[EO Chicago] Lessons on Leadership, Legacy, and Learning With Ben Altman

Ben Altman is the CEO and Chief Investment Officer of Altman Advisors, a multi-family office he co-founded with his father in 2016 that serves high-net-worth families. The firm provides comprehensive wealth management, financial planning, and legacy planning services. Under Ben’s leadership, Altman Advisors has built a multi-generational client base, established a ten-year investment track record, and is pursuing GIPS® certification to uphold global best practices in investment performance reporting. An active member of YPO (Young Presidents’ Organization) and EO (Entrepreneurs’ Organization), Ben is focused on integrating AI to enhance client service and internal operations.

Here’s a glimpse of what you’ll learn:

[01:24] Ben Altman shares how Essential AI transforms businesses at record speed
[03:54] Why anonymous feedback unlocks more honest, high-performing teams
[07:59] How Milton Friedman shaped decades of Ben’s modern financial thinking
[09:09] Ben explains Modern Portfolio Theory and its impact on investment strategy
[12:48] Why mastering AI is non-negotiable for staying relevant in 2026
[15:14] Inside the CRIT prompt system for sharper, more effective AI conversations
[19:17] How Ben built stronger relationships through rapid response and monthly check-ins
[33:30] Lessons learned from losing everything and the mindset needed to bounce back

In this episode…

What separates financial advisors who consistently thrive from those struggling to keep pace in a rapidly evolving market? How do top advisors build enduring client relationships while navigating volatility, risk, and accelerating technological change? Increasingly, the answer lies at the intersection of legacy thinking, economic discipline, and AI-driven efficiency.

Ben Altman, a wealth management expert with multi-generational advisory experience, exemplifies how disciplined investment strategy, rigorous diversification, and thoughtful technology adoption define modern financial advisory success. Drawing on lessons from past market cycles, Ben emphasizes the importance of avoiding concentrated risk. He also highlights the value of leveraging AI tools, such as voice-to-text dictation and context-driven prompting, to streamline workflows and enhance real-time client responsiveness.

In this episode of the Rising Entrepreneurs Podcast, Dr. Jeremy Weisz sits down with Ben Altman, CEO and Chief Investment Officer of Altman Advisors, to explore how family legacy, economic strategy, and AI converge in modern wealth management. They discuss how Ben utilizes AI to scale operations and the principles behind proactive client engagement. They also explore practical frameworks for building resilient, long-term relationships that prioritize personalized care, which is essential for trust.

Resources mentioned in this episode:

Special Mention(s):

Related Episodes:

Quotable Moments:

“If feedback is anonymous, it’s better because it’s more honest — people are more open about what they’re truly thinking and concerned about.”
“It’s not a question of whether AI can help you; it’s a question of how quickly we can learn before we become irrelevant.”
“Do what you say you’re going to do. All we have is our word, and repeating that enhances our relationships.”
“The hardest thing in business is to grow the business. Nothing starts until a sale is made.”
“If you’re not growing, you’re dying. There’s no coasting — if you think you are, you’re actually going down.”

Action Steps:

Embrace AI tools for efficiency: Integrate AI-driven solutions to streamline workflows and communication so you can keep pace with technological change and remain relevant as processes evolve.
Use structured prompts to enhance AI output: Apply structured frameworks when interacting with AI to generate clearer, more tailored responses that reduce generic output and improve decision-making.
Focus on relationship-building through accountability: Consistently follow through on commitments to build trust, strengthen connections, and sustain professional relationships in fast-paced environments.
Implement proactive client engagement: Schedule regular, structured client check-ins to shift from reactive service to proactive value creation and prevent issues from escalating.
Invest in personal and team growth continuously: Commit to ongoing learning and development to stay ahead of industry trends and support long-term adaptability and growth.

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Episode Transcript:

Intro: 00:02

Welcome to the Rising Entrepreneurs Podcast, where we feature top founders and entrepreneurs and their journey. Now let’s get started with the show.

Dr. Jeremy Weisz: 00:12

Dr. Jeremy Weisz here, Founder of InspiredInsider.com where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Ben Altman. You can check him out at AltmanAdvisors.com. Ben, before I formally introduce you, I always like to point out other episodes of the podcast people should check out, since this is part of you know, the EO series that I do.

Ben and I met through EO. It’s an amazing organization. I met some great individuals there. So, some of those I had Michael Attias, he started CaterZen, and he talked about transforming catering chaos into calm with his software. Matt Zalk. He’s in Tulsa. Key Renter Property Management. He’s all over Tulsa, Oklahoma City, and Arkansas. And you know Ethan King sticks out. I’ve learned a lot from him. And co-founder of Zeus Closet. And he talks, you know actually, Ben a lot about AI these days as well. I know you have some EO members you’ve learned from. You have a book there. Why don’t you talk about some of the EO people you’ve learned from?

Ben Altman: 01:14

Yeah for sure. Let’s see here. I have one from an EO member, Ab DeWeese. Which is.

Dr. Jeremy Weisz: 01:24

Essential AI.

Ben Altman: 01:24

Essential AI: Your All-in-One QuickStart to Using AI in Business and The Workplace. So I always like to read books from my friends. So that’s like that’s like I have like a whole section on my back that’s just like books that friends wrote, which I really love. And then let’s see here, totally on a different subject, but from about a friend’s dad, he was he was a survivor from the camps, and just how this kid, you know, survived and got through it somehow.

So this is a holocaust.

Dr. Jeremy Weisz: 02:01

The Little General who’s the author?

Ben Altman: 02:03

Yeah, it’s Robert Becker. It’s actually the kid, the child in the story. And it’s really put together by my friend Liz Becker, her daughter.

Dr. Jeremy Weisz: 02:19

While we’re on the book subject. Right. I always geek out on books. You have another book there that you’re loving right now. You want to talk about that?

Ben Altman: 02:27

Sure. So this is the one that I’m really on, it’s called the AI-Driven Leader. It’s by Geoff Woods. He’s made a career around using AI to help leadership teams specifically, and helping them sort out like goals and metrics, like with AI, which is, you know, I’m from the EOS world, and we do it like manually, you know what I mean? So we do it, but we do it by sitting for nine hours together.

So this supposedly makes it 90 minutes of just that. And it’s a game changer because what it does is it’s the key is this this is what really convinced me about this. If feedback is anonymous, it’s better, okay. Because it’s more honest. If you have six members of a leadership team and they’re all anonymous, anonymously entering their data into an AI platform, and then you let the AI compile it, show where you’re not aligned and where you are, and helps you determine what your goals should be.

So super interesting way to use AI to be anonymous with, you know, with, with what you’re concerned about. So that’s what I’m working on from Geoff Woods who’s a really inspirational guy in the AI space.

Dr. Jeremy Weisz: 03:54

Ben on the anonymous topic. So I’m listening to right now, I don’t know if you ever listened to Influence, Robert Cialdini, but there’s a new and expanded version which just came out. I think I have an hour and nine minutes left right now, but they talk about anonymous. If you don’t want a hung jury, don’t make people raise their hand and, you know, make it anonymous. I think that’s what they said in the book.

If I’m misquoting that, people can listen to the book and read it or whatever, but it’s a really good book. Influence: The Psychology of Persuasion the new expanded version they came out with. And then you mentioned, you know, EOS. So Gino Wickman and Traction, Gino Wickman on the podcast, people can go check that out.

And Verne Harnish on the EO topic of Scaling Up, and Verne was also on the podcast. So people can check that out. And he’s got a great book on scaling up. I think, Ben, you went to get another book. So I’m looking forward.

I’m looking forward to hearing what you’re hunting down there. So as you’re doing that, I’ll mention. So I also had Mark Winters who wrote Rocket Fuel with Gino Wickman. And that’s also a really good book of kind of the visionary integrator dynamic. So what do you got there?

Ben Altman: 05:05

I’ve got here Traction since you mentioned it. This is a formative book for me from the EOS world. And then a new one I read by it’s called Profit Works from some friends of mine, Alex Freytag and Tom Bower. So this one’s cool because it helps you rethink how you’re putting your comp plan together. So I love the whole series with EOS and Patrick Lencioni too.

We’re reading The Five Dysfunctions of a Team again. We have a couple new leadership team members that we’re rereading it and looking forward to that as well.

Dr. Jeremy Weisz: 05:38

I remember reading a long time ago, Death by Meeting by Patrick Lencioni. And the interesting part is I love his books because they’re, like, shorter. I can finish them, finish them quicker, and they’re easy. They’re easy to read.

So anyways, we’re going to launch into it. I just had to get your books on that note. And before, before I formally before I formally introduce Ben, this episode is brought to you by Rise25. At Rise25, we help businesses connect to their dream relationships and partnerships. We do that in a few ways.

One, we’re an easy button for a company to launch and run their podcast. We do the strategy, the accountability, the full execution, and production behind the scenes. We’re also an easy button for a company’s corporate gifting, so we make gifting staying top of mind for clients, partners, prospects, it could be even for staff from a culture perspective, simple, easy and affordable. Just give us the list of addresses. We do everything else. It’s been. It’s not like we send one-off gifts. It’s think we send three gifts a year for 4 to 5 years. Okay, so not just one-off gifts. So we kind of call ourselves the magic elves that run in the background to help it help companies build amazing relationships.

Because, Ben, I mean, we know each other at this point. Like the number one thing in my life is relationships. I’m always looking at ways on how I can give to my best relationships, and I personally have found no better way over the past decade to profile the people and companies I admire and share with the world what they’re working on, and to send them sweet treats in the mail so you can go to Rise25.com email support@rise25.com to learn more.

And I’m super excited. This has been a long time coming. Ben Altman combines a love for people with a passion for numbers, and he’s actually the CEO and Chief Investment Officer of Altman Advisors, and it’s a multi-family office he founded with his dad in 2016. He’s also a member of YPO and EO. So Ben, thanks for joining me and start us off with Altman Advisors and what you do. I’m going to. I’ll pull up the website.

Ben Altman: 07:42

Sure. So. Well, Altman Advisors, first of all, we’ve been in business for 49 years.

Dr. Jeremy Weisz: 07:54

Yeah, I was looking at this timeline here like on the Altman Advisors about I’m like, oh my God, this keeps going back.

Ben Altman: 07:59

I know, I know, it’s it’s it’s 1958. Look at that. Yeah, my father studied with a guy named Milton Friedman, which it was his kind of his idol. It’s there’s a famous book. I’m going to butcher it.

Capital and freedom or something like that. We’d have to look it up.

Dr. Jeremy Weisz: 08:21

I’ll look it up as you’re talking.

Ben Altman: 08:23

Yeah, that’s another that’s another good one. But the.

Dr. Jeremy Weisz: 08:27

He’s an American economist. It’s that one.

Ben Altman: 08:32

Tell me another one.

Dr. Jeremy Weisz: 08:33

He’s in. He’s an economist. Is that. Yeah. Yeah okay.

Ben Altman: 08:36

He’s he’s he was a Nobel laureate and University of Chicago. He’s part of the reason USC is so famous for their MBA school and yeah, Nobel Prize winner. Basically he’s a free marketeer. You know, you let the markets do what they want to do. That was the idea.

And that really influenced my father. And yeah, let’s see here if it says it.

Dr. Jeremy Weisz: 09:04

I’m looking. Capitalism and freedom. It looks like.

Ben Altman: 09:09

Capitalism and freedom. I said capital right. Capitalism and freedom. Right. So yeah, that was an influential book.

And he ended up catching him because Milton was still working at UFC at the time. So it was just, you know, some, some formative, influential things there. They also developed something called modern portfolio theory, which is really what we use. I empty is the acronym, but modern portfolio theory is the use of the markets to create, to choose where you want to be on what’s called the efficient frontier. Have you heard have you heard that term before?

The efficient frontier? I wish every person knew what this was. I mean, it’s really something that we should be teaching in school, but we’re not. Like to children to, you know, this this kind of like. But what it what it says is basically you a bond is less risk than a stock.

But if you combine 20% equities with 80% bonds, it’s actually less risk than 100% bonds. Okay. That’s interesting. And then you as you as you are willing to accept more risk, you’re you’re able to get more returns and you’ll you’ll make more over time. Depending on on how extreme the risk is, if it’s if there’s there’s issues with that, if it’s concentrated or you use leverage, it throws the whole thing out the window.

You know, you’re you’re going to be radically different and not predictable. But the When it comes down to basic asset allocation, it’s the it’s it’s the it’s you know, we use the term diversification all the time right. But what it means is how is your. Portfolio constructed. How is what which asset allocation is it.

So we have eight models. It’s from cash management to equity. The balanced ones are the most common. So we go from conservative to aggressive. And yeah a fixed income and equity and cash management.

So there’s five different balanced. And we’ve got a ten year track record at this point thankfully. And yeah we’re just kind of moving along moving along. We’re we’re getting what’s called Gifts Certified which is the global investment procedure standard. So that’s that’s what we’re working on right now.

But that’s It’s a major project to be able to show everything that you have in a in a way that’s accepted by the entire world and in, from a financial sense. So it’s the it’s the global investment, I think, procedure standards or something like that.

Dr. Jeremy Weisz: 12:03

I’m going to as you’re looking that up real quick.

Ben Altman: 12:07

I’m performance standards.

Dr. Jeremy Weisz: 12:09

You know, I know that AI is a big initiative. And we could talk about how you’re incorporating AI before you do. I just pulled up these are the books by Milton Friedman. He’s got a lot here. Capitalism, freedom.

So I’ll have to check on an audible because I listen to everything on audible. But capitalism freedom is here. Free to choose is here. Money. Mischief is here.

I mean, there is one, two three, four, five, six, seven, eight, nine, ten, 11, 12. I mean, there’s a lot they keep going here. So this is the second page I won’t go on. But you know, if you recommend capitalism freedom I’ll have to check that one out first. Yeah.

So talk about AI and incorporating AI in the company you mentioned with with iOS. How else are you incorporating AI?

Ben Altman: 12:48

Yeah, well, number one, it’s it’s it’s what I’m responsible for. I realize in 2026, you know, it’s not a question of whether AI can help you. It’s a question of how quickly we can learn how to make that happen before we become irrelevant, which is the risk. Basically, what Jeff Woods would say is the world’s changing so fast right now, and it’s not going to get any easier, like just get started. So I’m just like, you know, learning it’s it can be frustrating at times.

It can be, but then it’s very rewarding. You know, once you actually master something.

Dr. Jeremy Weisz: 13:33

What tools are you playing with? Yeah.

Ben Altman: 13:36

I love well whisper is the best dictation software, so I just love it. I mean, I it’s so cool to just change your keyboard and it actually works. And it actually fixes, you know, let’s say you stutter or you say something like, you know, something slightly off. It actually fixes your English. So it’s smart, you know, it’s the best one out there.

So I like that, that, that you can use directly with chat because we can speak a lot faster than we can type. So I mean it’s just an amazing thing and you know. It’s it’s a great tool. And, you know, especially if like you might have a certain like, you know, you might have a circumstance where you can’t type and so or, you know, you injured yourself or something like that and you got to do a shoulder surgery or whatever. Well, this is a total workaround basically.

Dr. Jeremy Weisz: 14:27

So yeah, I find it totally, really fast. And I look at I know we were talking before we hit record is what things can you incorporate use AI for to make things easier? Like for me I look at kind of 80 over 20. Where am I spending 80% of my time? I spent a lot of time, unfortunately, in email.

So what’s been a lifesaver for me is using whisper Flow and Gemini inside of Gmail because we use G suite and that’s been huge and speeding things up, right? Because like you said, I could just dictate it, go in there. It basically is what I wrote, but then it doesn’t, you know, it’s not run on sentences how I normally would type it and it formats it properly. Any other tools you’re playing with?

Ben Altman: 15:14

Yeah, I’m starting to use Plaud, which is this, this tool that’s for note taking, trying to incorporate that into my cloud right now. Let’s see what else. Playing with both Gemini and Chat. I’m using something you know I’m it’s it’s something I can’t believe I didn’t you know, it’s just I can’t believe I didn’t know. This is something called crit.

You’re familiar with crit. Okay. Context. Role. What role do you want the AI chat to play?

Interview. The key is we’re all using the chat software incorrectly. All of us. Why? Because we ask it questions.

So this reverses the table. It gets it, asks us questions before it spits out an answer which is much more consultative. You’re actually teaching it. So oh I want let’s see here context. Could be take any situation.

I, I want to teach about a mega backdoor Roth right. Because that’s a cool tool that we use.

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[EO Chicago] Lessons on Leadership, Legacy, and Learning With Ben Altman

[EO Chicago] Lessons on Leadership, Legacy, and Learning With Ben Altman

Here’s a glimpse of what you’ll learn:

In this episode…

Resources mentioned in this episode:

Special Mention(s):

Related Episodes:

Quotable Moments:

Action Steps:

Sponsor for this episode…

#1 Our Predictable Podcast ROI Program

#2 Our Comprehensive Corporate Gifting Program

Episode Transcript:

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