Wade Myers – Ex-Airborne Ranger, Now A Serial Entrepreneur, Investor, Advisor, Author, And Speaker

Most serial entrepreneurs have interesting back stories, but few can match that of Wade Myers. There has not been a single point in Wade’s life from when he was 6 years old that he has been held down to only one job. His entrepreneurial bent allowed him to weave his way out of childhood poverty in the Badlands of North Dakota to joining the Army, holding several key sales positions at Mobil, being sent to the Gulf during the first war there, going to Harvard Business School, and being a serial entrepreneur during the early days of the internet. Wade has probably held more than 30 roles in his professional career, and that’s barely scratching the surface. One hour is barely enough to get a sense of just how incredible Wade’s journey has been, but he attempts to give us the shortest version possible. We learn here that the key to Wade’s success is his willingness to take risks, seize opportunities, and break a few rules along the way. Join in and revel in Wade’s exploits in rural North Dakota, in the Army, in the volatile tech industry of the early 2000s, and in today’s business environment.

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Wade Myers – Ex-Airborne Ranger, Now A Serial Entrepreneur, Investor, Advisor, Author, And Speaker

On His Journey From Childhood Poverty To The Army To Harvard Business School And Beyond

My guest is Wade Meyers, who I met in business school. He is a serial entrepreneur, investor, advisor, author, and speaker. He has founded, invested in, and been a director of more than 90 companies and has completed over 100 financings and M&A transactions over the course of his career. He started his career as an Airborne Ranger in the United States Army in a mix of active duty and reservist time that spanned more than 15 years, including 6 months in the first Gulf War.

During his military service, he earned a number of awards and commendations, most significantly including a Bronze Star. Along the way, Wade spent seven years working for Mobil Chemical before earning an MBA from Harvard Business School. He then went to Boston Consulting Group before venturing out on his own and founding a number of tech-based startups, many of which he subsequently sold. In parallel, he became an investor, eventually starting a number of firms that invested in startup incubation, venture capital, private equity, hedge funds, real estate, and major motion pictures. He has also served on the boards of directors of several tech-based firms.

Along with his MBA from Harvard, from which he graduated as a Baker Scholar, Wade earned his Bachelor’s degree in Agricultural Economics from North Dakota State University and his Master’s degree in Computer Information Systems from Texas A&M, Central Texas. He has helped develop an executive education course for Harvard Business School and is also a Harvard case study author. He has published articles in Forbes, Huffington Post, and Apple News. He was featured in episode 4 of season 1 of The Curious Entrepreneur series on Amazon Prime. He lives in the Dallas-Fort Worth Area and has five children.

Wade, welcome. It’s great to have you on the show.

Thanks, JR. It’s great to be here.

In your case, to fully understand your journey, we have to start at the beginning. Talk about where you grew up and what your childhood was like.

I grew up in the Badlands of Western North Dakota in a little farm operation outside of Medora. Medora, North Dakota, is where Teddy Roosevelt ranched before he was President. In the Badlands, it’s semi-arid. It’s a lot like West Texas. It’s desolate and lonely. We were in the middle of nowhere. We did not have electricity, indoor plumbing, television, a telephone, or anything, and we had no income.

My mother was a Mennonite. We were influenced and raised in the Mennonite culture. We lived off the land. We had a trap line. We hunted deer, antelope, and game birds. We raised vegetables in a huge garden. It was a subsistence lifestyle. I went to a little country school with multiple grades per room for grade school. I went to a county school for junior high and high school. In my little country school, there were 5 or 6 of us per grade, roughly. In the high school, the county school, there were 34 of us in my grade.

You’ve previously mentioned to me that an early job was at a truck stop working the graveyard shift. What was that like?

We were in danger of losing the farm. In the sixth grade, I started working after school in construction. By the time I worked at a truck stop, I was a freshman. I had been working for a few years. I started selling door to door in the first grade. I would sell greeting cards and Spencer Gifts-like little supplies. I sold light bulbs and Christmas trees. I sold a lot of stuff door to door and made a lot of sympathy sales.

If we went to town, the town was 30 minutes away, [my mother] would drop me off at one end of town, population 1,500, and hours later pick me up at the other end of town. I would work my way door to door and sell stuff for money. By the time I was a freshman, I would work midnight to 8:00am. It was a truck stop. I showered in the trucker shower and raced to beat the morning bell at school. I’d go home to the little farm and fall asleep after school. I would sleep until it was time to get up again.

Homework happened when?

On the counter at the truck stop. The truck stop was sixteen fueling islands. Each island could have an eighteen-wheeler on each side. Oftentimes, in the middle of the night, at 3:00 or 4:00 in the morning, you might only have one truck or they’re might be a space between trucks. I’d usually have my books open on the counter. I’d run out, fuel a truck, come back in, ring them up, and so forth. It worked okay. The only difficulty was if I was changing a tire back in the big garage bay or changing the oil in a truck, I had to run out front to see if trucks were there, fuel them up, ring them up, and run back to the back. It was fun. I was the only one on that midnight shift but it was good training.

Clearly, you learned the value of a dollar early on. You learned about hard work and contributing to the family finances. It’s a unique situation to have been in as a child.

In the roofing job after school in sixth grade, I was paid $0.50 an hour. I worked for two hours after school. I got paid $1 working for an old crusty bachelor, hilarious. After we’d would do our two hours of work, it got too dark. We would go into the house and open a can of pork and beans. He’d spoon out half of it in a dirty old slimy bowl for me and half in a dirty old slimy bowl for him. We would sit there. He knew I was hungry. After giving me $1, he would feed me half of a bowl of pork and beans. As soon as I was done, he would set my bowl on the floor for his dog to lick it. That was my first job, $0.50 an hour.

Hopefully, he washed that bowl in between then and the next time he fed you.

I don’t think so. It’s like the old saying, “Do you ever wash this?.” “Yes, with soap and water.” When you’re done eating, he’d call his dogs, “Here Soap. Here Water.”

You entered the military when you finished high school. What led you to that path?

In those circumstances, I thought the military would be a good path out. I read a ton as a boy. I would read entire shelves at the county library. I read a ton of military history, fiction, and nonfiction. I dove deep into great American stories. I “A to Z” read whole sections. I wanted to go out and see the world, JR. I was anxious to leave my little hometown and North Dakota and see the world. The military was one way out. I enlisted in the Army Reserves and had the option to go on active duty but went to bootcamp and all that.

It was a fluke. I was working as a welder, and I thought, “That was the best thing out of high school.” I went down the vocational track in high school. None of us went to college. You went back to work for your dad as a farmer-rancher or on the oil patch. You did something like that. I learned how to weld at home on the farm. I was tired of making $2 an hour at the truck stop, and welders were paid $5 an hour. That was my limited vision. I was welding but went to bootcamp and enlisted in the Reserves. I had a little extra income. I loved the military and wanted to serve.

I happened to visit my sister in Fargo, at the other end of North Dakota, on the Minnesota border. She was in Fargo. I stopped to visit her on my way to Alaska, to my welding job on the Alaskan pipeline. She said, “I can’t believe you’re not going to go to college, Wade. You should. You’re smart. You’re selling yourself short by being a welder.”

Her husband was a welder, and she wanted something better for me. She took action and said, “I can walk you over to [the college] and help you register for classes. Why don’t you crash in my apartment? You can sleep in the baby’s room and babysit for me. I will cook you meals and do your laundry. Just do one quarter. Please do that.”

She walked me to one window [at the college] where I got a grant, a loan, and a check. I walked to the next window, signed the check back over, signed up for some basic classes, and was enrolled in college. I was crashing on a little cot next to her baby crib. Her husband worked at night, and she worked in the bank during the day. It was one of those, “young couple struggling” situations. She cared enough. I enrolled in college and thought, “I will do this for a while, and then I will go.”

I had $20 in my pocket. I had signed over the one check that I got for financial aid. I came back to her apartment. This was back in the old days, so I went to the classified ads in the newspaper. I took the first job and got hired, which was a breakfast and lunch cook at the airport in Fargo, Hector Airport. I took another job because I realized I couldn’t pay for anything. I worked and ended up working tons of jobs simultaneously. I would do all these little things and fall into different things.

I came home to visit and was like, “I’m not going to go back to college.” My mother, even though she was completely uneducated, a typical Mennonite background, she wanted her kids to have a better life. She called one of my high school teachers and said, “Wade is going to drop out. Please encourage him.” She told me slyly, “Mr. Vander wants to see you if you pop up to town.”

I went over there and knocked on his door. I was like, “My mom said you wanted me to see you.” He goes, “What’s this about you not wanting to go back to college?” He encouraged me. I ended up sticking and staying. I was enlisted in the Reserves. It was one of my many jobs, 1 or 2 weekends a month, and 2 weeks during the summer. I worked a ton of other jobs during school. I got through all that and went active duty in the Army after graduating.

Talk a little bit about what you were doing while you were on active duty.

It was one thing that would lead to another, and in some often cases, it was serendipity. I was a bit of a fast talker but I was enlisted in the Infantry Reserves. I was a machine gunner, and I loved the infantry. I loved running to the woods and camping out. I was like an overgrown boy scout, but I had this professor of Military Science in college. He said, “You want to go to the Corps of Engineers because you’re smart. Infantry, it’s low end. You want to be in the Corps of Engineers. It’s for smarter officers.” I’m like, “If that’s what you say.”

He was a branch engineer, and many officers want to influence you to go into whatever their branch is because of the confirmation bias of their experience. I went on active duty in the Corps of Engineers. I was in an Engineer Officer Basic Course in Fort Belvoir, Virginia, South of Washington, DC. I show up there and they go, “How many here studied Engineering? How many here have studied Math?” I studied Agricultural Economics. It was considered a soft science. They were down to 4 or 5 of us. “We don’t know what you guys studied but you’re going to be the ones that fail because this is a lot of engineering. It’s going to be hard.”

I had a blast that year. I learned a ton about explosives, military engineering, and so forth. I did well. I graduated at the top of my class and got a choice of what would follow. I could go to air assault training, parachute training or those kinds of schools. One of my friends who knew way more about the military than I did said, “Volunteer for Ranger School because engineers hardly ever get a ranger slot, but because you’re the number one grad, you’ll get your choice. If you get Ranger, they almost have to send you to Airborne School because what good are you if you can’t parachute.” I go, “I want Ranger.” Beware of what you asked for.

I went off to Ranger training, which was the hardest thing I’ve ever done. I’m a lean guy but I lost 49 pounds in Ranger training. It was rigorous. One little C-ration a day, no scheduled sleep for week after week. They are trying to simulate the rigors of combat. They are putting you through all these exercises. You are rotating leadership positions. It ate me up. I was hanging on by a thread. Only with the encouragement of a few fellow Rangers did I make it through.

There at Fort Benning, I graduated, and I was supposed to go on to my next post. I was thinking, “I want Airborne training now that I’m a Ranger.” I went over there to the Airborne school and said, “I’m supposed to go to Airborne training.” They said, “Where are your orders?” I was like, “They didn’t come in yet?” I was faking it a little bit. I exaggerated. They said, “We’ll call  and see if we can track down your orders.”

You were in the military. They have a captain that manages lieutenant careers. They get this captain on the phone. They say, “Lieutenant Myers is here. We can’t find his orders for Airborne training. Lieutenant Myers, Captain Lewis wants to speak to you.” He goes, “Lieutenant Myers, what are you trying to pull?” I’m like, “I’m sorry, sir, but as long as I’m here at Benning and as long as I’m a Ranger…” He goes, “I’m going to cut some orders. You can go to Airborne training but you’ve got to get going. Your unit is expecting you.” I show up and go to Airborne school.

I ended up, in a similar way, going to air assault training. I went through several demolition trainings. I went to atomic demolitions and nuclear surety training. I went through slurry explosives and liquid explosives. I kept volunteering for training, whatever I did. I was collecting merit badges. I was supposed to lead a regular Army unit. I show up at this base. This senior officer comes out, and he goes, “Where are you headed to?” He grabbed my military records, and I had all these delays where every time I was delayed, I got more training, like, “There’s an opportunity to go to atomic demolition training and become a certified nuclear weapons officer.”

I happened to run into this guy that said, “You should do this.” I show up, and this guy goes, “How did you get all this training? I command this special weapons unit. We have atomic demolitions. None of my officers have this training. How did you get that? You now work for me.” He trades the next two new lieutenants on post for me. He is on the phone with these two different battalion XOs going, “You can’t have him. I need him.”

I ended up commanding a special weapons unit for two full years because of all this training. While I was there, they sent me to a whole bunch more training. I went through scuba school and so forth because I was now diving with atomic demolitions and had teams that could parachute, repel out of helicopters, and dive with these atomic demolitions. It was all this cool training. It was during the Reagan buildup. We had an unlimited budget.

It was so much fun because we were trained and ready to deploy an atomic demolition anywhere in the world in a short time – be wheels up, be gone, and set off a small atomic bomb that would be able to wipe out a large target, both without creating too much nuclear fallout because it was considered tactical, not strategic. Not like an ICBM that would blow up half the world, but very targeted.

It was so much fun, and that same commander that had grabbed me and said, “You work for me”, he also said, “Myers, you need a grad degree, and by the way, you should get it in high tech.” I go, “Yes, sir.” Texas A&M had a little campus by this military base. It was in Fort Hood, Texas, North of Austin. He said, “There’s this program, Computer Information Systems. You should get a Master’s in that.” I signed up and was used to doing a lot of things simultaneously. I went to grad school while I was in the military. It worked out great but it was the encouragement of others, some good mentors, falling into things, and all of a sudden, I was in a completely different place than I was supposed to have been.

I really didn’t do anything the Army originally told me to do. I always had orders changed. I ended up having a lot of fun but it was peacetime military. It was boring in a way. I was like, “I’ve got all these merit badges. I’ve had a lot of training and worked with a lot of great soldiers.” Elite forces are fun. I’m hanging out with Rangers, Airborne, and all these special weapons guys. It was a ton of fun. At some point, you go, “I need to make a career. I’ve had fun. I’m going to head to the corporate world.”

You ended up working at Mobil.

There were these head hunters that focused on taking junior military officers out of the military, after 3, 5, 10 years, or whatever, and then placing them in Corporate America. Way back then, my goal then was to work for the biggest company possible that I could work for, work my way up the corporate ladder and retire with a gold watch after 30 or 40 years. That was the construct back in the day.

One of these headhunters came and did a presentation on campus, “As military officers, you have a lot of leadership experience. Corporate America values that. You’re going to jump in 3, 4, 5 years or whatever behind your peer group that went into Corporate America right after college but it’s okay. You’ll catch up quickly because of all your leadership experience. That will be great. You’ll have a good career.” I go, “That sounds good. I’m going to do that.”

I interviewed with a bunch of companies and was able to work for the plastics division of Mobil Corporation. It was great. There were lots of great training opportunities. Many of us in sales, marketing, and executive leadership were all former military. There was a strong bias for that. It was like an old home. We would go to national leadership meetings or sales meetings, and everybody would swap their different military stories. It was a comfortable place to be. I learned a ton and enjoyed my time with Mobil.

I know transitions out of the military for a lot of people are challenging. It sounds like yours went pretty smoothly.

Yes, for a couple of reasons, JR. One was that there were a lot of former military people at Mobil. I still had the feel of that camaraderie and esprit de corps that you get in the military. I still had that. I went right back into the Active Reserves. I joined the Reserve unit and immediately took command of a 160-man company. It was a combat unit. It was all men, and immediately I was working not quite half time but a lot of extra time command in this Reserve unit.

I still put on a uniform and did as many as three weekends a month. I had five full-time soldiers at the Reserve Center. I had to swing by the office 2 or 3 times a week to sign documents and check in with the guys that worked for me. I still was having very much a military experience the whole several years I was at Mobil.

It sounds like you were working, in effect, almost two full-time jobs. A military job and a civilian job all at the same time.

It was rewarding. I enjoyed it.

You got called up during the Gulf War.

I had been at Mobil for about six years at that point. The Gulf War broke out. If you remember, Saddam Hussein invaded Kuwait. The unit that I was in, in California, was on alert, “You’re about to go. Pack your duffle bags.” We were off alert and on alert, off alert. Meanwhile, we were sending tons of soldiers, sailors, and airmen over there. We were building up. The buildup took several months.

During that timeframe, I was constantly on alert and off alert. Finally, I said, “I’ll volunteer to go as an individual rather than with my entire unit. I’m happy to go and fight. I’ve got all this experience.” It was like I had dance lessons for a bunch of years. Suddenly, there was a prom, and I wanted to be at the prom. For some misguided reason, as a young man and even as a boy, having read all those military novels in historical accounts, I wanted to have a war experience. I was misguided, like the ignorance of youth.

There was a war, and I wanted to go serve. I wanted to do my part. I felt like, “I’ve had all this training, and I wanted to apply that for my sins.” I made it clear I wanted to go. I exaggerated again, and I feel bad about this, because I wouldn’t do this now. This is a fun story because it was a real career inflection point. I was at this Reserve Center, Presidio, in San Francisco. Where all the branches and military send people to learn a foreign language is in Monterey, California but in Presidio, we had a small language annex. I was there doing my reserve duty and happened into the office in the language annex that day.

The whole Gulf War thing was in the news all day long on CNN. We were building up. I’m looking up, and there are all these language courses. One was basic Arabic, like the Arabic 101 thing. It’s this big book. I had all kinds of cassette tapes. I was like, “That will come in handy in case I get called up.” I threw that in my briefcase, as I was checking out at the end of the weekend.

I was telling the personnel sergeant, “I can’t believe I’m not being called up because I have already been saying I’ll go as an individual.” He goes, “Captain Myers, you are incredible in terms of your experience. I’m sure you will get called up.” I said, “You do know that I speak Arabic.” What he heard was that I spoke Arabic, he said, “Captain Myers, I’m not sure we knew that about you.” I said, “I’m learning. I’ve got it in my briefcase. I can jump in. I can learn.”

Three days later, I was in Phoenix on business. I managed the Western third of the US for this division at Mobil. I was with my Phoenix guy. I get this call from my secretary going, “Are you Captain Myers?” I’m like, “Yes, it’s my Reserve job.” She goes, “You supposed to call right away, sergeant so-and-so.” I call him, and he says, “Captain Myers, you’ve got three days. You’re going. That Arabic thing changed everything.”

Back in the day, I had this Sony Walkman. I had three days to pack my duffle bag and report in. I’m listening to Arabic. I’m rewinding and listening. I’m going through the workbooks. Three days of prep and going through a little bit of indoctrination training for a week or two, and then I’m on different flights and so forth. I hit the ground in Saudi Arabia, and they rush me to the front because I speak the language. I’m an Arab Liaison Officer. Meanwhile, I don’t know hardly any Arabic. I’m trying to learn with the Walkman and these books.

The first thing I did was I found a wonderful officer that was also a captain but he was junior to me. He was Lebanese by birth and had grown up in Lebanon but was in the American Army. He was an American Army Officer that was working in the war. I grabbed him and said, “What are you doing? Where are you working? Work for me.” He became my language coach.

What I realized is that all the senior Arab officials speak great English. They have all been in the US military, to senior military training, and so forth. The junior Arab officials or junior military personnel did not speak English at all but as long as I knew enough Arabic to politely greet them and ask who I wanted to meet, I was ok.

Once I got into a senior Arab official’s office, we would switch to English and have a friendly chat in English. It worked out okay, and I had a wonderful experience, but regrettably, I exaggerated. I got into trouble a couple of times when I used the wrong words or said the wrong phrase, but I did learn quickly. I had a couple of different language coaches. This young captain interpreted all of my writing. I would do contracts, agreements, and so forth with Arab officials and the Saudi government. They would all be written out in Arabic by the guy that I grabbed to work for me. He would help me with the language.

What was nice was that the senior Arab officials, civilians, and military found it endearing that I was trying hard to learn Arabic and was trying to always greet them and talk to them in Arabic. They would always help me along and were very patient. I had a wonderful experience. It’s because of that that I got tapped for some diplomatic missions like, “Wade, we’re going to go over to Bahrain. You need to help us cross the border. We’re going to go over here.”

I got into Kuwait right after we liberated Kuwait. I was doing after-action meetings and had a lot of fun because everybody thought, “This guy is an Army Ranger. He’ll be able to protect our senior dignitaries and speaks the language.” I got tapped to do all these special assignments. It was a lot of fun. I experienced the war from a bird’s eye view. I was doing a lot of senior assignments. It was a wonderful experience.

When did the idea of going to business school pop up for you?

While I was in the Gulf War, which was a short war, I was there for many months afterward, cleaning up and all that. I had a lot of time for introspection and to think about what I wanted to do. I realized, “My career at Mobil was lightning fast. I had several positions. On average, every year, I got promoted and moved around all the time.” It was because I got promoted quickly, and I ended up managing a national business division and headquarters, that I didn’t have time to think, “Do I like this?”

There I am in the Gulf War and going, “I don’t like being a cog in a large machine. I want to run something.” I had been entrepreneurial during junior high and high school, especially in college. I was working tons of jobs. A lot of them were at-risk ventures. I was putting on dances and concerts for part of the gate. I was working on commission. I was like, “I want to be an entrepreneur.”

I had my desert experience like Moses, and it was like, “I want to be an entrepreneur.” I didn’t feel I had the skillset. When I got back, I immediately applied to business school. I took a flight, and found one of those Business Week editions that talked about ranking the top business schools. There were these articles about these business schools. One of them was to do a mid-career transition. I was 32 years old. I wasn’t that happy at Mobil Chemical, especially after having been gone for several months in the war and having that inflection point of excitement, being away from work and going, “I want to buy a company, start a company or something” but I didn’t know how to do that.

Hence, I made the decision within a few weeks of returning, to start working on my application. Back in the day, if you remember, we had to answer ten essay questions [for the Harvard application]. What it did for me is I went to the bookstore and bought all these books on how to apply to a top business school, how to write winning essays, and all that stuff. I went to school on it.

That process of being introspective was helpful to go, “Here are my strengths and weaknesses. Here is what I want to do.” It helped me. I didn’t want to be trapped in a corporate career, being dragged along, being promoted when other people thought I should be promoted, being told what to do or having someone write my job description. I was independent-minded and wanted to run something and be my own guy.

I applied, and what’s funny was back in the day, we had snail mail applications. You wrote to business schools, and they mailed you an application to fill out. I got applications from all the top five business schools, Stanford, Wharton, Harvard, Kellogg, and Chicago, and about another 10 or so of the top 25, some safety schools, and a whole pile of applications.

One of the books I read said, “Start with the Harvard application. It’s the hardest. It takes the longest. Once you’ve done that, you can copy and paste it for other applications.” I did that. All of them required the GMAT, except for Harvard. If you remember, the year we applied, Harvard had deviated and said, “We don’t think GMAT is indicative of student success. We don’t require the GMAT.”

I remember thinking, “I’m going to take a GMAT prep course, get some books, and study.” I was busy when I returned from the Gulf War at this new job at Mobil. I didn’t get a chance to study. I got down the wire. I finished the Harvard application. I applied to Harvard and thought, “I don’t have time to study for the GMAT. I can’t take the GMAT. I’ll fail miserably.” I ended up only applying to Harvard Business School because it was the only school that didn’t require the GMAT, and I hadn’t taken the GMAT.

I applied to Harvard. I thought, “If I don’t get in, I don’t go. There it is.” I really wanted to go to improve my skillset, to be an entrepreneur, to either start or buy a company and run it, and also to build my network. I realized that I had been at 1 company in 1 industry for 7 years at that point and then the military. I didn’t know anything about business outside that 1 company in that 1 industry. I had a limited view of business. I knew that I needed something to [be better prepared]. That’s why I wanted to go to business school.

I didn’t appreciate it when we were sitting in class together for that full first year that you had this strong entrepreneurial bent and desire. How did you end up deciding to go work for BCG when you finish school?

That first year was a lot of learning. I remember hearing about venture capital for the first time. I didn’t know what that term meant.  I remember hearing the term investment banker. I had no idea what that meant, “What’s an investment banker?” I was in learning mode about all these different things. Companies would come and present. There were all these jobs.

All the big brands like Procter & Gamble would come, and they would be interviewing for a product manager job. I’d already done that at Mobil. I was there for several years. I was a national-level executive at New York Headquarters. It was like, “I’ve already done these jobs.” A lot of the other students, as you remember, would all joke about how old I was. I was like Uncle Wade. I was 33 when we enrolled. Everyone else was about 25 to 27.

I thought, “The best way for me to land is to go to a market where I want to live and work for one of the large consulting companies to continue to improve my skillset. It’s like an MBA too.” To expand my network, I would try to find investors, and I try to buy a company in that market. I was very intentional about, “I only want to work for one of the big consulting firms,” because I thought all my skills could apply and it would be the best chance to meet people, investors, and so forth.

In our second year, I took Howard Stevenson’s Entrepreneurial Management class. One of the cases is about the search fund concept. I’m like, “That’s it. I’m going to do a search fund.” I was a BCG intern during the summer between my 1st and 2nd years. I heard they were opening a brand new Dallas office. I was like, “A startup. That’s cool. I’ll accept your offer if I can go to your new startup office in Dallas.” I had come from Texas to [business] school. I was living in Austin. I thought that would be cool. I’d buy a company in Dallas and work at BCG long enough so I could raise money or get someone to back me. That’s exactly what I did, except I launched in Minnesota.

I was at BCG for about a year and a half. I loved it. The intellectual ferment, all these super smart people solving problems, and it was at the time the internet was getting started. I worked on the biggest travel website, Travelocity.com. I helped American Airlines and Sabre put together the strategy for that. I remember thinking, “The combination of strategy, uniquely better value proposition, technology, business process redesign, sufficient capital, and great leadership. That’s the way to start a business or create a business that’s going to win in the marketplace and be successful.” I got excited because I got a chance to work on some cool assignments at BCG.

I had a friend from undergrad from North Dakota State University call me one day. We stayed in touch, and he’d always say, “What do you plan on doing?” I told him, “There’s a search fund concept. I want to try to get back in, buy a company and run it.” He called me one day, and I was working at BCG on the Baltimore Washington International Parkway. I was traveling heavily.

He calls me and goes, “How would you like to run a software company?” I go, “Yes.” I knew nothing about software, but running a company, yes. I wanted to be a CEO. He goes, “My brother is a venture capitalist, and he is looking to buy this company but the guy wants to retire. He remembered me talking about you because I had shared your search fund plan with him.” I’m like, “Wow.”

I flew up there and met with them. We had this unique experience where he went, “Can you help me diligence and negotiate this deal in Chicago?” I was working at BCG during the day and would catch an evening flight to Chicago. I would work on diligence, have dinner with the owner of the business, work it, have some after-action briefings and meetings, and then catch a midnight flight back or a super early morning flight back to Dallas. I did that for a month. I got burned out trying to hurry up to close this deal.

At BCG, we always had two clients simultaneously. It was different from McKinsey, where you usually had just one client at a time. I was wrapping up one of my assignments. I thought, “Now is the time.” I went to the guy that ran the office. He was a wonderful guy and former military as well. I said, “Ron, I’ve got a venture firm that’s backing me. I’m working on trying to buy this company. Can I please go halftime and not take another case on? I will work hard and finish well on this other case that will continue on for a few months, but can I go halftime?” He goes, “I’m excited for you. That’s fine.”

He answered pretty quickly. He was gracious, probably a little bit to his regret because this deal extended on. It was a Fortune 500 company spinning out of a division. It was a division they didn’t want anymore. I’m trying to negotiate with this CFO of a Fortune 500 company to buy this small division that he didn’t care about. It was like a rounding error. I provide a letter of intent, and he rejects it. I’m trying to negotiate the letter of intent to buy the business, and it goes on.

Finally, after about three months, the head of the BCG office in Dallas calls back, and he goes, “You’ve got to fish or cut bait. You need to either go back full-time and take on another case, or leave because we can’t keep doing this.” The Internet is starting to get pretty exciting, and this is a software company. He goes, “Everybody wants your gig. Everybody else in the office wants your deal, where they get to work on an internet startup halftime.” I said, “I’m sorry, can I get a few more weeks?” He goes, “Yes.” We agree on certain days.

I fly back to Minnesota. I sit down with the investor and go, “I’ve got to either quit BCG or quit this deal.” He goes, “I’m not sure this deal is going to close but how badly do you want to be an entrepreneur?” I said, “Bad.” He goes, “Is it bad enough to quit BCG and move here to Minnesota?” I’m like, “Yes.” He goes, “Why don’t you drop a few bullet points of what you’re going to pursue because we’re going to start from scratch, and this probably won’t close. Let me review it.”

I wrote up a two-page, bullet point summary of what I was going to do, what I thought about doing, what I needed for a maintenance wage to not quite starve, to buy a couple of businesses or whatever. Not even in signature block or anything. I flew back up and presented it to him. Over dinner, he said, “Move up here. Tell me when you can start, and I’ll start paying you.” He seeded me. That’s what launched my entrepreneurial career. He was a guy that believed in me enough to say, “I’ll pay you while you figure out what to do.”

We can’t even begin to scratch the surface of your entrepreneurial journey but when you think back to those early days, what did you do right? What did you not do right? How did you go on that successful run that you went on? The first 4 or 5 things you were involved in were all sold.

It was funny because one of the Howard Stevenson cases was all about finding an old business in a tired industry with long lead times and poor customer service, because if you’re average, you will do better than average. I remember him saying, “I wasn’t nearly smart enough to compete with all my classmates that went on to Silicon Valley or start tech firms.” I was thinking, “I’ll buy a manufacturing business or furniture business.”

This VC guy [Tony] said, “I’ve invested in over 100 businesses but all they do is software and information services. I’m going to talk you into tech-based businesses, especially software. Go do some research. They have the highest margins, the highest earnings, the highest valuations, PE valuations, earnings, and multiples. They are the best performing businesses.

I did. I came back. He goes, “Now I’m going to send you deals that don’t fit with our VC fund or that I know about that are struggling, that maybe we could buy together.” I didn’t know anything about software. He told me to read one book, and he highly recommended it. I read that book. I was like, “I don’t even know how to properly diligence a software company.” We bought 2 companies within 6 months. I merged them together and ran them. The mistakes were plenty.

I bought two businesses simultaneously. It would have been nice to pace them out a little bit. The timing happened. One was a Fortune 500 spin-out again. I got one of those purchased, and one was an owner-operator that was retiring because of health reasons. I immediately moved one out of the Fortune 500 company’s headquarters into the other. I was mixing up 2 different cultures and 2 different sets of employees, all in one building. It was quite messy because I didn’t know how to diligence software companies.

It took a little while. I was trying to sort through who all of our customers were after we did the deal. I got the deal closed. There’s a problem called “cave to close” in the deal world. It’s not perfect. You’re overpaying. You haven’t done enough diligence but you’re saying, “I’ll buy and figure it out.” We just paid them. We got these two deals done. I started figuring out it wasn’t quite as good as I had hoped. The sales pipeline was non-existent. We had issues. The software was buggy in both companies. A lot of the customers were late adopters to where it was like old code. I couldn’t exactly take that and sell that to any new customers.

I was sorting through that. There were two pivotal moments of learning. Here’s a funny thing. I had managed national sales force but I didn’t know how to manage a sales pipeline. I worked at a Fortune 500 company. I had never worried about cashflow, and all of a sudden, I’m running two small companies merged together, and cash is king. I’d have to wring my hands over, “Can I buy a new computer for an employee?” Compared to the old days, I had a massive expense budget when I ran a large business division for Mobil. I could fly on a private jet and take a customer golfing at Pebble Beach or Elk Country in Colorado. It was no big deal.

What I realized is that I didn’t know anything about an early-stage, startup, or small business environment. I knew nothing about managing cashflow. Each employee does a specific task, and if they’re sick, you get zero capacity for that particular capability. I’m learning all this simultaneously. I go to the 3rd or 4th board meeting, and we are completely out of cash.

I have to beg the investor to put more money in. He goes, “You’ve got to fix these cash problems.” I said, “If we can grow it, it will be fine.” He goes, “No, I don’t care how many zeros you add. If you can’t manage cash now at this size, your cash issues will be bigger if you add more zeros. Your problem is managing cashflow. It’s not the scale of the business.” I remember gulping, going, “Wow.”

He would sit there and look at the financials, income statement, balance sheet, and cashflow. He would be like, “What did you do here?” I’m going, “I don’t understand even how to read financial statements.” Yes, I went through a couple of classes at Harvard but I still had so much to learn.” He was such a great mentor. He said, “Here is our handshake deal.” He would put up all the money. He would help source deal flow. He would mentor me during diligence, negotiation, closing, and running the business. He would teach me to be an entrepreneur.

He got 80% of the company and I got 20%. I got 10% at closing anytime we bought something, and I invested the other 10% over five years. That was our deal, 3 or 4 bullet points. He cared. He was my lone investor. He mentored me. He taught me how to be an entrepreneur and how to manage a sales pipeline. He taught me everything I knew.

There is another one I bought. With this one, I thought, “It was all over.” I go, “Tony, I have analyzed every customer, product, software app we have, etc. I can’t grow this. I can’t. There are no new customers to go after. They are all using this old code, and it’s not scalable. It’s not repeatable. It’s highly customized. I’m sorry. I didn’t due diligence this properly. There’s almost nothing that we do with current customers that could be sold to new customers. I’m sorry about that. I feel bad.”

He goes, “No, here is the deal. You’ve got 40 to 50 employees. Some are software developers. You’ve got customer support. You’ve got the capability. All of this is paying your salary. Think of this as an incubator or skunk works. You go and create a new software app or a new software product that is going to serve Fortune 500 companies, with revenue that’s going to be recurring in nature. Something that is probably non-strategic that they would outsource to you. Go do that. Don’t worry about what we bought. It put you in this position. We have a data center. We have a lot of assets. Keep me posted and come up with some ideas.”

He goes, “You’re an expert at sales and marketing. You did a lot of stuff at Mobil. You had a couple of years at BCG. Just figure it out.” I remember walking out of there, going, “He’s patient. He sees something in me and is saying, ‘I’m still behind you 100%.’” I went out and started selling my time like a BCG consultant. I sold my time for $500 an hour. I went to all the biggest corporations in Minneapolis-St. Paul. I said, “I’ll study your salesforce and come back with ideas on how to reshape it. I’ll help you do a salesforce automation or CRM application review process and help you pick an application that is going to suit you.”

I sold sales and marketing consulting. I landed on this notion that a lot of them didn’t do a good job of analyzing all of their existing customer data and figuring out how profitable the customers were or doing a customer analytics thing. I did a lot of that at Boston Consulting Group. I thought, “This is what I’m going to do.” I ended up doing that for several Fortune 500 companies by hand, using Excel, collecting data and analyzing it. At a follow-on-board meeting. I said, “Tony, I’ve got it. We are going to do a marketing customer analytics play. Here is some software identified that I could license and host. We’re going to build a software-as-a-service market analytics play.”

Meanwhile, what happened is he would throw me companies that he had invested in that were running poorly, “Wade, can you run this publishing company? It’s struggling. The leader left.” I would move that into the same building, “As long as it’s a skunkworks.” I took over and ran that. I ran this other company. I took a little bit of the “ash and trash.” He would give me the upside, “Build this up and sell it. I ‘ll give you X percent.” I was like, “Awesome.”

I was improving and selling off stuff like that while I was building this new company. Finally, we got it to where Tony was excited. “This is fabulous. Let’s go out and raise external capital. You need to raise a lot of capital for this idea. Go to this guy. He is a local billionaire.” I had this guy in my office, and I’m telling the story of how this new idea is cool. He was looking around.

He goes, “I’ll invest a large check in you as an angel investor but move out of this office. Get new office space that looks way better than this. Only run this new idea. Start a new company. Hire someone to run this skunkworks thing with everything else, and then I’ll write you a check because this is clearly your idea. You are passionate about it. You are not passionate about this. Do that, and I will invest.”

I called Tony. He goes, “How did your pitch go?” This was my first pitch with an angel investor outside of Tony. I told him about it and he goes, “Do it.” I go, “really?” He goes, “Go lease a nice office over in Eden Prairie.” It was called Silicon Prairie. He goes, “You only have 2 or 3 employees helping you build that. Take them with you. Help me hire someone to run our core operation and go do that.” I did that.

It was the internet buildup. We raised $75 million for the business. Life was quite different then but we ended up doing 7 companies together in 7 years. In some of them, we immediately had someone else run it, and I was on the board. We had a mix of outcomes but overall, it was a good outcome for him as an investor. It was typical portfolio theory. That’s how I got my start.

Thinking back, you broke some rules when you were in the military, making up your Arabic language skills and getting yourself into Airborne school. You broke some rules in the entrepreneurial world too. It’s not supposed to be that easy to get funding. I’m sure you worked hard with those companies but it wasn’t like you had to go out and pitch for money again and again like a lot of entrepreneurs do.

I’ve got to tell you one story. I was far less successful than you might think at this point. The one that I raised $75 million for did not go well at all. The internet was melting down. Our customers dissipated. We burned through most of the cash. I got it slightly profitable and sold it to a publicly held firm but for us a song. It only returned a portion of the capital to my institutional investors. They were not very happy.

There I am, having sold off most of that portfolio that I helped start. I moved back to Texas to where I wanted to get back. Tony did not raise another venture fund. He was saying, “I’m shifting to creating an investment bank and so forth. I’m like, “I have to find a new venture backer.” I show up in Dallas, and I’m like, “Let me network around and try to find my new Tony. Someone that would back me for my next idea.” I’m embarrassed and ashamed about my experience. This is a funny story.

One of my friends lined me up for Ross Perot Sr. In those cases, you don’t meet directly with Ross Perot but with the chief investment officer of his family office. Ross Perot has great experience, is a billionaire, etc. I went to meet with his chief investment officer and was ushered into this nice conference room in his family office. This chief investment officer sits down and opens up his notebook. He take out his pen and says, “I understand you are a serial entrepreneur. Tell me about your experiences so far.”

Somebody had brought me a cup of coffee. I hadn’t even taken a sip yet. It’s still sitting there steaming, and I go, “I have taken a few hundred thousand and turned into a few million. I have taken several million turned into more million, and then I took $75 million and turned it into $5 million. Unfortunately, my largest capital raise was sort of dot-com disaster.” He folds up the notebook and closes his pen. He goes, “I can’t sell that story to Ross.” He stands up, leaves the conference room, and I’m going, “Wow.” Ninety seconds into the meeting, he is gone. I thought, “I’m going to have a sip of coffee.” I walk out, thinking “I’m gone. That was rather sobering. This is going to be a hard slog. This is a hard story to tell”, even though I took some modest sized investments, made a few million, and so forth.

I raised $12 million for my next venture but it was difficult because the whole internet market had melted down. We’re talking 2002 to 2003. All I had done was software companies, tech, and internet stuff. It was difficult. The next business I started after working hard to plan it. I planned it carefully and developed an extensive financial model. I was going to be a good steward of whatever capital I raised and carefully thought through every single aspect of what business I wanted to start. That business turned out unbelievably well, where my early investors got an 82X return. It was astounding.

I called two of my friends and said, “We are finally exiting the business after a bunch of years, and here’s the approximate amount you’re going to get wired.” They were like, “This can’t be real.” What I learned was that during those fast-heated days of the internet in ‘99 and early 2000, anybody wrote huge checks for any idea. You could walk into a VC’s office, and it was almost like they were begging you to take their money. Things started melting down only six months later. This was the opposite. They would crush you and wouldn’t even show up for board meetings. It was like, “We’ve already written you off. Just go die.” It was a weird environment.

I persevered, hung in there, and carefully planned the next one but with a whole different attitude. Any capital raise I do, I have an extremely high level of stewardship. It turned out much better. I would say that the first 10 or 15 years as an entrepreneur were way more struggle than success. I was learning a lot of lessons, and thankfully, I kept at it.

After that one big internet disaster, I was tempted to go back and get a real job. I thought, “No, I can’t. I’m ruined. I have been an entrepreneur for too long. It was in my blood. I had to try to find investors to back me one more time. Thankfully, I can do what I want now, and don’t have to rely on investors so much, but I do have a venture fund. I still beg for money for my fund and say, “Please trust me.”

Take us forward now. I’m conscious of time. What’s the mix of things you are doing at the moment?

I’m still an entrepreneur. I have a software incubator. I incubate software companies. They’re all my ideas. I found a company and have a team on them. I have a common team that develops across all the companies in the incubator. A passion of mine is constantly coming up with new ideas and working with the teams to build out software apps and launch them. I also have a venture fund. We have offices in Europe and US. We invest in the seed stage and series A stage. It’s almost exclusively software-as-a-service. It’s all I know. I learned to stick with my knitting as an investor.

I have a fund where we invest in multifamily properties. We’ve got quite a few units in the Dallas-Fort Worth Area and are expanding rapidly. I have a hedge fund. It’s public equities. It’s a long equity fund. That’s fun. I have awesome people I work with and awesome partners in my various funds. We are having a blast.

I’m exhausted listening to this. There has been almost no point in your entire life, from the time you were about six, that you only had one job at a time.

It has been fun. Some people would say I can’t focus.

I don’t know that I would say that. You have been a hustler since the very beginning.

The good Lord has given me a lot of fun experiences. It has been a very diverse set of experiences for sure.

When you look back, what are the things that stand out for you that you would tell your younger self or tell somebody who’s reading this in terms of how to think about letting your career unfold?

Take risks when you are young, and don’t be afraid of taking risks. We’re all brought up to try to avoid risks and make mistakes. Our loss aversion is higher than our desire to gain in many cases. My recommendation is to take risks when you are young and when you can. Everybody needs to become self-aware. Understand your skills and your biases. I had a real bias for sales and marketing. I was always drawn to that in business. I had to hire people that were stronger in finance, control, and ops.

Understand your stage of business. I love the early stage. Understand your role, what you’re good at, your skillset, what you’re not good at, how to surround yourself with good people, develop a growth mindset where you are always learning rather than a fixed mindset, and be aware of human flaws. The Nobel Prize-winning economist, Daniel Kahneman, would say, “We all make decisions emotionally. We must guard against that human flaw of not thinking deeply about things.” He has written about this prospect theory as opposed to utility theory on how to make decisions. Analyze all of that, understand who you are and find your place in the business world where you fit, and leverage that.

We will wrap it up there. We’re a little bit past the time that I promised you. I appreciate all the time you have taken and what an incredible journey you’ve had, only part of which I knew before.

Thanks, JR. It is a pleasure. I appreciate you.

Absolutely, Wade. Hopefully, I’ll see you soon.

—

It was great having Wade on the show and getting a chance to hear about his accomplished career journey and everything he’s learned along the way. If you are ready to take control of your career, visit PathWise.io. If you like more regular insights, you can become a PathWise member. It’s free. You can sign up on the website for the pathways newsletter and follow PathWise on LinkedIn, Twitter, and Facebook. Thanks. Have a great day.

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About Wade Myers

Wade Myers is a serial entrepreneur, investor, advisor, author, and speaker. He has founded, invested in, and been a director of more than 90 companies and has completed over 100 financing and M&A transactions over the course of his career.

Wade started his career as an Airborne Ranger in the United States Army, in a mix of active duty and reservist time for more than 15 years, including 6 months in the first Gulf War. During his military service, he earned a number of awards and commendations, including a Bronze Star.

Following his military service, Wade spent 7 years working for Mobil Chemical before earning his MBA from Harvard Business School. He then went on to Boston Consulting Group before venturing out on his own, founding a number of tech-based start-ups, many of which he subsequently sold. In parallel, he became an investor, eventually starting a number of firms that have invested in startup incubation, venture capital, private equity, hedge funds, real estate, and major motion pictures. He has also served on the Boards of Directors of several tech-based firms.

Along with his MBA from Harvard, from which he graduated as a Baker Scholar, Wade earned his Bachelors’ degree in Agricultural Economics from North Dakota State University and his Masters’ degree in Computer Information Systems from Texas A&M – Central Texas.

He has helped develop an executive education course for Harvard Business School and is a Harvard case study author. Wade is also a published author, with articles in Inc., Forbes, Huffington Post, and Apple News. He was also featured in Episode 4 of Season 1 of the Curious Entrepreneur series on Amazon Prime. He lives in the Dallas-Fort Worth area and has 5 children.