Pursuing an Acting Career After His MBA: Matthew E. May’s Favorite Mistake

My guest for Episode #39 of “the My Favorite Mistake” podcast is my friend Matt May, he's a multi-best-selling author and he's Chief Strategist with his firm Stratechia.

I've known Matt for a long time as a former University of Toyota educator, a Wharton graduate, and an amazing author. I've interviewed him many times before. I didn't know that he was formerly a theatre and television actor (including a stint on a soap opera — I don't have video clips of that).

Today, we talk about a few of his favorite mistakes:

• Not taking the traditional high-paying job after completing his MBA
• Leaving New York City for Los Angeles in the pursuit of his acting career

Matt and I also talk about mistakes more generally — when are they “happy mistakes?” Were there any acting gigs that were mistakes? How should we think about mistakes, as individuals and as organizations?

Update March 2023 — Matt has co-authored a new book, What a Unicorn Knows: How Leading Entrepreneurs Use Lean Principles to Drive Sustainable Growth available now — Watch my interview with him and Pablo Dominguez here via my Lean podcast.

You can listen to or watch the episode below. A transcript also follows lower on this page. Please subscribe, rate, and review via Apple Podcasts or Podchaser! This podcast is part of the Lean Communicators network.

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Automated Transcript (May Contain Mistakes)

Mark Graban (0s):

Episode 39, Matthew E. May, best-selling author and chief strategist at Stratechia.

Matt May (8s):

I was the only one to reject one of those nice high paying salaries that everyone else took.

Mark Graban (20s):

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 and professional success. Visit our website at myfavoritemistakepodcast.com. For links, show notes, and more, go to MarkGraban.com/mistake39 and now on with the show. Hi, welcome to My Favorite Mistake. I'm Mark Graban.

Mark Graban (1m 1s):

And today we're joined by Matt May. He is a recognized thought leader on business strategy, human centered innovation and lean operations is influenced by nearly a decade, spent as a full-time advisor to Toyota. And he's the author of five books. Books I've really enjoyed. They include the best selling “The Elegant Solution,” “The Laws of Subtraction,” and “Winning the Brain Game.” He's had articles in publications like the New York Times, HBR, and Fast Company. He has an MBA from Wharton and Matt is a founder of Stratechia, a Los Angeles based strategy and innovation firm. So with that, Matt, welcome to the podcast.

Mark Graban (1m 43s):

How are you?

Matt May (1m 43s):

I'm doing good. Thank you, sir.

Mark Graban (1m 46s):

So we'll dive right. And I'm sure you've got a good story for us. What is your favorite mistake?

Matt May (1m 53s):

My favorite mistake or best mistake is, is one that you actually just mentioned. I have an MBA from Wharton, pretty prestigious business school, always up there in the top five or so. I graduated too long ago to, to count the years. I want to just put, we'll put it at the mid eighties, but of the 750 or so graduates of my class. I was the only one to reject one of those nice high paying salaries that everyone else took. The at the time there were two industries that were probably the hottest one was investment banking and the other was management consulting.

Matt May (2m 41s):

I had worked as a, my summer job in between the two years of business school and the strategy department of a large pharmaceutical company and being a wise and wizened 25 year old. I just knew that I would die a slow and horrible death trying to claw and scratch my way to the middle. And so come graduation. I rejected all offers. I headed to New York with only an inkling of what I wanted to do other than become an actor and everyone, everyone that I knew, my parents, my grandparents, my classmates recruiters, you name, it told me that I was making the biggest mistake of my career.

Matt May (3m 32s):

If not life, why would you spend all that time and money going through two years? First of all, getting into Wharton was no easy feat completing the program. Why in the world, what what's going through your brain and just, should we check you in somewhere? So that is my that's my favorite mistake. And we can unwrap that a bit too. That's just the beginning of the story and how I got from there to here, if you want, or I'm going to leave it up to you.

Mark Graban (4m 1s):

Well, I mean, it seems like the first follow-up question is, did you feel like it was a mistake at the moment or at any point, if, if from people's outside judgment, that seemed like a mistake. You were following a path that you were clearly really, really interested in.

Matt May (4m 19s):

Yeah. I mean, mistakes. I think you can only identify mistakes retrospectively unless I miss my guess. So going into, I mean, we all go into things, not thinking that we're making a mistake. I had doubts for sure, because when you've got smart people and an influential people and, and all the world is moving left and you want to go, right? You think, well, what, well, maybe they're right. Maybe I should, maybe it's not too late. Maybe I should pick up the phone and, and, you know, Hey, I changed my mind. So I don't know that I thought it was a mistake, but I sure did have doubts.

Mark Graban (4m 60s):

And so then I don't know if I even, I mean, I think I remember a mention of, of you doing some acting. So how did that, that step? I wouldn't even call it a mistake, but that, that unconventional path, at least that first step out of Wharton, how did pursuing acting then lead to advising Toyota? I assume you, weren't giving acting lessons to Toyota executives. If, you know, forgive me joking, but

Matt May (5m 30s):

No. Well like many of the things in my life, it's probably a series of, of happy mistakes. If you look backwards on it, I'd love to tell you I've made grand strategies and plans, but almost everything that has happened that's of a good thing in retrospect has been a happy accident. So when I moved to New York city, I only had a few dollars in my pocket. I had enough probably for three months of, of lieu of living there in the summertime. I thought, well, gosh, if it doesn't work for these three months, if I can't get something going, I do have an MBA from Wharton and I will fall back on it. At the same time, I recognized a couple of opportunities.

Matt May (6m 11s):

One of them was to start my own educational consulting practice as a way to feed my foray into theater. What do I mean by that? In my second year, year of graduate school, as part of a work study and financial assistance program, I worked in the office of admissions. My job was to interview wait-listed candidates. Now, if you don't know anything about getting into business school back then, it's a little different than it is now. But back then, yeah, you have to take, you know, you know, a GMAT and a score, but really what they wanted was two years of experience beyond college.

Matt May (6m 53s):

So you didn't, you didn't leave college and go to a top 10 business school. It just wasn't, it wasn't go straight through. Yeah. And there was a Fairly healthy waiting list of candidates and understanding what then was behind the application process, the admissions process and what the admissions committee was looking for. You know, it was my job to read the dozen or so essays. I thought that I'm in New York City, there are a host of investment banks that have these two year analyst programs where they send their best and brightest to business school, to the best business schools.

Matt May (7m 33s):

And they come back at a higher level, you know, and, and, but, but that's dependent on them getting into one of those great business schools. So having that insight, I approached all of those associated analysts, junior analyst programs, basically in that training and education department of Solomon Brothers and Merrill Lynch and Lehman Brothers. And all the names that you know, are kind of merged now and said, listen, I will help your, your folks that you're sending off to business school, complete their applications as an advisor. I'm not going to write the rest of these for you, but I can lend my insight into what makes a good essay like that.

Matt May (8m 15s):

And that began my, that was how I, I made money that allowed me to pursue acting on the side. I did spend some time on TV and in commercials and in theater until I moved out here to our coast, the West coast, four years later, it Al it actually allowed me to write a book. It's a little known book, obviously out of print, but in 1990 at book called “The Admissions Guide to Selective Business Schools” came out. I had been one of those lucky folks that had gotten into the Harvard and Stanford's and Wharton's of the world. And so I had the both sides of, of the writing side and the review side. And that's how things began.

Matt May (8m 55s):

I sold that to a educational company. I was also teaching Stanley Kaplan, GMAT in the evening to support, to support myself and moved out here to the coast again, with no plan in mind and what we can pick up on that. But if you had a question on that path, that's how New York City worked out.

Mark Graban (9m 17s):

So you were able to pursue that path. And you were, you were getting by, is that the right phrase to use from these side gigs you were happy with at that point? It didn't feel like a mistake to you?

Matt May (9m 33s):

No, I wasn't waiting tables. Wasn't starving. Yeah. I wasn't waiting tables. Wasn't starving. Wasn't bartending. I, you know, I, it allowed me to have my own schedule. I could go on calls when I needed to. I met mostly in the evenings with, with these candidates and I made a trip out here to the west coast, 4th of July in 1989. And I decided I better move out here because I had just sold the practice, sold a book. What better time? It seemed like a turning point. I flew back to New York city, packed out my apartment, drove out here within a week and started all over. And the first thing I did was connect with my Wharton alumni network, met up with a company and a gentleman by the name of Dave Power, JD Power and Associates, the founder, and one, that was my foray into the automotive industry.

Matt May (10m 26s):

And I freelanced my MBA here on the West coast with JD Power and Associates with a number of performance improvement, consulting companies merits other big, huge companies that serve the automotive industry until 1998. When I got a weird phone call from Toyota,

Mark Graban (10m 46s):

That wasn't a mistake on their part. They meant to call you, right. How was that a happy, you know, that it was a different happy mistake. You, you, you, you take that call when it comes in, right?

Matt May (10m 59s):

Yeah. And I knew that gentlemen, and, you know, I had to be working under someone else's banner with Toyota and the University of Toyota, which was a newly formed entity as I was about to find out. But the phone call went something like this was just before Christmas. And the phone call went, something like this, Mr. May. My name is so-and-so. I am newly appointed Dean of the associate college of education, the University of Toyota. It's, I'm one half of the two-part university. We are getting together after the new year and a three-day offsite to figure out what we want to be, but is this a strategic initiative on Toyota Motor Sales part?

Matt May (11m 40s):

It's one of a seven prong strategy to move into the new era. We want to figure out what we want to be. When we grow up as a university, as a corporate university, we've made rounds and studied the best Crotonville and, and you know, Disney, et, etcetera. But we're not sure what we're all about. We were looking for the best possible facilitator we can find, unfortunately, he's not available. We heard you might pay. And that was the happy accident that began along a long run of, of over eight years. So,

Mark Graban (12m 14s):

So in your teaching and advising at Toyota, I know you learned a lot from that experience and, you know, Toyota is well-known for the Toyota Production System and an approach to management. That's often copied. I don't know how well emulated it is, but there are attempts to copy it. I'm wondering what are your recollections about Toyota's mindset around mistakes, as much as you can generalize cause you, one of the themes here in the podcast is learning by making mistakes. And when we try to improve our running experiments and trying new things, inevitably things don't work out and we could call those mistakes.

Mark Graban (12m 58s):

But I'm curious how that thought process might've worked at Toyota.

Matt May (13m 2s):

Yeah. And you know, my experience is outside of the production environment, but the challenge was, it was kind of a weird challenge for me in the, and the first challenge they gave me when, when something like this, we need to figure out a way to bring the creativity that's found on the manufacturing side of our business, into knowledge work. Because at the time, the end of the 1990s, there were roughly, if you were to count up all the A3s, you know, that had been printed and shared, there were probably upwards of, I dunno, 700, 750,000 of those per year being generated. The lion's share of those were in their production environment.

Matt May (13m 43s):

That included not just only factories, but that included logistics and warehouses and places like that. And the University of,

Mark Graban (13m 52s):

Sorry to interrupt. Can you do a quick verbal footnote for listeners or viewers who might not be that familiar with Toyota and A3 is in a nutshell, sorry.

Matt May (14m 1s):

Yeah. You know, an A3 refers to a paper size back in the day, an idea, or a piece of communication or a strategy was fit on the biggest size paper that would fit through a fax machine. Back then that biggest size was the international paper size of an a three. It is now, you know, short of shorthand for, and I always ask people that use A3s in their companies. Do you know what an, a three actually refers to? And no one knows. Yeah, but it, it is in the world of Kaizen or continuous improvement. One form of A3 is a story of a team they're going to call it as you know, they're, you know, they're affectionately referred to some, in some places in Japan as Kaizen newspapers, but it's on one sheet of paper, there's an art to folding it, but it tells the story of, of a, of a theme or a problem, what the conditions of that problem are, what the analysis of the causes of that problem might be, what the alternatives in terms of concepts and solutions and ideas might be to counter that problem.

Matt May (15m 10s):

And then a plan for experimenting with that solution, which lands us on the doorstep of mistakes because in the, in the, in the world of Kaizen and continuous improvement, lively well in Toyota and other places following World War II, it was all about small nested experiments done as, as close to the frontline, as you can, before you went nationwide or company wide or department wide on anything, you would ask the question, you know, what would have to be true for this to be a good solution on a broader scale. And you would test out the weak parts of that solution, get proof of concept essentially.

Matt May (15m 52s):

And the difference between an experiment and a pilot would be, we're trying to make sure this isn't a bad idea rather than, Hey, this is a great idea. How will it spread? So the weird project for me was how to get the creativity out of the factory and into the knowledge side in the United States, Toyota motor sales is one of a number of distributors if you will, of Toyota products that are made in the United States and everywhere else, but they were basically the marketing arm, sales and marketing arm, the major one in, in the US so when I say knowledge working about sales, marketing, HR, legal, finance, all of the things that are, that are kind of outside production.

Mark Graban (16m 34s):

Yeah. And, and it's funny, I mean, you know, I've started my career in manufacturing as an engineer, and you'd think there would be a perception that people in quote, unquote knowledge work would be more creative than I did in the factory. That would be a stereotype or maybe incorrect perception, but that might've meant that would be a mistake to think that.

Matt May (16m 53s):

And th well, that's why I thought it was weird because I'm like, well, wait a minute. You know, how guys putting on a windshield wiper all day long? How creative is that? And meanwhile, I got these guys doing projects, you know, in sales and marketing, and they're doing these grand, you know, marketing campaigns and they're one-off, and nothing's the same thing. And they're project based. And well, lo and behold, there was sort of a fear of failure on the knowledge side of the business, where there didn't exist on the production side of the business. So there was an, it was a hearty challenge and it took several years. And I was, you know, I've told you this story before, but there came a point midway in that eight or nine year run, where I was ready to walk out the door because I was ready. You know, I just threw up my hands in the air.

Matt May (17m 34s):

I just didn't know what to do. You know, a couple of epiphanies happened, but so back to your question, you know, in the kind of sales and marketing world, there wasn't that embrace of, of failure. You know, the old fail fast and learn mentality was not there. My client, the Dean of the university saw that as an opportunity to really carry out the mission of the University of Toyota, which was to spread and emboldened the tenets and philosophies and the methods and practices that had brought Toyota, w w M was bringing them to, and they hadn't been, become the biggest yet, but certainly it was the halo years of Toyota as an automaker.

Matt May (18m 17s):

So it was an interesting, interesting project to have.

Mark Graban (18m 23s):

Yeah. And you also do a lot of strategy work, and I'm curious, maybe as a final topic to dig into here, when, when a company invents a new product line or pivots, or goes in a new direction, I wonder as much as you can generalize or what your perceptions are, how often is that really planned versus it's some sort of mistake, it's a discovery that couldn't really be put into a five-year plan as something, well, in year four, we're going to innovate and do this.

Matt May (18m 57s):

Yeah. So that's kind of a loaded question because I had another happy accident happened to me, that concerns strategy, you know, and I'll try and short cut the, the story, but I hated strategy and business school, the way it was taught, it was very left brain. It was very, let's start with an analysis squat, right? Strength, weakness, opportunity, and threat. I didn't like that. I didn't like, and strategy was synonymous with a plan or a documents that told who was going to do what by when, with what resources

Mark Graban (19m 32s):

Logical well-reasoned mathematically determined market research driven plan. Yeah.

Matt May (19m 36s):

I hated it. It just wasn't creative to me. It was, I have, I have an underdeveloped left brain. I have an overdeveloped right brain. I didn't like it. I didn't like it until I ran into a gentleman by the name of Roger Martin. And we met each other 11 years ago when we had a book out at the same time, his was called The Design of Business. Mine was called. It was my second book. It was called In Pursuit of Elegance, a business book. BusinessWeek had recognized those two, those books with a passel of others as being worthy of mention for creativity and innovation and in organizations. And we got to meet each other that way and maintain sort of an arm's length appreciation of each other.

Matt May (20m 18s):

Obviously mine for him, more than the other way. He's, he's a brilliant guy. He, he helped run monitor rope was the Dean of the Rotman School. University of Toronto. He's now retired, but he taught me a new way of strategy is called playing to win what he used to advise Proctor and Gamble. And that simple framework of what's your winning aspiration, where will you play? How will you win? What capabilities do you need and what management systems are required. And then what would have to be true for those choices to be successful. And how will you test out your assumptions was an epiphany to me on strategy. So from 2012, to now, I have a completely different view of strategy than a plan.

Matt May (21m 1s):

Plans are great. There's a place for them. But when you say strategy to me, it's about the choices that you make not necessary, not necessarily the plans that you make plans may be explicit about those choices, but more often than not, they don't, because they don't tell you the important part of strategy, which is the things that you choose not to do. They imply them, but they're not explicit about it. So when you ask me, well, how many times is it an accident? I don't know. I have been doing a great deal of work with venture backed, small companies, startups, and more often than not, you know, the work in the garage is no one has a plan.

Matt May (21m 47s):

They're forced to create a plan to get venture backing. They, they have, they have identified a problem. They believe they have an elegant solution for it. And they have a passion for bringing that solution to the world that more than anything drives them. And they're in a constant iterative mode until they get to the point where they need that maturity and discipline, where someone's going to throw money their way. So I get to see a lot of those companies and it's super refreshing. Do they have a plan? Yeah. Do they have a strategy? Usually not usually. Not, not in the way that that I've come to define strategy.

Mark Graban (22m 26s):

So if people want to learn more, they can Google Roger Martin “playing to win.” Good, good. That's a good topic to dig into.

Matt May (22m 34s):

Absolutely. Yeah. The book is called Playing to Win. It's probably eight years old. He, he's always, there's a thing called thinkers50.com that has the, you know, top 50 thinkers. And he's always in the top. He's always got a podium position. I think he was number one or two years ago. Maybe dropped down to number three or something like that. But brilliant guy got a new book coming out, Mark that you and I should probably talk about it because he really takes to task the whole notion of efficiency as the wrong way to go incorporate it.

Mark Graban (23m 4s):

I, I wouldn't, I wouldn't disagree with them. I would rather use words like effectiveness and other.

Matt May (23m 10s):

Yeah. It's an interesting, it's an interesting book. I'm not sure what to do with it. He's asked me to take a look at it and do something that I'm not sure what it, because half of me says, well, gosh, I don't know that that's maybe my own bias is being revealed. Hmm.

Mark Graban (23m 26s):

Well, we'll, we'll, we'll take a look at that again. At some point when, when that book is out and we'd be good to chat about that as we wrap up here, I'm going to hit you with kind of an odd ball question here on, on the question of mistakes. And you mentioned acting, give me, I'm gonna try to hit you and get an honest answer. Any acting gigs that you took that were mistakes because he ended up hating the role or the project?

Matt May (23m 51s):

No, but I will tell you that the acting mistake that I did make was leaving New York city for the west coast. There's a, this is kind of off topic, but since you asked in New York City, there is more of an artistic intention purpose about acting. You go to acting classes a lot, you take, you take dance classes, you take improv classes, you try and develop yourself as an artist. When I moved out here and as you know, being a West coaster, we're in the shadow of Hollywood and everyone wants to be famous. I don't care about the art of it. And I realized when I moved out here that I had probably made a mistake leaving New York City.

Matt May (24m 33s):

I wasn't ready to do that. I ended up ditching my acting bent and habit within three or four months of moving out here and never looked back. Have I used that skill? Absolutely. I speak a lot. I facilitate a lot being in front of people, being kind of raggedy sometimes and in front of people is doesn't daunt me. So that answer, I guess that's an okay question. I mean a good, it was an okay. Answer to your good question.

Mark Graban (25m 6s):

That's right. Questions. Don't always lead to sometimes the direct answer. Isn't the best answer. So that's interesting, but you, you call me a west coaster. This is still very new for me. And when I see driving around LA is what? 90% of the billboards, at least, or about this new show, this new movie, it's all, it's all just, Hey, watch this, Hey, vote for this and these awards. So that's, that's my observation for being here. Not a mistake to move out here to LA so far by, by any means, even though I clearly I did not come out here to pursue acting or being famous. Good.

Matt May (25m 42s):

There are enough starving actors out here,

Mark Graban (25m 44s):

I think. Gosh, so, well, Matt, Hey, this has been a lot of fun. Thank you for, for, for doing this. And let me put you on the spot to talk about mistakes. Our guest again has been Matt May. He's the founder of Stratechia. Matt, what can people do if they want to learn more about the firm, give us the website.

Matt May (26m 5s):

It's Stratechia.com and that's spelled, it's kind of a mashup of strategy and technology with an Italian flare. So S T R a T E C H I a.com. And you can find me on LinkedIn as well. I write articles there and on medium.com. So give me a search.

Mark Graban (26m 22s):

Yes. Your techie pronounced differently. Sounds like a delicious flavor of gelato, right? Or a mispronounced flavor of gelato. I'll take a scoop of Stratechia. And so, Matt, thank you. Thanks again. We'll talk to you soon.

Matt May (26m 40s):

Thank you. Bye bye.

Mark Graban (26m 42s):

Thanks for listening. I hope this podcast inspires to pause and think about your own favorite mistake and how learning from mistakes shapes you personally and professionally. If you're a leader, what can you do to create a culture where it's safe for colleagues to talk openly about mistakes in the spirit of learning, please subscribe, rate, and review the podcast. Our website is myfavoritemistakepodcast.com. See you next time.

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