Meet Ben Wolkov

We had the good fortune of connecting with Ben Wolkov and we’ve shared our conversation below.

Hi Ben, what is the most important factor behind your success?
For me, it all comes down to authenticity. The way we operate at Caldera Law is very straightforward – we tell people exactly what they can expect from working with us, whether they’re clients or members of our team. And then we actually deliver on that.

I think people can feel when something is real, when a relationship or an experience is rooted in honesty rather than performance. That has shaped the way the firm works and the way we show up in every interaction. Authenticity isn’t something we talk about; it’s just who we are, and it’s been the backbone of Caldera’s growth.

What should our readers know about your business?
Caldera Law works at the intersection of business, culture, and community. We focus on hospitality, food & beverage, real estate, entertainment, and with high-growth ventures – industries that are shaping Miami in real time.

What sets us apart is our philosophy of leadership and service. One of the biggest challenges of growing the firm, and of my own growth, has been learning how to balance individual ambition with the collective interest. It’s the classic leadership crucible: shifting your mindset from “What do I want?” to “What does the team need? What does the community around us need?”

That shift doesn’t come naturally. It requires you to make it less about you, while still making sure it remains true to you. I won’t pretend that’s comfortable – it’s not. But it’s necessary. And it’s been the most defining part of building Caldera: learning how to assume and embrace leadership while staying anchored in authenticity.

What I want people to know about us is simple: our work is driven by relationships, real values, and doing things the right way. That sounds basic, but in practice, it’s rare. And it’s the reason clients trust us and the reason we’ve been able to grow the way we have.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
If we were lucky enough to time the visit to one of Paya’s legendary weekend Block Parties in Miami Beach, then we would start there. It doesn’t happen often, but when it does, it’s one of the best vibes in Miami – great crowd, music, and pure energy. And a great place to catch up with your creative friends driving Miami’s culture.

Little River is a must.
We’d spend time at The Garden, a neighborhood space curated by my friend and Miami culture legend Max Pierre. It’s intimate, music-driven, and beautifully unpredictable. You can walk in on a random night and end up in a conversation with someone fascinating or take the wheel spinning 45s. It captures the spirit of Little River perfectly.

For music lovers:
A monthly ritual is the Arthur Baker DJ set at Dante’s HiFi. Arthur is a legend and a friend, and his set is one of those Miami experiences that feels both timeless and hyper-local. If it’s late October, then the Despacio tent at iii Points!

Food-wise, Miami never disappoints:

Sunny’s – an essential.
Hiyakawa or Ogawa – when I want to impress someone.
ZeyZey – the music bookings have been on point lately; incredible acts in a small space.
Stubborn Seed – Chef Jeremy Ford is a genius and a good friend.
Barceloneta – my longtime neighborhood spot; too many good nights and memories there.

For grounding and community:
We’d close out the week with Yoga at IMA, the best yoga studio in Miami. It’s the kind of place that reminds you why people fall in love with this city – the community, the warmth, the sense of belonging.

Cup of Joe:
Imperial Moto Cafe in Little River. My home away from home.

That’s my Miami: culture, music, great food, and the kinds of spaces where you feel connected to the people around you. It’s a city with real soul if you know where to look.

Who else deserves some credit and recognition?
There are three people I feel especially grateful for when it comes to my story and the early days of starting my own practice.

The first is Ira Coleman, Chairman of McDermott Will & Emery. When I left the firm to start something on my own, I walked into my tiny shared office on day one and saw this massive orchid arrangement sitting on the desk with a handwritten note wishing me luck. It was such a simple, but remarkably classy gesture, especially coming from the leader of a firm I had just left. That level of graciousness left a lasting impression, and it’s helped shape how I approach professional relationships, particularly in challenging moments.

The second is Chris Mehringer, Co-Founder and President of Park Street – my very first client. Completely unprompted, he sent an email to his network explaining that I had gone out on my own and recommended me. That single act of friendship and belief opened the floodgates for me and helped create the foundation of what ultimately has become Caldera Law. Park Street remains a client today, which speaks to the strength of that relationship.

And finally, Kevin Fitzgerald, the Founder and Chairman of REIC, a mentor, client and friend. I have learned more about business from Kevin than just about anyone else–he has been a massive advocate for me in my legal career.

Ira, Chris and Kevin played different roles, but they each showed up for me at exactly the right time. I wouldn’t be where I am without them.

Website: https://www.caldera.law/

Instagram: https://www.instagram.com/caldera.law/

Linkedin: https://www.linkedin.com/company/calderalaw

Image Credits
Courtesy of Caldera Law; Photos with World Red Eye watermark are Credited to World Red Eye