Preparing Advisors for the AI Era at Future Proof Citywide with Chris Cherry

The Future Proof Festival took the industry by storm in such a fresh way a few years ago, and now there's Future Proof Citywide as well. For those who have only heard the buzz about Future Proof Citywide, how would you describe it in everyday terms?

[00:00:55] Chris Cherry: Citywide in everyday terms. So look, I think Festival, like you said, kind of took everybody by surprise and became a huge hit.

So coming out of the first year in '23, where we hosted the breakthrough meetings, we had an overwhelming response where people wanted to have the meeting program again, do we have to wait a whole year? And so our team kind of saw the demand and said, let's have a second event, a second large scale event where we won't be kind of limited with space because if you think about Huntington Beach, we literally build on the parking lot from the ground up. But we're limited there. And we did it. We succeeded. We have 5,000 people there, and the event is a huge success. But we really can't go beyond that. So going to the East Coast, in South Beach specifically allows us to grow the event not only on the beach, but into the city.

So, Citywide is giving us the opportunity to not limit and say we can only have 5,000 people, but maybe in three, four, or five years we have 10,000 people. Think of it like South by Southwest, maybe we kind of take over into South Beach, into all the venues. There's some beautiful venues, restaurants, places to activate and for the industry to take advantage of all those people in one place. So we called it Citywide for that very reason, for the vision to kind of take over South Beach. Not just on the beach, but over into the land as well.

[00:02:19] Doug Heikkinen: Everyone always asks the difference between Citywide and the original festival, and you said, besides we can grow bigger, is there a different vibe and ambition behind the format at Miami Beach?

[00:02:31] Chris Cherry: Yeah, so I think that's a good question. The format, the approach is the same, meaning let's take all the things that we didn't like about traditional conferences and go against that, which is get people outside, get people in a more casual, relaxed environment.

Those things remain the same. The way that we interact when we're there are the same by using the breakthrough platform. But, Citywide has a different theme, right? So we still have the same ecosystem of financial services, but this year, what we are focusing on, ai, why?

Because it's the hot topic. Hot, it's not just hot, but it's, what is affecting our industry and our daily lives, like immediately. So we saw the need to kind of own that narrative and make sure that we're bringing education. To not just our advisors, but our entire ecosystem. Matt, he put an open invitation on LinkedIn and said, I want to talk to anybody who's using AI, is implementing it in their firms.

And so he's been on the phone all day, every day, just understanding what, who is saying they're afraid of it, we've only done this. And then there's other people that have built their entire AI agents, agentic AI, if you know what that is, of course you do. But, so I think Citywide allows us to change the themes for the future and evolve instead of just having an event that's focused on just one product. So with Citywide we can evolve the themes, to whatever is happening in our industry currently, which as we know now is AI. So, I think that allows us to bring the same community, similar community, but maybe different segments.

You might have different people that would come from the same companies to Citywide.

[00:04:15] Doug Heikkinen: So there's four key themes for this year: invest, build, grow, and live.

How do these themes play out in real experiences for the guest? Got a favorite example of where these themes meet the energy of the event?

[00:04:29] Chris Cherry: Yeah, so, I have one. It's a, I can't tell you what it is, it's a surprise, but it's going to be a a, very cool, one of our sessions is going to be really cool.

But look, I think when we left the festival, no matter what the theme was, we had M&A topics, we had practice management, we had all kinds of topics, but we almost always, in every single session somebody brought up AI on stage at Festival. And so it's not about just getting on stage and talking about AI, it's really understanding how it's affecting everybody in their practice or in their, even us, Future Proof, we're building agents for our different sections of our business. So we're actually not just talking about it, we're actually doing it. So it doesn't matter. And sometimes someone will say, well, we're not using AI, or we don't have an AI product, so is Citywide for us? And we'll say, well, absolutely.

You have to be part of the conversation. Even if you are not building an AI product, it's going to affect your life, right? So let's bring those conversations so that everyone can be understanding together. Who's using what, what's safe, what's compliant, if I'm not using it, am I going to be left behind?

So when someone says, they're not using AI or, and I say, well, you should at least be part of the conversation. Come and be educated on how you can use it and make a decision for yourself. So I think there's still people that are scared of it and our goal is to have people come to citywide and just feel more confident about, even if they're not ready to use it yet, but to sit back and say that they're not going to use it, I think is, it might be a little naive because it's going to affect all of our lives. And that's why we included Live with AI, right? Because it's not just about work, it's about everyday life. It's going to somehow be changed. It is the future.

[00:06:19] Doug Heikkinen: You are going all in on AI on Citywide, but there's a lot of other things that are happening there besides ai.

So what are some of those things?

[00:06:27] Chris Cherry: So we have, look, we have quite a few partnerships that we have that are happening. And I had said earlier how we could build kind of across the street into Ocean Boulevard and beyond. I always mess it up. I think it's Ocean Drive. Anyway, so we have some partnerships with F2. They're our wealth tech community. So they'll be having some content sessions. A pre-event kind of cocktail reception the night before. So their partners are our partners as well. And so we have, having everyone together allows them to kind of activate across the street and bring all their partners in one place.

That's happening. We, last year we had a women's lounge. We had the Versace mansion where we had several of our partners do things over there. So that was our first year, obviously, and so this year we're going to make that even bigger and continue to grow across the street as well. The, did I tell you about the AI playground yet?

[00:07:18] Doug Heikkinen: You haven't.

[00:07:20] Chris Cherry: So we're building this 20,000 square foot huge tent that's going to have all kinds of things to learn about AI. So some of our, like usually where we would have FinTech kiosks, some smaller booths and AI companies will be there as well as a small stage kind of doing show and don't tell.

We'll have some round tables where advisors can learn from each other about who's using what in AI. And then we'll have some, secret surprises in there coming too. But we just want to create an environment where everyone can come and feel comfortable about what is AI and how is it going to affect them.

So even if you're not using it, our goal is to give people the confidence to try it and to

understand how it's going to affect their businesses.

[00:08:05] Doug Heikkinen: If somebody asked you, who hasn't been to one of these, what's actually different about Future Proof Citywide compared to the usual financial conference circuit?

How do you answer? Are there any moments that really capture the difference to you?

[00:08:19] Chris Cherry: Yeah, look. Well, I don't know that anyone else has ever said, let's take everything we have and go out on the beach, on the sand and work, right? I think no one's ever done that before. I mean, I think it's even a challenge to go to the beach for the day and bring your lunch and your speaker and your umbrella.

So imagine if you're saying, we're going to go live out on this beach for three days. So, we put so much into building kind of that space and an experience, and there's something special about being outside next to the ocean, but you're actually at work. So I don't think anyone's ever done that before. And to explain the vibe, when I'm talking to someone new, I'll often, I have photos and I'll say, can I just share my screen?

Because you talk about it, and yes, it sounds cool, but when you see how people are engaging, and just business actually gets done. I think it's helpful to be in more casual clothes. And at first, my first year here, I would convince people like, it's not just a party, like people are working.

It's okay that you can wear a golf shirt in a baseball cap. You actually feel more natural and you're more relaxed. And I think that's helpful when you're bouncing around to different exhibit spaces and breakthrough meetings and food truck areas. I mean, there's nothing that we have is even close to what you would see at some of the other industry conferences.

So extremely different format than what anyone is used to going to in a huge hotel or conference room. You're just taking people out of that cold, kind of stiff, heels, suits. Yes, there's a place for that, but when you talk about future proof, that's not what we're about.

[00:09:57] Doug Heikkinen: You mentioned the breakthrough meetings, so let's talk about that.

What makes these one-on-one group or group sessions feel authentic as opposed to just another form of speed dating?

[00:10:09] Chris Cherry: Yeah, so look, I think it's putting the work and the effort in beforehand, it's literally like using a dating app. You're not just saying, Hey, we want to meet with, advisors that are interested in private credit. Send people our way. You actually have ownership in using our program ahead of time. So, you have to put the work in. But it's, different than I, years ago I would go to a conference and, oh, I hope I run into this person and I'm going to go to this happy hour and meet this person. And that still happens.

There's a ton of organic networking. But if you put the work in ahead, you might sit down with 14, 16, 18 people. Like, quality one-to-one meetings. You know that five days before you even get there. So you build your profile, you make outbound requests based on your filters. So you might say, I want to meet with East Coast advisors that manage more than a billion that are interested in private credit.

And then you make your outbound requests. You're then able the following week to see inbound requests. So people who are interested in meeting with you, you can say yes or no. The next week the algorithm runs and based on, there's a lot of factors that matter, but based on how interested you were, timing, and then you are actually, your calendar is populated with these meetings.

So it's, it leaves out a lot of chance of kind of just hoping you meet the right advisor. And it allows you to really only accept meetings that are quality and that will make sense for you. And it's a numbers game. if you sit down with 18 and five, were good. Six, were okay, but nine were amazing and you have a second date.

That's a huge win. So I think the breakthrough really did put us on the map and all the other stuff is icing on the cake. We're outside. We have fun. We have a concert. The energy is, you can feel it when you're there. But the breakthrough meetings really proves the ROI. It allows you to go home and say, I met with all of these people at Futureproof Festival in '26.

I met with all of these people at Futureproof Citywide in '25. And now you can compare it with your CRM and see did those leads really convert? and that, our clients have continued to grow based on that. We're able to really show ROI, which I think was hard in the past. You'd say, well, I met this person here, I met this person here.

But you can download your report and really show you actually met those leads at our events, and that's helping us continue to grow our partners.

[00:12:34] Doug Heikkinen: We've heard attendees gush about the unique ways Citywide sparks meaningful connections, not just transactions, and you were kind of talking about that, and it's probably due to some, the environment you're setting.

Share with me a favorite story or a result of one of those meetups.

[00:12:50] Chris Cherry: So. Last year I was walking down the main path at Festival and someone stopped me and introduced himself. He said, I'm Broderick, I'm from PodPony, and I just want you to know that you changed my life. I came here two years ago and I met my first client and my podcast took off. And if it wasn't for Future Proof and these breakthrough meetings, I would have a totally different life.

And he meant it and he was so sincere and kind, and it just made my day. And I hugged him. We took a picture together. I had never met him before. And I was like, wow. It just, it felt good to know that what we're doing is, it matters. Even my own, in my own personal life my partner, he's a lawyer and he will use the meetings program and he's met some amazing people that are constant referral sources for him, and it's literally changed his life as well.

So I think, and that might sound a little dramatic, but it's true, like these are real meetings that are happening in breakthrough.

[00:13:46] Doug Heikkinen: All right, last one. Finally, why do you think this March, right at this inflection point for AI, is the moment for industry leaders to gather at citywide? What do you hope they walk away with after long after the event wraps up?

[00:14:00] Chris Cherry: Yeah, that's a great question. I hope that they feel confident that AI is not doomsday. It's not something to fear, but it's something that's going to allow us to work more efficient, to make us stronger. I think that being part of that, whether you're comfortable using it right now or maybe it's not part of your life at all right now.

I think being at Citywide, being part of those conversations is going to help you get comfortable with it. Or maybe you've already been using it for two years and you can share your experiences and some of the different situations. Whether that's coming in to speak on stage or in one of our, in the AI playground and just engaging with everybody in our industry so that we can all learn together.

So I think leaving there with confidence that AI is a positive force, not just in our industry, but in our lives, it's going to affect all of our lives. I think that will be a success for us.

[00:14:55] Doug Heikkinen: Yeah, it's figure out how to use it or be left behind.

[00:14:58] Chris Cherry: Yeah, exactly. Yeah. I was in a meeting with one of my clients and she said, the people that resist it and don't want to use it are afraid of it.

And the people that say, I'm going to make this work for me, and I can't use all the language that she used, but basically she said it's propelling her in a way that makes her more efficient, makes her better at her job. So if you sit back and say, I'm afraid of it, or it's not going to be compliant, or I can't do that.

Like you said, sadly, it's not even, you're going to be left behind, but it's going to affect you somehow. So you'll either use it to your advantage or it's going to affect you in some way.

[00:15:37] Doug Heikkinen: Chris, thanks so much for being with us. Good luck at Future Proof Citywide.

[00:15:43] Chris Cherry: Thank you. We'll see you there.

[00:15:45] Doug Heikkinen: I'll be there For more, information about Future Proof and to register, please visit FutureProofHQ.com. We are on all social media platforms @Advisorpedia. Please give us a follow. For our producer Tory Miller and everyone at Advisorpedia, thank you so much for listening.

Today's podcast was sponsored by Fidelity Investments. If you would like to learn more about Fidelity's top performing mutual funds and ETFs for financial advisors, visit i.fidelity.com/top funds.