CEO and Investor Kurt Wilkin on Why Being a “Proud Mistake Maker” is Key to Business Success

CEO and Investor Kurt Wilkin on Why Being a “Proud Mistake Maker” is Key to Business Success


Check out all episodes on the My Favorite Mistake main page.

My guest for Episode #193 of the My Favorite Mistake podcast is Kurt Wilkin, a co-founder and CEO of HireBetter and managing partner of Bee Cave Capital. His bio says he's “coach, mentor, entrepreneur… and proud mistake-maker.”

Prior to founding HireBetter, Kurt founded and led The Controller Group (TCG), a professional services firm focused on accounting, technology and recruiting, which was acquired by Tatum in 2006.

He’s the author of a new book, Who's Your Mike?: A No-Bullshit Guide to the People You'll Meet on Your Entrepreneurial Journey. You can learn more at His quiz that he mentioned in the episode: WHOSYOURMIKE.COM/QUIZ.

In this episode, Kurt tells his favorite mistake story about not having a complementary “execution partner” to help him run a business. How (and why) did he adjust? Why did he step aside from the CEO role and what did he learn from this entire experience that serves him well today?

We also talk about questions and topics, including:

  • What does it mean to you to be a “proud mistake maker”??”
  • How do you try to create a culture where people can also be proud mistake makers? Leading by example?
  • Investing in people who are humble enough to learn…
  • Learning from mistakes vs. avoiding company-killing mistakes?
  • You’ve said that you saw your dad struggle as an entrepreneur. Were you able to learn from any of his mistakes?
  • You joined a failed startup in the dot-com bubble… any lessons learned from that?
  • Mistake to try to swing for the fences vs. lifestyle cashflow positive business
  • TELL US ABOUT THE BOOK: A business book for people who hate business books?

Scroll down to find:

  • Video of the episode
  • Quotes
  • How to subscribe
  • Full transcript

Find Kurt on social media:

Watch the Full Episode:


Here's a great two-minute clip:


"I very much have the belief that we learn best from our own stories, our own experiences, and definitely from our own mistakes — If we have the right attitude"    Kurt Wilkin
"I like to say 'the bigger the shit show, the bigger the lesson I'm gonna learn.' So it just allows me to learn." Kurt Wilin
"I think if, if we only look at our successes and pat ourselves on the back, we're never gonna get better." Kurt Wilkin
"The more I embrace my mistakes, the more authentic I become to myself and to others." Kurt Wilkin
"If you don't make mistakes, you're not trying, you're not growing. And if there's anything I could impart on my team and your team is to try make a mistake, learn from it, move on. If you don't make mistakes, you're not entrepreneurial enough, you're too safe. And if you don't learn from your mistakes, then we've got a bigger problem." Kurt Wilkin
"But I want you to make mistakes. I want you to learn from it. And I want us all to acknowledge, don't hide from your mistakes. If you hide from your mistakes, then you're a coward."  Kurt Wilkin

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Automated Transcript (Likely Contains Mistakes)

Mark Graban (0s):

Episode 193, Kurt Wilkin, CEO of HireBetter and Managing partner of Bee Cave Capital.

Kurt Wilkin (7s):

So, My Favorite Mistake, my biggest mistake is trying to do this without an operating partner.

Mark Graban (17s):

I'm Mark Graban. This is My Favorite Mistake. In this podcast, you'll hear business leaders and other really interesting people talking about their favorite mistakes because we all make mistakes. But what matters is learning from our mistakes instead of repeating them over and over again. So this is the place for honest reflection and conversation, personal growth in professional success. Visit our website at For more information about Kurt, his companies, his book, and more, look for links in the show notes or go to Thanks for listening.

Mark Graban (57s):

Well, hi everybody. Welcome To My Favorite Mistake. I'm Mark Graban. Our guest today is Kurt Wilkin. He is a co-founder and CEO of the company, HireBetter, and he's managing partner of Bee Cave Capital. So prior to founding HireBetter, Kurt founded and led The Controller Group, or TCG, a professional services firm that focused on accounting, technology and recruiting. It was acquired in 2006, and he's the author of a new book, it's titled, Who's Your Mike? The subtitle is, get This A No Bullshit Guide to the People You'll Meet On Your Entrepreneurial Journey. So you can learn more, or kurt

Mark Graban (1m 37s):

It's W I L K I N. Look for links in the show notes. So, Kurt, welcome to the podcast. How are you,

Kurt Wilkin (1m 47s):

Mark? I'm doing great, man. Thanks for having me. I love what you're doing to highlight mistakes and learning from 'em.

Mark Graban (1m 51s):

Well, thank you for that. I'm looking forward. It's gonna be a no bullshit conversation, right?

Kurt Wilkin (1m 57s):

I love it. I love it.

Mark Graban (1m 59s):

Now, you know, Kurt's bio says, I love this. It says, describes him as coach, mentor, entrepreneur, and proud mistake maker. So I you're you're in the right place.

Kurt Wilkin (2m 11s):

Hey, man, you talk about mistakes, I absolutely in the right place. So thanks. I feel like I'm in my second home.

Mark Graban (2m 16s):

Well, I'm, I'm happy you're here and look forward to talking about your book and, and other things from your career. But as, as we, we normally do here, proud mistake maker, what would you say is your favorite mistake,

Kurt Wilkin (2m 30s):

Man, you know, with the, the controller group that you just described. I had a partner and he was really the guy that got stuff done. And my execution partner, I was the idea guy, maybe decent sales biz dev guy. We had a great run, as you mentioned earlier, was a successful exit. When I bought HireBetter, I didn't quite appreciate how much Brett brought to the table and how much I needed that execution partner. So My Favorite Mistake, my biggest mistake is trying to do this without an operating partner. And boy, I spent five years beating my head against the wall until I finally re realized what I was missing and went out and found one.

Mark Graban (3m 10s):

Wow. So I think there's a lot to, to dig into. I mean, I appreciate you sharing the mistake and let, let's, let's talk about, you know, I, I guess first off, before, maybe this ties into how did you come around to realizing the mistake? I know you said it took five years. Like what, what were some of the symptoms? I mean, looking back at it now, what were some of the things that were going wrong or not happening without that execution partner?

Kurt Wilkin (3m 37s):

Yeah, you know, we, we were growing rapidly and I, I'm very open and honest about this in my book by the way. But very, we were growing rapidly at HireBetter, growing 30 or so percent per year, which is pretty good for a services firm, but we weren't profitable. And I kept telling myself, oh, we're just scaling. We're, you know, building for the future and, you know, all this crap that, and I'm not a very good manager of people or just manager of details. And I, I just kept telling myself the story that we were spending money as investments and really we were just pissing away a lot of money. So that was one. And we see that a lot with our clients. If you are reach some sort of plateau or if you realize you're just not profitable or maybe you could be much more profitable, those are generally symptoms.

Kurt Wilkin (4m 22s):

The other was, man, I had a list a mile long of projects I wanted to do, and why don't we do this and we need to start implementing this. And, you know, I just, I made the team like a five year old soccer team where you're kind of chasing the ball and really no true team. And, and it was just a bad leadership on my part. And, and maybe, maybe bad followership on their part, I'm not sure. Maybe they were good followers because they did what I asked them to.

Mark Graban (4m 50s):

So, tell us, I'd like to hear a little bit more of the context when you talk about buying the company. Was a founder still involved, or I'm just curious to know some of the dynamics of that transition.

Kurt Wilkin (5m 4s):

Yeah, yeah. Great story. Great, great question. So with the controller group, I founded it with, with partnered with Brett Lawson and Kathy Shrock. And then when I left there, I was really looking for what I wanted to do next. And there's a longer story, but the, the short story is I, I, I tried to buy a couple of companies that were more tech focused and not people focused. I was, I was tired of dealing with people, people suck. So wanted to find something that wasn't focused on people. And I realized at the end of the day, I'm not a tech guy. And I, I kind of stumbled upon HireBetter, and it was a, a recruiting firm, and I, I, they did things differently. And I think the recruiting industry's broken, but it was a very small firm at the time, there was a founder involved.

Kurt Wilkin (5m 47s):

I was going to buy it and put one of my former employees in charge, and I was just gonna be a chairman or, you know, passive investor. And after about six or nine months, months, I realized that the founder was as great as he was, and smart as he was, he was unemployable. And so we, we parted ways and I just, I dug in and, you know, five years later I look up and like, wait, I was supposed to be a passive investor. Yeah.

Mark Graban (6m 10s):

So you, I mean, you, you not only survived you, you, you said you were growing as this realization of the mistake or what was lacking really, really sunk in. Like, was was, was it a gradual recognition? Was there kind of a, a big aha moment and, and you know, either way, how did you adjust? Did you bring in that, that kind of person?

Kurt Wilkin (6m 35s):

Yeah, you know, I, I, I probably had a solid operating partner all along, but she didn't push back against me as much as she needed to, which I think you're strong, your operating partner needs to, so if I disagreed with her, even if I was super friendly about it, she would go along with it, right? And so we just didn't make, with Brett, we kind of fought a lot, but we always came up with the right answer no matter, you know, what the right answer was. And I, I dunno if it was gradual. I, I, I think the first three or four years you're like, Hey, we're just paying myself nothing. Credit card bills going up. And, and just the story I kept telling myself is, we're investing for the future.

Kurt Wilkin (7m 15s):

And then I looked up and realized we're, we're really not building something for scale. We're not building systems and processes and structure, we're just fighting fires. And that's probably the aha was like, oh crap, my credit card debt is, is through the roof. I'm not making any money. I'm busting my ass. And as I say in the book, I had built a lifestyle business for everybody but me. And that's a quote from a good friend who came in and, and dug in and, and, and tried to help us understand what our challenges were.

Mark Graban (7m 42s):

So you, you mentioned the woman that was working with you here as operating partner. Were you able to work with her so she could adjust? I mean, I dunno if she would come on and say her favorite mistake was not pushing back hard enough on Kurt. Was, was there a matter of making an adjustment or bringing in somebody different?

Kurt Wilkin (8m 2s):

You know, I, we probably, if knowing now or knowing then what I know now, I think we would've been able to adjust. But at the time, I think neither one of us really understood what was going on. And then later I read Rocket Fuel by Mark winners, and Gino Wickman, if you've read that book, it's a great book about the difference between the visionary and the, what they call an integrator. If I've read that before, it would've been eye opening and maybe we could have made some changes, but she, she actually had a chance to go back and run her family business, and it was a opportunity of a lifetime. And I, I certainly wouldn't have wanted to go in the way of that. So it really worked out best for all involved at the end of the day, and it allowed me to go find, you know, the right longer term operating partner.

Mark Graban (8m 44s):

Hmm. And so then how much longer has, has, has that person been in place? Is that playing out the way then the, the, the way you would've wanted?

Kurt Wilkin (8m 53s):

Well, it's, it's great that you ask Mark, because we've talked about favorite mistakes. Let's talk about a little bit deeper and I'll, I'll share what I can. So long story short, we were wasting money, as I mentioned before, were inefficient. And then we brought in an operating partner who came in and she was a great turnaround person. She cut costs, she right sized the team. We raised prices to be where we needed to be. We cut costs. We were very, very profitable for a couple of years under her guidance. But what I learned was she wasn't a growth partner, she was a, a turnaround partner and you know, there's a, a different person for every season.

Kurt Wilkin (9m 35s):

And I, I learned that, that she was great for that, but she wasn't great for growth. So we, we ended up parting ways and, and I'm so excited and happy that we worked together because she really saved our bacon. And then I brought in a friend from YPO who came in and did a great job on the growth side, and he had some health challenges. So he, he decided to step away. And then about two years ago, I brought in Ciscos Casa, who is, I liked him so much that he, I made him my CEO about a year ago, a year and a half ago. And so I've stepped aside from the CEO role, which is been really great for me to go do what I really enjoy doing and love to do, and not the, not run a run a company that's not my bag.

Mark Graban (10m 18s):

Yeah. So, you know, I mean, you know, our, our, one of our themes here on, you know, My Favorite Mistake is, you know, embracing the learning from the mistakes to not beat someone up for making mistakes, but, you know, to acknowledge them and, you know, so I wanna come back to that phrase you used of being a proud mistake maker. I was wondering if you could elaborate on that, like what that means. That phrase means something to me, but I, I want, I want to hear what it means to you.

Kurt Wilkin (10m 49s):

You know, I'm very, I, I very much have the belief that we learn best from our own stories, our own experiences, and definitely from our own mistakes. If we have the right attitude, and I like to say the bigger the shit show, the bigger the less I'm gonna learn. So it just allows me to, to learn. I've, I've tried to make that into a calling card, both for myself and this book. So it's really, this book is a series of stories from other other people. Hopefully you can learn from their mistakes and their stories, but I think if, if we only look in at our, at our successes and pat ourselves on the back, we're never gonna get better. And I'm a lifelong learner.

Kurt Wilkin (11m 29s):

I wanna, I wanna learn. And, and a couple years ago, I think I learned, mark, that the more I embrace my mistakes, the more authentic I become to myself and to others. And so that's really been my mo is try to tell people we all make mistakes. Everybody, your listeners aren't sitting there think thinking, oh my gosh, Kurt and Mark, they're perfect bullshit. We're so flawed, it's ridiculous. And I want everybody to know that, that they're flawed and that's okay. And it's what we, it's not the mistake we make, it's what we learn from it.

Mark Graban (11m 59s):

And so that, and that's powerful. And I'm, I'm, I'm curious, you know, with within HireBetter, or you know, previous companies that you were involved in, do you think being a proud mistake maker is part of that, to set an example for others, do you wanna create a culture, a team of proud mistake makers? Tell, tell us more about that.

Kurt Wilkin (12m 21s):

Yeah, you know, in my perfect world, we we're an entrepreneurial company and, and many of your listeners probably are too. And if you don't make mistakes, you're not trying, you're not growing. And I, if there's anything I could impart on my team and your team is to try make a mistake, learn from it, move on. If you don't make mistakes, you're, you're just, you're not entrepreneurial enough, you're too safe. And if you don't learn from your mistakes, then you're, we got bigger, you know, another problem. But I want you to make mistakes. I want you to learn from it. And I want us all to acknowledge, don't hide from your mistakes. If you hide from your mistakes, then you're a coward.

Mark Graban (12m 56s):

Yeah. So, I'm, I'm curious, you know, in your role now with Bee Cave Capital, how, how does that mindset that you have affect decisions on either making an investment or how you are involved in, in coaching or mentoring a company you've invested in? Are, are you looking for companies where, as you put it, there's a bit of a shit show? Is that an investment opportunity? To an extent.

Kurt Wilkin (13m 22s):

You know, I, I invest in people and if the people are hum humble enough to recognize their mistakes and, and, and be a learner, that's one thing. If it is a shit show, which, which some of them can be, I try to, I try to avoid because that just means it's, sometimes it's too hard. But if, if a, if a founder is, you know, the type mark, they're too proud of themselves. They're the smartest person in the room. You, you're, they kinda look at, poke their nose up at you. If you have a, you know, Arkansas Benner in the background, cuz I went to Arkansas, you know, I want to be around people who are willing to make both make mistakes, but then also accept that they do make mistakes.

Mark Graban (14m 7s):

And I mean, it sounds like there's a, a matter of degree, I'm curious to hear your thoughts on the idea of there are small mistakes, early mistakes that you can learn from, that you can build upon. But here's what I, I would propose wanna hear your reaction, the idea that we're gonna learn from mistakes and embracing that doesn't mean we can do any wild, irresponsible, stupid thing. It's like, well, I'll learn from it. Like how, how do you find the balance between, let's say, you know, embracing and celebrating relatively small learning experience mistakes versus avoiding looking to avoid something that would say a mistake that tanks a company.

Kurt Wilkin (14m 44s):

That, that's a great, great point. And I, look, I'm not sitting here saying everybody just make mistakes all day long. That's not what I'm saying at all. But let me, let me tell you what I tell my boys. I've got three boys and they're all in their late teens, early twenties. Now what I tell them is, I want you to make mistakes. I'm here to help you make mistakes, but I'm also here to help you not make the life altering mistakes. So that's what you're talking about, you know, getting somebody pregnant or getting in a drunk in a car with a drunk driver. You know, things that are gonna change your life in a negative way. Those are the mistakes to avoid kinda the same thing with your team. If it's a matter of, you know, saying yes to a 10% discount to a client all day long, if you, if we don't like it, we'll talk to you later. But to, you know, hide something material from a client or from from us is big mistake.

Mark Graban (15m 31s):

Yeah. Before we talk about the book, and again, our, our guest is Kurt Wilkin. The book is Who's Your Mike? You know, two other things stood out to me, you know, from, from your bio, Kurt, when you talk about learning from other people's mistakes or learning from mistakes, you, you, you talk about seeing your dad's struggle as an entrepreneur first off, and then you talk about being part of joining a fail, what turned out to be a failed startup in bubble. I'm, I'm wondering if one or both of those, you know, I guess observing your dad and living through that in a way, like how, how did that influence your view on mistakes or help you as an entrepreneur and investor?

Kurt Wilkin (16m 14s):

Yeah, I, I may have interesting stories for both. Lemme start with my dad. My, my dad was probably the smartest person I know, but my dad was, was very, very cheap. And he wanted to, he wanted to do everything himself. And so the mistake that he made was not have an operating partner like I've talked about, or really being, being too proud to, we're not proud enough to, to delegate some of those other tasks to people who are better than him and frankly, a lot cheaper than him. And so he struggled. It's hard to be a, a one man entrepreneur if you're not delegating anything. And I honestly, I don't think I learned that until much later in life. But now that I kind of put two and two together, that's definitely a lesson learned on the other.

Kurt Wilkin (16m 59s): just the biggest lesson there was, it heyday, late nineties, early two thousands, and we were a licensed sports product. We're selling on the internet or e-commerce licensed sports products like COOs and has and t-shirts, whatever for football, baseball teams. And we, we raised 5 million bucks on the back of a napkin. We, we launched and we knew we needed to raise money in late, late 2000 or something like that. And I was, I was not on the board, but I was like the finance guy sit around the board meetings and we were needed to raise money and all the board members were like, no, we're not gonna raise money until we're a million, a hundred million valuation.

Kurt Wilkin (17m 40s):

And there was one board member that says, guys, if we can raise money now on a 20 million valuation, let's do it. Because you never know when this thing's gonna dry up and everyone I'll poop. You know, this is things going on fire, we're gonna a hundred million. And as you know, the, the, the bubble burst and we ran outta money, couldn't raise money. So just a lesson learned that sometimes, you know, take, you know, never know what tomorrow's gonna look like.

Mark Graban (18m 5s):

Yeah. And it seems like there's, you know, a lesson you brought up earlier this, this question of spending money to invest in the future versus trying to become cash positive or at least break even. I mean, you know, there, there's, there's a big, I'm I'm, I'm curious how you think through this big decision for a startup or a company that is still growing really quickly, how do you think through this question of really, let's say swinging for the fences as some people might put it versus saying, well, we're stable and we can fund our growth, but we might be growing smaller there, there it could be a mistake one way or another, right?

Kurt Wilkin (18m 48s):

Yeah. You know, honestly, I think that's a, a choice for the founders and, and the investors. What I mean by that is there are times when I working, you know, 20 hour days for two weeks straight where I'm like, well, why don't I just make a lifestyle business and, and just make this a cash cow and live happily ever after? And I see people doing that, and on the one hand I'm envious of them. On the other hand, I, I wonder what they could do if they, if they did the other, and we, we made the choice to grow as fast as we could and, and build it and sell it with tcg, HireBetter. We're, we're just, we're trying to grow and be a successful company, but it's not necessarily a lifestyle business, it's just we're not trying to grow it to flip it.

Kurt Wilkin (19m 30s):

So it's a choice, I think. Yeah. And it's not for

Mark Graban (19m 33s):

Everybody. Yeah. But when, and there, there's, it seems a dynamic when, when a founder or founders bring on investors now, it's not strictly their decision anymore.

Kurt Wilkin (19m 42s):


Mark Graban (19m 43s):

Your investors hopefully are aligned with what that decision's gonna be. Right.

Kurt Wilkin (19m 48s):

And I, I'm glad you said that and I wanna make sure that, that folks know that when you bring on investors, you are, treat it more than more sacred than you would your own money.

Mark Graban (20m 2s):

So with the book with Kurt, you know, you describe it as a business book for people who hate business books. Do you, do you generally hate business books? You mentioned one that you really liked, but,

Kurt Wilkin (20m 14s):

You know, well, I wouldn't tell Mark Winters and do you know what to their face? But I think just the first three afters is phenomenal. The best. Right. The rest of it, eh, you know, and that's generally how I feel about a lot of business books. I, I believe even when I was writing this book, you know, my, my friends said, Kurt, you need to write a book about networking and connections and whatever. You're so good at that I'd read that book and I'm like, guys, I got 30 pages of that and then the rest of a 200 page book, I'm just making full of stuff full of crap. And I think that's what a lot of people do. They've got a nugget, really cool nugget. They wanna get out there and they have to fill a bind to sell a book. And there are good ones out there. Don't, please don't get me wrong.

Kurt Wilkin (20m 55s):

So what I tell people is 20% nugget treat mine the same way, 20% nugget. I, i, I wrote it in ways that you could really divide each chapter. Say I wanna read a chapter about a legacy employee you outgrew that's in finance or accounting. Well that's chapter one. If you wanna read about the big swing and you know what sales guy you're bringing from the outside who's puff full of puffy and never gonna deliver, that's chapter seven. That's pipeline Paul. So each chapter is a different archetype that you're gonna meet on an entrepreneurial journey. And it's just a fun way to learn these stories from o from other people's successes and failures.

Mark Graban (21m 30s):

Yeah. So I know that's one thing you focus on is, you know, kinda thinking about the role of certain key employees as a company grows or, or progresses, use this phrase where, you know, yesterday's hero might become today's liability. Can you, can you share, you know, kinda what, what, what's, what's a common situation there? Somebody who is, how common is it where somebody's a great fit for let's say the very early days of a startup? Everyone's gotta do a little bit of everything. And as, as opposed to getting into a mode now where it becomes a little bit more, if you will, professionalized and certain functions where you maybe want expertise as opposed to being able to do the jack of all trades or Jill of all trades.

Kurt Wilkin (22m 14s):

You just nailed it. Everybody who's an entrepreneur has or will have that challenge. And as you're getting off the ground, you need people with that entrepreneurial grit that will roll up their sleeves and do anything you need to go visit a major customer one day. You need to go sweep the floors the next day. You need to whatever the next day. Those are great guys and gals to have when you start. And not to say that those folks can't grow into your VP of finance or VP of sales or whatever it is down the road. It just doesn't happen that often. And it's, as you grow and, and really go to try to scale, to use that term, you need that specialization in certain areas.

Kurt Wilkin (22m 57s):

And not that you can't do it, I, I like to tell people, if you've got a six person leadership team and you're all going through this for the first time, you're gonna learn a bunch of lessons the hard way. But if two or three of you have done this before in their, you know, with similar type company, you're gonna, you're gonna get there faster and more efficiently with fewer heartaches. Yeah.

Mark Graban (23m 18s):

And you know, we've had a few guests on the show here frame their favorite mistake as, you know, a hiring mistake or not reacting to their perception of a mistake quickly enough. What, what's your advice if you've hired somebody look great on paper, you thought it was gonna be a great fit, and then early on you think you're, you're starting to have second thoughts. Like when, when do you sort of lean in and try to coach your way through it or, or fix the situation versus realizing it's a mistake? There's really no real good option other than finding somebody different?

Kurt Wilkin (23m 55s):

Yeah, I'll, I'll say a couple of things. First, there's a book out there called Hire Slow Fire Fast, which is a great thought. You know, hire slow, make sure that they're a good fit, both with their experience as well as your skill set and fit into your culture. And then when you realize that it's not, then, then terminate quickly. The caveat is did you, did you set 'em up for success? And if, if you didn't, then there might be an opportunity to do that. And if you did, obviously move quickly. The other thing is Mark, look in the mirror, there's a epilogue to the book called When You're The Problem, the last chapter of the book is called, when You're The Problem, you could have the best candidate of all time, they're a perfect fit, but if you can't get it outta your own way and get outta their way, you're gonna be in this followed cycle for, for years.

Kurt Wilkin (24m 47s):

So that's where you need to learn some lessons yourself and acknowledge when you might be the problem.

Mark Graban (24m 52s):

Yeah. And it might not even be a matter of a pattern then you might really say, well, hmm. If if somebody says, you know, I I keep hiring people who don't work out, if there's a pattern then that maybe points you more in the direction of looking in the mirror and and deciding who the problem is. It's probably harder to figure that out if it's a newer business and there's not yet a pattern that's been established. If it's the first time where it could become a pattern if you don't learn from it and adjust, it seems like that would be a harder situation to diagnose or come to terms with.

Kurt Wilkin (25m 29s):

Yeah, but even still, we all have stories we tell ourselves about why so and so didn't work out and you know, we have a story for each one. The, the thing I wanted to mention, one of the common ones for your entrepreneurial companies and and listeners is in sales. So as an entrepreneur, oftentimes we are the main sales agent, the main rain rainmaker, and we can sell because it's our baby and we can overcome objections, we can change prices, we do whatever we want, right? And we bring in a salesperson and we, we, we just say go sell without giving them the tools and the case studies and the marketing collateral and the system and the CRM and all that stuff.

Kurt Wilkin (26m 9s):

And they try to sell like we do and they struggle. And so we get frustrated. So then we try to get a more, you know, get somebody from Dell or some big company and they come in and they can't sell you what you're doing either cuz they're used to selling big company, they can't sell your well crappy startup. So it's, that's the biggest challenge many of our, our clients have in many of your listeners probably have.

Mark Graban (26m 32s):

And that's a situation I've seen. Right? So I've, I've worked for two startup companies, both were founded in, in Austin and the, the, the one company, this is going back to 2000, 2001, it wasn't, it was more of an enterprise software startup. So there were different dynamics, but there, the company churned through a lot of sales people. And I recognized the one issue of someone who had come from a bigger, really successful company who was seen as more of a order taker and that didn't translate well into a startup. And I, you know, that don't mean that's a sound Well no, I guess that phrase was used in a disparaging way of like, well, and it didn't mean that it was a bad person.

Mark Graban (27m 19s):

I think it was more a matter of bad fit.

Kurt Wilkin (27m 21s):


Mark Graban (27m 22s):

And then one of the people, back to, back to the subtitle of Kurt's book here, the people you meet in your entrepreneurial journey, one, one of those salespeople that didn't work out was of the big swinging bleep variety people can fill in. They know the phrase, I don't want to have to tag the episode as explicit maybe. Well you already said

Kurt Wilkin (27m 43s):

It, but I'm sorry, I'm sorry.

Mark Graban (27m 44s):

No, it's fine. Yeah, it's not, it's

Kurt Wilkin (27m 46s):

Not that bleep out.

Mark Graban (27m 47s):

No, that's my mistake. Getting hung up over that. But this, this guy, this guy was a jerk and was abusive. You know, I was working in like a sales engineer role. I'm not trying to turn this into a counseling session, but like, there's this question at one point, at what point are there behaviors that are just not acceptable compared to are you delivering or not? And this, this guy had a Super Bowl ring and that was his, I dunno if you've run across if this is one of the people you've met, but I I think he, he banked a lot on that Super Bowl ring was gonna impress people and it didn't always work out that way.

Kurt Wilkin (28m 21s):

Sure. I, you know, not this specifically the super Superbowl ring, but everybody or a lot of these guys and gals have a proverbial Superbowl ring they're swinging around with, with stuff. Yeah. Yeah. It's interesting, you, you mentioned, what kind of things might they do that make them, maybe you didn't quite say this, but not a good culture fit. Maybe they're successful financially for you, but they're not a good culture fit. That's a that's another question you have to come across. You have to answer for yourself, are you willing to put up with it? And the good salespeople are gonna have an edge and they might not be the same docile, you know, personality that your office manager has. And that's okay because you don't want that as your salesperson.

Kurt Wilkin (29m 2s):

So man, it's, this ain't easy, let's just put it that way.

Mark Graban (29m 6s):

There's, there's a lot of room for mistakes. But again, as, as you're emphasizing Kurt, and we try to focus here on the podcast, you're gonna make those mistakes, but admit them, learn from them, don't repeat them. That seems to be the

Kurt Wilkin (29m 19s):

Key. Love it.

Mark Graban (29m 20s):

Love it. So one thing I wanted to ask about the book, you know, it's kinda a broad statement related to the book where you're saying, you know, the, the modern workplace is a dumpster fire. So more specifically, like what, what are the biggest sparks of said dumpster fire in a modern workplace? The, the fire starts somewhere somehow.

Kurt Wilkin (29m 40s):

There's just a lot going on, obviously with the, the out output of the, of the pandemic and, and with this whole great resignation and now this quiet quitting and, and work from home, work from the office. If you read Tim Ferris's four Hour Work week, that's a bane of a lot of entrepreneurs existence, you know? So we're just trying to deal with people, as I said before, people suck, but also the most beautiful thing in the world, but it's hard to wrangle, you know, and build a good team.

Mark Graban (30m 11s):

So this, this phrase I'll, I'll ask you before we wrap up here, quiet, quitting. Is that a real thing or is that bullshit? Is that a bullshit phrase?

Kurt Wilkin (30m 18s):

Well, I don't know who, who trademarked it. You know, the guys at TikTok do a great job with that, but, you know, I think it's been going on for years and, and we, we probably have a lot of it in our organization and you do too. They're just kind of coasting is the way I, I put it. And like I mentioned with Tim Ferris's four hour work week, those, he, he basically encourages people to work as little as possible on they, you know, but have as much fun as possible. And on the one hand, I'm, I'm envious of those guys that, you know, take every Friday off and don't work on the weekends and don't pick up their laptop after 5:00 PM And so who's, who's to blame 'em. On the other hand, if I'm paying you for a full job, I I wanna get a full job. Right. What your full effort during that time period?

Mark Graban (30m 59s):

Well, and there's a question, how do we define full? Is that a 40 hour work week does a startup environment require, does, does is the, is the bare minimum for that? What might be considered above and beyond in, in a different workplace, kind of an older, bigger corporate setting versus not being a co-founder, but being an early employee, are you willing to, to grind or hustle or, you know, all these different words that are used to really, to really make that succeed? Or is it just a job?

Kurt Wilkin (31m 30s):

Yeah, I think you said it, if if you're gonna be working for an entrepreneurial company, you better have a little bit of that, that hustle, as you said. And it's not a, it's not a lifestyle, it's not a, when I say lifestyle, it's not a nine to five is not a 10 to four or whatever, you know, kind of term you can use. But it's also tremendously fun and exciting and, and you might have an exit. And so there's, there's lots of good things that come with that as well.

Mark Graban (32m 1s):

And then the other phrase, you mentioned the great resignation. There's some people saying, well, that's been going on for a long time as well. Do you agree or is that a new, are there elements of this that are a new dynamic?

Kurt Wilkin (32m 12s):

You know, I think it's kinda like quite quitting. It's a great buzzword that gives press clippings. It has the number of people who have resigned and has been increasing over time. So that's not new. What happened was, during Covid there was a big stop. Everybody, no one moved. Everyone was afraid to move. And so then the next year it was just exacerbated by so many people that, that were really looking for something new. So what they are looking for, we, we do know this, what they're, for the most part, generally speaking, they're looking for purpose, they're looking for, for mission. They're looking for a place that has values that align with them. So that part has been growing and is here to stay. I believe a paycheck is obviously needed, but it's not the only thing for most people.

Kurt Wilkin (32m 56s):


Mark Graban (32m 58s):

And, and back to the subtitle of your book and the, the, the title of the book, again by Kurt Wilkin, Who's Your Mike? A new a no, A new, that's my most recent mistake, not a new bullshit, a no bullshit guide to the people you'll meet on your entrepreneurial journey. And it sounds like you've described some of those people, some of the people you'll meet, share the passion or willing to put in, you know, a lot of work to grow a business and there's some people you meet who are just in a different place looking for something that is not as demanding time wise. And, and as with all things, I'm sure it's a matter of just finding the right fit for the right situation, whether you're that job seeker looking for a change or an entrepreneur looking to hire for your team.

Kurt Wilkin (33m 44s):


Mark Graban (33m 46s):

So Mike, well, or Mike, another mistake. This is a Friday afternoon podcasting adventure. I've long gotten over trying to edit out my mistakes, but the author and our guest is Kurt Wilkin. The book is Who's Your Mike, I'm gonna try to say it correctly this time. A no bullshit guide to the people you'll meet on your entrepreneurial journey. And I've had fun saying no bullshit. So Kurt, it's been fun having you here. I really appreciate everything you have to share today.

Kurt Wilkin (34m 15s):

Hey man, mark, thanks so much for having me. I really appreciate you applauding and the, the, the concept of the mistake and help people that learn from it and being okay with that.

Mark Graban (34m 24s):

Well, thank you for being okay with it, leading by example and, and sharing your stories. Really Appreciate it. Thanks again. Awesome. Well, thanks again to Kurt Wilkin for joining us today to learn more about him, for links to his own website, his book, his companies, and more. You can look for links in the show notes or go online to As always, I want to thank you for listening. I hope this podcast inspires you to reflect on your own mistakes, how you can learn from them or turn them into a positive. I've had listeners tell me they started being more open and honest about mistakes in their work and they're trying to create a workplace culture where it's safe to speak up about problems because that leads to more improvement and better business results.

Mark Graban (35m 7s):

If you have feedback or a story to share, you can email me And again, our website is

Mark Graban is an internationally-recognized consultant, author, and professional speaker who has worked in healthcare, manufacturing, and startups. His latest book is Measures of Success: React Less, Lead Better, Improve More. He is author of the Shingo Award-winning books Lean Hospitals and Healthcare Kaizen, as well as The Executive Guide to Healthcare Kaizen. He also published the anthology Practicing Lean that benefits the Louise H. Batz Patient Safety Foundation, where Mark is a board member. Mark is also a Senior Advisor to the technology company KaiNexus. He is also a Senior Advisor and Director of Strategic Marketing with the healthcare advisory firm, Value Capture.