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Michaels Andrews

Co-Founder and CEO

Michael Andrews Bespoke

New York, New York

Past affiliations include Founding Partner & General Counsel, Chandler Park Ventures

JD  Northwestern School of Law

MBA Kellogg School of Management

BS Georgia Tech

Well-suited for a new entrepreneurial career

michael andrews headshot

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Full Transcript

EXJ: I’m just astounded by your background. You have a degree in industrial engineering, a law degree, and an MBA, and you have law firm, in-house and business founder experience. Then you made the great change and did something completely different. What the heck?

Michaels Andrews: [A chuckle and a pause] Well, I’m not quite sure how to answer that.

EXJ: Why don’t you take me through where you were going? You started off with these different degrees. Did you have a plan in mind?

Michaels Andrews: No. I wish I could claim that I had the foresight to have somehow intentionally woven all this together, but I didn’t. Honestly, I was trying to figure out what I wanted to do. I was intellectually curious, and I just had certain opportunities present themselves. Growing up in Georgia, I had a full scholarship to Georgia Tech. It was the top industrial engineering program in the world, so I thought, well, I’m here, I might as well be an industrial engineer. I also minored in economics and philosophy because I thought the topics were more interesting than engineering.

EXJ: You didn’t go to law school directly after graduating from Georgia Tech. So what did you do?

Michaels Andrews: I did what everybody of my generation who didn’t know what they wanted to do. My parents’ generation joined the army. My generation went into consulting. I did that for several years, then did the natural progression to grad school.

EXJ: Why law school?

Michaels Andrews: I have a family full of lawyers and the only reason I went to law school, to be honest, was to piss off my father. I got tired of losing political debates to him because his response was always you’re not a lawyer, but if you were, you would understand this, that and the other thing. I remember coming back home for what was probably Thanksgiving after my semester of constitutional law and just ripping apart one of his arguments. That was the downfall of my relationship with my father, but boy, it felt good. So, in fairness, the law degree was a little bit of an accident.

EXJ: I know what you mean. Every kid wants to be as smart or smarter than a parent. I had the Nazi war criminal prosecutor Telford Taylor as my constitutional law professor.

Michaels Andrews: Wow.

EXJ: So what happened next?

Michaels Andrews: I finished my JD MBA and was running a tech startup company. This was 1999-2000 when half my classmates were dropping out of business school after their first year to go do a Silicon Valley startup. So I, like every one of my classmates, was doing some form of startup. Then the dot-com bubble burst. My startup lasted about six months. I folded it and figured I’ll go practice law for a year or so while all this mess shakes out. Eight years later, I finally left the law.

EXJ: Did you always want to have your own business?

Michaels Andrews: Yes, I’d always wanted to be an entrepreneur. It runs in the family. Nobody in my family likes working for somebody else. The business opportunity is really what confronted me here. Unlike for a lot of people who leave to go start something, starting my company wasn’t a passion project. I started it as a business. I didn’t actually intend on doing it full-time. When I started the business, I hired a couple of people and I was doing this kind of on the side as part-time CEO overseeing these folks, but I realized it was more complicated than I had anticipated.It’s hard to hire people that aren’t seasoned entrepreneurs to startup something where there’s a lot of ambiguity. So, I ended up much more involved than I had intended on being.

EXJ: So you didn’t just quit law and open a business. How’d you go about it?

Michaels Andrews: For about two years I did double duty. Once it became clear we actually had a real business that was growing fast, it became unsustainable for me to both run the business and practice law. So early in 2008, I entered the business full-time. That was just before the financial crisis hit. I remember at the time thinking, oh my God, I’ve made the biggest mistake in my life. But the complete opposite ended up being true.

Ironically, in terms of percentage growth, we had our best growth year ever in 2008 right in the middle of the financial crisis. At the time, as everybody was getting laid off, career counselors would tell you “Well, if you just got fired, the first thing you need to do is go buy a new suit.”

EXJ: I guess you need to look successful. A well-fitting, well-crafted suit speaks success.

Michaels Andrews: Leading up to 2008, everybody was increasingly casual, but after the financial crisis, people started getting dressed up again. The irony was that before joining my law firm, I was wearing shorts and flip-flops most of the time (classic tech entrepreneur attire). Then I end up at one of only three major firms in the city at the time that were still full business dress five days a week, and I was the most outspoken critic of the firm’s dress code. Then I ended up moving from a law firm where I’d been forced to wear a suit to selling suits full-time.

EXJ: Did you have an “ah ha” moment when you said to yourself, “You know, I don’t want to do law; I want to do this.” Your business is far outside your realm of experience.

Michaels Andrews: I didn’t have an “ah ha” moment. So, the nexus of the business itself was I worked for a law firm that required associates to wear a suit to work every day, and I started getting mine custom-made. As a first-year lawyer with student loans, I didn’t have a lot of money so I started getting my suits made overseas when I would travel. I had clothes made in India, Thailand and Hong Kong, and I fell in love with the idea of custom tailoring. I really enjoyed the process of picking fabrics and picking the details and all that. But I wasn’t satisfied with the quality and the fit. And obviously, when you’re traveling, if you’re not happy with the suit, you can’t simply go back and deal with it, right?

EXJ: That’s true. I see the kernel of a business idea forming here.

Michaels Andrews: Right. So I thought there’s got to be some opportunity here between overseas production, bringing a level of quality and service, and taking the headache away. None of this really existed at the time. Indochino and Proper Cloth were also just starting, and Suit Supply hadn’t come to the U.S. yet, so the market at the time wasn’t very competitive.

EXJ: I remember my father went to China and had his measurements taken. He would pick the fabric and they would make the clothes. So he had all this custom clothing, and it really did make a difference. He used to joke that the custom fit made him keep in shape because otherwise the clothes wouldn’t fit right. How about the guys who come in from Hong Kong?

Michaels Andrews: There were those traveling Hong Kong tailors that had been around for a while. They’d see you in a cheap hotel room and they had no personal sense of style whatsoever. They didn’t bring samples with them, just fabric swatches and you couldn’t see the work. You didn’t really know what you were getting. And I wasn’t super impressed with what was available in the market. I thought that there was just an opportunity to do it better.

Sure enough, I was right. When we started, there really wasn’t very much competition. And then, within a few years, there was a whole lot of competition.

EXJ: Interesting. Did you always have an interest in fashion and design?

Michaels Andrews: I did. I mean, not from a career standpoint, but I’d always loved clothes. I was voted best dressed in high school, but that’s not so impressive. I went to a public high school in rural Georgia. In the land of the blind, the man with one eye is king.

EXJ: So you liked design, you liked fashion, and then you kind of brought it all together. But you actually studied it too at FIT.

Michaels Andrews: I didn’t earn a degree at FIT, but I did take a couple of classes in FIT’s menswear program to build a foundation and to really understand what high-quality custom tailoring was. I learned very quickly that most of what was being sold out of Hong Kong, China, Thailand and all those other places by all the traveling tailors was mostly crap. I mean, there’s a reason why they were selling their suits for $400 to $500 and on Savile Row, a custom suit was $5,000, right? There was a big difference.

EXJ: So, what was it like going back to school after you’d worked for years?

Michaels Andrews: It was really fun. I enjoyed it. I’ve always enjoyed being a student, clearly, as I’ve got about half a dozen degrees. I took three or four classes on Saturday afternoons. It was the first time I’d done something that was so hands-on. You’re cutting and sewing and all of that, which was great.

I remember being really pissed that you actually had to be a full-time student to take the pattern-making class, which was the one class that I really wanted to take. Aside from that handful of classes, most of my experience has been learned on the job. I’ve probably fit more people than just about anybody out there. I’ve personally dealt with well over 10,000 clients.

EXJ: The patterns are huge, and the cutting is so important. You have to get that right. I took sewing in school and what we made, we had to wear. I folded my fabric in half without realizing that the pieces weren’t lined up, so the back was shorter than the front. So I had a very short dress to wear in the fashion show. It was a little embarrassing, but the dress sure looked good.

How about other careers, were there any other out-of-the-box careers you were looking at?

Michaels Andrews: I dabbled in a bunch right out of school. When I was in school, I worked in the marketing department at Delta Airlines as a co-op. So I had a couple of years of experience there. When I graduated, I went into consulting for several years. Then I ran a startup in the dot-com space before practicing law for almost eight years. I moved from King & Spalding in New York to Fried Frank in London. I dabbled with the idea of going into finance and interviewed at a bunch of investment banks, but I just couldn’t really bear, at 30 years old, going back and being a first-year analyst at some investment bank.

EXJ: Looking back at your time practicing law, would you have stayed in law if something didn’t just hit you as something different you wanted to do?

Michaels Andrews: I left King & Spalding the second time and went in-house at Siemens. So I did the in-house thing and I’d been seconded at Henry Schein out on Long Island. I enjoyed being in-house, but I knew I wasn’t going to be a lawyer forever. I was either going to go into the business side with a client, as almost every one of my friends from law school had done, or I’d start a business. I kind of always had one foot out the door. It was really a question of what I was going to end up doing.

EXJ: So, did you just quit law and start Michael Andrews Bespoke? How did you go about making the change?

Michaels Andrews: I started it two years before I left the law. But once it really became clear that this business had legs and was growing to the point that there was an opportunity to do it full-time, I took that opportunity.

EXJ: Is that what you’d suggest to people who are considering leaving and starting a new business, to start up while you still have that income? The financials of changing your career entirely are a huge challenge.

Michaels Andrews: Yes. So, there are a couple of answers to that. If someone is thinking about leaving the law to go do something completely different, something entrepreneurial, the first thing I always suggest is to read Michael Gerber’s book E-Myth Revisited. In a couple of hundred pages, Gerber tries to talk you out of being an entrepreneur because most people become entrepreneurs for the wrong reason. The example he uses in the book is a person who loves baking but hates the boss at their bakery and decides to go start his or her own bakery. Well, if you love baking and you start a bakery, the last thing that you’re going to be doing is baking.

As a business owner, your job is sales and marketing and HR, accounting, finance and taxes, and everything except baking. The easiest thing in the world to do is hire somebody to do the baking. You’re going to end up doing everything else. If you really love baking, find a bakery where you can work where your boss isn’t a jerk. If you like being a lawyer, find a law firm that you like working at.

EXJ: You still have to manage the people, the accounting and so much more when you have your own business. What were the most challenging aspects of opening and operating your business?

Michaels Andrews: I would say there were all the usual challenges. Starting any business is difficult. You have to find the right partners, the right vendors, and the right employees. You have to manage your cash flow. The thing that kills the vast majority of startups is that they’re underfunded.

I think the fact that I sort of dipped my toe into this made a big difference. I didn’t just leave law. If I had just left the law, we would have gone bankrupt early on because I didn’t have enough savings to continue to fund the business. For two years, I continued in law while I built my business. I was lucky. It was right when law firm bonuses really started going through the roof. I plowed my first couple of big bonuses right back into the business. If it hadn’t been for that, we wouldn’t have made it. So, you want to make sure that you have the funding.

EXJ: What else will be important in considering whether to open your own business?

Michaels Andrews: You want to make sure you’re leaving for the right reason. Most people leave their job because they’re unhappy. That’s the worst reason to leave because you’re going to make bad decisions. People need to be strategic about when and why they leave. They need to leave for a better opportunity. Then leave when they find that. Don’t just leave because you feel you can’t take it where you are one more day.

EXJ: Right. It’s a big challenge. You want to love what you do and that’s what you should be doing every day as much as possible, but you have to set yourself up for success. What do you feel helped to make you successful?

Michaels Andrews: I am fortunate in that I actually love being an entrepreneur. I think that part of the reason we have been relatively successful is I’m not a fashion designer, I’m not a tailor. I don’t pretend to be either. Most people who are going to start clothing companies are usually one of those two things. They’re not business people. A handful of folks that really have been super successful are the Michael Kors or the Ralph Laurens of the world. They are incredibly savvy businesspeople.

EXJ: [You have business acumen and understand your clientele. You’ve been in their world. You’ve lived their lives. You understand how they want to look.

Michaels Andrews: I have. I don’t think a lot of designers sit down and say, all right, who’s the client? Who’s the customer that I’m designing for? Instead, they’re designing for themselves. If people like it, they’ll buy it. I think designers like Ralph Lauren and Michael Kors have had great success because they know their customers and they design for those people, not simply for themselves.

EXJ: That’s a good point.

Michaels Andrews: We take a client-service approach here. We’re not in the business of designing clothes. Our clients design their clothes. We’re in the business of making sure that we facilitate the client in making good decisions, and then we make sure the trains run on time. If we tell you your suit will be ready in six weeks, it will be ready in six weeks.

EXJ: What do you wish you knew before you started your business?

Michaels Andrews: How much money lawyers would be making today? Actually, I’m really glad I didn’t know that.

EXJ: Yeah, you might not have made a change. You might never have left law practice. What warning would you give those considering leaving law?

Michaels Andrews: Anybody who thinks that leaving the law to become an entrepreneur is going to mean fewer hours is high on something. People are always asking if I left because I hated law practice. I was overworked and overpaid. But if you think all the hours you work at a firm were terrible, I can honestly tell you that my worst week at the law firm would have been a vacation week compared to the first couple of years when I started my business.

EXJ: If you want to be successful, you have to put that work in. But how did you manage it?

Michaels Andrews: I was doing double duty for the first two years, but that’s what allowed us to survive. I wouldn’t wish those two years on my worst enemy. I worked 50 to 60 hours a week as a lawyer and then put in another 40 to 50 hours a week as an entrepreneur on top of it. I was working 18 to 20 hours a day, seven days a week, 364 days a year. My hair fell out, I gained 15 pounds, and it certainly was not enjoyable.

There’s not much reward in the first couple of years in the business because you have to figure everything out. You don’t know much, and you make every mistake that you could possibly make. You’re going to make mistake after mistake after mistake after mistake, and you’ve just got to be prepared to keep going and take those body blows. It was probably about two, two and a half years into it when almost overnight we turned a corner, and all of a sudden it was like we’d gotten over this learning curve and had a real business.

EXJ: I think factoring in the learning curve is essential. You really need to do your homework and study in advance to understand the market, to understand whatever your product is that you’re offering, the costs, what you’re going to need to invest, and the skill set required. You need all of that. And that’s where I think people really underestimate what’s involved.

Michaels Andrews: And I think it’s very easy to underestimate what’s involved. Building a business is hard. Like for anything else you ever really wanted to accomplish, you have to put in a lot of hard work. It was much harder and more painful than I was expecting. You can’t imagine how hard it will be until you’re in it.

EXJ: You have to train in business, learn the necessary skills and keep exercising them to get better and better at it. So those are important considerations to keep in mind. Any other advice?

Michaels Andrews: Being an entrepreneur is absolutely not for everybody. You have to really be comfortable with risk and with failure, and the fact that you are going to be dealing with headache after headache after headache. About 90% of startups are going to fail. Then, even the ones that do succeed, if you’ve left a good law firm it’s not very likely you’ll make more money than you did as a lawyer. I’m a very successful entrepreneur, but still I make less than I would as a partner in a big law firm today. Hopefully, that won’t always be true, but 15 years in that’s still the case. So, if you’re leaving law for financial reasons or if you’re doing it because you’re unhappy, those are the wrong reasons to do it. You need to be someone who enjoys being an entrepreneur.

EXJ: But you love what you do and that has to count for something. What do you enjoy most about your business?

Michaels Andrews: I always have new things that I’m working on and new problems to solve so it’s constantly mentally stimulating. I love that no day is the same as any other. Everything is a challenge.

Also, I’ve had the opportunity to build a team of people that I really respect and admire and enjoy working with every day. I have a level of control over my destiny, which a lot of folks don’t have. I’ve taken real enjoyment in building a company that I’m proud of and a place where I really enjoy coming to work.

EXJ: That’s great. How about strategies to avoid failure or at least position yourself for success? One of the things is preparing financially. What else?

Michaels Andrews I think you need to make sure you’re not underfunded. If there’s one thing I could go back and undo it would be falling into a little bit of the artist trap. You can’t fall in love with your product for the sake of the product. Artists that fall in love with their art forget about who their client is. And ultimately, the measure of the value of your art is what people are willing to pay for it.

I think a focus on profitability, on the bottom line, from the beginning is critical because the profits that your business generates are what give you the flexibility to do what’s needed to help the business to grow and to give you the lifestyle that you want to enjoy. If you get too wrapped up in your ego, doing things not for the reason of ultimately making money, that’s a recipe for disaster. First and foremost, you need to make sure you’ve got a healthy, profitable business that is going to sustain itself. And you need to make both short-term and long-term decisions that will protect the financial viability of the business.

EXJ: I totally agree. This is all great advice. I think that it applies to any business you’d want to do, anybody who wants to get out of law. Your advice and admonishments really apply across the board to anything a person would decide to do.

Michaels Andrews: Absolutely. I mean, I could have been just as successful starting a company that made widgets as in clothing. I happen to be passionate about clothing, and I think that is a huge plus. But again, I don’t try to pretend to be the designer, I’m not doing this because I’ve got this just unending passion for clothing. I love clothing and it’s great to do something that I’m passionate about, but I don’t get too wrapped up in that. If I spend all my time focused on trying to design the coolest clothes in the world, I wouldn’t have enough energy and focus left to run the business.

So the idea that you should go find that thing that you love and start that business is a little bit misleading because, again, starting a business is really about all of the other tangential things. If you really just love designing clothes, you need to go work for Ralph Lauren or someone like him and design clothes for a big company where you can focus on design.

EXJ: You need to get the necessary background too, finance, marketing, product development, etc. You really used a wide variety of skills to do what you do, from business to the law, and a whole bunch of other skills.

Michaels Andrews: That’s right. If you want to be a designer, if you want to make cakes, you need a very specific skill set and you’ll know very quickly whether you’ve got it, whether or not somebody will hire you. Ralph Lauren would never have hired me as a designer.

EXJ: [It’s the whole package, your skill set, that has enabled you to be successful. Are there any other points that you’d want to call out for these lawyers who want to leave law to do something else?

Michaels Andrews: [The single biggest piece of advice is if you’re looking to make a change if you’re not happy with what you’re doing, you should make a change. But you need to be patient. Don’t just jump at the first thing because you can’t take it anymore where you are. That will set you up for long-term problems. The most successful people I know are people whose every step in their career path was a step forward. They didn’t make emotional decisions along the way.

EXJ: [That’s great advice. I really appreciate your time. You’ve given excellent advice for those who really are struggling and want to make a change. So I truly appreciate that.

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