Michael Geroe’s legal journey saw him work from the West Coast to the East Coast, as well as a good chunk in the middle of the country. This taught him a ton of powerful career lessons, which greatly helped in building his own startup. He joins Joseph Schohl to look back on his story so far, filled with learnings about resilience, reinvention, and fulfillment. Mike also shares how he shaped himself to become an effective problem solver for his clients and found the best opportunities in the most unexpected places.
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Kansas City Here I Come: Mike Geroe’s Coast-To-Coast (And In Between) Legal Journey
My guest is Michael Geroe. In this episode, we follow Mike from his California roots through a fascinating career that takes him from the West Coast to the East Coast and back again, not before spending a good chunk of time in the middle of the country. Along the way, Mike shares candid stories from his time in big law, his leap into startups, and the lessons he has learned about resilience, reinvention, and finding fulfillment as a legal professional.
Whether you are a sitting or aspiring general counsel or simply love a great journey, Mike’s story offers inspiration and a few laughs along the way. Here is Mike’s bio. Mike Geroe is a seasoned technology executive and former general counsel of Ad Knowledge, where he oversaw all legal compliance and corporate affairs during a period of rapid growth and innovation.
A graduate of Columbia Law School, Mike and I were in the same class. He began his career in private practice advising technology and media clients on complex commercial matters. He later founded his own startup, giving him a rare dual perspective as both entrepreneur and legal strategist. We will hear more about all that on our show.
Mike, welcome to the show.
Thank you for having me.
Mike’s Childhood And Educational Background
It is great to have you. For our audience, Mike and I went to law school together back in the late 1900s. We recently connected at a little Columbia Law School reunion that we had. He would be a great guy to have on the show. Mike lives down in San Diego. Is that where you grew up?
I was born in Hollywood, but that was before Hollywood got split in two. My dad was in San Diego in the ‘70s. We moved down from LA. I stayed here through high school and did not leave until college.
Where did you go to college?
I was a bit of a collegiate vagabond. I actually started at UCSD. They had a program as seniors. You could be enrolled as a freshman at UCSD.
As a senior high school?
As a high school senior. This was in like 1985 or 1986. They had a program where you could apply and, contemporaneously, be enrolled as a freshman and a high school senior. I did that. At the end of my senior year in high school, I am like, “I already spent a year at UCSD.” I transferred from UCSD to Cal. I wanted to be like every teenage guy in California at that time.
I wanted to be an electrical engineer. Everyone was reading about Apple Computer and the fight with IBM. That was going to be the future. I was very interested in that. I had taken math and science classes in high school. When I got to Cal, I realized that the level of math skill necessary to be an electrical engineer was just a few orders of magnitude above what I was ever going to have.
The level of math skill necessary to be an electrical engineer is extremely advanced. Share on XI thought, “You already transferred once. That is how you got here. Let us do it again.” This time, I transferred to Georgetown. I went from one extreme, like math and science focus on the West coast, to the opposite of that, which was a history major. I became a history major out east at Georgetown. That was it. I transferred to Georgetown as a sophomore. I graduated from Georgetown. From there, I went to law school.
Did you go straight from Georgetown to law school?
I did. There was a summer of my senior year at Georgetown. I was in some special program at the US Department of State in the Main State down on East Street. I was very much thinking of taking the Foreign Service Officer Exam and becoming an FSO, if I could. I had an incredible experience, a bunch of mentors. It is me in the special programs. I am always in some weird special program. Georgetown had a special program where you could apply early to Georgetown Law and get admitted like super early if you were already a Georgetown undergrad.
I had done that. I was sitting on an offer from Columbia. I wanted to take the foreign services exam and not go to law school. Every person I respected at the State Department basically said, “You are a fool if you stay here and do not go to law school.” They are like, “Go to law school.” If one mentor had said, “Take the exam and stay,” I would have done it.
I would have done it. There was this other lady I was working with who was not a lawyer, but apparently, at the time State Department was under a consent decree for not offering sufficient career advancement to women. She was aware of this. She was in the same honours program at State. She said, “I am totally going to take advantage of this. I am going to take the Foreign Service exam. I am going to be a fast track on a fast track career. I am basically going to lap you because of this consent decree.”
The running joke we had. At some point that summer, we had lunch. I am like, “Are you signing up for the exam?” It was time to sign up. She is like, “I decided I am not going to stay.” She decided she is not going to stay. Between that and what all my mentors said, I was like, “Yeah, not going to take the Foreign Service exam. I just accepted the offer from Columbia.” I was like, “Georgetown law was great, but I’ve already been at Georgetown.
I had already been in DC. I had never lived in New York.” The opportunity to do that was very attractive to me. It was something for it. That is what I was doing as a kid. If I were in San Diego, I would want to be in San Francisco. If I were in San Francisco, I would want to be in DC. It was like a natural progression. If I were in DC, why would I want to stay in DC? Let me go to New York. That is what I did.
Mike’s Journey From West Coast To East Coast
When you graduated, though, you did stay in New York for a while, right?
Of course not. I knew you were with Dewey, not the New York office.
I was. On paper, my duty station was in Washington, DC. I had spent a lot of time in the New York office. Clearly, I spent more time in the DC office, but there were a lot of projects that either required me to go or that I volunteered to do that brought me back to New York.
What work were you doing at the law firm?
At Dewey, it was this weird combination of Title II and Title XIX work. Title II work was this super niche federal election law thing. That stemmed from my mentor at Dewey Ballantine, who is a legend, a gentleman by the name of Miles Link, who at one point was president of the DC bar. Anyway, he did Title II work, which meant that I did Title II work. Again, on paper, I was in a group called the International Trade Group.
Eighty plus percent of that work was Title XIX work, which was all like anti-dumping and countervailing duty and trade compliance. That bled into allied compliance-type work. I did some antitrust compliance. I did dispute resolution, which was litigation. I did different kinds of litigation. A lot of it was before Article 3 courts.
Mainly the Court of International Trade, but some of it was like NAFTA panels. We do NAFTA appeals at the time. Dewey Ballantine historically represented petitioners, meaning American industry. We represented the lumber industry against Canada or Quebec. We would represent the steel industry against steel manufacturers from around the world, from the UK to France and China. You name it.
We had specialties like photographic film and paper. We represented Kodak in disputes against Fujifilm and paper. It was a highly specialized practice. It really only existed in Washington, DC, and in New York. At some point, I realized that I was really driving myself into a very small niche. My ability to find clients was going to be negligible. I took opportunities. Did you work for a big firm out of law school?
I did. It is funny because my path was five years in big law, corporate M&A. This was the plan from the beginning. I am going to do a five-year corporate M&A. I am going to go in-house. I am going to rise up and become a GC. Hardly anybody. I thought that was just like the normal path. Hardly anybody I have interviewed.
They did not get that memo. Joe, why didn’t you call me? That would have saved me a lot of time. Trust me.
What I thought of as the traditional path to the GC chair. This is what is fascinating to me is like, we are right now in DC, early in your career. How did you get from there to a GC job? That is what fascinates me.
The reason I ask you this question is because I am sure the same thing happened to you, is you would be working and then just in an email, it would go to everyone, not just you, “Would you like to help with Project X? You would have to go to the New York office.” Everyone got those emails. My Neanderthal mind was like, this is a career-limiting move here.
If you are only going to do Title XIX work and you are only going to do Title II work, you either like better have a lot of beer buddies who are like presidential candidates or like steel magnets or something like that. Short of that, you are going to get stuck. I started volunteering for these projects that had a broader application. They would bring me into contact with a broader array of corporate executives, not like super-specialized people.
That got me into very large, complex litigation suits. A lot of them were life sciences-oriented, large pharmaceutical companies, health insurance companies, etc. I also tried to volunteer in DC at the local government level. It was called an ANC commissioner. I was an ANC commissioner. People would come to the commission for various reasons. That brought me into contact with some local executives.
That is when I started meeting people face-to-face who were not introduced to me by the firm. This was, smash cut to the late 1990s, at this point where AOL was just bursting at the seams. People were leaving the company and creating their own startups. All those startups were like Northern Virginia and Metro DC.
If you were going out to bars and restaurants and doing the business development circuit, you would run into those people. Just by doing that, I got a small group of half a dozen little startup clients that were interested in legal counsel. I excitedly talked to partners at Dewey Ballantine about it. They would roll their eyes. They would be like, “We are not interested in your little start-up. Could you please go?”
We certainly do not want the conflicts.
I was just super naive. I did not have your play sheet about the five years or whatever it was. I was struggling. There was a smaller firm, a Richmond, Virginia-based firm by the name of Williams Mullen, which will market not this thing basically. Fortune 500. They had Fortune 500 companies, but not as many of them.
Your entrepreneurial instincts, which are going to take you far, as we are going to hear.
That is when I jumped ship from Dewey Ballantine to Williams Mullen. As you may or may not remember, depending on how involved you were with tech. That is when the Internet bubble burst. AOL was shrinking. These startups were dying on the vine. Just as I had made partner at this new firm, it took a little bit of time to work through the system, but collecting bills became harder. Hard luck stories became more frequent.
These entrepreneurs and executives were people with whom I had become friends. I had known for years from my time at Dewey Ballantine when I brought them over with me to Williams Mullen. Busting their chops to try and ring a few grand that they did not have anyway. That whole arc started to sour. That was around the time.
I am accelerating this here from a summary standpoint, but I got a phone call. Everyone was getting phone calls from headhunters. I would field calls from headhunters. Most of them were totally irrelevant or not of interest, or I was utterly unqualified for them. There was this one where the guy kept talking about being a GC for a hotshot internet company that was funded on Madison Avenue. That seemed interesting.
As time went on, he would call me back every month just to check in on the job they were still being interviewed for. I finally said, “Let us talk. Let us have a more serious conversation about it.” At that point, I learned that the Madison Avenue that he was talking about was not the Madison Avenue in New York, which he, of course, understood was my assumption that it was the Madison Avenue startup in Manhattan. However, it was on Madison Avenue in Kansas City, Missouri.
The other Madison Avenue.
I said, “That is probably not going to work. I do not have any ties to the Midwest. It is not going to work.” He was persistent. He kept calling back. My situation kept looking darker and darker. I talked to my wife about it. She was not that interested. I did not know what to do. What I did was I gave the guy terms and a number that I thought would make him go away.
I said, “I am happy to help these people as outside counsel. We could kick the tires with each other. I can work from Williams Mullen. See if they paid.” When that did not work, I just said, “Here is what I need. Here is my salary number. Here are the stock options I want. Here is the housing accommodation I need.” I figured I would not hear from them again. He called me back 60 days later. I am like, “He is agreeing to all of this. Let me go out.” They flew me out. They put me up at a nice hotel.
I met the founder. We hit it off. To make a long story short, I said yes. Part of the terms was that I would need time to relocate my family and find a house. They put me up in nice corporate housing for a while. I was using that time just to make sure that I could cash the checks. They were not bouncing. The salary was what we had agreed. The stock option agreement was signed. That was it. The bottom line is the fellow I ended up working for and with, an entrepreneur by the name of Scott Lynn. He was the real deal.
Look at that. Your family followed you. You were a Kansas City resident?
I was in Kansas City. I was a pretty open book. I said, “I would probably only keep my wife here for about three years.” He laughed at me. He said, “Mike, in three years, we are either going to IPO, be rich and retired, or completely unemployed.” That is all the runway I’ve got. I do not have more than three years. Of course, that did not turn out to be exactly accurate. I spent the next 10 or 11 working with him. Indeed, after about three and a half years, I left Kansas City. I was working from Southern California.
What’s the name of this company?
It does not exist anymore, but it is called Ad Knowledge.
What did you guys do? What was the product?
It was an advertising tech play. It was really a two-sided marketplace between advertisers and consumers, basically. Its mission was really to show the right ad at the right time. It was employing novel advertising technology to get the right ad in front of the right person. The compliance regulatory work that I had done with the agencies, not exactly the antitrust work, though there were some antitrust issues that came up in later years.
They were minor, but certainly the familiarity with working with federal agencies and state agencies on compliance was enormously useful. The experience of working on complex cases at Dewey and to an extent, at Williams Mullen, there were complex litigation issues, some complex contracting, but the bread and butter work at Ad Knowledge was really licensing and a little bit of prosecution, maybe some collections work, but a lot of defence. A lot of getting accused of being email spammers. A lot of litigation around that.
The familiarity with working with federal and state agencies on compliance is enormously useful when working as a lawyer. Share on XWhat led this recruiter to you? Why did he reach out to you?
He reached out to many people. I do not think he just reached out to me. How he specifically found me, I honestly do not know. This was like in 2003 or 2004. Actually, I do not think I started at Ad Knowledge until the summer of 2004. 250-foot level details, I do not remember, but I do remember he was one of many recruiters that I was in touch with.
The one thing I remember about Dewey Ballantine was great. I worked my tail off. I did a lot of hours, but they gave me two weeks of vacation. They would tell you, “Take the two weeks because the rest of the time you are ours.” I would totally take that vacation, no matter how complicated my matters were.
I remember we had to do those matter sheets, like refer this back to whoever would be like these intricate multi-page emails that you would internally send out, like who was covering for you when you were on these vacations. I would take them. While I was on these vacations, that was the time I had to talk to recruiters because I was not in the office. I would be in Europe. I would be on some crazy vacation, but I would be on the phone trying to talk to a recruiter about a job. I do not remember exactly how or when this particular guy came across my resume.
I do remember those matter sheets and who was covering for you on each matter. Now it is like you are covering for yourself when you are on vacation, because we are all. How did that job end? Did the company get bought?
That company was headquartered in Kansas City, Missouri. As I told you, on day zero, I warned Scott that my shelf life in Kansas City was going to be more or less three years. After three and a half years with his cooperation, I came to California. He did not even have an office here at the time. He is like, “Mike, you are my GC, really? You are not going to go to a city where we do not even have a freaking office.”
He opened an office in LA, in West LA. Long story short, I would commute to that office. I worked there for years until they closed. It was a sales office. At some point, the executive management team and the investors were like, “We are going to IPO. It is time to IPO.” At that point, they wanted the management team back in Kansas City. They called it the cockpit. They are like, “Everyone has got to be in the cockpit.
I cannot try and do a dog and pony show. Get people to invest in the company. Try and go public. Have like my GC out in some outpost somewhere. You have got to come back to Kansas City.” The executive summary was that my family did not want to go back to Kansas City. It was a nice place, but we had no ties to Kansas City. We only spent three years there. I have got two daughters. They were like super young when they were in Kansas City, but at this point, they were in school.
They had friends. Breaking that up became problematic. Again, long story short, I helped interview, hire and train my replacement. Basically, I trained them for two years. I walked out the door. That was basically December 2014. It was amicable. Scott and the company gave me a lot of runway. I was like, “What do I do now?”
Starting His Own Startup Firm
What I decided to do was take what I had learned about Ad Knowledge with a focus on compliance and apply that to some branch of ad tech advertising. That is what this startup was by the name of Optincall. What would happen is I would have friends and colleagues who I knew over the years, either from my time before AdKnowledge, sometimes from my time at AdKnowledge, other alums who had left the company, and they would call me up.
They would be like, “Mike, I know you are doing this startup, but I could really use a hand on this little project. Could you help me with this little project? I will pay you for it.” I was trying to spend all my time growing this startup, but what I realized at some point in time was really keeping the lights on. The mortgage was paid, was all these little side projects I was doing. I was running into a lot of trouble on the startup because what I knew how to do was be a lawyer. That is what was in my DNA.
Tell me about Optin.
OptinCall is a startup that is focused on giving consumers the tools to inform decisions on complex purchases. The business focuses on about a dozen verticals, complex products or services. Insurance products, health insurance products, or education, for-profit education, nursing, for example. We connect consumers with service providers or product providers anonymously. Meaning the consumer can speak directly to a service provider, get their questions answered, but not give up their phone number or, frankly, even their name.
It is extremely helpful for consumers if they can connect with service providers without having to give up their phone numbers or names. Share on XSimilar to Ad Knowledge, it is a two-sided marketplace. Still, all the advertiser knows is that whenever it is they decide to launch their advertising campaign, they will be connected to someone interested in their product or service. Still, they will not have the name or contact information of that person. We connect them over the phone.
If the consumer likes what they are hearing, and it is a good conversation, the consumer can share his or her name and contact information. They can continue that discussion to make the purchase. The use case here is people who are going through some career or life change. Someone who is getting married. Someone who is getting divorced.
Someone who is moving because they just got a new job or they just lost a job. They either need insurance or they need auto insurance, or maybe they are trying to put solar on their roof or some home remodel, but its focus is something that you cannot just go to Target or Walmart and just buy off the shelf. It is something that is more expensive, more complicated. You are going to want to do some research about it.
The consumers are people who want to do this anonymously for personal reasons, or they do not want to be bombarded.
Exactly. It is to protect their privacy. They do not want their, like, when was the last time you looked for auto insurance or home insurance, but if you do it over the internet, often you end up filling in a lead gen form, or even a mortgage, sometimes if you do not go directly to a conventional bank. They will have you fill out these lead sheets. They will sell the data and the lead sheets.
I have experienced that right on the mortgage side.
The question is, how can you learn what you want to learn, but not get spam phone calls or spam emails? How do you just get the info you want, but then have the freedom to make your own decision without getting harassed by other service providers we solve for?
How do you guys get paid by the service providers?
Basically, if the connection lasts longer than 60 seconds, they pay us a flat fee for each connection. If they get an answering machine or if one of the kids picks up the phone, they can hang up within a minute. There is no charge. They call it whatever they want. The salespeople can call on a campaign. Maybe they are at the airport. Their flight is delayed. They want to do some work. They can just dial into the system. It is all automated. It is patented. It is not even patent pending. We have got patented system to handle all.
You co-founded this company, and how long have you guys been at it?
Since I left Ad Knowledge. I took six months, maybe a little bit longer, to just cool down. Find my bearings. I connected with an old buddy. That is when we started to spin things up. It was not literally after I left, but pretty close thereafter.
You have the law offices of Mike Geroe, right?
I hung out my own shingle. That is what my mom told me to do. My mom wanted me to be a doctor, but I was not good enough for that either. This was the next best option.
What Mike Is Looking Forward To
What are you most looking forward to?
I really enjoy the different challenges that this entrepreneurial space has. I have been doing it since Ad Knowledge. It is like a different cast of characters and a different set of challenges. It is all in the same sandbox. It is. How do you raise money to fight another day? How do you comply with this changing montage of regulations?
What is old is new again. I just enjoy doing what I am doing. At this point, I feel like I have been doing it for so long. It is not that I can do it in my sleep, but I know what is in my wheelhouse. I try to stick to my lane. Over the years, I have found other colleagues in private practice who are good at what they do. It is tax law, insurance law, or 33, 34 act stuff.
I know who to go to. I got my own little network. I continue to be active in the in-house bar, the Association of Corporate Counsel, where I swap stories and headaches with other startup GCs. I am also a member of the ABA, although I have not had time to travel as much. For the ABA, you have to travel more. The ACC activities are more like those in your city, in your town. Plus, the ACC national comes to San Diego every few years. I just keep doing what I am doing. So far, so good.
Mike’s Advice To His Younger Self
What advice would you give to your younger self? Maybe the younger self when you were feeling a bit pigeonholed.
The starkest contrast to me from being outside counsel and being in-house was the following. When I was at Dewey and at Williams Mullen, I was with a team of super-talented people. The people in general, the people with the same level of experience, we were all in the same class. We were the same age, not necessarily, but we were in the same partnership class.
At some level, each one of us understood we were competing against each other for a very limited number of slots. We were not all going to make partner. If your long game was a partnership over as the years passed, that competition was going to sharpen. When I was at Dewey, the partnership track was like 7 or 8 years. When I was there for seven years, I knew people in New York because I had spent so much time in New York.
I knew people in DC, of course, because that is where I was. I had friends and supporters. I had made successful inroads to branch out of Title II and Title XIX, but they wanted me to, like, take another lap, like take another year or two, before they were even going to consider me for partnership. That is when I moved over to this other law firm. As a partner, the dynamic was a little bit different, but it was still high-level.
It was still very much a, what have you done for me lately kind of atmosphere. When I moved in-house, at the time, I was one of one. I was with a bunch of talented people. None of them was a lawyer. I was the only lawyer. That was the weirdest thing. It probably took me two years to get used to that. I would have never admitted it at the time. I was like, “Where are my colleagues?” They were all other managers of other departments, but none of them were lawyers.
Without knowing, it lifted a type of pressure, whether you were competing to make partner or whether you were competing to make sure your yield was sufficient. Your collectibles were going to clear for what the partnership expected. All of that just dissipated. It is not that there were not other kinds of pressures, but frankly, the way it felt to me, the pressures I had moved into versus the pressures that I had been experiencing for the last ten years, it was like a cream puff.
It was like, “Are you kidding me? Like what?” I had the mental real estate to really enjoy being a lawyer in a way that I never let myself do while I was in private practice, because I was always thinking about something else. Again, it is not like Ad Knowledge was like a fricking trip to Disneyland or Candyland or something like that, because there was absolutely pressure for the business. You wanted to figure out how to make contracts work.
How to mitigate the risk, but it was all like a different order of magnitude from the weight that I felt had lifted from me. If I could go back and tell my younger self anything, what I would have told myself, and I do not know how I would have done it, honestly, would be to try to lift that weight. Try to just focus on being a good lawyer and trust that the rest will take care of itself. I was so stressed. As I indicated at the beginning of this call, I still had no plan.
It is not like I had a plan like you did, like five years and then jump ship. That just did not occur to me. I was too dumb. I was billing too many hours to spend time thinking about it. What I should have done was to try not to worry about that at all. I was a good problem solver, but maybe I would have been a super duper problem solver for the clients. Maybe that would have made me invaluable in a way that I otherwise was not able to do because I had this other weight I was constantly dragging around.
Super interesting, with the benefit of hindsight, you realize how much of that was self-imposed because you were the same person in a new environment. You did not have it.
Episode Wrap-Up And Closing Words
That is a great place to leave it. I love the wisdom in there.
It is wisdom that takes years to accumulate.
Thank you for the opportunity to share it and to reconnect. It was great seeing you.
Likewise, Mike, thank you for being on the show.
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Here are my biggest takeaways from our interview. Number one, focus on developing your skills and being a truly good problem solver for your clients, rather than getting lost in competition or pressure. Trust that opportunities will follow from your genuine value. Number two, embrace flexibility and resilience. Mike’s path shows that taking risks, learning from setbacks, and building on every experience are key to long-term growth in both business and law.
Number three, be open to new places. Mike’s willingness to relocate across the country, even to an unexpected destination, led to invaluable career experiences and personal growth. Sometimes the best opportunities are found when you are willing to step outside your comfort zone and embrace a new environment. Until next time. I would love to connect with any in-house lawyers or outside lawyers serving in-house lawyers who are interested in maximizing their full potential. Please reach out to me on LinkedIn to start a conversation.
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About Mike Gero
Mike Geroe is a seasoned technology executive and former General Counsel of AdKnowledge, where he oversaw all legal, compliance, and corporate affairs during a period of rapid growth and innovation. A graduate of Columbia Law School (Mike and I were in the same law school class), he began his career in private practice advising technology and media clients on complex commercial matters. He later founded his own startup, giving him a rare dual perspective as both entrepreneur and legal strategist.