Michael Alter, Clinical Professor of Entrepreneurship at Booth School of Business

Michael Alter, Clinical Professor of Entrepreneurship at the University of Chicago’s Booth School of Business, joins J.R. Lowry on our first episode to share his career story and the things he learned along the way. Michael talks to J.R. about how his bachelor’s degree in economics from Northwestern University and his MBA from Harvard Business School equipped him with the skillset he needed to jump into the startup world. He takes us on his experience as a consultant in McKinsey & Company and the lessons he brought with him that helped him fulfill his roles as the Chief Executive Officer of The Tie Bar and SurePayroll. Michael’s career success continues to serve as an inspiring feat for young dreamers of today. Join us in our first episode as Michael talks about his childhood dream, his first job, and advancing his career through business school.

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Michael Alter, Clinical Professor of Entrepreneurship at the University of Chicago’s Booth School of Business

This is a new series, one I’ve wanted to do for some time. I am delighted to welcome Michael Alter, who I’ve known for too many years. Michael is a Clinical Professor of Entrepreneurship at The University of Chicago Booth School of Business. He is also a three-time CEO, a member of multiple boards, a fundraiser for the Juvenile Diabetes Research Foundation and he’s married with three children. Michael, welcome. It’s great to have you here.

J.R., thanks for having me.

Thanks for being the first guest and being willing to be the guinea pig. Let’s get into it. You’re from Highland Park in the Chicago area. When you were young, for a little bit of fun, what did you think you wanted to be when you grew up?

After I got past the fireman and policeman phase, I wanted to run a business at some point, whether that was as an entrepreneur or an operator. We had a family business growing up. I got to see that and hear about it around the kitchen table. That was what I knew.

From fireman, policeman to CEO, that’s the natural progression for most kids. What was your first job?

I was a schlepper. That was the official title. I worked for a wedding and bar mitzvah photographer in the Chicago area. I would carry the lights before the big weddings and events and set them all up. I schlepped all the boxes, so I was the schlepper.

How old were you when you were doing that?

I was fifteen and old enough to be able to get a job. I was very much interested at the time in photography. There were 2 or 3 photographer “studios.” I walked in and said, “Can I work for you?” One of them hired me and it turned out to be something that I did all through high school. I went to college in the Chicago area. I did it through college and it helped to pay for a portion of my education. It was a great experience.

Is photography something that you still do?

I do some but not to the same degree that I did. I progressed and became a full-fledged photographer working for this company. It became a little bit too much of a job and not as much as an avocation, which is a little unfortunate.

That’s always the challenge with things that you love to do. Are they better off as a hobby, not as a job? It’s something a lot of people wrestle with when they’re trying to decide whether they want to make a hobby into a career. You went to Northwestern and studied economics. Why did you pick economics?

Part of it was I wanted to do liberal arts and I was also interested in business, so economics was a natural fit between those two. It’s a happy medium. I almost had a minor in US History too, which I was also interested in.

You went to work at IBM. How did you decide to go to IBM? What put you there?

When I was leaving, it was not where I was thinking that I would end up for my first job. I got some great advice from a mentor and family friend who said, “You’ve got to learn to sell. Go get a job that teaches you to sell.” I was fortunate at the time to get an opportunity from IBM when they had a strong sales training program. Fundamentally, it was foundational for me and my career going forward. It’s like a mini MBA.

Speaking of MBAs, you went to business school. What drove your decision to go to business school? Something a lot of people in their twenties wrestle with is getting an MBA as something that they should go do? What factored into your decision?

For me, it was a little bit of advancing in my career a bit more. I could have stayed in the sales organization at IBM as an account marketing rep which means I was a salesperson. I moved up that career ladder but I wanted to be a bit broader than a salesperson. There’s nothing wrong with being a salesperson but I was looking for more responsibility and opportunities. Going back and getting an MBA helped that. For me, the bigger question was, “Do I go part-time or full-time?” It turns out that some of that is based on the choices you have in front of you. Having gotten into Harvard to get my MBA felt to me like a no-brainer.

Looking back, was it a good investment for you? It’s expensive. A lot of people question whether the top business schools are good investments anymore.

I teach at one of the business schools, The University of Chicago. For me, it was hugely worthwhile in so many ways. A lot of my career is a bit of the Chutes and Ladders and left and right. The foundation that you get from getting an MBA in a school like that is helpful. The other thing is it’s like a Grade A union card. Nobody can take that away from you. As you try to take some more risks and be more entrepreneurial, you can always get a job because you have that stamp.

You chose one of the traditional post-business school paths and went into consulting. In your case, it was McKinsey. How did you decide to go to McKinsey after school?

I could tell you a great fancy story about how it makes sense and how this next career step was to go do that but the reality is my wife was a year behind me in business school. It was expensive to be in business school. We didn’t know what city we wanted to be in when we graduated. I had a choice between consulting firms that pay you a lot of money and if you leave after 1 or 2 years, your story is, “I didn’t like to travel.”

Nobody ever questions it. I could have been a research assistant at school and stayed another year. I would have hated that. I took the opportunity that helped me pay for my MBA. It was right in front of me and I would figure out what my options were later. To me, the fascinating thing was I figured I would leave within 12 to 24 months and I stayed for almost six years because I enjoyed and learned a ton. I didn’t get there on a fancy path.

What are the key things that you took away from your time at McKinsey?

I took away a series of things but the biggest one is structured thinking and structured communication. I can be put into a situation where I don’t know what is going on and be confident that I can ask enough questions and get up the curve enough to understand what decisions we might want to take or not take. Also, more importantly, to structure the thinking to understand that there are a hundred things we could do. These are the three that matter and to get there quickly.

Entrepreneurship: You’re not always supposed to have all the answers. That’s not the best way to run a company. Instead, you should listen to your team and understand what ideas and what advice they have.

That skill set has helped me as well. It’s helping me now, being in a new place, coming up the curve, learning how to build relationships and getting a handle on what matters the most.

I also joke, I’m good at PowerPoint now, too.

Do you still have a copy of Say It With Charts or The Pyramid Principle? Those are a couple of McKinsey standbys.

I’m sure I do.

You jumped into the startup world and went over to SurePayroll during the dot-com boom. You were there at the beginning.

I was there at the beginning. It wasn’t my original idea. There were three other folks that were starting it and I became the fourth person. One had the idea. They were more senior serial entrepreneurs that had done well and were looking to mentor some folks to build the business. I was brought on to get customers and my partner was brought on to do the operations and technology. It wasn’t a company when I joined. It was an idea.

That’s about as different as it gets from being in a big strategic consulting firm but what was that transition like for you?

It was jarring. I had been entrepreneurial in college. I mentioned the photography piece. I did my own photography business and some real estate photography and things. I knew what it was like to be on your own. [McKinsey was] six years of working for a big company with all of the resources and leverage that you have. On the first day [at SurePayroll], I got to figure out how to set up my email and do everything all over again with limited resources. In the first month or two, I was looking at myself in the mirror going, “What the hell did I do?” Once I got past that, it turned out to be a great opportunity for me.

Did you foresee that you would end up as CEO a few years later?

At the time, I didn’t. It was the four of us. We were a band of brothers marching forward. We didn’t care about titles and it didn’t matter. It was only as we moved forward and had some institutional money and venture investors that the more formal structure seemed to take hold.

What do you think it was that put you in that role?

Some of it is luck, happenstance, timing and a bunch of other things. The reality is that the two original founders who were already successful didn’t want to run the business full-time. They wanted to move to the board. My partner had left the business after about eighteen months because he’s a startup guy. He likes that early-stage bubblegum and Band-Aid stage. Now, he’s a successful venture capitalist in the early-stage stuff and it’s where he belongs. We brought in an outside CEO from a public company into a business with 18 to 20 people and it was an absolute disaster. She left relatively quickly on and it became my problem at that point. I was not a great CEO when I started.

What are the things that stand out for you that you learned about being a CEO with a growing enterprise?

There are a couple of things. One of the biggest things I learned as a CEO is a little different than what I was taught or what I thought, which is that you’re always supposed to have the answer. You ought to be able to rule on high and say, “We’re going left. We’re going right. Here’s what is happening.” What I learned was that it’s not the best way to run.

I needed to listen to my team and understand what ideas and advice they have. Once I hear some perspectives, I can decide if I’m going to make a decision, if I’m going to leave them to make the decision, or if I’m going to let the decision play out a little bit longer. It was a hard thing to realize that as the CEO in control, it doesn’t mean you have to steer the bus all the time.

A lot of founders and CEOs of companies, as they grow, hit a point where they can’t do that anymore but they’re still trying to. It becomes an issue for the company when they try and keep too much control over things even as it gets bigger.

Culture and managing people that are not McKinsey consultants is a different game. Thinking about how you manage, motivate and drive a business forward with a myriad of people that you have that are diverse, are bringing different perspectives, and are critical to the company is different than an environment where you’ve got a relatively narrow set of folks who are all going to work as hard as they possibly can no matter what.

In some ways, being an engagement manager at McKinsey is an easy job. It’s a lot of hard work but everybody who is working for you is going to knock themselves out.

It’s figuring out how you motivate and get the best out of your teams. People are motivated differently, whereas, in my previous jobs, they were relatively similarly motivated.

How did you do that? What worked for you?

To me, it was a lot of listening and understanding what matters to different people, letting the people know that they mattered and we cared. Some of these things are simple and it’s amazing to me that people don’t do it as much.

As an example, if someone was doing a great job in the payroll business, the year-end is busy. Our Head of Implementation would work tremendous hours to make things happen. I could give her a bonus and we certainly paid people well but I knew that she was a fan of country music. We paid up and got her third-row center tickets to her favorite artist when they came to Chicago. There’s a limo, a hotel and a dinner and she took her husband. There’s no way she’s ever leaving us because we understood what mattered to her and figured out how to deliver that.

She would never have paid for that herself if you gave her the money.

We created these memories. I’ve found that a fabulous way to motivate people. We had a senior technologist that we sent to Disney World with his family. On and on the list goes. I’ve found it to be a great way to motivate and manage people because it shows you know them and you do what matters for them.

Entrepreneurship: Being the CEO doesn’t mean you have to steer the bus all the time.

You had to weather some downturns in there too. There was the dot-com bust in your first year and then the financial crisis years later.

Don’t forget almost going bankrupt before that, not having to do with any of that stuff. I joke that being an entrepreneur is it’s not “up and to the right” until you’re done and then you can tell the story. It’s a heartbeat. My experience was certainly that. We were raising money on Sand Hill Road the week in March when the NASDAQ fell at the end of the dot-com era 1.0 happened. At the beginning of the week, everybody would talk to us. People were going to get us term sheets. We were the coolest thing they had ever seen. We flew back home early on Thursday morning because nobody would talk to us by the end of the week.

I remember that period well. It was a crazy week and one of several weeks like that which we have had in the past twenty years. You were CEO until 2014. You sold the company to Paychex, a larger provider of payroll services. What drove the decision? Why then?

We sold the business in 2011 and I ran it as a division for them after that. As you’re growing the business, at some point, you’re hopefully making the right decisions for the business more so than anybody else and what is right to grow and build this business. We all believed in what we were doing, the clients we were serving and the people we were creating jobs for. Our biggest opportunity was we were in this huge market but nobody had ever heard of us. We did a bunch of research and learned that when we got to compete for a deal, we won our fair share.

Even if we won our fair share, it was a good business. We won against our competitors way more than we lost. The problem was there were so many deals happening where nobody had heard of us. We weren’t at the table. We had an awareness problem and the question was, how do we generate more money to drive awareness? We were in a little bit of a box that we could spend money on marketing and awareness but it was only based on the cash we generated. We generated some cash and were running this as a profitable operating business with real margins and real constraints like every business. Then we stepped back and said, “How do we scale this? What do we need to do?”

The reality is we needed more money to drive awareness. Some of that was marketing, some hires and a bunch of different things. It made sense that the natural owner of this business was not us in our capital structure. It’s a question of who is the best owner. When we put the business out to get a new partner, we looked at private equity and strategics. I don’t think it’s surprising that the strategics wanted to pay a lot more than private equity. You would have to ask the folks at Paychex but [I think] they’re quite pleased with their acquisition. Going on years later, it’s a good business for them.

You built a lasting enterprise.

Quite honestly, it feels pretty cool.

Most people can’t say that.

There are a ton of people that built that. Success has many fathers and mothers.

What led you to The Tie Bar, your second CEO gig?

It’s a natural career progression from a B2B payments business to a B2C consumer men’s accessories business online. [Smiles.] It’s not even close. Part of it was when we sold SurePayroll, I was trying to figure out what I wanted to do next. I didn’t feel that the right long-term place for me was in a larger company. I have nothing against Paychex, which is a great organization I have a lot of respect for. It just wasn’t where I was going to get my energy from going forward. I had gotten involved in some other businesses. I had a friend from business school who was the senior partner on the private equity firm that had bought The Tie Bar.

We always wanted to work together. He asked me to get involved and coach this young CEO they had hired, so I did. I was on the board and engaged in the business. They weren’t thrilled with the results and the execution. One weekend they asked him to leave and called me up and said, “Do you want to run the business?” I was thinking, “When else am I going to get time to completely change my career from business-to-business payments and software to consumer internet?” It seemed interesting to me. It was an interesting growth story at the time, brand and business, so I jumped.

How did that second experience differ from the first one?

The start was obviously different because it was an existing business that was generating cash and making money. Having said that, the size and scale of the actual business were much smaller than I expected or was the right place for me longer-term. What I mean by that is we had logistics and a significant number of people in our warehouse but the best answer there unfortunately for those folks, was to outsource it.

I joined a business with 100 employees and within 4 to 5 months, we were down to 12 or 18. We rebuilt back from there and [focused on] the areas that were growing and scaling the business. [The] founder and his wife who built the business had scaled it with them and a lot of worker bees. We didn’t have an infrastructure.

A lot of my time was building out the people and the technology, expanding us into retail stores and things like that. After a period of time, the business became a fashion and marketing-focused business. The things that I love to do like the go-to-market stuff, sales stuff and partnership stuff, weren’t a big part of the business.

It wasn’t a place I was going to get a lot of energy from in terms of what they needed and the right thing was to keep scaling the business going forward. There were skillsets I didn’t like. I’m not that fashionable. We transitioned the business over to our Head of Merchandising, who became the CEO. She did a great job and her first love is that stuff. That’s when I transitioned out.

You took some time off and then went in for round three.

The biggest lesson to me in that transition or in some of those things is that there’s an old saying with venture businesses and startups, which is, “Do you think it’s the horse or the jockey that makes the business?” Is it the market or the horse or is it the jockey or the team? I used to believe that if you had a great A-plus team, they would figure out how to move you into the right market. Therefore, you want a great team. I’m now a firm believer that I want to start with a great market first because it’s way better and easier when you’ve got so much open runway to run.

I certainly don’t want a bad team but to me, the market is the first thing. I think about payroll and the opportunity in payroll for small businesses in that market and opportunity. We were primarily a tie company when I joined The Tie Bar. Nobody wears a tie [anymore]. It’s a lot harder in a shrinking market. That was a big lesson for me about where to where to go.

The other big career lesson to me was to take a bit more of a breath, think through some of the opportunities, and be a bit more patient than jumping back in. I didn’t want to take time off. I could have left SurePayroll and done some stuff for a year or two to find the right thing but I  jumped right to [the next thing]. Taking some time with a process in mind of what I was looking for and what I wanted and would be good at next was important to me. It was hard because I didn’t have a lot of patience but it paid off for how my career moved forward.

Did you do that in between being at The Tie Bar and joining Vanco?

I did and I spent about a year figuring out what it is I wanted to do. That’s how I simultaneously got involved at the University of Chicago, teaching and helping on the board at Vanco. When we had a transition with our CEO at Vanco, I stepped in as the Interim CEO with the idea that we would bring in a new CEO. I didn’t join as the long-term CEO.

Entrepreneurship: People are motivated very differently and you need to figure out how you motivate and get the best out of each of them.

I stepped back and said, “What do I want to do?” One of them is, I don’t want to be on a plane all the time. My wife lives in the Chicago area and this business was based in the Minneapolis area. She wasn’t moving, so I wasn’t moving. It was fortunate that I didn’t have to do that. I said, “I’ll do it for a while until we can find the right person and get them embedded in.” It wasn’t a long-term plan for me.

You went full-time into teaching since then. How was the transition into academia?

I love it. I didn’t think I would end up teaching or if I did, I figured I would do it when I was 60. I started teaching in my late 40s full-time. I get a tremendous amount of energy in what I do. I love the flexibility. I love how it’s fresh and new and how it gives me a platform where I can now do lots of things. Part of the way in, I stumbled into this idea that I’m going to take some time and let things play out a bit more. I had been involved at The University of Chicago Business School through one of the faculty members, Steve Kaplan, who runs the entrepreneurship program. He’s a successful tenured chaired faculty member in the private equity and the finance world.

I had been hanging around the hoop at the University of Chicago. I was involved in their advisory program for the entrepreneurship world. They made me an entrepreneur in residence. The idea was, you’re meeting with students and helping them think through their business ideas versus you’re spending your time coming up with your next idea. I enjoyed that. I got a chance to see that. Along the way, I had been pushing Professor Kaplan that we needed to have a program that taught students how to sell because we do a great job in the entrepreneurial world of helping them build a business plan, think about the strategy, how to launch it and how to raise money.

All of our other classes are about, “Once your company is big, here’s how you organize, do the pricing, and all this stuff.” We don’t do anything, “From PowerPoint, I raised $5 million. How do I get any revenue?” This was back when I was at SurePayroll. They ended up creating a course called Entrepreneurial Selling and hired a great professor, Craig Wortmann.

He built this awesome class. I used to speak in his class occasionally. Craig moved across town to Kellogg, where he was from. It was right before Thanksgiving 2016, and Steve called me up and said, “Michael, you’re not doing anything right now. Craig moved across town. I need you to take over the class.” I was like, “I’m not doing this. I don’t want to do this. I want to go run another company.”

Steve had his own plan, “Why don’t you teach in the evening program? You will teach it once in the winter and see what you think. Maybe you will do it again in the spring.” I did and I fell in love with it. I was fortunate that they made me this full-time offer, so I jumped in full-time. What I love about it is I’m now able to work with a lot of early-stage businesses and growth-stage businesses, either as an advisor or a board member. That balances with my teaching because I stay fresh, learn what I’m teaching and have a variety of examples. I can use that variety of examples to help the companies I’m involved in. It’s a good fit for me personally.

You can combine past experiences, the board roles, the students and the things they’re thinking about, and your teachings. All those things start to come together into a nice portfolio. You’re on and have been on a lot of boards. What advice do you have for people who want to get onto boards and in terms of being a good board member?

Those are two different things. To get onto boards, there’s a little bit of, “Once you get your first one, it’s easier to get your second one.” It’s because a lot of people like in most jobs are looking for experience and proof points. It’s the first one that is the hardest one to get on. I would encourage you to be thoughtful about what board you get on and whether there’s a good fit with your skills and the chemistry of the organization.

Some of it is the stage, size and scope of a company that fits what you’re doing. If you’re an enterprise sales leader and you’re going to go into an early-stage startup, maybe it’s not the right thing. If you’re a cybersecurity expert and you’re going to go into a retailer that doesn’t have eCommerce, you’ve got to make sure you have those skillset matches. There are a lot of ways to find boards through recruiters and a series of advisory board online services. I don’t think I’ve ever found one that way.

I find it much more from my network of VCs, private equity and folks that I know in the startup community around. I don’t have the perfect advice, except it takes time and it matters that you pick the right one. You’re going to be involved in these for many years usually and you can only do so many of them. You want to make sure not just that there’s upside but that it’s a good place you want to spend time in, you can add value and you feel like it’s the right fit.

What do you do to add value?

I’m not on a Fortune 500 board, so the level of engagement and where I am is a few levels lower because of the nature of the businesses I’m involved in. Growth-stage and early-stage businesses require their boards to provide practical and strategic advice that can be down in the weeds if you need to be. It’s not to say that people on a big Fortune 500 board are not giving practical advice but they tend to be more strategic, longer-term direction setting. They are a little bit more balanced towards governance than in a smaller organization where governance matters but it’s not the same level of governance in terms of, if you’ve got $5 million in revenue, your audit committee is not that sophisticated.

Some of it is situational and figuring out where you want to play. They talk about “elbows in and hands out” around the board table. It’s the idea that you’re not running the business. The toughest thing for me in becoming an advisor, because some of it is not a board role but an advisor to a board or the company, is the balance. When I was the CEO and I said, “We’re all going left,” everybody had to get on board and go left or we got new people.

As an advisor, I can say the answer is obvious that we all need to go left but I have to be okay that sometimes they’re going to still go right. It’s the difference between influencing subtly the directions of where you want to go and leading through the charge. It’s not being a general, it’s being more a diplomat. I find that I ask a lot more questions and I try to work with others to get to the answer versus directly saying, “Here’s what the answer is.” That’s a balance.

The other thing is, I’m particular before I get on a board to make sure that there’s the right chemistry between the CEO and myself and that he or she will value what I’m saying. It’s not that they’re going to take everything that I say as gospel and do anything I say, but that we have a good give and take. Also, that they genuinely want interaction and help because you can’t coach somebody who doesn’t want to be coached. That was a hard lesson for me.

That gets us up to now. When you look back on your career, how intentional would you say that you’ve been in managing your career and how opportunistic?

I could look back and tell you a perfectly intentioned story that makes total sense…

It’s like your perfectly intentioned reason for joining McKinsey.

I can do that but it wouldn’t be true. My career has been reasonably opportunistic in that I don’t believe you can always plan everything. A lot of life is timing and the decisions that you make. The result of those decisions is more about how you act and play once you’ve made that decision and what you do with the decision you make than [it is about] making that decision. I have a friend who has a saying that I adopted as my own, which is, when you’re playing life, it’s a little bit like when the tray of cookies comes around. If there’s an oatmeal raisin cookie on a tray and you like it, you’d better take it because when the tray comes around again, it might not be there.

It’s this balance between, “I’ve got some rough idea what direction I want to go but there’s an opportunity in front of me and I better take it.” When I decided I want to leave McKinsey, it was a bit like taking a cookie. There were a whole bunch of things that came at me that I could take and they didn’t come at me like when you’re graduating from college or business school, where it’s very much a parallel process to recruiting. It’s serial and you’ve got to make decisions. When the SurePayroll opportunity came up, it met enough of my criteria.

Entrepreneurship: Be very thoughtful about what board you get on. You want to make sure that it’s a good place where you want to spend time and where you can add value.

I felt like it was the right thing, so I took the cookie and made the leap because if not, they’re going to hire somebody else. If you move forward, you could say the same thing about how I moved to The Tie Bar and what I do now in teaching at Booth. Originally, I could have stayed as an adjunct and taught a couple of sections a year. That’s a part-time adjunct but they made me an offer to be full-time. I knew that if I didn’t take it, somebody else will. It’s not the opportunity, at least for me, that’s going to come up every other year. These are roles that don’t come up that much. I was fortunate enough to be in that position. I took the cookie.

You’re in a great business school.

I can’t complain about it. The idea of, “Do I pass on this now and go run a company for another five years and then come back?” You don’t know if the opportunity is there. My big lesson has been to think but don’t be afraid to leap.

Was there a point in time where you felt like, “I know what I want to do,” and you figured yourself out? When was that?

It was months before the pandemic started. As I’ve gotten my sea legs in teaching, I may not be the best but I’m better than I was. I got comfortable with how it works and how to be a teacher in this organization. It’s different than what I had thought. The setup that I have for me that fits what I like to do is that I get bored easily, so I love this breadth versus other people who love to run one organization, drive that hard, and move that forward. It took me a while to become comfortable with it, stop making excuses, and say, “I’m teaching now. We will see what happens.” It’s like when we were all at McKinsey and we would say, “I’m here now but I’m going to be leaving at some point,” to say, “This is right for me. This is a good fit.”

You’re talking about a portfolio play, which is career portfolio versus career path. This concept is getting a lot more attention as the gig economy grows. We’ve got this Great Resignation going on and people are off trying to figure out what they want to do and thinking more about purpose. What is your take on the career portfolio approach to your career versus having one thing at a time?

The advice I give a lot of folks that I’m involved with is to make sure that you’re learning from what you’re doing and that you can feel passionate about what you’re doing. If you have those two things, you can keep going and growing. It can be fun, energizing and exciting. If you’re not, life is too short. We all know it. We all looked back. The biggest challenge is that we all get on this rollercoaster and compare ourselves to everybody else, which you shouldn’t do but you do.

We all have friends that have been successful who are doing all sorts of interesting things. You start to say, “Maybe I should do those interesting things.” The reality is if that’s not where you’re going to get your energy and what is going to be passionate for you, it’s not the right thing. It takes a while to figure out that’s okay because, in the end, we all end up in the right place if we’re willing to take those chances.

It’s a rare person who comes out of college or high school and knows clearly what they want to do and does it for the rest of their life. Most people change, grow, and evolve.

The biggest lesson is you can do that. When you’re trying to decide between the seven good opportunities when you’re graduating college, what if you pick the wrong one? You can change it. Do your best and then jump.

You have the ability to interact with a lot of people who are in their twenties and are successful enough to get into The University of Chicago Business School program. What other advice do you impart on them in your class? I’m sure you go deep on entrepreneurship but in general about managing their careers – what else do you teach them?

Clay Christensen, who was a professor at HBS and passed away [a few years ago] wrote a book, How Will You Measure Your Life?. I don’t know if you’ve ever read it.

I have.

I’m taking a class through it on the last day of class because it’s important to think about the choices that we’re making now and the trade-offs we make. It’s not wrong to make trade-offs. We need to realize the consequences of trade-offs, make sure that they’re the right things that we care about, and understand what it is that we care about. It can change over time but where you choose to put your resources and invest, where you plant will grow and where you don’t water and the plant will not. Make sure you’re making the right choices around that and consciously doing that, so you don’t wake up 20 or 30 years from now and go, “It’s not where I want to be.”

Entrepreneurship: Taking time to process what you’re really looking for, and what you really want to be good at next is important in moving your career forward. Take a breather, think through opportunities, and be a bit more patient rather than just jumping back in.

Are there any other final thoughts to share, books you’re reading that you would recommend or podcasts that you listen to?

A book that I’ve read is a simple book. It’s James Ryan’s Wait, What?. I don’t know if you’re familiar with it or know the history of it. He was the Dean of Education at Harvard School of Education. He gave a graduation speech years ago. It’s all about the five questions and a bonus question we all should learn to ask. It became this book, which has a phrase from one of his questions. One of his questions you should all ask is, “Wait, what?” It’s like how your teenager would ask it.

It’s fascinating in that way of making sure that you’re present in all your interactions. As a teacher and an advisor on boards, these five questions are all I use. It’s interesting. It’s a 70-page book. It will not take long to read. You can watch the YouTube video of his speech, which is even shorter. It’s insightful in terms of how you engage and interact with people. I found it to be hugely helpful.

I’ll have to check it out. Are there final thoughts or anything else?

I appreciate you having me on. It’s exciting to be the first. Hopefully, I didn’t set the bar too low that it will be good.

You’ve been a great guest. We have covered a lot of ground. There are a lot of things that anybody reading can take away from the episode. I appreciate you being willing to be the first, Michael. It means a lot to me. I want to thank you for that and for sharing your career story and the things that you’ve learned along the way. For those of you who are reading, I would encourage you to visit PathWise.io, the website. If you would like more regular career insights, you can sign up for the newsletter and also follow PathWise on LinkedIn, Twitter, or Facebook. Thank you, Michael, and happy career planning. Take care.

Thank you.

Important Links

• The University of Chicago Booth School of Business
• Juvenile Diabetes Research Foundation
• Say It With Charts
• The Pyramid Principle
• SurePayroll
• Paychex
• Vanco
• Steve Kaplan
• Craig Wortmann – LinkedIn
• How Will You Measure Your Life?
• Wait, What?
• YouTube – Dean James Ryan’s 5 Essential Questions In Life
• PathWise.io
• LinkedIn – PathWise
• Twitter – PathWise.io
• Facebook – PathWise.io

About Michael Alter

Michael Alter is a Clinical Professor of Entrepreneurship at the University of Chicago’s Booth School of Business. Michael was the Executive Chairman (and former Interim CEO) of Vanco, the largest provider of electronic payment solutions to the faith-based and education communities. Previously, he was the Chief Executive Officer of The Tie Bar, LLC – the #1 e-commerce destination for stylish men’s accessories.

Prior to The Tie Bar, Michael was a co-founder and CEO of SurePayroll, a SaaS technology company that is now a wholly owned subsidiary of Paychex®. Michael co-founded SurePayroll in 2000 after six years as a consultant with McKinsey & Company. Prior to receiving his MBA from the Harvard Business School, he worked in various sales positions at IBM. He holds a bachelor’s degree in economics from Northwestern University.