What do leaders sometimes miss when everything feels positive inside the company?

A lot of times culture feels great and people feel great during good times. The question really though is how resilient is that culture going to be when things start to break

and even in the best successes things are going to break because the way that you're organized might work for let's say from you know 50 to 200 employees but some point the way that you do things is going to have to change. And so the big question isn't just how great it can feel when you're on top, but how resilient is your culture and the things that you hold most dearly and your values. How resilient are those things going to be when things are difficult?

Yeah. Okay, cool. So, um, as we close out this interview, I just want to ask you a couple general entrepreneurship questions. Uh, one of the questions I really wanted to ask you before you go is that you've said many founders overestimate risk early on. M

can you talk to us about what you mean by that? Well, I'm not sure I mean it that all founders overestimate risk. I think a lot of people who when they question whether they should be entrepreneurs overestimate the risk of taking the leap. And

I think that's particularly true when you're early in career. The specific example I'll give to make this point, my wife was a senior executive at a at a company with a big brand. And so we got to go to cool things and we're at the Seal concert, met Heidi Clume. It was wonderful. And there were all these MBA interns there. And this MBA intern engaged in conversation with me. She says, oh my gosh, you started two companies. That's so cool. I'm like, thank you. She goes, you know, I've always kind of wanted to be an entrepreneur, but I don't think I could because I'm too riskaverse. And I said without thinking, I said, well, I don't know. I think I became an entrepreneur because I'm riskaverse. And she's like, does not compute. And upon reflection, I think I said that because I wanted to be more in control of things. I wanted to like control my environment, build a workplace I wanted to be in. Like when you go work at a

company, there's a lot of things out of your control that may be really suboptimal. And the other thing I'd say on the risk thing is that if you're in your 20s

and you go start something, the upside is massive. The downside is you got incredible experience that makes you probably more employable, probably makes your business school essay better. You know, it that riskreward equation can change once you have a big family and a big burn rate. But but certainly before you have those things, I think that people way overestimate how risky entrepreneurship is.

Yeah. And nothing's permanent either. I remember I was an entrepreneur right out of college and when I I got I was like 27 when I got my first corporate job and I thought I was going to be so behind everybody and I get into corporate and I was doing great in corporate even though I started as an entrepreneur. So you can kind of be an entrepreneur, go back, be an entrepreneur again. Like

there you go. It's nothing's permanent. Um, okay, cool. So, I end my show with two questions that I ask all my guests. Uh, the first one is, what is one actionable piece of advice that you can give our young and profits so they can be more profitable tomorrow? What is one piece of actionable advice they can do today to become more profitable tomorrow? I think if you look at all the money that you're spending money on, it will be pretty clear that there's 10% of those dollars that is essential that you can't touch and that there's probably 10% of dollars that maybe you don't need to be spending today. And then there's a lot in the middle. And so one way to be more profitable is simply to be a little bit more efficient with your resources. And I think that on a regular basis, look at all the subscriptions, all the software you use. Look at all the employees that you have and are they all like playing

at a high enough level? Like there are sometimes teams with 10 people that would be better with eight people

because coordinating things with eight people is easier than with 10 people and your highest performers get a lot more energy when they're surrounded only by high performers than with people that aren't as committed as they are. And so I think there are always opportunities to uh or there are often opportunities to improve profitability by asking questions like that.

I love that. And what would you say your secret to profiting in life is? And this can go beyond just business.

I think that it gets back to this ego and ego cracking thing. Like what I've realized is that and this is going to sound I don't know how it'll sound but what I've realized is like the more energy I can just put out there to employees to friends to our customers to the world just sending energy out without without a transactional mindset without expecting anything back the more energy comes back to me often in very unexpected ways and sometimes with great time delays like people that you know I did It's something business-wise 10 years ago where I could have optimized for the transaction, but instead I like

just made sure that they felt good about things coming back 10 years later with a new opportunity that wouldn't have existed if they felt anything less than great about our interactions. So, there's so many things now that I'm 50ish where just putting great energy out there on a routine basis, not being so focused on what is going to come back to you is the way to be. And uh I don't know, try it out. I think you'll see that uh the universe works in mysterious but wonderful ways when you do that.

Yeah, I mean it I hear you on that. Like basically optimizing for relationships and not necessarily the bottom line every time. I think that's so important as an entrepreneur,

but I think it helps the bottom line over the long term. Like those things can hurt the bottom line in the near term for sure, but over time it always comes back sometimes multiple multiple times over.

Yeah. Uh, Mike, where can everybody learn more about you and everything that you do?

Well, I encourage you to visit justworks.com to learn about our company because this is where I'm focused, but you can also see me on LinkedIn, Michael Seckler at LinkedIn, CEO of Just Works. And uh

but yeah, thanks for listening today. Thanks for having me on. Yes. Uh, it's really cool to be able to talk to you and thanks again for, uh, being a Just Works customer. I mean, you're a very successful entrepreneur and that you choose us means a lot to me.

Thank you. This is such an awesome conversation. Thank you for all your wisdom and thank you for coming on the show.

Awesome. Thank you so much for having me. Well, young and profiters, there you have it. What an incredible conversation with Mike Seckler, a true masterclass on resilience, adaptability, and leadership without ego. Mike reminded us that entrepreneurship isn't about getting everything right the first time. It's about developing what he calls intellectual stamina, the willingness to take a few steps forward, learn fast, and pivot without any of the drama. Growth happens when you move with curiosity instead of fear and when you stop treating course corrections as failures and understand it's just part of the process of being a successful entrepreneur. He also showed us what customer obsession really looks like. Even as a CEO of a $300 million plus company, Mike still spends time every single week and day talking directly to customers, joining sales calls, handling escalations himself from time to time.

Because when leaders lose touch with the people they serve, the company will lose its compass. So stay close to your customers no matter how big you get. Like Mike said, the edge of the balloon is where the truth lives. And I also loved his honesty about ego and energy. He said, surviving the dot crash cracked his ego wide open and that humility turned him into a better leader. The best founders don't lead from pride, they lead from purpose. They make hard calls with transparency. They protect their teams during downturns and they take care of themselves so they can show up calm and grounded for everybody else. So here's your challenge this week. Yeah, fam. Audit how you lead. Where do you need to pivot faster?

How can you spend more time listening to your customers? And are you managing your energy like the leader your business deserves? If you take just one insight from this episode, let it be this. Success isn't about avoiding the storms. It's about learning to fix things before they break. All right, young and profits. That's all the time we have for today and now I want to give a special shout out to one of our amazing listeners who keeps this community thriving, Muhammad J. Rasheed who shared, "I initially started following Hala on LinkedIn and then I started listening to her podcast. I enjoy listening to it and I always feel like I'm learning something new and getting value."

Muhammad, that's exactly why we do this, to bring value to driven learners like you. So, thank you so much for listening to the podcast. And if you want a chance to be featured in our next outro, be sure to drop us a five-star written review on Apple Podcast or Spotify and tell me what you're loving most about the show. All right, guys. Until next time, this is your host Halataha aka the podcast princess signing

Questions about this episode

Who speaks in "Mike Seckler: How to Build a Business That Thrives When Others Fail"?

Hala Taha (Host), Mike Seckler (Guest).

What is "Mike Seckler: How to Build a Business That Thrives When Others Fail" about?

Mike Seckler, CEO of Just Works, discusses the importance of resilience and adaptability for entrepreneurs and small business owners in a rapidly changing environment. He emphasizes the value of genuine company culture, customer loyalty, and strategic decision-making, drawing on his extensive experience navigating various business cycles to offer advice to young entrepreneurs facing challenges.

What is mentioned in this Young and Profiting episode?

10 people, works and ideas are mentioned, including Just Works, Mike Seckler, ADP, Workforce Now, Anne Winblad, Yap Media. Each one on this page links to its own page with every episode that mentions it.

How long is "Mike Seckler: How to Build a Business That Thrives When Others Fail"?

The episode runs 1 h 10 min; the transcript is about 13,930 words in 171 timestamped sections.

More from Young and Profiting

About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated February 3, 2026.