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Gary Sinderbrand joins Warren Kucker to discuss The Surprising Way Personality Types Can Boost Outreach Response Rates to 30%. Key takeaways include AI can be used to identify psychological fit and improve prospecting outcomes. and Personality matching and psychological alignment can enhance client management and coaching..

EP. 27 45 min July 22, 2026

The Surprising Way Personality Types Can Boost Outreach Response Rates to 30%

with Gary Sinderbrand

"I should spend more time finding people that look like people I already enjoyed dealing with."

About This Episode

Gary Sinderbrand, a 35-year wealth management veteran, explains how he built the Rainmaker app to score psychological fit between financial advisors and prospects using Carl Jung's archetypes. He walks through how the app profiles an advisor, finds and researches compatible prospects, and mines existing clients' networks for warm introductions. He also covers Ask Archie, an AI coaching companion built on decades of his own training content, and where personality matching could go next.

About the Guest

Gary Sinderbrand

Gary Sinderbrand is the creator of the Rainmaker app, which uses AI to match financial advisors with prospects by psychological fit. He spent 35 years in wealth management at Merrill Lynch and UBS, where he was one of Merrill's youngest million-dollar producers and co-built a training program that shaped more than 10,000 financial advisors.

Key Takeaways

  • ✓ AI can be used to identify psychological fit and improve prospecting outcomes.
  • ✓ Personality matching and psychological alignment can enhance client management and coaching.
  • ✓ The future possibilities of personality matching and prospecting are vast and evolving.
  • ✓ Outreach built on shared values and interests, not a product pitch, lifted cold connection rates from about 3% to 30-40%.
  • ✓ Asking happy clients for permission to use their name with their own connections roughly doubles response rates again.

Chapters

00:00 Introduction to Rainmaker App
01:39 Gary's Career Journey
03:07 Understanding Client Fit
06:36 Development of Rainmaker App
12:12 Prospecting and Personality Matching
30:18 Client Management and Coaching
37:56 Future Possibilities of AI

Show Notes

A better book of business starts by giving clients away

Gary Sinderbrand spent roughly 35 years in wealth management, mostly at Merrill Lynch and later UBS private wealth in New York City. A year into the job he was ready to quit. A mentor taught him the work was solving problems, not selling product, and that solving problems meant listening to people's fears, goals and aspirations.

The bigger lesson came in his third year, when a manager told him to give up half of his accounts. His last five accounts looked very different from his first five: larger, with much better relationships. Not everyone would follow his advice, so rather than forcing it, Sinderbrand recalls being told

I should spend more time finding people that look like people I already enjoyed dealing with.

He handed back half his accounts, and the following year came close to doubling his productivity with far fewer relationships. His conclusion is that an advisor chooses who to work with: someone you can help, who will follow your guidance, and whose outcome you are willing to own. His top clients brought unsolicited referrals and more assets, so he says he never had to make a cold call.

That approach became a training program. He and a colleague piloted it on 50 advisors against a control group of 50, McKinsey analyzed the results, and for about ten years he and Bob Payne split their time between managing money and teaching advisors an outcomes-based process. Its core idea: the top hundred households in a book drive most of the business, so that is where the focus belongs.

Fit depends on who the advisor is, not just who the prospect is

Working as a consultant, Sinderbrand kept hearing the same question: how do you find the right client? About two years ago he reframed it. What one advisor considers a great client isn't what the advisor across the street considers one, so the starting point is understanding the advisor.

He turned to Carl Jung, less for sorting people into archetype buckets than for the shadow self, who people are when nobody is watching. He loaded Jung's Red Book into Google's NotebookLM, asked how Jung's 12 archetypes relate to money and professional relationships, and had it draft questions to determine an advisor's archetype. Convinced by the output, he started building in Lovable, writing the first code himself before engineers refactored it.

He uses his own profile to explain the matching. He tests as a Sage: he loves to teach and explains risk and return with charts and logic rather than sales talk. Sages fit other Sages and Rulers, and CEOs are predominantly Rulers who want clear, concise information to make their own decisions. So his natural fits are CEOs, COOs, accountants and estate planners. A Creator archetype, by contrast, fits people judged subjectively, such as marketing executives, screenwriters and film directors, and adding a secondary Jester archetype tilts the list toward fiction writers.

How a psychological profile turns into a 30 percent connection rate

The Rainmaker app starts with 13 questions, each with 12 possible answers, where the advisor picks a primary and a secondary. Scoring produces one of 144 primary and secondary archetype combinations. The advisor adds a LinkedIn profile and answers 14 or 15 questions about outside interests such as military service, sports and travel.

The output describes how the system sees the advisor, blind spots included. Sinderbrand says advisors found it uncomfortably accurate, especially on warnings like a tendency to overexplain after a prospect has already decided to trust them. The system then plots traits such as trustworthiness and ability to communicate, and suggests professions that correlate with them. The advisor sets a location and narrows to a target such as chief marketing officers at web-based companies.

Each prospect is researched with tools including Apollo, Gemini and OpenAI. In Sinderbrand's example, the system surfaces the CEO of a local bearings company who is an avid skier. Sinderbrand teaches skiing in the winter, which adds a second connection point to a Ruler and Sage pairing. The generated LinkedIn message compliments how the CEO holds everyone accountable and offers to trade stories. He says this lifts first-touch connection rates from about 3 percent to 30 to 40 percent, because

I didn't reach out to that person and say, hey, let me talk to you about your 401k.

The message aims for a connection, which might become a conversation and then a coffee. Sinderbrand tells advisors to collect people they could help someday rather than pitch an account on day one.

Warm introductions from the clients you already like

The second side of the app, Gatherer, starts from a client the advisor already loves. It maps why the two get along, then scans that client's first-degree LinkedIn connections for people who look like a good fit. The advisor asks the client only for permission to use their name as a reference, and the app writes the outreach. When Sinderbrand puts the question to Kucker as if he were that client, the answer is an immediate yes.

On cold intros, using the hunter side of the equation, response rates are around thirty percent. On warm introductions, they're closer to sixty.

Kucker ties this to selling in general. Sales usually means solving a problem and finding the job titles likely to have it. Everyone says people buy from people they like, but it is mostly lip service, and those judgments get made subconsciously on a single call. Sinderbrand's method adds a narrowing step sales and marketing usually skip. Kucker notes it only works now because most prospects have an online presence that didn't exist in the yellow pages era, and that it lets an advisor go from liking half their clients to liking all of them.

After the close, the content is the advantage

For managing clients after they sign, Sinderbrand built a coaching companion called Ask Archie. His training material from decades of group sessions, Zoom consultations and several hundred videos was scattered, so he transcribed two to three hundred hours of recorded Zoom calls where advisors reported back on applying his methods. He used Claude Cowork to turn that into a retrieval-augmented system that chunks the content for vector search, and added an ElevenLabs clone of his voice.

Advisors get one, three or five minute coaching answers that use their name, know their archetype, explain what to say and how to measure it, and remember every earlier conversation. Sinderbrand says the answers are often better than his own because they surface things he said on a call twelve years ago. When he demoed it to senior executives at a large wealth management firm, one said he had been dreaming of something like it for six years. Sinderbrand's point is that budget and engineering are not the hard part:

if you don't have the content, the underlying intellectual capital, all you're doing is building a shiny toy.

Looking three to four years out, he expects archetype matching to become table stakes. The next step is finding connection points that only show up at the level of personal values, such as a cause both people care about, and shortening the time between first contact and the feeling of having known someone for years.

Full Transcript Show

00:15 Warren Kucker: Hey there, and welcome to another episode of Selling AI. Today we're getting into what happens when you point artificial intelligence at the human side of selling instead of just the busy work. My guest Gary Cinderbrand, founder of Archimatch and creator of the Rainmaker app, is here to talk about how you can prospect better by understanding what personality types fit best with the personality type that you can service. He spent 35 years in wealth management. He was one of the youngest million dollar producers in Merrill Lynch. And he co-built their training program that shaped more than 10,000 financial advisors. here's what makes it interesting. Gary took the Carl Jung archetypes and fed them into an LLM. that's probably minimizing it a bit, spent a lot of time feeding it into an LLM. but he ran a research project with across 150 plus professions alongside Duke and built a tool that he thinks can take the outreach response rates from like three percent to north of thirty percent. So we're gonna dive into how you score psychological fit before that first conversation, why a rep's existing network kind of beat any cold list, and really his contrarian take on how you could find the right prospects to work with to win more work and make work more fulfilling. All right, let's get into it. Gary, thank you so much for being on the show today.

01:32 Gary Sinderbrand: More, pleasure to be here. Thanks for having me.

01:34 Warren Kucker: Awesome. Well listen, let's start with your career arc. Thirty five years in wealth management. That's a ton. Give us the shorter version of that journey. And then what was the kind of the through line that pulled you from coaching advisors into building software for them?

01:49 Gary Sinderbrand: God, it's a great question. sometimes I look try look back and connect the dots and I realize there was really no plan to do that. where I wake up every day is I would say a bit of a surprise. the good news is I wake up wondering what I'm gonna learn today. And I always approached it that way, understanding that the older I would get, I had to acknowledge the the the less I knew. So for me, even from the outset in my career, it it didn't become a task of finding answers, much more so posing the right questions and constantly questioning what I was doing. So when I started in wealth management, I went through six interviews with Merrill Lynch. They hired me at age twenty-three, I believe, telling me that I had basically no chance to make it, but I kept passing all their screening interviews, so they were gonna give me six months or so. one year in I was ready to quit. because anyone that gave me their money, I gave them back less because I was trying all sorts of crazy things to make that work and realized very quickly I didn't want to live my life that way. fortunately I was mentored properly after my first year and understood it wasn't about selling product and creating transaction fees. The job was really about solving problems. And I knew that to solve problems I needed to shut my mouth and listen. To what people's fears were, what their goals, their dreams, their aspirations were. And that really formed the the rest of my career. by my third year, I was doing very well. And a manager came to me and basically knew that I had pretty high aspirations in the business and told me that if I was really serious about it, I would give up half of my accounts. And I thought he was kidding. And he explained to me that the last five accounts I opened looked very different than the first five accounts I opened. They were much larger. I had much better relationships with these people. And if I wanted that trend to continue, I had to be able to understand that not everyone I would talk to would basically follow my guidance or advice or even listen to what I had to say. And rather than trying to force someone or selling them anything, I should spend more time finding people that look like people I already enjoyed dealing with. So he made me a bit of a bet, which we both ended up winning. I gave him half the accounts I was covering for redistribution. And the following year I came close to doubling my productivity, with far less relationships than I had before. And that was the first time I recognized that. In financial advisory, you have a choice of who you're gonna deal with. It shouldn't just be someone that agrees to deal with you. It should be someone you feel as an advisor that A you can help and B is gonna follow your guidance and you're willing to make yourself responsible for that outcome. As a result of that, I was able to grow my practice pretty dramatically and with a focus on the top clients across the board. Several years l several years later, I was complaining to the director of training. that I thought the training was completely inadequate for where the firm said they wanted to go. This was prior to financial planning. This was prior to working for fees instead of commissions. You could still do that stuff, but it wasn't the main focus. So I was asked, well do you think you can do something better? Why don't put a pilot together? We'll test it out. So we came back to them and with one other fellow we put a pilot together. We tested it on 50 advisors. We did a control group of fifty similar advisors that did not go through the program. And three months later they came back to us and said, this stuff really works. It was analyzed by McKinsey and we'd like to know how much time you can give us to make this a reality. So for the next 10 years or so, myself and one other gentleman named Bob Payne spent half our time as producers managing other people's money, and the other half working with financial advisors, many of whom were senior to us and were making a lot more money than us. And we went and explained how we were following this very specific process, how it was all outcomes based. We had a lot of disciplines around it. But most importantly, you couldn't do it for 400 different people. Since the top hundred in your book were giving you most of your business anyway, that's where your focus had to be. So became successful in teaching that program, teaching that process, while at the same time maintaining a relatively small book of business, as far as households go, that had ever increasing amounts of net worth. And I found that the better aligned I was, the more I serviced these people, the better I got to know them. The more they would offer unsolicited referrals and bring me any funds that they had. So I never had to make a cold call. So this whole concept of if I want to have a perfect book of business, a perfect set of clients, could I define what those parameters looked like? And the answer is, yeah, I could. So I didn't realize at the time that there were ways to actually quantify that. And even more importantly, there were ways to put that into computational models which could pre-identify and increase the likelihood that the people you'd be talking to would fit that model. It was just pie in the sky. So fast forward, I'm spending the next three or four decades. I'm doing I'm in production. I worked primarily at Merrill and then UBS private wealth in New York City. But the the parameters were still the same. Everything worked the same. came out of the business about 10 years ago as a producer, launched a small startup, and then following that decided I either am going to go back into business as a producer or I'm gonna start to do some consulting work. Because I always enjoyed the teaching aspect of it. So started doing consulting work about six or seven years ago, working with a lot of financial advisors I had trained several decades ago, but that problem was still out there. How do we find the right client? How do we understand? Who's gonna fit where? And then maybe two years ago, I started to think maybe I'm looking at this incorrectly. Maybe it's not finding the right prospective client. Maybe what I need to focus on is how I'm different as an individual than another advisor that might sit across the street, and that what that person considers to be a great client and what I consider to be a great client aren't necessarily the same. So, this whole concept of alignment. I'd always been fascinated with the work of Carl Jung. not for the simplicity of putting people into separate archetype buckets, but kind of the shadow self. Like what governs us? Well, who are we when nobody's looking? What are we doing when no one's paying attention? And everyone falls into one of those 12 major archetypes. So I started to do look at that, and then I started to play around a little bit more. early with what AI might be able to do. I didn't look at AI and say, hey, this is super cool. Let me build a product and see where I can plug it in. I said maybe AI can give me a better understanding of Young's work as it relates to professional relationships. So I got a hold of the Young Red Book, which is kind of a overall tone. I think I initially loaded that into the the notebook LM product, Google's product. Which was very early on, and I started to pose questions to it, and it came back. It was giving me some pretty reasonable answers. It was exciting. I said, Well, can we transition it to people's characteristics as it relates to money? It said, Well, yeah. I said, Well, if you wanted to determine, let's say, an advisor's overall archetype from a financial advising standpoint, could you develop a set of questions to do that? And I said, Yeah, here's the questions. And I the more I looked at it, the more I was blown away. So I realized, well, maybe there's something I can do here. Now, vibe coding was not a thing. So I talked to my son-in-law, who is way out on the bleeding edge of a lot of this stuff. And he said, Well, you have two choices. You could spend a couple million dollars to get a bunch of geeks to write the program, or you can check out a program called Lovable. It's like, Lovable? What what's that? And that basically sent me down the rabbit hole of AI. And I didn't approach it from the standpoint of, hey, AI is going to solve this problem. I approached it from the standpoint of this is a problem that is pervasive in an entire industry that no one has yet to solve. So what if I could figure out a way to determine ahead of time who, as an advisor, I would best get along with as an individual? And that led to a series of discoveries, tests. And things that came back that basically allowed me to not eliminate the risk of soliciting an unknown prospect, but to approach that prospect with knowledge about that person at a far deeper level than I ever would have been able to do bef do before. And plus how that prospect's values, history, profession, or all the rest of it would align with me personally. And that's where the idea for Rainmaker initially came from. started out on Lovable and then when I knew it was gonna work, got serious and I would write the initial code, which my tech people would make fun of. They would refactor it and give me something that worked. And that's kind of where we are now. We're just about to launch that product formally. So it's kind of a short version of where I've been, what I've done, what I'm about to do.

11:54 Warren Kucker: That's an awesome, awesome life career arc there. so let's dive in a little bit deeper here. So in particular, you built this with mm financial planners in mind, right? Or wealth managers. I know we've talked and we'll get into a little bit some broader concepts that Rainmaker may translate into, but let's focus on on that specifically. Obviously the core of what you're getting at is you will make more money and do better work if you're working with people that fit your personality type or your archetype, which is probably a little bit too vague. Let's dive a little bit deeper into that. How do you feel? What are some examples of like some of Carl Jung's kind of what drives the human spirit and personalities and like what's a good match, what's a bad match, what's a little counterintuitive? I think the the core of what you would assume is that a financial planner, someone wealth management has to be able to get along with everyone and has to work really well with anybody that comes along. let's shred that a little bit. What are the types of things that are compatible or incompatible.

12:55 Gary Sinderbrand: Great question. So let's break it down a little bit. next to people's health, money is number two. And most people who are successful, they they're successful, they find some way to create wealth, either through savings or through equity in a variety of different ways. How they manage that wealth, more often than not, is utilizing their most recent experiences. as well as their personal beliefs. So we get into these biases, confirmation bias, recency bias. It's what defeats most individual investors. Because managing wealth is a science. And if you stick to the discipline, no matter what that discipline is, you will do better than if you try and do it by the seat of your pants. So I recognized as we went through, as I went through and I tested myself in the system, I came up repeatedly as a sage archetype. Now, the Sage archetype loves to teach. I like to get down in the details. I like to explain a lot of underlying concepts using charts, graphs, logic without any sales bullshit at all. I want people to understand how risk and return are related. I want people to understand the difference between a real bond and a bond mutual fund. These are basic things I need them to understand. So I was very, very set on being able to educate people. Now When we looked at that, we then said, okay, as a sage, who would I correlate or correspond with most closely? Well, people that had a sage archetype on the other side, I would car I would correspond with because these are people that appreciate knowledge. These are people that like to understand things at a higher level. But I'd also correspond with rulers. CEOs are predominantly rulers. They have to make decisions based on whatever information they have. They don't want any BS, they want to explain to them clearly and concisely so they can reach their own approach. So I correlated very well in my own personality with CEOs, COOs, accountants, estate planners, people that worked in definitive. It either is or it isn't. And I need the baseline to be able to make that decision. So when I would search using Rainmaker for potential prospects. My traits would appear on the screen. This is who I am. This is where my strengths are. And it would automatically surface the traits and characteristics I'd be looking for. And then right next to that would be the underlying professions that would be there. And if I was looking to deal with people that had the ability to make quick decisions, obviously CEOs would be there. So I'd click CEOs as a category, I put a geographical category. Ring fence around it. And it would give me, initially on the search, it would give me a list of, you know, 25 or 50 CEOs. Some of them looked interesting, some of them didn't. If I wanted to go further from that point, I would dig further and say, okay, this person looks interesting. Let me see how I line up with that person. Now the system knows all about me, just doesn't have my archetype. It's got my LinkedIn, it's done a deep dive on Google Gemini to know everything about me. You can find out online. It understands my value system. It really understands who I am. Now we're going to do a similar amount of research on this particular individual. And let's say it's the CEO of a local bearings company. And it comes up and I find out that this guy has had a variety of jobs along the way. And it also shows me that he is an avid skier. I find that out. He's very family-oriented. And his kids are involved in sports and athletics. So I have all this information in front of me, and I look at this and I say, this sounds like a guy I might like. I might really want to get along with. And I'm going to reach out to him with a message that's automatically generated on LinkedIn. And it's going to say, you know, hey Warren, I noticed on LinkedIn a lot of the work you've done, you know, at the Rawlings Bearing Company. And I really admire how you've held everyone accountable, starting with yourself all the way down. I approach things in a similar way in my own business. I'd love to connect and and kind of trade stories. Would you like to? Something like that. And all of a sudden, instead of a 3% response rate, we're getting connection rates in the 30 to 40% on that initial cold connection. Why? Because I didn't reach out to that person and say, hey, let me talk to you about your 401k. Or let me talk to you about, you know, how you're invested currently. Or what do you think of the market? I took the time to learn about that person and reach out to them on a level where I would probably respond positively. what else do we have in common? Well, he likes to ski. I'm a ski instructor in the winter. So there's another connection I can put in there. So now I've

18:06 Warren Kucker: Yeah.

18:07 Gary Sinderbrand: got good data on both sides. I've got a correspondent archetype with my own. He's ruler, I'm sage. And all I need to do is to get that initial connection, which might lead to a conversation, which might lead to a cup of coffee, which ultimately may or not may or may not lead to a professional relationship. But I don't look at it from the perspective of soliciting a prospect to become a client. My approach is I want people in my business to collect people, find people that are like you, find people you might be able to help. Maybe not today, maybe down the line. And maybe it's not, but with them opening an account, maybe there's something else you can do for them that they can then do for you. And that mimicked how I built my own book, except now I could do it electronically. So that's how we connect it along those lines.

19:05 Warren Kucker: Before we get into like the business use case on this, I just want to pull out the the archetypes example you gave there just a little bit further. So what would be like another common like personality type for financial planners that would be let's say on a different end of the spectrum than Sage? And so like and then what what would they who would they fit compared to a ruler? Give me another example of like that that kind of like fit.

19:28 Gary Sinderbrand: So you could you could come in, yeah. You could come in as a creative, right? You like to basically fashion things that no one's thought about before. your dominant archetype is you're a creative. You're not going to look at the same problem the same way twice. At that point, you could correspond very well with people who are in roles where they're pretty much judged subjectively. people who write ad copy, executives that are in the marketing area. People that admire screenwriters would be a good example. Film directors would be a good example. Anyone that's trying to basically build something that comes out of an image in their mind, a creative archetype would get along with. Now, you could pair creative, depending on what you're doing, with let's say jester, which means you're looking at the world, your secondary archetype is jester, you're looking at the world with kind of a smile on your face and a wink in your eye, and that may indicate that you'd probably be. more attuned to going after fiction writers, people who write books, people that are interested in history but like to put historical fiction together, people with vivid imaginations. So creative can correspond in that area as well. So every one of the underlying archetypes that we map for has multiple professions that they correspond to. Not to confuse matters further, But this is all in the kind of what we'll call the cold zone or the hunter zone. This is identifying

21:02 Warren Kucker: Okay, right.

21:03 Gary Sinderbrand: people by profession and then getting to know who they are personally using two or three different tools. Apollo, we use Apollo, we use Gemini, I think we use OpenAI in some cases as well. But we also have the ability to take a client that you currently have that. You love. They're just they're the perfect client. We can put that client in another side of the application. That side of the application is called Gatherer. And basically it's going to map out the characteristics between the FA and the client as to why they get along. What what are the underlying things that connect them, other than just the archetype? From there, assuming that client's on LinkedIn, the advisor can go up. look at that client's LinkedIn and look at their first degree connections and identify people that in all likelihood this person knows. We can then

22:04 Warren Kucker: Right.

22:05 Gary Sinderbrand: generate an outreach. And you're one of my better clients and the outreach is, hey Warren, I notice you're connected to you know Joe, Sharon, and Tony. These look like people I'd really get along with. May I use your name as a reference when I reach out.

22:20 Warren Kucker: Mm-hmm.

22:21 Gary Sinderbrand: Now, you and I have had a great relationship. What's your response gonna be when I ask you for permission?

22:27 Warren Kucker: Of course. Yeah. Be happy to introduce you

22:28 Gary Sinderbrand: Yeah, that's it.

22:29 Warren Kucker: directly. Yeah.

22:31 Gary Sinderbrand: That's known. I'm not asking you to do any work. All I want is your permission to use your name as a reference. Now I've got three warm introductions. On cold intros, using the hunter side of the equation, response rates are around thirty percent. On warm introductions, they're closer to sixty. So anyone with a book, they can identify who their best client is, look at their LinkedIn connections, get permission. We do the outreach, we write that for you. You've got all the data on those people first because you've researched them. And you see it's almost like a dossier. And it looks, you know, this guy looks like somebody I would like. Somebody I could help. I want to reach out to him. But first I'm going to use and get Warren's name to act as a reference. So here we're just again, we're using alignment, but we're using it from the back end. We already know we get along with that particular client that we're soliciting.

23:31 Warren Kucker: Right. That's great.

23:33 Gary Sinderbrand: So it's a completely different way to build a practice.

23:38 Warren Kucker: Yeah, absolutely. That's what I'd say is like as a founder slash salesperson, you get reminded regularly that something that is often easily forgotten is that all you're really doing when you're looking for a job or trying to sell a product or you're trying to solve a problem and you're trying to bias a product or service is you're out there in the market talking to someone and being like, Is I have this valuable thing, are you willing to exchange some money for it? Right. Why? Because I can't build a house or grow food. I need to do whatever I do well to solve a problem you have so I can buy a house and grow food. Right. So like what I end up doing from what you do from a sales standpoint is you solve a problem and then you look for personas, job titles of people that are likely to have that problem. And that's all sales is, right? If you do that well, you solve a problem well and you figure out who has the problem, that's how you narrow that market down. What's interesting is that you're taking in a additional narrowing cycle, right? In that like we f fre we say this all the time, but we don't it's more lip service than anything, is people buy for people that they like, right? So like and most of the time that like is subconscious. Most of the time it judgments made quickly, probably too quickly sometimes because all you have is a conference call to figure that out. But like sales and marketing almost completely ignore that interrelationship part along the way. And like that's i I find it interesting that like It's additional slice and it's a slice that we could take. You probably couldn't do this when you were selling through the yellow pages, right? Like and there wasn't a lot of public information. And people with wealth and wealth management in this type of space didn't have a huge online presence. Most people you're reaching out probably have an online presence. They talk about what they work on and have some a aspect to it. What I really like about this again is that like AI is kind of like helping illuminate the human relationship in a way that hasn't been done before. Secondarily you create like an environment of people you like to work with, right? Like what better than having like liking half of your clients from a personal perspective to liking all of your clients from a personal perspective? It's really fascinating. Talk about the inputs. Let's say you're I'm I'm your client. How would you figure out what archetype I was? what's the what are the inputs there? Do you use something deeper than you would when I'm doing outreach?

25:52 Gary Sinderbrand: So the first thing I would do if you were now if you were my client from being an advisor or a potential investor. Okay. So if you're going to use Rainmaker app, the first thing you're going to do when

25:59 Warren Kucker: The Rainmaker app. The Rainmaker side. yeah. Yep.

26:05 Gary Sinderbrand: you come up is you're going to answer a series of questions. And each of those questions has 12 possible answers. And you can select a primary answer and a secondary answer. And a lot of them are pretty close. a lot of them are subjective in nature, you're really gonna have to think through how you want to answer them. Each of those individual answers gets scored on a matrix. Depending on the overall score, each question attaches to one of the 12 underlying archetypes. So you can answer, you answer all 13 of these questions, we end up with 144 possible combinations of primary and secondary archetype. Once those questions are answered, we ask you to give us your LinkedIn So we can take a look at that. And just as a side note, what we will do is after we run your full profile, we'll look at your LinkedIn and we'll say, you know, your LinkedIn says the following. we think using this language probably expresses who you are a lot better. So we'll rewrite the LinkedIn for you if you want to copy and paste. That's up to you. Now, from there, we'll ask another 14 or 15 questions about outside interests. What do you do? When you're not thinking about being an advisor. What are you involved in? Were you in the military? Yes or no? What sports are you involved in? Do you travel? If so, where do you like to go? So we're developing this entire dossier on you as a financial advisor because downstream we're looking to be able to connect that to other points that we might find in clients you're looking for. At the end of it, the first page is gonna come up. is it's going to give you the results of that testing. And it's going to give you kind of a brief document that says, all right, you're testing initially as everyman. Secondarily, you're testing as creator. It's creative. So that's your dominant archetype. And then based on what you've told us, if you expand it, there will be a variety of things that talk about and describe how the system perceives you. These are things we think you're really good at. And a little list. We think you're really good at presenting. We think you're really easy to talk to. We think that sometimes you may overexplain things. When we were doing our initial testing with advisors that I do consulting with, I would say, tell me what this got right, tell me what it got wrong. And it was scary how accurate it was, especially in some of the areas we'd identify and say, here's what you need to be careful of. Pay attention to the body language of the people you're talking to because you're gonna get to a point where they're gonna understand you know what you're talking about. They've made that decision. They don't need to pass a test on the on the subject matter because they now trust you. Be aware of that. And a lot of FAs would go, yeah, I get too long, I overexplain. So we'll get all that out there and you'll see exactly who you are. From there, we plot your traits, trustworthiness, ability to communicate. there's five or six different traits that we plot. We then say, okay, let's go find somebody that fits with you. You hit the prospect column. From there, you put a location in that you want to go after. And we give you, let's say, based on your traits, there might be four or five rows. In each row, there might be six or seven professions that correlate with the traits we've identified for those underlying archetypes. You can switch them on and switch them off. Let's say you only want to go after CMOs, chief marketing officers at web-based companies. Well, we can skinny that down. That's all you're gonna see. Then the names start to come up, and then you decide who you wanna dive deeper and deeper on. You go through alignment and then messaging, and you then copy and paste and reach out to try and make that happen from there.

30:00 Warren Kucker: Great. Let's talk about how does this type of like personality matching. I apologize. I'm grasping for a different set of terms than I've used. how does it how does it kind of manifest itself once you've landed the client? I know you're focused on the the hunting or gathering part of the aspect. How what's the continual usage? How do I continue to make myself a a better thought partner for my client so long?

30:28 Gary Sinderbrand: You couldn't ask a better question. 'cause I don't even think we discussed this when we spoke the several days ago. so I've been training advisors since the nineties. either in large group settings, six hours at a at a dose, individual one-on-one consultations through Zoom, or in a variety of videos that I've created, several hundred videos I've created. So I realized that this stuff was completely disorganized. It was everywhere. And there was it was voluminous. And to try and organize it and make something out of it, I thought was pretty impossible until I started to educate myself on the use of how a rag would work. So get a little bit geeky here because I didn't know any of this stuff two years ago. So when you ask ChatGPT or anthropic a question, it knows everything and it tells you nothing. It scours the world in their large language model. all information is there and it tries to give you an answer that's germane to what you do. But if you want something that's somewhat specialized and contained, you want to be asking that that resource a question that's within the boundaries of what it knows. So it doesn't go wander off left and right and give you a bunch of stuff that's useless. So I thought, well that's pretty interesting. So I started to take, I think two or three hundred hours of Zoom calls that I'd recorded. And those Zoom calls were the actual application of the things I trained being fed back to me by the advisors that I've trained and hired me as consultant. So it was, hey, I told you to do this, what happened, how'd it work out, boom. And these Zoom calls would take place over periods of time. So I was able, using AI, to transcribe every single Zoom call initially. Took a while. They were all transcribed into this giant mass of continuous text that made no sense whatsoever. From there, and I did primarily I used Claude co-work to do this because co-work can wander all over your computer. And I said, here's what I want to do: I'd like to create a resource where I can pose a question and get an answer. That would sound a lot like the answer that I would give if the question were being posed to me directly. And it walked me through everything I needed to do, including a voice clone on 11 Labs, which sounds more like me than I do. so we built something called Ask Archie. And Ask Archie is a companion program which answers that question. It's like, okay, I got the fish, you know, to to use a fishing metaphor. The fish came up, looked at my fly, it took my fly. What do I do now? Right?

33:25 Warren Kucker: Mm-hmm. Okay.

33:27 Gary Sinderbrand: How do I play this fish and not kill it? Or whatever it might be. And I started to ask it questions and it would respond in one, three or five minute live coaching, using my name, knowing my archetype, and explaining exactly what to do, what to say, and how to measure it, and then whether or not I was going to hold myself accountable. And every time I would go back up and hit ask Archie, it knew everything I'd done before and it never forgets. So it's an ongoing memory bank of questions. Which would coach me through the entire relationship. Now what makes this different is and rag is just retrieval, augment, and generate. We're working in a closed unit where the tech is not nearly as important as the content. And I had massive amounts of content. Disorganized? Yep. But the AI was able, and again, I don't know how far down the tech rabbit hole we want to go, but it was able to basically reorganize it into chunks where we could do a vector search and pull a piece here, a piece there, and a piece there. And the answers that came back oftentimes were better than I would have given myself. Because I forgot what I said twelve years ago on a Zoom call. And it would pull

34:49 Warren Kucker: Yeah, right. Yeah.

34:50 Gary Sinderbrand: something out or and it blew me away. When I demoed it to some senior execs at one of the largest wealth management firms, the exec looked at it and basically said, I've been dreaming about something like this for six years. Now, even though they have the money and the tech to build it, and this is important, if you don't have the content, the underlying intellectual capital, all you're doing is building a shiny toy. So Ask Archie will be a companion right alongside Rainmaker. Now the other thing that's interesting about this is when we filed our patent, the patent was filed identifying and engaging a professional prospect. wasn't necessarily plugged into what we're doing here. And what makes it unique and less obvious is that we're using psychological alignment as our primary vector, as opposed to

35:56 Warren Kucker: Okay.

35:57 Gary Sinderbrand: what's not patentable, which is, you know, two plus two equals four.

36:00 Warren Kucker: Mm-hmm.

36:01 Gary Sinderbrand: When I started to look at what this could do, I realized that this Ask Archie container has 40 years of experience. But a lot of that experience ended up as wisdom. So to me, wisdom is the ability to have the experience and reflect back on it. And as you have more experiences and more reflection, you become more wise. Not just my experiences, but the experiences I've shared with hundreds and hundreds of other advisors. The more this thing interacts, the smarter it gets, but it only gets smarter for that user. So if you're

36:44 Warren Kucker: Right.

36:44 Gary Sinderbrand: the FA and you're the client, you're having an extended conversation with me. And it will evolve. It will get smarter

36:52 Warren Kucker: Mm-hmm.

36:53 Gary Sinderbrand: as we go. And it will hold you accountable. So once I plugged that part in and understood how I wanted to do that, that started to give me this concept of creating an advisor operating system from inception all the way through ongoing care. how we're treating the data inside the rag. The ingestion is portable. Take any expert, if they've got sufficient content in any form, we can replicate their expertise in a personal way to any user. So Archie's got a lot of possibilities beyond just what we're doing with it.

37:37 Warren Kucker: That's awesome. that's a really good segue maybe to my last question. Let's let's fast forward three to four years now. you've developed your tech further. LLMs have probably evolved to be somewhere between fifty percent to a hundred percent better than they are right now until they kind of level off along the way. What do you think might be possible with this type of like let's say pr like personality matching, who you work well with, prospecting. client management coaching kind of paradigm that you've we've kind of combined here. What do you think might be possible that just isn't wasn't even really fathomable two, three years ago?

38:16 Gary Sinderbrand: So the LLM on identification of archetypes and corresponding archetypes is pretty baseline. It's kind of table stakes. But when we go out and we start to look more deeply into the individual, we don't have enough information on the web, no matter where we pull it from, we don't have enough information to really infer kind of a deeper meaning or kind

38:37 Warren Kucker: Uh-huh.

38:37 Gary Sinderbrand: of things that I may have to discover are really important to that prospect that I didn't indicate before. And maybe it's just something off to the side. That I don't pick up on. So there may be that this particular individual is a regular donor to the Alzheimer's Association, just by way of example. And the FA has Alzheimer's in their family and is actively involved. That's a great connection point. It doesn't surface at the archetype level, it surfaces at the human level, at the value space level. So what I'd like to be able to see is not necessarily less hallucinations. But more connectivity points beyond just the obvious. So I think the better the LLM gets and the better we can train these train our own LLM and train our own software, the higher the probability is that when an FA reaches out to a prospect, there's a shorter timeline between initial contact and feeling like you've known that person forever. We've all had that experience. You meet somebody and two minutes in, you say, I'm gonna know this person for a really long time. I'm really glad I met them. Or you're looking for the exit route to get out of there. It's kind of a visceral

39:51 Warren Kucker: Right. Yeah.

39:52 Gary Sinderbrand: feeling. I wanna be able to quantify that further.

39:57 Warren Kucker: That's awesome. That's really interesting. And a common theme is just again that AI, you know, we're worried that it might shred the what is core to like human relationships, but there's a really a lot of areas where it should elevate them. And so, it seems like a foreign concept. It seems like this should be a natural process. But knowing that you like someone two minutes into an interaction rather than hours on end, there's a lot there's something valuable to that, right? in a world it's increasingly more disparate. So that's awesome. Gary, maybe a last thing, where can people find you? Where do you post content? Where do you talk about what you're working on? where can our listeners find you?

40:34 Gary Sinderbrand: So the easiest way to see what's up, and I'm updating it pretty regularly, is just go to my website. It's archimatch.com. That's arch e for archetype. AR-C-H-E-Match.com. there's a variety of things up there. I'm updating it pretty frequently. We're going to be onboarding our first real clients probably within two months. I'm very close to inking an enterprise deal to run a pilot for one of the largest firms out there. And I'm highly confident that that pilot's gonna lead to a larger engagement. they can find me there. they can drop me a note if they want to get on kind of the early wait list to come up for the product. I would say we're probably within a month to six weeks of buttoning it up and taking it from beta version point eight to version one, which I'm pretty excited about.

41:30 Warren Kucker: That's great.

41:30 Gary Sinderbrand: We're working very hard to find all the little nuances with our test guys where we can button things up. But Archimatch.com is the best way to go. You can also find me on LinkedIn, just under under my name.

41:43 Warren Kucker: Awesome. And in case you didn't want to plug it, I believe you almost your own podcast. What's it called? And what do you talk about?

41:48 Gary Sinderbrand: So that's a completely different deal, but thank you for mentioning it. I built my book by listening to other people's stories because I found a couple things. When people give you the opportunity, when you give people the opportunity to tell you their story, there is a natural affinity for the listener. So I cooked up this idea of everybody's somebody else before they become the person that everybody knows. And there's always a story there. And there's lots of life lessons there. So I came up with this idea that If the public only knew, Data I thought, what the backstory might be on the guy that invented Love Pop, which are greeting cards, or Love Sack, which is furniture, or came up with the concept of Zico Coconut Water and what they were able to do there. How did they come up with that idea? What did they do? So I have a variety of tremendous guests. I think right now shows I record today are gonna be out in November. I've got a great backlog. I don't solicit people. I get people ringing me up all the time. Hey, I listened to your show. I want to come on board. What it does, Warren, is it renews the belief that we're pretty much capable of anything. And that if we decide the world sucks and the world's gonna suck. If we decide that there are things out there that we have yet to discover, and all things are possible. If they matter enough to us, this is the podcast you want to listen to. Because those are the people I have on. So I'm really enjoying it. So it's called If the Public Only Knew, they can get it on Spotify. They can get it on Apple Podcasts and all the rest of it. And so far it's, I guess it's I'm told it's doing really well. I've got a lot of listeners and

43:36 Warren Kucker: Good to hear.

43:36 Gary Sinderbrand: a lot of downloads. I don't pay attention to it. I'm doing two later today. And I I'll make this a formal invitation. I'd love to have you join. Love to have you on and hear your story.

43:45 Warren Kucker: I love to be on. I really appreciate. Love the perspective. And everyone should listen. It's it's a great perspective. I think my core takeaway, I think about this all the time. We people often forget that their current state is not their final state. Honestly, like most of the time you go through several major life transformations along the way, and it always seems like whatever you're doing now is what you're gonna be doing forever. And it's really not true. it changes wildly. I imagine you thought you might be retired sipping coconut water somewhere and now you're building AI applications. there's no way five years ago this is what you were thinking about doing. So things evolve quick and means that you could always change what you don't like about what's going on right now. So that's a great that's a great perspective. And so I appreciate taking the and our listeners should listeners should listen in.

44:33 Gary Sinderbrand: Warren, really a pleasure to talk to you. Thank you so much.

44:34 Warren Kucker: Awesome. Gary, same here. looking forward to seeing how the launch goes.

44:39 Gary Sinderbrand: Great deal. Thanks, buddy.

44:40 Warren Kucker: Take care.

44:41 Gary Sinderbrand: You too.

Account ExecutivesSales Managers

About the Host

Selling AI is hosted by Warren Kucker, founder of Topiq. Each week he sits down with revenue leaders, founders, and operators to unpack the strategies, tools, and stories behind selling AI products and using AI to sell smarter.

Warren Kucker — Host of Selling AI

Warren Kucker

A revenue leader and entrepreneur who founded Basiq.work, focusing on conversational AI for sales teams. Previously served as VP of Sales and CRO at Series B companies, scaling revenue to $2M+ quarterly bookings. His exits include Shelly.ai (ML email automation) and Boxton (digital freight platform). Started his career at Apple managing a $100M shipping efficiency program.

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