Robert Wynn – Climb USA

We’ve all been given good advice when we were young, sometimes even when we aren’t so young.  Many of us, myself included, didn’t take all of the advice I should have.

This is especially true in regards to the advice given about investing. The advice can be summed up into two words, do it.

Robert Wynn has taken the idea of given advice and brought it to a whole new level.  He has founded Climb USA, which teaches children how and why to invest.  He uses real life examples and allows the students to learn, first hand, what it takes to make their money work for them.

Listen as Robert details the joy of teaching, the power of investing and one way he has chosen to make the world a better place.


Visit Robert at:
Authentic Business Adventures Podcast

Podcast Overview:

[00:02:30] Real estate ownership realization post dad’s death.
[00:03:03] Learning about investing from dad’s savings.
[00:07:42] “Stock Selection Guide” used for value-based investing.
[00:10:23] Discount brokers revolutionized investing, now diversified.
[00:15:40] Business life cycle and investing strategies explained.
[00:20:53] Fascination with short selling, not promoted.
[00:23:24] Community organizations teach personal finance, sometimes investing.
[00:25:28] Virtual focus on Wisconsin, equity in investing.
[00:28:39] Financial literacy and changing behavior trends.
[00:34:06] Family starts finance-focused non-profit with relatives.
[00:37:00] Youth learn investing through Stock Market Experience.
[00:38:55] Programs develop student leaders and investment enterprises.
[00:43:43] Nonprofit empowers youth with virtual meetings.
[00:46:38] Teaching basics of stock market, progressing slowly.
[00:49:32] Young lady buys affordable headphone stock, sells.
[00:53:32] Pipeline for financial services career hopefuls.


Business Podcast Transcription:

James [00:00:00]:

You have found Authentic Business Adventures business program that brings you the struggle, stories and triumphant successes of business owners across the land. Downloadable audio episodes can be found on the podcast link found at My name is James Kademan and we are welcoming, preparing to learn from Bob Wynn, the founder of Climb USA. So, Bob, how are you doing today?

Robert Wynn [00:00:27]:

I’m doing well today. Thank you very much.

James [00:00:29]:

Thanks for being on the show. I was poking on the website that you have, and I think the gist is it’s helping kids with investing in financing or finances, I should say.

Robert Wynn [00:00:40]:

Is that right? Yes. Generally, financial literacy and specifically, we’re focused a lot on investment, education, and wealth building.

James [00:00:48]:

That is awesome.

Robert Wynn [00:00:49]:

Yeah. And of course, the name of the organization, I like to say, describes who we are and what we do.

James [00:00:55]:

All right.

Robert Wynn [00:00:55]:

Lime is actually an acronym. It stands for communities learning to invest and mobilize for business. I think it’s important that people approach their adulthood in that sequence, learning about business, finance, and investing, and then eventually entering into business and hopefully do it on a community mobilization basis as well.

James [00:01:18]:

Nice. I love it. You know, it’s funny, it is rare that I don’t have a conversation with someone where we start talking about money or investments and stuff like that. And we always talk about how we never were taught this in school, or how it’s never just like, how do people know this? Or you’ll be talking with a financial planner, or there’s a time I had a financial planner that didn’t do so great for me. And I was like I joked with him because I’m like, I can lose money on my own. I’m really good at that.

Robert Wynn [00:01:45]:


James [00:01:45]:

I don’t need to pay somebody to lose money for me. And it was one of those things where I’m like, I don’t know if other people would have even been aware. And it was just well, it was the John Oliver thing that made me look a little deeper. He had a little thing about financial planners and all that jazz anyways, the whole financing, investments, even just the power of a dollar kind of thing, I don’t believe that many schools are really teaching that. And it’s one of those things where I’m like, that’s pretty important.

Robert Wynn [00:02:15]:

Well, you’re making me remember how I got started myself.

James [00:02:19]:

All right.

Robert Wynn [00:02:19]:

Growing up, I just remember big box stores, sears and some of the other big companies. I never thought about the fact that somebody owned those.

James [00:02:29]:

Oh, sure.

Robert Wynn [00:02:30]:

Or you see real estate and people were living in apartment complexes, et cetera, and you just never really thought about the ownership behind those things. Like you said, no one in school was telling you about business and ownership and all of that. It was really only after my dad passed away, and that was in 82. And then my mom I’m the only son and a lawyer by training, so my mom wouldn’t listen to anybody else’s advice. And she had been a traditional mom. She worked outside of the home as a teacher, but she just never dealt with the finances.

James [00:03:02]:


Robert Wynn [00:03:03]:

So she was starting from a pretty elementary basis of understanding. And I had a job by then, but I didn’t really know that much about money. But then realized that my dad had saved kind of quietly for his limited income and all that he had on him financially. I was actually impressed with the fact that he had enough that you could have called them investable assets, because saving beyond what he needed for emergencies, his house was paid for. And it just occurred to me a whole family could have been a lot better off if we had been investing. All right, so I knew somehow along the way learned that there was something called investing, but I didn’t know that much about it myself. So, at the time, Merrill Lynch had a book called how to Buy Stocks, and it was a thick, like, 300 page book, and it was boring, but I plowed through it because I wanted to talk to my mom about maybe taking a slight different turn and go beyond just saving and investing a little bit. But we had to really educate ourselves. And then through that whole process, I began to get fascinated by it myself. This, again was in the early to mid eighty s. And I opened up my own account because I actually wanted to take more risk and just be more experimental than I thought I could advise my mom to be. And as I learned more and more about it, I just became not only smitten by it, but also very concerned and passionate that everybody should know the basics about investing and how the stock market works. Because so much financially revolves around what we call the capital markets.

James [00:04:51]:


Robert Wynn [00:04:51]:

And so I ended up getting involved in state government with economic development, not really because of the investing, but it sort of helped to broaden my understanding of what business was all about and especially how important capital was. And of course, capital comes in different forms.

James [00:05:13]:


Robert Wynn [00:05:13]:

Debt as well as investments or equity. And I just felt like I was being empowered by what I was learning and just felt that more people could do more for themselves if they learned about investing.

James [00:05:28]:

Yeah. Interesting thing here as you’re talking 80s versus today, investing is a totally different game.

Robert Wynn [00:05:36]:

Very much so. There’s some things that are similar.

James [00:05:38]:


Robert Wynn [00:05:38]:

Yeah, sure.

James [00:05:39]:

But today it’s much easier for me to get on my phone, open up an account, and just start trading away. Right. I can be a day trader in less than less than a day.

Robert Wynn [00:05:50]:


James [00:05:50]:

We’re in the 80s. What did you have to do to trade a stock?

Robert Wynn [00:05:53]:

Well, again, funny that you would ask, because Charles Schwab pioneered discount brokerage I would say probably in the early 80s. But before that, you just basically had full service brokerage companies. And that just meant that there were these account executives, or we call them stockbrokers, and they made their money by recommending people to buy and sell stocks. And then they made a commission off of those buys and sales. And oftentimes, sometimes the advice dovetailed with the financial incentive for the individual to make money off of those decisions.

James [00:06:37]:

Sure. Wolf of Wall Street, right?

Robert Wynn [00:06:39]:

Yeah, that’s right. So, collaterally. I was approached by a good friend to start an investment club. This is more of a do it yourself approach to investing.

James [00:06:50]:


Robert Wynn [00:06:50]:

And again, this was in the mid eighty s. And it was literally 1987, the summer that we started this investment club in Wisconsin. And we connected immediately with a major nonprofit that supports the training of people who want to learn to invest for themselves. The organization back then was called National Association of Investors Corporation, and everyone referred to it as its initials, NAIC. They had a magazine called Better Investing and later changed the name of the organization to what’s now called Better Investing and Website is

James [00:07:29]:

All right.

Robert Wynn [00:07:29]:

But because I was so interested anyway, I went to their meetings, which were all physical. There was not much on the Internet back then in the 80s.

James [00:07:39]:

No, I don’t think there was not a useful one anyway.

Robert Wynn [00:07:42]:

Exactly. But they had a lot of sort of manual education programs that even showed you how to manually keep track on the investment club accounts. That’s a whole story in and of itself because it was just a long form accounting ledger that people had to be trained on to maintain so that the several members, oftentimes 15 or so members, could track what amounts they were putting in and how that amount would grow based upon the investments that the portfolio as a group was making. So all of that was pretty complex. But they had a tool that was actually pioneered by a broker from the 40s. It was a gentleman named George Nicholson. I only heard about him. I met his family, but he had passed away, I guess, by the time I got involved with Better Investing. But it was called the Stock Selection Guide, and we call it, for short, the SSG. And basically it is what we might call a value based Warren Buffett approach to investing, where you’re looking at just the fundamentals of a company, a publicly traded company, their sales growth, their earnings growth. And based upon that understanding that when we’re buying shares of stock, we’re really purchasing a piece of the profitability of that company. That’s why we would purchase them. And so you’re trained to analyze the potential profitability of that company going forward and then determine whether or not that’s a good company to buy, and if so, whether the stock price is trading at a level that would make it a buy as opposed to a hold or sell. And that was called the stock selection Guy.

James [00:09:23]:


Robert Wynn [00:09:24]:

So I was on their board of directors for over 15 years into the mid 90s.

James [00:09:30]:


Robert Wynn [00:09:31]:

And it’s a very great organization. I’m still good friends with most of the people who are still associated with it, but it doesn’t outreach as deeply into the underserved communities as I was interested in. So that’s what led me to start a couple of other nonprofits that were really taking a lot of what I had learned from better investing and trying to bring that knowledge into communities that just don’t touch or connect with people who know a lot about investing and business and things of that nature.

James [00:10:07]:

Okay, so interesting. So mid 90s, you’re talking when the Internet came about for the masses, I should say, and I imagine second only to porn on the Internet was probably how to make money. Yeah. Because I remember is ETrade.

Robert Wynn [00:10:23]:

Yes, ETrade. And I think TD Ameritrade and a lot of other they all popped up. That’s right. I guess back then, ETrade was like how Robin Hood is today. Sure, it was very popular. But before that did come the discount brokerage services. And that was really important because it did make investing a little more affordable and sort of maintain people were able to maintain more of their investment profits as opposed to commissions. So that was really important. I always like to recognize Charles Schwab for really swimming upstream in that whole discount brokerage arena. But like you say afterwards, there was a proliferation of support organizations and access by virtue of the Internet. And one of the newcomers at that time was Motley Fool. Oh, yeah. Actually, one of the founders, at least is from my alma mater, University of North Carolina, David. And I didn’t know it at the time. He’s younger than me, so we didn’t overlap in college. But better investing had invited it’s. Two brothers that started Motley Foo had invited them to one of the national conventions, so we were able to meet them as well. And so it’s a huge world out there now. And now, of course, you’ve got a lot of different investment vehicles. Mutual funds begin to proliferate. And now we’ve got ETFs, which are exchange traded funds. And then along the kind of sidelines, you’ve got a lot of the cryptocurrencies, the most popular of which is Bitcoin, but there are a number of others out there. And through myself and Climb, we don’t venture into the cryptocurrency arena at all. And with mutual funds, everybody inevitably is going to invest some in mutual funds, but we don’t focus on that with our programs or our education because there is an extra layer of understanding and education that occurs when people learn how to invest or analyze an individual company. If you’ve talked to a lot of entrepreneurs, then you know that those entrepreneurs are hyper focused on their cash flow management, their profitability, their attractiveness to investors and all of that you get a sense of if you are an investor in a publicly traded company. So we think that part of what we’re doing is training the next generation of entrepreneurs to hit the ground running in terms of their understanding of those sorts of things.

James [00:13:07]:

It’s funny you say that about entrepreneurs being focused on the cash flow. I know they should be. I know some that aren’t.

Robert Wynn [00:13:15]:

There could be a couple of reasons. One is that they are flush with cash or another is they just hadn’t gotten a memo.

James [00:13:22]:

Right. They have too much money. I don’t even know how to start to count it. And others are like, I don’t have any money, I’ve already counted it. It’s all in my pocket three quarters. So it’s interesting, but I like the idea of teaching people stocks because that’s way fundamental and I imagine it’s to a point a little bit easier where you look at a mutual fund and you have to compare all of their holdings.

Robert Wynn [00:13:47]:


James [00:13:47]:

You’re also trusting who’s ever running that mutual fund that they chose some good holdings.

Robert Wynn [00:13:52]:


James [00:13:52]:

And I imagine that’s another hand.

Robert Wynn [00:13:54]:


James [00:13:55]:

To be the more people that you have making decisions for you, whether that’s a broker or a mutual fund advisor or the team advisors, that’s more hands in the pot kind of thing, right. Where stock is just a stock.

Robert Wynn [00:14:10]:

Yeah, it is. There’s an important aspect to diversification.

James [00:14:16]:

Fair, totally fair.

Robert Wynn [00:14:17]:

And so mutual funds can give you that much more efficiently because your first purchase is spread over so many stocks that the fund itself owns. But all the other things that you mentioned can be a problem or a concern in terms of someone else managing that you have to pay for. Sometimes funds are managed by committees. That means there might be multiple folks that have to be paid for it. But then again, I think that if one never learns to analyze an individual stock, they just miss that depth of understanding of what goes into making a good company.

James [00:14:55]:

It’s interesting you say that, because I invested in GE.

Robert Wynn [00:14:59]:


James [00:14:59]:

And I lost.

Robert Wynn [00:15:02]:

That depends on when you invested in it.

James [00:15:04]:

I would say past few years.

Robert Wynn [00:15:06]:


James [00:15:07]:

So in my mind, GE diversified company jet engines and light bulbs. Right. There’s two opposite ends of a spectrum. And I felt like it’s one of those companies that just couldn’t go away. I’d read a few Jack Welch books and most of them I thought were pretty good, or the content I thought for the most part was really good. And so I thought, this is amazing. But then I learned that GE is not a sexy company. It’s not a Tesla or a Bitcoin or something like that. So it’s just like jet engines. How boring, right?

Robert Wynn [00:15:40]:

Well, it’s so much there. Number one, for a very long time, General Electric had been a member of the Dow Jones Industrial Average, which is a select 30 companies longer than any other company. Full disclosure, I had owned GE as well and probably didn’t own it at an Opportune time because I sold it and I don’t think I made any money off of it either. Yeah, exactly. But businesses have their life cycles and so GE was on the very mature end of its life cycle, and unless they’re able to continue to renew and reinvigorate their business model, like many mature companies, they’re just going to fall by the wayside. We can think of many that have done that. But whereas when you mentioned a Tesla and what have you, I mean, they just got started based upon a premise of the future, that cars will be electric as opposed to combustible driven. So that’s sort of another piece of the analytical process where you want to look at the overall economic environment and see where the opportunities are, what are the trends that maybe are going to cause companies to fall by the wayside. And there was some evidence for GE just almost got over conglomerated, you might say, especially because so much of it had to do with finances as well. But that’s part of the excitement of being an investor. You have to look at the world with a more critical eye, in more depth, and then begin to understand the interrelationships between politics and science and so many things that drive the possible profitability of these companies. And that’s another reason I really enjoy it for young people, because sometimes they’re not necessarily motivated by what they are seeing and hearing in the classroom. But once they sort of realize that you can actually make money based upon what you do understand about the world around you, then they want to pay a little bit more attention because there’s something that’s a little more immediate that they can benefit from if they understand that.

James [00:18:02]:

All right, so it sounds like there’s both the math to figure out what’s going on with the financials of a given company.

Robert Wynn [00:18:07]:


James [00:18:08]:

But also somewhat of a gut check for where you think that company is or can grow.

Robert Wynn [00:18:14]:


James [00:18:14]:

I suppose if you have the most profitable typewriter company yeah, you’re still typewriter is going to be limited. Whatever.

Robert Wynn [00:18:23]:

But funny you mentioned that because I’m sort of intrigued by IBM.

James [00:18:27]:

All right.

Robert Wynn [00:18:28]:

It’s a big old publicly traded company at one time. It Literally Used To be Called International Business Machines. And they are hanging in there. They are right now. It’s not one anyone should go out and buy right away without doing their own research. But I don’t own it. But I look at it and I do admire it from afar because they have really weathered the storm of change, I think, quite a bit. And you will see these companies and even Apple is morphing a little bit right now from where they were emphasizing equipment sales, and now they’re sort of morphing into becoming more of a service type business. And then now you’ve got these amazing trends that are right on the sort of precipice of the future. One would be the electric vehicle or green energy trend, and every day now we’re hearing about artificial intelligence.

James [00:19:28]:

Yeah, you can’t go a day without it.

Robert Wynn [00:19:30]:

Exactly. And then there are these things I know less about, but the biotechnology trends that are out there these days, it’s just some tremendous change that’s going to lend themselves to investment opportunities. The more people can study it and understand it, there’ll be some false starts, too. And people who get out there too far out front sometimes don’t have the success because a company that you think might do very, very well ends up being maybe too far afield from where the economy really does exist. Yeah, and I can remember one of my early investments was in Wang Wang computer.

James [00:20:14]:

Oh, wow, that’s a while ago.

Robert Wynn [00:20:17]:

But fortunately, somehow I think they did big mainframes. And you hear this is maybe a little further afield than I talk about generally, but one thing that really added to my enthusiasm and intrigue about investing was in 1987, just as I had started. And of course we were in a mild panic because of the I think they call it Black Friday. The stock market crashed on Friday in October.

James [00:20:51]:

I was just going to ask you about the timeline there.

Robert Wynn [00:20:53]:

Yeah, so we had just started investing so we didn’t have too much at risk. But I’ll never forget being at lunch at a place on State Street in Madison, and I just overheard two guys talking at the other table about one of the guy’s brothers was making a ton of money as the stock market was crashing. And of course, then you learn about the ability to sell short. That just really fascinated me. And that’s why I got so passionate about investing, because I realized that you can make money if the market is going up or if the market is going down. Again, I have to emphasize that we do not promote or even teach about selling short. We have a stock market game, and it’s an allowable strategy because it is a realistic strategy that does exist, but we don’t teach it because it is much more risky. And one can end up losing almost like theoretically an infinite amount of money because whereas on the downside, a company has a finite amount, they can lose zero, go to zero.

James [00:22:01]:


Robert Wynn [00:22:02]:

But on the upside, theoretically, there is no threshold of conclusion at the upside. So we don’t teach it. But I only brought it up just because I decided I wanted to experiment with it. And I thought Wayne would be a company to experiment in selling short. And sure enough, if I remember correctly, I sold it first at around 60 something a share. And then I was able to buy it back at 30 something a share. So I made some money, all right. But I felt very uncomfortable when I look at my account and see you have a lot of money there because you’ve sold these shares. But you know, you’ve got to save some money because eventually you’re going to have to buy the shares back and you’re going to need money to be able to do that repurchase. And I just thought, I don’t want to put myself in a position where I might get overly enthused about money that really isn’t mine. So I don’t have much experience in selling short, but the market offers a lot of different strategies and avenues for making money.

James [00:23:11]:

Oh, my gosh, there’s a ton making or losing, right?

Robert Wynn [00:23:13]:

Yes, that’s right.

James [00:23:15]:

So I want to talk about the people that you have as students. One, let’s just start with how do they find you? How do they know you exist?

Robert Wynn [00:23:24]:

It’s word of mouth, but also a lot of community based organizations, just as you were saying early on, it’s very uneven in terms of what is expected to be taught in the schools. More and more there is a movement to teach personal finance, which sometimes includes a tad bit of investing, but not a whole lot. And so a lot of times, community based organizations have youth development programs and they have a lot of flexibility in what can be incorporated into their curriculums and so on. So oftentimes we fit easily there just because there are fewer decision makings in the process and what can be brought to the young people. So that’s one of the major ways. And then the other is not through formal parent organizations, but very frequently you will run into parents who say they never learned about investing, but they want to be sure that their children learn. So they come to us or someone very often someone may be talking about investing. Then they say, well, you really ought to connect with Climb USA or connect with Bob Wynn or something of that nature. So it’s just very organic. At this stage. We hope to get larger and be viewed more as sort of a clearinghouse for getting started, for investing and so on. But right now we’re in our third year and not widely known.

James [00:24:58]:

Okay. And is this mostly Madison based or is this national?

Robert Wynn [00:25:02]:

Our organization is based in Madison, Wisconsin.

James [00:25:06]:


Robert Wynn [00:25:06]:

And we serve a lot in Milwaukee because all of the jobs I’ve had in the past, I’ve developed a lot of familiarity with Milwaukee. Okay. We have done a little bit in some of the outer lying areas as well, but because we got started right in the heart of the pandemic, everything’s been virtual.

James [00:25:27]:


Robert Wynn [00:25:28]:

Yeah. And I say everything. We’ve done a few things live lately, but our platform of operation is pretty much virtual. So while we promote and focus on Wisconsin, we are accessible throughout the country and eventually we hope to be evenly involved with organizations and other groups throughout the country as well. We just think that one of the areas of equity that we want to address is the fact that some people understand investing and some people do not understand. And yet we have a very prolific efforts around workforce development and we want people to have jobs. But to have those jobs and not know that you should proactively open up your 401 or you have a right to open up an IRA, even if you’re young and babysitting, you can open up an IRA. People who know how to do that at an early age are going to end up so much better off generally than those who had not. At least the history of the stock market has proven that people who have been long term investors have done well in building wealth, as opposed to those who just work very hard, live paycheck to paycheck, but never really learn about investing.

James [00:26:54]:

Yeah. It’s interesting. When I was in college, I had a guy tell me that I got to start investing. Like invest now, you’re in your 20s, perfect time because it’s just going to grow from there. You can afford to make some mistakes, essentially. And I was living essentially hand to mouth. So I’m, like, invest. What?

Robert Wynn [00:27:10]:

Yeah, exactly.

James [00:27:12]:

Am I going to get generic rolling? What am I going to do here? So it was one of those pieces of advice that I should have took. I should have taken, but I just.

Robert Wynn [00:27:21]:

Well, I was going to say, you’re a very lucky guy to have someone to advise you.

James [00:27:25]:

I was like, I suppose almost every kid where I thought, I know the world. I got it all figured out. Just ask me, right?

Robert Wynn [00:27:33]:

Yeah. And I didn’t know a thing that reminds me of my dad. Like I said, my dad was pretty special because he worked very, very hard and put four kids through college nice. And like I said, paid for his home and saved tens of thousands of dollars he had in the bank when he passed away. And I think I was in my 20s, early twenty s. And one day I was home just visiting from college. He says, you need to start thinking about well, he actually said, you need to come home and stay longer when you come, and that will give us a chance to talk. And I said, talk about what? And he said your retirement. I thought he had lost his total mind. I mean, there was in my early twenty s and that sounded like the craziest thing in the world to start talking about my retirement. But here I am now, just a couple of years from retirement, and I’d have been way better off if I had stayed there longer and had that conversation.

James [00:28:38]:


Robert Wynn [00:28:39]:

And so you’re exactly right. You know, it you know, you have to be open to the information as well. And that’s actually something that we’re grappling with quite a bit, because another one of my mantras is young people need to know how to buy Nike stock as easily as they know how to buy Nike shoes. Yeah, well, if there’s a shoe giveaway or shoe sale, it’s huge demand. But if you’re somewhere saying, hey, I want to show you how to buy some stock, people just don’t flock to your door. And so that whole idea of how to take that advice that you received, that I received, or that these younger kids, some of them are lucky enough to receive, how do we really get them to listen and engage in the behavior that’s going to help them get an early start to building wealth? And that’s where some of the trends in financial literacy are today. We’re looking at not just what should go into a curriculum or even how to deliver the curriculum, but how do you convert that knowledge into behavior. That’s something that consumer scientists are looking at in a lot of depth, and people haven’t totally figured it out yet.

James [00:30:02]:

So I think it’s interesting that you say all that, because I had to have a mindset shift to get myself to invest. Because when I was a kid, when somebody said investing, I assumed I just went directly to that’s. A rich person making more money, which it’s not wrong, but that’s not exclusive to the rich people. I mean, that can be you can invest anything. College. We’re talking early 90s. So Internet wasn’t really a thing, right? I shouldn’t say it just became a thing. So it was still it was like the bottom of the ocean, right? We don’t know what’s down there.

Robert Wynn [00:30:38]:


James [00:30:38]:

So we’re not going to go quite yet anyways. It took me way longer than I would have liked it to, to realize that I’m not investing to become rich. I’m investing just to get that money, to make more money.

Robert Wynn [00:30:52]:

That’s right.

James [00:30:53]:

So I gave myself a goal of investing, and the goal was not to be rich. The goal was we like to go out for breakfast on Sundays. My goal is to have my investment pay for breakfast.

Robert Wynn [00:31:04]:

I love that.

James [00:31:05]:

So I need to make $20, $40, depending upon where you go, to take my family out to breakfast. And it was interesting when I made that little mindset shift, instead of like, I need to pay for my retirement, so I need to pay for me to live for 30 years without a job, I need to pay for my breakfast, like, oh, I can figure that out. And it wasn’t that big of a deal then. There wasn’t all this pressure, like, don’t mess up, right? You can lose a couple of bucks on GE and you win some you lose some kind of thing. And it wasn’t such a huge burden, right. But in the end, it was the same action. Right. You’re just investing. You’re doing your research, figuring out what to do. It was just that little shift of like, this decision means that you can work or you don’t have to for the rest of your life.

Robert Wynn [00:31:50]:


James [00:31:50]:

Don’t mess up.

Robert Wynn [00:31:53]:

Just makes it too intimidating.

James [00:31:54]:

Yeah. So you just don’t even want to start because you’re afraid of failure or you’re afraid like, oh my gosh, I can’t retire ever because I got in the investment game and I lost kind of thing.

Robert Wynn [00:32:03]:

Well, that’s why I really appreciate better investing and what I learned through them through this investment club methodology. And we are promoting that through Climb USA as well. And basically it’s a model where and this is what we did in 1987, it was about usually 15 or so people. In our case, I think we started with 17 that come together and agree to put in $25 per month, and then they go through the stock selection guide training and just gradually build a portfolio. And I got so smitten with investing that I ended up getting my broker’s license at one time.

James [00:32:44]:

Oh, wow.

Robert Wynn [00:32:45]:

Talking about brokers jumped in. Yeah. So I got my series seven and so on. And by doing that, you’re not expected to be in a club because somebody who is a licensed professional could cause too much sway in decision making, et cetera.

James [00:33:00]:


Robert Wynn [00:33:01]:

So after about 1015 years, I had pulled out, but I stayed in touch because this club was started in Madison, and in the year 2021, in September of 2021, I checked in with the club because they let me join or attend whenever I care to, and the club had peaked at $951,000.

James [00:33:24]:


Robert Wynn [00:33:25]:

That was after 500,000 had been taken out, and they quantified how much had been putting in. Had been put in. It was only about 500,000. So the club, once you let it grow for several decades, does become a little bit like a money making machine.

James [00:33:45]:

Yeah, I bet.

Robert Wynn [00:33:46]:

And that’s assuming the stock market continues to return 8% per year, which historically it has.

James [00:33:53]:

Don’t look at this year.

Robert Wynn [00:33:54]:

Yeah. Last year was very troubling and very, very difficult. And we started a club with my family because I worked my 1st 25 years with the state of Wisconsin.

James [00:34:05]:


Robert Wynn [00:34:06]:

And then I decided I was going to go into the community and start a nonprofit and help a lot of community people to learn about financial literacy and investing. And my family was uneven in their knowledge, and I said, well, we got to bring my family along if I’m going to do this. I have some siblings, they have children. And so it was about nine of us that came together and said, we’re going to form this family club and put in $25 a month. We had a few youngsters, and the parents would put in the 25 for the children that were under 20 or so.

James [00:34:41]:

All right.

Robert Wynn [00:34:41]:

And we have today about $180,000 in that club. And that’s after about 70,000 has been taken out.

James [00:34:50]:


Robert Wynn [00:34:51]:

And then my sister is a treasurer and keep track of how much we put in as an aggregate family. And the family has grown. So it’s now 13 that are members, and that includes husband, wife being one member.

James [00:35:04]:


Robert Wynn [00:35:04]:

And we have put in about 61,000 of our own money, and we have 187,000. And that’s after 70,000 has been taken out.

James [00:35:14]:

Holy cow.

Robert Wynn [00:35:16]:

Yeah. It went up to over 200. Then a couple of people took money out. But for what we call wealth building activities, we always promote home ownership as another way to stabilize a family financially. We had two family members that took out about 25,000 each to put in as a put down, as a down payment for a home that they wanted to one to build and then the other to purchase. And then another took out about 8000 for an entrepreneurial project. I think it, too, had to do with real estate, and then another was older and just wanted to derisk some of her own assets for retirement. So those are the kinds of things that this club model can generate for people’s future. But again, we started that family club in the year 2000. So it’s been two decades now.

James [00:36:06]:

All right.

Robert Wynn [00:36:06]:

Yeah. So that’s the thing that we’re still needing to understand how to message through Climb USA that we think that we are bringing the community a solution that can be transformative in 20 years.

James [00:36:22]:


Robert Wynn [00:36:22]:

But we can’t promise anything spectacular in year two, three, or four. And so a lot of sort of, like, community and charitable work are looking for outcomes that are measurable within a very short period of time.

James [00:36:40]:

Oh, wow.

Robert Wynn [00:36:41]:

Whereas with what we do, it takes a longer period to really show the results. You actually see the results more in the students understanding and appreciation for what they’re learning than you do in the money itself over the shorter period of time.

James [00:36:59]:

How do you measure knowledge, Kenneth?

Robert Wynn [00:37:00]:

Yeah, exactly. But if you talk to them and one day we’ll do a podcast with the all right, because when you talk to them, you’ll see that these are special children because of what they have been learning. And so Climb really has sort of a sequence of three programs that we are trying to present to the community sequentially. And the first is this stock market simulation, which is each person’s given $100,000 fictitious money, I was just going to say. Right. And then they just get a chance to play around with that money and even sell short just for the fun of it and see how it works. And then at the end of the investment period, we just do it during the summer. Right now, we give prizes and we give real cash prizes to the winner. And this year, we’re offering $1,000 to the youth winner that’s a person under 18 and then $1,000 to the adult winner. We used to not have an adult category of competition, but every year when we would do the summary because this is our fourth summer doing this, we heard so many testimonials from the staff of the organizations that were bringing the youth to USA, say, hey, I never learned about investing. And during the summer, I actually opened up my first brokerage account or I bought my first stock. And we just started hearing so much that we decided we wanted to give adults a platform to continue their learning as well. So that’s our first program, the Stock Market Experience, we call it. And then the second is this Klein Youth Leaders Program, that’s one that meets on a regular basis during the school year for once a week. And we just have different conversations about money, investing, entrepreneurship. And those students, because it’s treated more like a club, can stay in it multiple years.

James [00:38:55]:

Oh, nice.

Robert Wynn [00:38:55]:

And once those students have been in that leadership council for at least two or three years, their conversation level begins to change, their understanding begins to change the way they see the world and see themselves and see the future changes as well. So you can really see the benefits of doing that. Then the third program is this investment club initiative. Because, as I was telling you, with our own family, you can see how the building of those funds not only creates the understanding, but also the capital and the wherewithal to go out and do other wealth building activities like buying a home or having money to pay for your education and things of that nature. We’re actually helping to change the narrative of how you talk about those investment clubs because they’re not just social, they’re really contributing to the economic fiber of communities that we bring them to. So we call them now community based investment enterprises so that people in the first instance can understand that these truly are businesses. And you talk to entrepreneurs. Maybe we’ll have to talk to an investment enterprise group, too, because they actually are businesses, and they have to get a tax ID number, brokerage account. Okay. And they’ll run just like a business. They’ll have a president of the investment enterprise, vice president, treasurer, secretary, meet monthly, have minutes to the meetings, et cetera.

James [00:40:25]:


Robert Wynn [00:40:25]:

And one of the things we’re doing is pioneering the model to accommodate youth. It has been an adult model because technically, you got to be 18 to I was going to ask you anything.

James [00:40:37]:

Yeah. To tell me about the ages of these groups.

Robert Wynn [00:40:40]:

So we target a lot of our education for middle and high school students.

James [00:40:44]:

Okay, so you’re talking 6th, 7th grade.

Robert Wynn [00:40:45]:

Yes. That’s the ideal time to start. Okay. This summer, our roving reporter for our summer stock Market Experience, I think is going to be a 7th grader. I think he’ll be going to the 8th grade oh, nice.

James [00:40:56]:

Okay. Next year.

Robert Wynn [00:40:57]:

But when we organize the youth leaders to be part of an investment enterprise, we have to be sure that the parent signs on behalf of the youth so that it’s sort of like a custodial account equivalent to how that would work. But obviously, if you get the young person investing at an earlier age, they can have more later on. So that’s one reason we wanted to pioneer it. But I brought it up only because in one of the clubs that we got started in Milwaukee, it’s only about seven years old, and it has about $30,000 in it. Right now, we just assigned or voted in a youth. He’s under 21, but he’s in college, a freshman who’s going to be the secretary of the club. And then we have a gentleman who’s also a college student who’s the vice president. So the adults are still sort of guiding them, trying to teach them. It’s so funny because we do use Robert’s Rules of Order like you would in any business. All right, so my name is Robert. Little did I know this one, 8th grader, when she was telling someone what she was doing, and she says, and we use Mr. Bob’s Rules of Order. And I say, no, they’re not really.

James [00:42:09]:

My rules.

Robert Wynn [00:42:12]:

But they’re learning how to make a motion and get it seconded and passed and so on. So all of those things are great training for just being a great civic leader and citizen of your community.

James [00:42:26]:

Yeah, I remember the first time that I was on a board and somebody had mentioned that the Robert Rules of Order. And I was like, Who’s Robert? Who is Robert? I didn’t know it was some universal thing.

Robert Wynn [00:42:39]:


James [00:42:41]:

Sharp guy.

Robert Wynn [00:42:42]:

Well, when I go to restaurants, I ask the wait staff or what have you, what’s the history behind the name of the restaurant or what have you, just always kind of curious how they got that. And so teaching the kids Robert’s Rules of Order, I actually looked it up, and there was some army or military leader that was I think his name was Robert something, and he was very structured in just how he conducted meetings and got a lot of efficiencies around decision making and so on. And that’s why they call Robert’s Rules, because he’s the one that got that started.

James [00:43:19]:


Robert Wynn [00:43:20]:

Yeah, that’s pretty cool.

James [00:43:22]:

So when students sign up with you, are you giving them one on one, or is it in person? Is it zoom or how are you?

Robert Wynn [00:43:31]:

Well, it’s funny because we’re sort of riffing on how we do this. Just trying to figure it out.

James [00:43:38]:

Yeah, we all are.

Robert Wynn [00:43:39]:

Yeah. So a lot of what I do is you might call group mentoring.

James [00:43:43]:


Robert Wynn [00:43:43]:

Before the pandemic, even with a different nonprofit, we met in small groups in mostly Madison and Milwaukee and did our education live. But once climb got started, everything and I was not really that knowledgeable about zoom and was just trying to really figure it out, but have learned that you can access a lot of people through a Zoom meeting or some sort of different virtual platform. And because I have gone to a number of different schools where some of my colleagues have become pretty successful, I’ve actually been able to zoom in really high level professionals that are excellent role models and expertise, providing expertise for the young people that we serve. So our zooms are usually weekly in some cases. Most cases they’re weekly. We do them differently in the summer than we do in the fall, but they’re generally weekly. And then we normally will conclude a program at the end of the summer or end of the school year with what we call a capstone. And in those cases, we’re preparing the young people over several weeks to come up with their own topic that they want to present, and then they present back to the teachers and facilitators on a topic that is interesting. To the young people because they learn so much by doing their own research, preparing their own presentation, and then having to articulate ideas in their head in the way that they want to articulate them. So it’s sort of that combination of back and forth and trying to keep engagement. And through the zooms we’ve had presenters from seattle, washington, from california, from New york, atlanta, from florida. We’ve got a nice colleague, cadre of colleagues down in South Florida. So we’ve been able to zoom back and forth with them as well.

James [00:45:49]:

All right, I want to ask you, how do you get these middle schoolers to be interested in the financials of a company?

Robert Wynn [00:45:56]:

Well, number one, like I say, the parents are very influential in bringing the youth to us. And so, like I say, I can’t say that students just walk in off the street or call us up because they want to learn this information.

James [00:46:16]:

Yeah, let me look at the prospectus.

Robert Wynn [00:46:19]:

Usually it’s a parent that has gotten them to cooperate, to be involved with our program. And then at the middle school level, we’re not going to teach them in depth on some of the financial analysis.

James [00:46:37]:


Robert Wynn [00:46:38]:

It’s more just general conversation around the stock market. In general, like the 7th grader, I was explaining to you, I was on a private one on one zoom with him. We don’t do a lot of that, but from time to time and I was just explaining to him what the SP 500 is and the Nasdaq, and then training him on where to find it on Yahoo finance and then let him look it up. So this Friday, he, along with a couple of other students, we’re going to be on a virtual platform and just let him practice saying the numbers. It’s funny sometimes when you see that big number 10,000,700,000, what have you, people don’t know how to pronounce those numbers sometimes if they’re not used to them. So we’re just getting them used to a lot of just basics. That is a foundation for the kind of further learning that we want them to have. Quite honestly, I mentioned you that stock selection guide that’s sort of like the pinnacle of the learning that we have to offer. And there’s not a lot of students yet that have gotten to that stock selection guide level of understanding yet. We are still trying to get there. We do a lot of education on Yahoo Finance. Okay. There is a website that’s specific for investment education called Investopedia, so we use that quite a bit. And then I learned a lot on Value Line, which is a subscription service that’s available through most public libraries. So we do some training of the young people on how to decipher that. Once you’ve got that foundation, then you’re ready to learn the next level, which is the stock selection guide process. And we’re still not teaching as many that level as I would like.

James [00:48:33]:

All right. Does Reddit get involved in that?

Robert Wynn [00:48:37]:

Well, not normally, but you might remember, was it early 2021 when AMC and what was the other stock? One of them just went crazy.

James [00:48:49]:

GameStop, right?

Robert Wynn [00:48:50]:

Yeah, GameStop. Yeah. Well, yeah. And so there was actually another little stock that had a very funny move, and it was a Wisconsin based company. It was a headphone maker out of Milwaukee. And because they were in Milwaukee and the stock price was very affordable, I had just bought some of that for myself and for one of our investment clubs, as well as a couple of the students. We’ve helped a couple of students just open up their own account beyond the investment club just so that they have their own little account that they can play around with. And they’ve shown responsibility enough that we would help them to open up their own account in consultation with their parent.

James [00:49:32]:


Robert Wynn [00:49:32]:

And so the one young lady I had bought some of that headphone maker just because it was very affordable and that stock was zooming up. It went up close to 70, 80 points in a day or two, just like GameStop did, but it never made the news quite as much. All right, but I sold some and oh, as a matter of fact, the young lady, she at the time was like a junior in high school, maybe. We work a lot with Charles Schwab just because we know the people there in Madison and Milwaukee and they’re very friendly to us. So the broker at Charles Schwab was nice enough to call her and let her know that her stock had gone way up. And it was a fast move, so it could also go down real fast. So she called me up and said, mr. Bob, the guy at the brokerage firm told me that my stock went way up. What should I do? And I told her, sell.

James [00:50:32]:


Robert Wynn [00:50:33]:

So she sold, and then I was able to sell some as well, and that was real exciting.

James [00:50:38]:

So was that related? Like, why did it go up so high so fast?

Robert Wynn [00:50:43]:

Why did GameStop go up so high? You asked about reddit. Yeah, I think the Reddit type game yeah, it was the Reddit type people that probably caused that stock to move so fast. Yeah, I think there was sometimes you just don’t know what’s going on behind the scenes, so to speak.

James [00:51:03]:

Well, I think there was a little bit of some of the people on Reddit were trying to.

Robert Wynn [00:51:10]:

Well, they were.

James [00:51:10]:

Actually they’re playing a game.

Robert Wynn [00:51:11]:


James [00:51:12]:

Which kudos to them, but the headphone manufacturer in Milwaukee, I’m like, is that even on the radar?

Robert Wynn [00:51:17]:

Yeah, I’m going to let people look that name up.

James [00:51:19]:

Okay. I’m going to have to do that because that’s interesting that that happened so close to home.

Robert Wynn [00:51:24]:

Yes, it did.

James [00:51:26]:

But I bet that girl, she made the money on that, whatever it was, she’s probably like, oh, this is fun.

Robert Wynn [00:51:32]:

Well, you know, it’s funny you mentioned that, because when we met her, she wanted to be a nurse. I can’t remember exactly what type of nurse, but a nurse. And she always came to our programs, which is always relating to business and finance. And we even do a little entrepreneurship program called Go for It. And that culminates with a pitch competition, because you hear about generator and all these other organizations, they’re always doing pitches. So I’m like, I want to get some of these community kids ready to be at the big pitch competitions. So we’ve done quite a few. So she wins all the pitches, and I just thought, like you say, she’s learning so much. She’ll probably be fascinated with the industry and want to become a financial services person.

James [00:52:18]:


Robert Wynn [00:52:18]:

But she has not swayed. As a matter of fact, her name is I Am Unique, and she has distinguished herself as being, I think, the first high school student in Milwaukee to go through a special nurse training program where she graduated from high school and had her nursing certification before she graduated from high school.

James [00:52:38]:


Robert Wynn [00:52:38]:

So what we did with her the year she graduated, to keep her engaged with what we’re doing, I said, Why don’t you use as a summer project to study publicly traded healthcare stocks, all right? And then give us a capstone report at the end of the summer? And sure enough, she researched them UnitedHealthcare. And I remember another one was the one that I think does like healthcare uniforms and so on, and she did a very nice presentation. It’s actually on our website, on the bottom of the Climb Youth Leaders page, where you can see the 1 hour presentation that she did. And shortly after that presentation, she called me up and said, mr. Bob, I can’t remember the name of the company, but it was the same Caremark. That was the name of the company.

James [00:53:32]:


Robert Wynn [00:53:32]:

And she said, I saw a truck and it was Caremark. And that was one of the companies I studied. And so it does, again, just open her eyes to even know more about the industry that she is interested in. We are hoping that we become a little bit of a pipeline for more individuals joining the financial services ranks because there’s going to be tremendous turnover and a lot of opportunities in the financial services arena, and it’s a great lucrative career path as well. So we’re hoping that some of the young people that we work with will choose to go into that arena. We have another young person who, in high school was not clear about what he was going to do after high school. I came up from a family that the expectation was automatic. You’re going on to college, but a lot of children don’t grow up with that background or expectation. But after being with our program, he was part of the Climb Youth Leaders, and several of his peers who were Climb Youth Leaders were in fact, going to college. So he ended up applying and going to college. And now, to my pleasant surprise, he has said he wants to major in economics. And I think he got his taste of economics through our program.

James [00:54:57]:

That’s awesome.

Robert Wynn [00:54:57]:


James [00:54:58]:

I love it.

Robert Wynn [00:54:59]:

Bob, how can people find you on our website? Climb USA. Climb

James [00:55:06]:


Robert Wynn [00:55:06]:

That’s the easiest way to find us.

James [00:55:08]:

Nice. And are you for students and all that kind of stuff? Can they sign up or register?

Robert Wynn [00:55:13]:

They can. The summer program is the one that we’re looking to build participation in for now, and that’s on our Summer Stock Market Experience page. We used to call it Summer Stock Market Experience, but just the Stock Market Experience page, there’s a registration for our orientation that’s coming up on May 23. And then the program kicks off with a virtual program on the 13 June, and then the trading will occur from June 26 through August 4.

James [00:55:45]:

Nice. I love it. Bob, thank you so much for being on the show.

Robert Wynn [00:55:48]:

Well, thank you very much. I thoroughly enjoyed it.

James [00:55:51]:

This is cool. I love what you’re doing. You’re making the world a better place. You’re helping some people make some money.

Robert Wynn [00:55:55]:

Well, we’re trying.

James [00:55:56]:

It doesn’t hurt, right?

Robert Wynn [00:55:58]:

And we’re really trying to grow the next generation of entrepreneurs to be better prepared, knowledge wise, as well as having some capital that they can leverage for their future.

James [00:56:08]:

That’s cool. I love it.

Robert Wynn [00:56:10]:

Thank you very much.

James [00:56:11]:

This has been Authentic Business Adventures, a business program that brings you the struggles, stories and triumphant successes of business owners across the land. We are locally underwritten by the bank of sun prairie. If you’re listening or watching this on the web, you could do USA huge favor. Give us a big O. Thumbs up, subscribe and of course, comment below and let us know what your experience has been either trading, buying, selling stocks as well as the business. And of course, I guess I should say most importantly, if you could share this with all your friends and the kids that you know that could probably use a leg up in their life, which is all of them.

Robert Wynn [00:56:41]:

And thanks to Bank of Sun Prairie, they have actually hired one of our Climb Youth leaders as an intern. And I’m going to try to look him up, see where he’s at today. But incredible. Sun Prairie, I understand, has been very supportive of some of the youth leaders that we have worked with.

James [00:56:57]:

Oh, very cool. Just down the road. I love it. My name is James Caterman and Authentic Business Adventures is brought to you by Calls on Call, offering call answering services for service businesses across the country, on the web at callsoncallcom, as well as the Bold Business Book, a book for the entrepreneur and all of USA available wherever find books are sold. We’d like to thank you, our wonderful listeners, as well as our guest Bob Wynn, the founder of Climb USA. Bob, what’s that website?

Robert Wynn [00:57:24]:

One more time

James [00:57:27]:

Awesome. Past episodes can be found morning, noon and night. The podcast link Thanks for listening. We will see you next week. I want you to stay awesome. And if you do nothing else, enjoy your business.

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