Ep. 298: AI Is the New Rainmaker: Smarter Client Matching with Derek Notman of Couplr

The advisor-client matchmaking process is broken. Most firms still rely on cold outreach, mass lead-gen tactics, and outdated “Find an Advisor” tools that rarely convert. In this episode, Derek Notman, founder and CEO of Couplr, joins the show to explore how his platform is reimagining the experience with psychology-driven matching and how AI is reshaping the future of advice.

From boosting lead conversion rates by over 500% in a proof of concept with Liberty in South Africa to navigating the ethical pitfalls of AI-driven marketing, Derek shares insights that every RIA and enterprise firm needs to hear.

Key Takeaways

  • The Advisor Matchmaking Experience Is Broken
    Most firms still rely on cold calls and static advisor search tools that frustrate consumers and result in low conversion rates.

  • Couplr’s Approach: Psychology + Data
    Instead of focusing on ZIP codes and assets, Couplr uses preferences, personality traits, and shared experiences to match clients with advisors.

  • Real-World Impact: 525% Increase in Conversions
    A proof of concept with Liberty in South Africa delivered more than 2,000 leads and dramatically improved client experience.

  • Avoiding the ‘Creep Factor’ in Lead Gen
    Derek warns against AI tools that scrape data and bombard consumers with unsolicited outreach—because creepy doesn’t convert.

  • AI Is Here to Stay—But Human Connection Wins
    AI can enhance advisor efficiency, but trust and rapport remain the foundation of successful relationships.

Notable Quotes

“The advisor-client matchmaking experience is broken. Couplr replaces cold outreach with psychology-backed introductions that actually work.”
Derek Notman

“People want help with their money. Why not empower them to make a decision when they’re ready, instead of trying to cold call?”
Derek Notman

“Don’t be creepy with AI. Find tools that enhance human connection so you can be a better advisor.”
Derek Notman

Topics Mentioned

  • The Advisor-Client Matchmaking Experience Is Broken
  • Integration with CRMs Like Redtail and Wealthbox
  • Why Avoiding the ‘Creep Factor’ Matters in Advisor Marketing
  • Insights from the Liberty Proof of Concept in South Africa
  • AI, Behavioral Coaching, and the Future of Advice

Podcast Intro

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Episode Transcript

Craig: I’m excited for our next guest. Allow me to introduce my good friend, founder and CEO of Couplr, Derek Notman. Derek, hey, what’s going on?

Derek: Craig, good to be with you, my friend, again. We just saw each other last week.

Craig: Yeah, it was good. At the Asset Map Mastermind event in Philadelphia.

Derek: Yeah, that was pretty cool. It was an amazing event. A lot of great thought leaders, awesome engagement there about what the future of advice is going to look like.

Craig: That was a lot of fun. I thought it was great that it was very different than a lot of other events we go to.

Derek: It was refreshing. It wasn’t too long, but I think we got a lot out of it. And it’d be cool to see what the, I think they’re putting a white paper together, right?

Craig: On all the information. We’re all going to be authors, fully authors of a white paper.

Derek: Pretty awesome.

Craig: Future of advice or advice 2030.

Derek: Advice 2030. What’s it going to look like five years from now?

The Advisor-Client Matchmaking Experience Is Broken

Craig: Well, I want to know what advice is right now, Derek. I need advice right now. Give us the 30 second elevator pitch for Couplr.

Derek: So the advisor client matchmaking system experience, whatever you want to call it, is broken. And what Couplr does is that we replace the cold outreach and mass lead gen tactics that are being used today with psychology backed introductions that work.

Derek: Right. Money is emotional. Money is private. A financial advisor, we even discussed this in our event last week with Adam and Asset Map, the future, and even today, is human advice. Humans are wired to connect on more than just my zip code and 401k balance.

Derek: And at the end of the day, I mean, I’ve been an advisor for 20 years. I’m a CFP. I’ve been around the block a while. I understand this. And the best client-advisor relationships are ones that are built on rapport and trust. Rapport and trust are built on shared commonalities, preferences, personality, traits, shared experiences, and so forth.

Derek: So that’s what we’re doing. We’re speeding up that whole process so clients and advisors can match faster and get business done.

Craig: So you mentioned matching and lead gen, but a Couplr doesn’t generate leads, right? You take leads and organize them better and match them with the right advisor better. Can you explain the difference?

Derek: Yeah, so a lot of companies, whether it’s from a solo advisor all the way up to a large national insurance broker dealer, wire house, whatever, they all do lead gen activities, whether that’s social media marketing, paid organic ads, SEO, all of that good stuff.

Derek: The problem is, is that the lead conversions are terrible. The, there’s, I don’t know what the statistic is, because it varies from firm to firm, but most of those leads never become a client. And so what Couplr does is that we change that experience to drastically increase conversions.

Derek: So when a lead comes in through whatever channel it is, instead of, hey, Craig, give me your name, phone number, email address, we’ll contact you. You know, that doesn’t feel good to a consumer. That’s clickbait, it’s transactional, I’m giving away information I don’t want to give away just yet.

Derek: Instead, imagine an experience where, hey, Craig, click here and get matched with the top three advisors at our firm and only connect with them when you’re ready. And we’re going to do it on a much deeper level than how much money you have and where you live.

Derek: All of a sudden, we’ve empowered the consumer. And so it’s all about lead conversions because if we improve the client experience, that will flow downstream and it’s a better experience for everybody else involved.

Craig: It sounds good to me. I mean, there’s so many leads out there. I was just telling you before we started the recording that we’ve got an RIA client that had tens of thousands of leads just stuffed into database. And they weren’t using them or did not have a very good success rate closing them. And we’re still buying more every month from the usual suspects. So certainly they could use a tool that could increase their closing rate.

Derek: Well, that’s it. I mean, I don’t know any advisor that became an advisor to become a marketer or a cold calling expert. They became an advisor because they want to help people with their money. So let me leverage a technology that helps me do more of that with the type of people that I want to work with. And so that’s what Couplr does.

Derek: Even another way that Couplr can be used is to solve the orphan client problem, which is similar to what you’re talking about, these tens of thousands of leads this firm has but doesn’t know what to do with. Why don’t we go re-engage these people in a way that’s not, hey, you have to meet with us today, but hey, why don’t you click here and try getting matched with an advisor to see if this feels good, right? Totally different experience.

Integration with CRMs Like Redtail and Wealthbox

Craig: So how does your, so the technology, if I’m an advisory firm and I want to sign up with Couplr, how does that, how does technology integrate with what I have?

Derek: So we have two main integrations right now. One, I should say we are a white label tool. So our sweet spot is RIA firms with at least 50 advisors all the way up to national companies, you know, the insurance broker dealers and so forth.

Derek: And right now we have CRM integration with Redtail and Wealthbox that’s live. And it’s a two-way thing. So it’s not just single sign-on type of thing. This is data exchange where we will push all new leads into the CRM as a new opportunity. So the advisor knows, hey, this lead came from Couplr. This came from Couplr through Bankrate. Okay, cool. I know this information.

Derek: When I updated in my CRM, that data pushes back into Couplr. So I can track how long did the lead take to close? What’s my ROI on the lead based upon what I spent for the Couplr service? And so on and so on. So we have those integrations done. We’ll consider others.

Derek: We also have a cool feature where you can put in a tech link. So for example, Asset Map. An advisor who’s using Asset Map can put their discovery link. So Asset Map advisors out there know what this is. They can put that in so that once a lead contacts an advisor, that link will become active. And the lead can connect with the advisor, but can start the discovery process with that advisor right off the bat. We’ve got it all built in and working.

Craig: That is nice. I don’t know any of the products that’s doing anything similar.

Derek: I don’t either.

Craig: They’re doing similar, but not exactly the same way.

Why Avoiding the ‘Creep Factor’ Matters in Advisor Marketing

Derek: Not exactly the same way. You know, you’re making me think, Craig. One thing that we did a hard line in the sand with is that we did not want to be creepy. We made a very clear decision.

Craig: Good in all cases, especially.

Derek: I know, right? Creepy is not good anywhere at any time. So we wanted to make darn sure that our product was not a creepy experience for anybody. And as you say, the usual suspects, some of those usual suspects are doing data gathering, scraping, right? Of publicly available information. And then selling that information to advisors as enhanced, you know, lead info. But the advisor is still reaching out.

Derek: So, hey, Craig, I just got your information. It looks you just bought a house. You just changed careers. You just got inheritance.

Craig: You give a lot of money to your alma mater, blah, blah, blah, blah, blah. Hey, you want to get together and meet?

Derek: And Craig’s, who the hell are you? And how did you figure out all this information about me? That’s creepy. So we’ve made a very clear point that in anything we do with our tech, we do not have a creep factor.

Craig: And we’re going to see a lot more of that because we’re seeing so many of these AI lead gen tools that are all about, well, they all pitch themselves as where we can monitor money in motion. And we’re going to highlight that. We’re going to send automated emails to anybody who we think has got a dollar or got some money that came in. Either they got options, they sold a business, something.

Derek: And everyone’s going to have these automated tools.

Craig: They’re going to work a little bit in the beginning, but once everyone’s got it, we’re all going to be overwhelmingly flooded with emails from everybody once any sniff of an asset transfer, an equity liquidity event occurs.

Derek: That’s exactly right. And what will happen? Unsubscribe, unsubscribe, unsubscribe, right? That’s what’s going to happen.

Craig: I need an AI agent to unsubscribe me from everything.

Derek: I know, right? You have to build one just for that, which could probably be pretty easy. You’re right. And what’s interesting though, I think people forget, people want help with their money.

Craig: A lot of them do.

Derek: And they’re searching to the tunes of tens, if not hundreds of millions of times a month on financial products for education, insight, guidance, whatever. So why not just empower them to make a decision when they’re ready instead of trying to get creepy and cold call?

Craig: I think I wrote an article. Maybe five or more years ago, it was titled, Don’t Be Creepy, How Advisors Can Use Social Media, but Avoid the Creep Factor, right? And that’s just becoming more and more prevalent. And these AI tools make it easier and easier for anybody selling anything to act Facebook and just plug into every single thing you’ve got.

Craig: I was doing something in chat, so I used ChatGPT and Claude for AI, and we subscribed to both, and I bounced back and forth because they change, and they’re better at strengths and different things. And I was searching for, so I’m looking to go on a trip with my brother into British Columbia, along the northeast coast, which is bad service. So I asked ChatGPT about, start buying Starlink. I didn’t go anywhere else. I didn’t search it. I didn’t Google it. I didn’t go anywhere else. On my phone, I said, what’s the price of Starlink? I had no idea. Where can I get it?

Craig: I switched to Instagram. The very first thing in Instagram feed was the Starlink ad. That wasn’t a coincidence. I’ve never looked for it before. I’ve never talked about it. Never Googled it. Never. So clearly something’s going on there. I said, ChatGPT, are you selling my data? It goes, no, I’m not selling your data. I promise. And I’m, BS. I’m calling BS on that.

Derek: Yeah. Those AI, you know, as they’re getting more and more evolved, they’re getting better at hiding their mistakes, but also lying about things. You know, we have to take it with a grain of salt, for sure. That’s funny. But did you get it? I have Starlink. I love it.

Craig: I’m going to get it. I don’t want to make the Starlink ad. Where’d you buy yours?

Derek: Online. Just went to the websites that I wanted. They shipped it to me. I had it in a few days. Bob’s your uncle. Is it the mobile one or is it the RV one or the… No, this one I fixed to the top of my house, but with four bolts I could fix.

Craig: In the house. So I want a mobile one, in the car.

Derek: You can do that, but this one even, I can unbolt it, and I can bring it anywhere in the world. It’s got a little stand that I can put anywhere I go. So I can go camp in the middle of nowhere, stand, as long as I’ve got a power source, I’m good.

Craig: All right, we’ve digressed a bit.

Derek: Yes, we have.

Insights from the Liberty Proof of Concept in South Africa

Craig: But it’s good for the audience that they want to learn about that. Good. So let’s talk about, speaking of remote areas, that’s a good segue. So the Couplr recently did a proof of concept in Africa.

Derek: Yes, we did.

Craig: So that’s a bit remote from us, although they’ve got certainly many metropolitan and urban areas as well that have good internet access. But what were you doing over there? What was this proof of concept? And what data did you glean, and what value is it to us here?

Derek: So interesting. And for anyone to ask, why the heck is Derek and Couplr in Africa? Well, we’re in South Africa. And South Africa is where my mom is from. So I’ve been going there my whole life. I know a lot of people there and a previous company I had that I sold did a deal down there in the same industry. So I had connections.

Derek: And so we ended up doing a POC with a company called Liberty and consider them a New York Life or Northwestern Mutual here in the States. You know, that size of company, insurance, wealth management, kind of the whole gamut. They’ve got about 8,000 give or take advisors, you know, around the country. So pretty large group.

Derek: And we went to them and we pitched this guy. We talked before is, let’s fix your find an advisor tool on your website. Let’s fix that experience. And so what we did with the POC is we just basic, we added what they called it match me. And they added that to the homepage above the fold. So it was very simple to see.

Derek: And it just talked about, hey, why don’t you match with one of our advisors instead of putting your postal code in. And through that POC, we generated over 2,000 leads. And we increased conversions from their existing tool by over 525%.

Craig: Wow. Well, 500% on what was the base? Was it one? One conversion?

Derek: No, no, no. I mean, no, it was more than one. They were, I can’t remember what the numbers were, but it was remarkable. Let’s just put it this way. It was enough of a delta where we’re going to a full-on partnership with them.

Craig: Excellent.

Derek: Yeah. So, I mean, they’re going to stroke a check, right? Every year for our technology, because they totally saw the value of it. And what was cool is that I did my own, you know, external, feedback loop with advisors and clients, but they did it internally too independent of us. And all of, they shared all the data with us, all, they came back overwhelmingly positive responses from clients and advisors.

Craig: They just love the experience.

Derek: They love how it worked. They loved how Warren leads came in instead of having a cold column. And then we learned some interesting things too. So down in South Africa, talking about ethnicity gets a little touchy given their history. And so we instead of, so in the States, we asked about ethnicity as one of our questions in our algorithm.

Derek: But in South Africa, we asked about native or home language, and there’s 11 of them down there. And so we, through all these leads, we started to learn who are these consumers and what are they looking for in an advisor? And so overwhelmingly, the top three were English, which is pretty prevalent down there, but then Afrikaans and then Xosa.

Derek: Those were the top three languages that consumers wanted their advisor to speak. The consumers wanted their advisor overwhelmingly to be under the age of 45. They wanted help with financial planning, investment management, and life insurance. And then when gender mattered for the advisor, they wanted a female advisor.

Craig: So interesting stuff.

Derek: And we gather a lot of other data in addition to that, but that was just some interesting insights that we gained, but not only our partner Liberty gained, oh, that’s interesting. We should maybe adjust our marketing, our recruiting efforts, product development, all that kind of stuff.

Craig: So when you talk about all those efforts, is that a big change for them, or is it just a smaller change?

Derek: What do you mean a change?

Craig: When they’re changing their marketing, are they readjusting their whole marketing budget, or is it just a small portion of it?

Derek: To use our product, you mean?

Craig: No, you said the data that you gave them made them change the way they’re doing marketing.

Derek: Oh, well, no, it gives them insights to be able to change. Well, I mean, let’s face it, these things are large, slower-moving entities, but the marketing department’s always looking for reasons to justify itself and its actions. We’re giving them data to help support them and fine-tune what they’re doing. A simple one is 72% of our customers are dog people.

Craig: We should probably put more dogs in our ads, right? Okay.

Derek: Simple stuff, even that. I mean, but it’s simple because that resonates.

Craig: Dogs attract consumers?

Derek: Hey, dog people, if I see an ad for a company, it’s a dog, or I’m a dog person. I grew up with cats, but I love dogs. I’ve got two. I’m going to instantly be more drawn to the dog. It’s just human nature.

Craig: Right. You’re a dog person. Would that work across categories? Does it work for advisory firms that if I see an advertisement for an advisor with a dog in it, I’m more likely to click it if I’m a dog person, which I am, than a non-dog advisory? Do I associate dogs with advisors in France?

Derek: So you touch on an interesting point, and it goes back to the humanity of the work that we do, and that we even talked about this last week, that financial planning is more of a verb than a noun. And at the end of the day, clients more than ever are paying attention to the meaning of their money and working with an advisor that they feel understands them on a deeper level.

Derek: And how do advisors differentiate themselves to make that connection? It’s through things, hey, I’m a dog person, or I love surfing, or I love mountain climbing, or I’m into martial arts, or world travel, whatever, the list goes on. When you connect the consumer with an advisor that, instantly there’s, oh, I like the vibe here. This feels good, right? So it may seem, it is simple, but it’s yet powerful if done well.

Craig: Makes sense to me. So this could revolutionize the way advisors advertise and market to prospective clients. We think so. Do you see yourself as a marketing company in that respect?

Derek: No. Well, I see ourselves as lead gen and a data company. Because we’re gathering so much data. Although we do touch marketing quite a bit where we end up working with and talking to the different web teams, the digital teams, the marketing teams, and giving guidance and suggestions based upon what we’re seeing.

Derek: There’s another firm I can’t list yet that it looks we’re going to be doing a full-on relationship with here in the States, a large RIA. My initial three, four conversations were with the chief marketing officer.

Craig: Right?

Derek: Which makes sense.

Craig: It makes sense. It all becomes linked in one way or the other, right?

Derek: It does. It does. And that’s, again, while we took a strong approach on we wanted to be white label, because a lot of these companies are doing a good job on the marketing and lead gen side. So I don’t want to try to fight it or compete against that. I want to leverage it and then just drastically improve that final bit of the conversion that’s missing.

Craig: Yeah. How many advisors are currently on the platform? What’s in the U.S.?

Derek: In the U.S., we are close to 1,500 as of today. That’s excellent.

Craig: And it’s mostly enterprise firms?

Derek: Yeah, yeah. That’s, I mean, up until about two weeks ago, you couldn’t even sign up with us directly. But that we’ve got our partnership with Bankrate, we are opening up a small amount of room for individual advisors to come in that way and sign up for that. But that’s it. Otherwise, you’ve got to come in through an enterprise.

Craig: So tell me about the Bankrate and the American College partnerships.

Derek: So Bankrate’s exciting. It’s cool what we’re doing there. So it’s different. So people know Bankrate. I mean, they get 100 million visitors a month on their combined channels. And they’ve sold leads before to our industry. That’s nothing new. But the way that we’re doing it is we’ve embedded a Couplr call to action within a specific user flow for people looking for advisors.

Derek: More for users. And connecting them straight into that experience versus making it a manual thing where the lead was just sold to someone and they had to call it. So we’re bypassing that whole manual process and automating it. So cool that it’s early days still. So we’re starting to get some data, but we’re seeing leads and matches happening, which is pretty cool.

Derek: So that’s exciting. And there’s plenty of room to grow there because I think, I mean, if it works for Bankrate, it can work with Money.com, NerdWallet, the list goes on and on and on and on.

Derek: And then with the American College, excited there, they have something called Your Advisor Guide, which they’ve had for years. And it hasn’t gone anywhere. So they brought us on after looking at the market, they ended up doing a deal with us where we are powering that experience for the matchmaking purposes.

Derek: They’ve recently just relaunched that website, which looks amazing. And starting, I believe, late September, early October, a multi-seven-figure marketing campaign to drive leads for advisors.

Craig: And that’ll all go through Couplr.

Derek: Yeah.

Craig: Oh, and all go through. So it will go through Couplr.

Derek: Yes, it will. Yeah. Because we’re embedded on their site.

Craig: So it’s just so cool to be able to even, we’re going to see what’s going to happen there.

Derek: So that’s awesome. And so any advisor that has a designation in good standing with the college can get onto Couplr through them right now.

Craig: Nice. That’s a great benefit.

Derek: Huge benefit. Yeah. I mean, it’s great for us. It’s great for them. They’re forward thinking about trying to drive leads. It’s a win for everybody.

AI, Behavioral Coaching, and the Future of Advice

Craig: All right. We are running out of time. I wanted to wrap up with a couple of questions about AI. So you guys are using AI. It’s in the name of the firm, Couplr AI.

Derek: Yeah.

Craig: But talk about where you see AI going and how you see it. We talked about this last week at the Mastermind, but share a minute about your thoughts. I don’t think we were at any of the tables together, so I didn’t hear what your thoughts were when it comes to how AI is going to change advisors between now…

Derek: I think advisors need to be paying attention and need to be careful. AI is growing a lot faster. I don’t think exponential is the right word.

Craig: It’s so fast that it’s growing. Geometric.

Derek: That’s it. Thank you. Yeah, it’s going that fast and that it will start to overtake all aspects of our lives. And do I think Skynet’s going to completely take over? I mean, if you read the AI 2027 white paper, that is one scenario they talk about.

Craig: It’s kind of total news day. It’s a fictionalized.

Derek: Total fictionalized.

Craig: That’s right.

Derek: But it is interesting to hear that story play out. I don’t know if that’s going to happen. I mean, my crystal balls never worked. But I think advisors need to get comfortable with the idea that AI is here. It’s not going away. And that they have to use it in a variety of ways to run their practice.

Derek: And I always go back to Craig, whatever. Whether it’s AI or some other tech, find something that helps enhance your human connection so you can be a better human advisor. Because we also talked about that’s where I think it’s going. It’s more behavioral coaching, counseling, having these meaningful conversations with clients.

Derek: But AI can help facilitate that a lot. If we’re putting our head in the sand and sticking to yellow pads, I think you’re going to go out of business. I do. I love AI. I think it’s a great tool, but it needs some guardrails and it can be extremely powerful if used correctly. Don’t be creepy with it.

Craig: Don’t ignore it. Yeah, that’s my two cents on it at this point, at least. All right. Also, before we go, let’s do a plug out for your podcast, Rethink, with some guy. With some guy you’re doing that with?

Derek: Yeah, some guy. My brother from another mother, Adam Holt over at Asset Map. We’ve been doing Rethink, the financial advice podcast for a couple of years. Craig, you have been on that podcast with us.

Craig: Sure. So…

Derek: Yeah, it’s a lot of fun. We’re just, we’re rethinking things and looking at it, you know, it’s interesting. It’s starting to take more of a global perspective, too, because we’ve got a lot of folks from different countries on.

Craig: Yes, just the WealthTech Today podcast. We were, we were, we’re top 50 in a number of countries, some top 10 in a couple of countries that we pop up.

Derek: That’s awesome.

Craig: That’s awesome. No, no good reason. We don’t, we don’t do any advertising or marketing overseas, but it just, the power of the internet spreads it around.

Derek: And great content. Well, that too.

Craig: Well, that.

Derek: That helps.

Craig: And one last thing to plug is Rebel Dads. What the hell is that?

Derek: And why should I care? Well, you are one of the OG Rebel Dads, my friend.

Craig: Yes. So, I’m excited to have you coming back with us this year, too.

Derek: Rebel Dads is a community for fathers who also are business leaders and entrepreneurs, where we focus on being the best leaders at home and at work. And supporting each other through this community, exciting stuff going on. We meet annually on Necker Island with Sir Richard Branson, and we have a book, which Craig, you are in, that we’re working on with Richard right now, special book project coming out. So exciting stuff going on there. It started as just kind of a bucket list thing, it’s turned into a cool community.

Craig: I’m working on my, I’m going to start pounding on the bike to get that. Oh my gosh.

Derek: That first year when you and I did that, Craig, that is the worst bike ride I’ve ever been on. I was not in good shape at that point either, so I’m in better shape, so I might take you up and go again. I thought I was in decent shape, but that’s straight up the mountain bike ride. Hardest bike ride of my life.

Craig: And Richard smoked us.

Derek: He did it, he does the whole thing nonstop.

Craig: Yeah, he’s 70, he was 72, it three years ago, right?

Derek: Two years ago. Yeah. And he smoked us. Yeah, totally, yeah. It just goes to show you, health is important, huh?

Craig: There you go, man. Cool. All right. This has been fantastic. Where can the audience find more information about Couplr?

Derek: Yeah, Couplr, just go to couplr.ai, C-O-U-P-L-R.ai.

Craig: We had to spell it weird because it’s a tech company. And then you can check me out on LinkedIn too.

Derek: Very active there.

Craig: He’s super active. 33,557 followers on LinkedIn.

Derek: Love your stuff there. Thanks, brother.

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The Wealth Tech Today blog is published by Craig Iskowitz, founder and CEO of Ezra Group, a boutique consulting firm that caters to banks, broker-dealers, RIA’s, asset managers and the leading vendors in the surrounding #fintech space. He can be reached at craig@ezragroupllc.com

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