Inside Out

A Manhattan startup superlawyer who talks like a mindfulness guru might sound like a character from Silicon Valley, but it turns out he actually exists. Randy Adler navigates personal trauma, overblown egos, and the depths of his own insecurity as the protagonist of this powerful parable on the human condition...

Randy Adler bucks the superlawyer stereotype. He wears his heart on his sleeve. He gets deep without hesitation. He talks freely about insecurity (mainly his own), the importance of honest communication, and the necessity of feeling loved. He’s an open book, in part because he has come to terms with a foundational tragedy that, in many ways, made him who is he today.

His ability to deal with his own demons fortifies a career handling the egos of other hyper-ambitious people. Adler is one of the top startup lawyers in New York City, specializing in high-growth technology companies. In 2009, he established his own startup firm, RK ADLER, LLP, which he branded as “a startup for startups.” Its fast success attracted the attention of Dentons, the world’s largest law firm, which acquired RK ADLER in 2015. He now serves as co-chair of Dentons’ startup practice, and has represented countless startups including Vine, Homemade, Exo, Snappette, Influenster, ThreatStream, and Jopwell. He has also served as Chairman of the Board of a charity called A Caring Hand, which uses a unique psychological method to help young children and families who have lost loved ones. 

Adler’s path has been treacherous, lined with tragedy and temptation. Even after moving past his childhood trauma, there was a time in adulthood when he indulged in a lifestyle that could have destroyed him. Once again, however, he dug into himself for an answer.

It’s this ability–to peel back the layers of his own motivations–that makes speaking with Adler so interesting. He’s like a psychological gold miner, plumbing the depths for finds that will enrich not only himself, but the clients he serves and the children he mentors. We took some of these gems and put them on display in this Breaker interview with a powerfully open mind… 

As a master adviser to startups in New York City, do you have a strategy for dealing with big egos?

I would say “debunking them,” because egos are blinding. They create huge blind spots. In fact, I don’t believe that people have really changed since man stood upright, in that hubris leads to man’s downfall time and again.

I’m susceptible to this too. Luckily my girlfriend keeps me in check. We need people in our lives that keep us humble.  Humility is extremely important, as ego blocks our ability to listen to others. Being confident is not the same as having a big ego. You can be confident and be filled with humility. 

Speaking of ego, it seems like psychology is a recurring theme in your life. A Caring Hand also deals with psychology, right?

Yeah, maybe. A Caring Hand is a charity that helps children who have lost parents or loved ones. Psychology almost feels too artificial. To me, A Caring Hand is more organic. It’s letting children be children, and letting them relate to one another. On some level is that psychology? Sure, but then I would say, what part of life isn’t? 

"Egos are blinding. They create huge blind spots...We need people in our lives that keep us humble."

Why is A Caring Hand so important to you? 

When I was seven, my dad passed away. I looked at my father like a hero, as many young boys view their dads. He worked at IBM, which is probably where I get my love of technology. One day, December 16th, 1987, my dad had a heart attack in the middle of the night. I woke up to my mom doing CPR on him and the paramedics carrying him down the stairs. They took him to the hospital but couldn’t revive him. A super traumatic incident for a young child to see. For me, it was an event that shaped my life.

Because I share my father’s name, I saw myself as the standard bearer to his legacy, which is not a burden any child should have to take on. My childhood went from happy carefree playing-all-the-time to super serious, working for success, and I should tell you why. We were fairly well off, like a Ferris Bueller’s Day Off family on the cul-de-sac; a classic Connecticut family.  My dad had started in the mailroom at IBM and worked his entire career there until he was in upper management. But when he died, he had forgotten to sign a few papers that would have given my mom his pension, so we went from this position of great comfort to my mom going back to work, and us ultimately having to sell the house. My sister left home; my other sister decided not to move in. That sort of thing.

What A Caring Hand does is gathers kids under the supervision of a psychologist. All different age groups meet and talk to one another, play games with each other and try to relate and talk about their losses. It’s kids helping kids. When I was a kid I saw a psychologist, but that’s not really the best way to open up. When you lose a parent as a child, you feel so shameful and so different. I can still remember my dad dying. Everyone came to the house, and I hid behind one of the couches. I was so ashamed that everyone was paying all this attention to me. I felt so different.

Adler witnessed his father's death at age seven, an event that majorly impacted the trajectory of his life.

Adler witnessed his father's death at age seven, an event that majorly impacted the trajectory of his life.

How did you ultimately learn to live with it?

It’s just like a wound: if you don’t let it heal, it’ll only get worse. You need to talk about it and acknowledge it. Like this interview—I could have never done it ten years ago. Never. It would have been so uncomfortable for me. It’s a sad event for me still, but it’s now something that’s more factual. It is what it is. I’m not debilitated thinking about it. And that’s probably as a result of my involvement with A Caring Hand, which helped me to confront emotions I had unhealthily suppressed. It really does bond people and get them to open up.

When you were a kid and you envisioned that success you were driving towards, what did it look like? 

I saw myself being very wealthy—which only came out of the insecurity I had because money was such a sore subject. I craved the security of money.

Then there was this man my mom dated years after my father died. His father was a well-respected attorney in our town, and that really resonated with me. People would always come to him for advice and for counseling on things, even unrelated to law. He was a consigliere-type figure with a rational and balanced mind. That’s when I decided I wanted to be that. It’s kind of difficult to describe that moment when you you’ve found your calling or passion, but looking back I can really recall that moment as the moment.

"When there’s a legal dispute, a lot of that has to do with human emotion. It doesn’t necessarily have to do with what’s written in a document."

What made you so good at it when you got older?

I think I’m good at what I do because I actually try and help people as human beings as opposed to helping them narrowly with a legal issue. So, in other words, when there’s a legal dispute, a lot of that has to do with human emotion. It doesn’t necessarily have to do with what’s written in a document. Some of it may, the legal part may, but the overarching issue most likely has to do with the relationships between folks. What are they experiencing? Are they being heard? Whether they feel disrespected. A lot of times, people will feel a certain way and the other person doesn’t even realize it. A lot of times, communication is what’s needed most to solve these problems. My awareness of these underlying issues lets me help people get to those problems.

It resonates with me when you say that, while on the surface being a lawyer is about dealing with these technical things, at its core the job is to provide understanding and communication between the parties. And I think a lot of people in similar positions aren’t as successful because they don’t understand that. They get bogged down. It’s like a doctor. A great doctor has a great bedside manner, because really, what people need is to be cared for…

I totally agree. I run a small team of people and I try to instill that exact belief. I teach them to relate to people, to focus more on being holistic service providers and less on the technical skills. You have to have the technical skills, of course, but people respond better to that other stuff. 

Randy and his father

Randy and his father

Digging a little deeper into your own psychology, you said that you were driven by wealth because you wanted security. Once you had wealth, were you happy? Or was this also a stage when you started to “rebel?” 

I started to rebel when I was hanging around with people who had a lot of money. You know, the kinds of things people do when their families have built buildings that they live in. You can just use your imagination, and that’s the kind of stuff I started to get in trouble with. Initially it was rebellion, but when things start to become a problem, it’s something deeper. In the end, I believe that anyone who gets into that scene is self-medicating their pain. Once we try to deal with that pain, then the need for self-medicating goes away. I think that my years of rebellion were really about medicating a bunch of pain that I hadn’t dealt with.

"Once we try to deal with that pain, then the need for self-medicating goes away."

The pain from your father’s death?

From my father’s death, yeah. I mean, there’s a lot to unpack there; a lot of things happened: my father died; my sister left; our financial situation changed; my mom went back to work and back to school, and so on. Essentially, I went from security and comfort to insecurity and fear.

When you’re partying with these people who have their own buildings—are they medicating too though? That question always bothers me, as someone who definitely indulges a lot. If the most successful of the successful, or at least the luckiest, are the ones who party the hardest, how could it be that they’re self-medicating?

That’s a very interesting question, but the answer is yes, they are medicating. We’re all medicating something, and it usually has to deal with—and I’m not a hippie – but as my girlfriend tells me all the time, it all comes down to love and feeling loved. A lot of children of extremely wealthy people do not feel loved or worthwhile. Doesn’t have to do with the facts, but with the feelings. There are different burdens that we all have. Mine was that my father was taken away from me, so I have to redeem that loss. For others, they may think—my father made a few billion dollars, how am I going to ever compare? In the end, it’s really important that we listen and hear people so that we can support each other as best we can. Nowadays, I have friends from all walks of life, at every reach of the world, and with absolute certainty I can say that we’re not that different. It’s the human condition that we’re all living. That inspires a lot of my advice as well. 

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