In this episode of GC Sidebar, Paragon Legal CEO Trista Engel sits down with Michael Stein, General Counsel at Gambling.com Group, for a candid conversation about the realities of legal tech adoption, the all-hands nature of being GC at a small company, and the career role that changed everything.
Michael shares a pragmatic view on how to cut through the hype around legal tech by weighing cost, ROI, and implementation against real business needs. He offers a behind-the-scenes look at what the GC title actually entails in a lean organization—where “other duties as assigned” can mean anything from complex negotiations to making sure the coffee is hot and the meeting runs smoothly.
From negotiating Britney Spears’ first Las Vegas residency contract to navigating the transition from Big Law to in-house, Michael reflects on the moments and mindsets that shaped his career, plus why he sees himself as a trusted, quiet voice of reason in the room.
Watch the full episode.
Prefer reading over watching? Below is the complete transcript from our GC Sidebar interview with Michael Stein, General Counsel at Gambling.com Group
Trista Engel: Hi, I’m Trista Engel, CEO of Paragon Legal, and welcome to GC Sidebar, a short and sharp conversation series with today’s most forward-thinking general counsel.
In just four questions, we cover the legal industry, leadership, careers, and a little fun.
Today I’m joined by Michael Stein, General Counsel at Gambling.com Group, a provider of marketing and sports data services for the global online gambling industry.
Michael spent a good chunk of his career at DLA Piper, focusing on corporate governance, M&A, and capital markets work for public companies. He later moved in-house to Las Vegas, holding legal roles at Caesars Entertainment and Everi Holdings.
Fun fact, while at Caesars, he negotiated Britney Spears’ first residency contract with Planet Hollywood.
He boomeranged back to DLA for a year and a half before joining Gambling.com as GC in 2021.
Michael, I’m excited to have you. Welcome, and thanks for joining me.
Michael Stein:
Thank you, Trista. Great to be here.
Trista Engel:
Let’s jump in. What’s the biggest challenge you see facing GCs and in-house legal teams today?
Michael Stein:
I think one of the biggest challenges at the moment is this whole push-pull, both publicly and in the sales channels, for so-called legal tech. Everyone says you must implement legal tech, and if you don’t, you are almost a pariah.
I think there are so many aspects to consider. One is cost. Two is the effect on budget and EBITDA, particularly if you’re a public company and you’re adding costs to your budget. How do you calculate ROI? And implementation. How long is it going to take to implement? How many hours is it going to take?
And finally, does it actually do what it says it does?
Trista Engel:
What part of your job would surprise people the most?
Michael Stein:
I think the most surprising aspect of the role is that people hear “General Counsel” and might picture a high-and-mighty lawyer. That’s certainly not the reality.
In a small company, in my opinion, it’s pretty much all hands on deck for anything that comes up outside of your legal duties. You simply do what needs to be done.
Sometimes that means helping HR collect computers from former employees who won’t respond. If you’re on a business trip, it might mean making sure the meeting runs smoothly, ensuring the meals are correct, there’s enough coffee and water, enough plugs, and that everyone is set up.
You do what you have to do above and beyond all the legal work you handle on a day-to-day basis.
Trista Engel:
What’s one career moment that changed your trajectory?
Michael Stein:
I don’t necessarily think it’s one single moment, but it was certainly one job.
As you mentioned in the introduction, my experience with Ms. Spears during my time at Caesars was transformative. Professionally, Caesars had just gone public, was over $20 billion in debt, and was majority-owned by Apollo and TPG. It was a very complex global company with a complicated capital structure and debt stack.
It was also the perfect transition role for me into an in-house position. I moved from a capital markets and M&A role at DLA into a role that also included entertainment contracts, a big selling point for me as a music fan.
Working closely with the entertainment team, who were entrenched in the industry and worked with big-name musicians, was both exciting and fun. It was my entrée into in-house practice, and it really opened my eyes to how things are done differently compared to a law firm.
That role was a seminal moment in my career.
Trista Engel:
What’s something people might not know about you?
Michael Stein:
Most people know I have a wonderful and supportive wife and two amazing boys, and I wouldn’t change a thing.
Before starting my family, I did a lot of hiking and biking. I’ve been to Mount Everest base camp, reached the top of Kilimanjaro, and was planning a trip to Aconcagua.
As they say, the best-laid plans often go awry, and now we’re happily settled in Texas with a wonderful life.
Trista Engel:
And the bonus question. Who is your favorite fictional lawyer?
Michael Stein:
Most fictional lawyers are litigators, defending the indigent, the downtrodden, or someone wronged.
I’d have to say Tom Hagen. Putting aside the illegal activities, Tom is described as a logical, gentle voice of reason for the Corleone family.
I like to think of myself as logical and a voice of reason. On the transactional side, and especially in-house, that role of trusted, reasonable confidant who moves in the background without making a lot of noise in the foreground can be a big asset.
Trista Engel:
That was really fun, Michael. Thank you so much for sharing your journey and your thoughtful answers.
Michael Stein:
Thank you. It’s been a pleasure to be here.
Trista Engel:
All right, that’s a wrap on today’s episode of GC Sidebar. Catch more great conversations on our website at paragonlegal.com. Thanks for tuning in.
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