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Welcome to the Jason and Scott Show. This episode is being recorded on Friday, October 10th, 2025.
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I'm your host, Jason Retail Geek Goldberg. And as usual, I'm here with your co-host, Scott Wingo.
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Hey, Jason, and welcome back, Jason and Scott Show listeners.
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Well, Jason and listeners, we have a real treat for you on today's episode.
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Jason and I have both known Kevin Ertel for about 15 years each.
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So that's about 30 years by my calculations, Jason.
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Yeah, it probably fell longer to Kevin.
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It did. It probably felt like 60. We get a 2x multiple. The two of us together are a lot to handle.
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And we'll get into his amazing career. But what's really exciting is he has
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a book dropping, and we were able to get him, due to that 60-year relationship,
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on the show to tell our listeners about it.
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The book is called The Strategy Trap, Why Companies Fail at Execution and How
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to Get It Right. Kevin, welcome to the show.
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Thanks, guys. Great to be here. It's been a bit since I was last on and I'm excited to be here.
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Yeah, yeah. We had the interns looked and they couldn't find it. It's been that long ago.
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Yeah.
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It predates recorded history.
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Yeah. It was chiseled on a tablet somewhere. We'll have to dig it up, literally.
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Yeah. So as you alluded to, Kevin, this is not your first time on the show.
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If memory serves, the first time you were on this show, you were with Sir LaTabla
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at the time. Is that correct?
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Yeah, that's right. It was, yeah, back in 2015, I guess. But yeah,
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a few things have happened since then.
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Yeah. And weirdly, our careers like overlap and coincide for many years before
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that, which maybe we'll explore another time.
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But as we always like to do on the show, kind of remind the listeners what your
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e-commerce journey was prior to writing the book.
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Yeah, I mean, I spent most of my career in retail. I started,
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you know, on the very ground floor as a clerk at Tower Records.
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And I really had all my formative years there. I spent 20 years at Tower Records,
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started as a clerk and left as a senior vice president and led the team that
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built the first TowerRecords.com, you know, when it was mostly people on dial-up modems coming in.
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And I remember, you know, kind of obsessing about the image sizes that,
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you know, would download quickly.
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And fun fact, Tower Records was, of course, like an icon, a public pop culture
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icon, but it was run by one guy that owned 100% of the company and it was wildly successful.
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And he, inside baseball fact, he did not like ties.
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No, he did not.
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And so if you were so silly as to show up in his office wearing a tie,
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he would cut it off and pin it to his wall. And I know this because one of my ties is on his wall.
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Oh, I don't think you ever told me that. You got your tie cut off.
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Yeah, and I was totally punked. My co-workers who sent me like a lamb to slaughter at this meeting, like,
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I guarantee you were completely aware of what was going to happen and like,
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led me to believe that I should wear a tie to meet the billionaire owner of Tower Records.
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Hey, you know, I mean, a lot of people consider that a badge of honor to be
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in that case of ties. So congratulations to you on that for sure.
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I'm certain it was not the nicest time. So I distracted you,
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but of course, beloved, beloved music store featured prominently in a lot of
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America's greatest movies.
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Yeah. And I mean, just it was the greatest company to work for.
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I absolutely loved my time there.
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But, you know, as you said, it came to an end. So then I went to Borders,
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you know, which was still doing really well at the time. And I first went there
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to lead the building of the loyalty program, Borders Rewards,
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and then also led Borders.com.
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Did that for a while, left there and moved on to the vendor side for a little
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bit as the VP of retail for 4C Results, a company that measured customer satisfaction.
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And so I worked with more than 100 retailers and helped them understand customer
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satisfaction and how to respond to what they learned about what their customer
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experience was and how to make it better.
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From there, I went to Online Shoes as a CMO, got me to Seattle and moved on
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to Sur La Taub from there when we talked.
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And at Sur La Taub, I ran digital, but also marketing and technology for a while.
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And then I moved to Nike and I spent seven years at Nike, three different jobs there.
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Initially as sort of the GM of the digital business for the running category globally.
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Then I led global online or global digital operations. And then the last job
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I had there was leading global retail operations. So stores,
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a little bit of a full circle all the way back to that.
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And Kevin, for all of our young listeners that only wear contemporary shoes,
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remind us what Nike does.
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Yeah, right.
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You know, a few shoes, a little apparel, sweatpants, that sort of thing.
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That's a great idea.
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Yeah. You've heard of it?
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I have. You could probably have a mild success in that industry.
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Yeah. Seems like it did pretty well. They've done well for themselves.
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As long as you don't hire any eBay people to run it.
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Oops.
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This is where I'm going to go no comment.
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Fair.
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Pleats the fifth pretty early. This may be a record. Yep. Okay. I have to get this.
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Yeah. I'm going to have to on that one.
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And then after I left there, I started Mystere Advisory, a consultancy where
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I focus on three things, helping people with strategic execution,
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which we'll talk more about.
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I do executive coaching and also do some advisory work with a variety of different
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companies, software companies.
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And all that's led me actually to what I'm doing right now also is working with
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the Minnesota Timberwolves and leading the ticketing business there.
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Oh, neat. I didn't know that. That's new information.
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Breaking news for.
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Me and all of this is a side hustle for your main gig which is a musician is that correct.
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That is correct yes all supporting that yeah still playing music all the time
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and working on getting a new band together here in cleveland and of course you
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guys i think have been there we play that gig every year in new york right after
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right as part of nrf and we'll be doing that again this year at the cutting
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room in new york looking forward to that that.
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Is the The best event at NRF when I can stay up late enough for it.
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Yep. Drink your coffee. Have an extra one.
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That is a safe bet. And I believe you've even passed the music bug on to the next generation.
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Oh, it might. Yeah. Not so much in my house. They listen. They don't play.
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Awesome. So we want to jump into the book, but before we get too deep,
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just please tell me it's not a deep dive case study in all of my failures.
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Absolutely not. In fact, you do appear in the book as a kind of a hero, really.
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Yes. So, it's a fiction book. Awesome.
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It's entertaining reading.
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I was certainly entertained. So, before we jump into the content of the book,
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like, Like, you know, Scott, Scott kind of alluded to it in the intro.
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What, what inspired you to write a book?
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Is it the money?
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Yeah, right. I had thought about it for a long time.
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And, you know, I've been writing blogs for a while and sort of got a few people
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had said I should write a book.
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And I finally just decided, you know, to take that seriously.
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And then I really had to think about what was a topic I wanted to write about.
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And something that I'm really passionate about is the fact that,
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you know, most strategies fail. And there's a lot of data about that.
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And the number one reason they fail is poor execution.
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So I really wanted to focus on that. And, you know, I mean, there's a million
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books about strategy and how to write a strategy, but there's not that many
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about execution, funny enough.
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And most of the ones that are out there are written by consultants and academics.
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And so I wanted to write this really from an operator's perspective and really
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somebody who's sort of been there and has the scars from it.
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But I also didn't want to just make it, you know, my perspective.
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So I interviewed more than 60 operators, people who had been there and done
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that across a ton of different industries. I actually started in retail,
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but as I started to ask people who they knew who were successful executors,
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it just sort of passed me on.
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And before you knew it, I was talking to people in just about every industry
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you could imagine, you know, in content, media, tech, healthcare.
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I talked to a guy who does like public utilities in Australia,
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you know, so really kind of covered the gamut.
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And what I found in doing that is it just was a lot of commonality in the things that work.
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So that's what got me really inspired to kind of make this a book to put it out there.
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Cool. One of the things I like about it is how you structured it.
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So you've got kind of two chunks, you know, phases, phase one,
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setting the stage and phase two, showtime.
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And then you go through basically, you have six C's and each one is basically
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a C word and how you and then a trap that kind of goes along with it.
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So for example, I'll just pick one.
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Part two, clarity, escaping the complexity trap.
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Part five, coordination, closing the silo trap. And the reason I like this is
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this, it's kind of book, some books you read once you're like,
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okay, I had some good takeaways.
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And then others, like one of my favorites is this Ben Horowitz book called Good to Great.
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And it's, it's kind of similar where it's like a collection of case studies
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so you can read them linearly.
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But then you're always like, what was that case study? Oh yeah, it was in that book.
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And then you can jump right to it. Cause I, cause I feel like people could read
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this and then be, they, a lot of times you don't know you're in the trap or it's coming.
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So, so I think they'll, they'll get into the trap and they'll be like,
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I think I'm in one of those things Kevin was talking about.
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And they'll look it up and be like, oh crap, I'm in the ivory tower trap.
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And then, then you give them, you can like help them get out.
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So I think that'll be handy when, when people actually get their hands on this.
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Was that intentional? You try to make it a reference and a read?
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Yeah, totally. I mean, I very much wanted it to be practical.
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So I wanted to make sure that there were lots of how-tos in there and lots of
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things that you could take away and go execute right away, you know, kind of make it happen.
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So very much wanted to make it easy to reference, different sections that you could go to quickly.
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At the end of every one of those parts, there is a checklist that you can use
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to kind of go through and kind of see how you're doing and rate yourself.
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So yeah, I wanted to make it super usable.
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Yeah, I can even see, I've been in companies where we do little book clubs,
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and this would be kind of a good one for an executive team or even a team to
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kind of have as they felt like they weren't being as effective on the execution as they wanted to be.
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You should do the reading club follow-up. That way you can sell another book.
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Yeah, I love it. Let's do that.
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The workbook. so you kind of stated this but just so listeners can tie it together
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i'll ask the question what is the strategy trap.
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Yeah i mean the strategy trap is when leaders get kind of obsessed with the
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idea and even the presentation the idea maybe the slide deck but they don't
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spend nearly enough time focus on creating the conditions for the people on
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the team to actually bring that strategy to reality.
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And that is the fundamental problem that sort of leads to all the other traps.
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How do, so I've always had this trouble, this challenge.
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So I'll, I'll talk to them blue in the face about our vision and I'll even tie
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it into, you know, the plan and everything.
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And then we'll do these employee surveys and now everyone's always like this division isn't clear.
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I'm like every quarter I go through this, like, why is this not landing?
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What am I doing wrong, Kevin? Which trap am I in?
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Well, I mean, you know, this, the vision is only part of what you need to execute.
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So that in the end it's you know this you want me to go through the six c's
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would it help to kind of give the big picture yeah yeah.
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Let's let's hit the c's.
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You know you talked about the two phases setting the stage and then and then
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uh show time but in setting the stage the sick the first three c's are co-creation
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clarity and capacity and those three are super super critical Co-creation is all about, you know,
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bringing the team at multiple levels within multiple functions in to help develop
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and create the strategy.
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And what you get out of that when you do it that way is, you know,
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alignment and buy-in. You get people really kind of owning it a little bit.
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You get validation to make sure that this plan that you're putting together
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is going to be workable. And then you get commitment.
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And so partly people are sort of fully understanding the strategy then and then
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really buying into it and really saying, I'm ready to go.
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Clarity is about simplicity and it's about meaning.
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So it's about helping people understand it, but really understand and connect
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their personal meaning to it, which really helps retention right on it.
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And then capacity is super critical you can't
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just drop any new strategy on top of people's existing work
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and just expect it to get absorbed within and and so that becomes a real problem
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if you don't do that so taking the time to create space for it really really
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matters those are all setting the stage that gets you set to kind of move into
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showtime and actually start to go on this thing and so the three c's there are
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communication coordination and coaching,
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communication you know is an is a non-stop thing so to your comment a little bit.
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I actually heard this. I was at a Nike conference a few years ago,
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and Kara Lawson, who's the head coach of the Duke women's basketball team and a former WNBA player,
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she talked about her concept she tells her players of early, loud, and continuous.
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And she's talking to them about that in the context of basketball you know hey
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like you got to tell people if a pick is coming get there early the arena is
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really loud so you've got to be loud and you got to continually talk about it
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because they didn't hear it the first time,
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and i think that applies to when you're communicating a strategy to get in there
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early talk about it even before that vision or the idea was was fully formed
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you know so people can understand the why,
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but then be loud, talk about it in every forum, in every way,
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and in every different method you can think of.
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And then continuous matters because you can't stop.
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There's like this thing called the Ebbinghaus forgetting curve that says people
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forget 90% of what they heard within 30 days if it's not reinforced all the
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time. So you kind of have to do that.
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Coordination then is about having checkpoints and just ways along the path to
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make sure that you're sort of organized and implementing this thing and people
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understand the why and what their component of it is at any given moment and
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how it fits in the big picture.
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And then the last but not least is coaching, which is a component of leadership,
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but not all of leadership. It's a specific one about creating culture and how
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do you do motivation and incentivizing people to do the work.
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But all of that reinforces the vision that you're talking about at the beginning.
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So I find having that structure across all those six C's helps people understand
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the vision better, helps them understand their role in executing in that vision
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and reminds them and motivates them along the way.
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Yeah, I think I'm already stuck in the first one. So you can't just tell people
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what to do and they just do it like the whole.
00:16:24.724 --> 00:16:25.204
Yeah, not so much.
00:16:25.624 --> 00:16:31.284
I was going to say, like, I didn't want to pick on Scott's incredibly successful managerial style.
00:16:31.284 --> 00:16:35.364
But when he did that survey and they said the vision isn't clear,
00:16:35.644 --> 00:16:39.724
what they actually meant is they didn't get a chance to co-create that vision.
00:16:39.864 --> 00:16:41.064
And so they weren't committed to it.
00:16:42.484 --> 00:16:45.084
It is entirely possible. Exactly.