
In this episode of the "Parents, Is Your Teen College Ready?" podcast, host Shellee Howard interviews Annaline Dinkelman, a former Wall Street professional who now runs Teach Me Wall Street, an online education platform that teaches high‑school students, middle‑schoolers, and adults how to invest and understand financial markets. Annaline shares her personal journey from South Africa to a decade on Wall Street, her transition to day‑trading, and the creation of Wall Street Walks, which pivoted to online classes during the pandemic. She describes her hands‑on, interactive teaching style, emphasizing short 2‑hour sessions over two weeks, covering market players, news impact, stock selection, and portfolio building. Her summer program includes four modules: Wall Street 101, Investing Week, Cryptocurrency (focused on the technology rather than speculation), and Budgeting. She also offers a weekend "Wall Street 101 for Adults" course. Annaline discusses the importance of teaching financial literacy early, the distinction between investing and speculating in crypto, and offers practical advice on work‑life balance, setting technology boundaries, and learning from failure. The episode concludes with a call‑to‑action directing listeners to teachmewallstreet.com for enrollment.
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Parents, is your teen college ready? Are you feeling overwhelmed, stressed out, or excited about your teen applying to college? Do you know what colleges are looking for? And if your kid gets in, do you know what you'll pay for it? College admission has never been so competitive or expensive. Shellee Howard will take you on a journey to help you and your teen get college ready. Now here's your host, Shellee.
Hello, this is Shellee Howard, and I am coming to you from the podcast Parents, Is Your Teen College Ready? And today I have a wonderful guest who is going to blow your mind. She's going to teach teens, young adults, how to invest. She was in Wall Street. I'm not going to steal your thunder. Welcome, Annaline Dinkelman.
Hi, Shellee Howard. Thank you very much for having me. So, I always, before I talk, I tell people I'm originally from South Africa. That's where my accent is from. But I am a resident of New York City. So, we moved here about 25 years ago, and I used to work on Wall Street. But after 10 years there, I was just tired of the long hours and and I quit and I became a day trader. And day trading is fun. I still do it today. But it's really lonely. So after 2 years on my own, I started doing tours about Wall Street and the stock market. And I created a company called Wall Street Walks. And that's— when I started that, I thought I would be teaching many tourists from around the world, showing them around Wall Street. But I had many student groups, not just from the US but from around the world, taking my tours. So in the pandemic, when everything came to a grinding halt, I took the classes part of my business online, and thus is Teach Me Wall Street. So I teach students about the stock market, Wall Street, and investing.
That is so incredible. You took a life experience, and now you are enlightening and empowering young people. So as a parent of 4, I'm thinking, how do you do that?
You know, students love money. I think they are frustrated. Sorry to be— you're a parent, I know, but they're frustrated because you won't give them the money they always want. So students look at the stock market and they think, I can make money. So they eager to learn and invest. And then when the students in my class are really interested, and some already have custodial accounts, so they are investing. Like one student told me, my grandpa gave me $500, and he said I can invest that in the stock market and we share the profit. So that kid was just after the half of the profit that he could be making. And my classes are hands-on and interactive. I teach the students to work on stock charts, and they not like sitting to a lecture. We do it hands-on.
I love that. So what age is like the best time? I, you know, again, I'm working on my mom mindset here, and I'm like, I know at least 2 of my 4 would really enjoy this. But when is the best time to introduce this? To a young, you know, to a student teenager?
I focus primarily now on only teaching high school students.
Okay.
But during the pandemic, I also had many middle school students, and they are ready for it. So when they— like, you have to start the conversations when they're young as a parent and trying to help them. Like, you probably teach your students, like, or your children, save some, invest some, and then spend some. So that saving part can become investing and already grow and work for them while they're at school.
I love that. I mean, it probably freaks teenagers out a little bit when you, when you explain you can use your money to invest and make more money. I mean, what, what is the, the length that of time it takes to teach a student the, the class or the program?
So I have, um, I teach my programs all online, and 2 hours is sort of the golden time that teenagers could sit still and be engaged. So I have it over 2 weeks in, um, where we cover like who are the players about the stock market because what people don't realize, it's the news that makes the stock market go up and down. So you need to understand who are the newsmakers, who should you listen to, and then we also focus on understanding how to buy companies, which are good companies, put them together in a portfolio. And after my summer programs end, I have a stock market club for the students where we have 8 weeks of of implementation because you only really learn by buying and selling stocks and gaining experience. Sometimes the market beat you up, but sometimes the market gives you a gift and you make a little profit.
Wow.
So, and then from there, students just have to keep practicing. And I realize they have school, so I teach my students to buy value stocks or things that don't need daily hands-on management.
Right, that's super important. So, but I think of summer coming up, and that's why I thought having you on the show would be brilliant timing-wise. I have students who may want to become entrepreneurs or go into business or finance or accounting or, you know, the, the financial side, and typically it starts with, I'm really good at math and I don't know what to do. So what does— do you have a summer program and what would that look like?
Yeah, I have a summer program that I teach in June, July, and August, and my summer program runs 10 AM Eastern and then also 10 AM Pacific. My very first class, I had students from California and they were like, for them it was 7 AM. So the program runs twice a day, and students can alternate their classes. If they oversleep or something, they can just come later. And the foundational week is Wall Street 101. Who are the players? What they do? What are the financial instruments, stocks and bonds? And then I have an investing week where we focus on choosing companies. Why would you choose this company? Most important, when would you buy and when would you sell? Because many people buy a stock and then it goes up and then they just watch all their profits disappear as they wait. I'm gonna buy it when it goes back up. What if it never goes back? So I teach my students like discipline, like have your rules. And then those are my two staple main programs. And then I also added a program on cryptocurrency. Because that is right now in the news a lot. But crypto students don't realize that that is where the jobs of the future lie. If you've taken a photo of a check to deposit at the bank, you are using what they call fintech, financial technology. And crypto technology is part of that renovation of the technology that drives Wall Street and the financial services industry. So, and then I round out my program with budgeting because you can make all the money, but if you don't understand how to manage your money and look after your money, you're going to just lose it all. So those are the 4 programs in my summer program.
That is amazing. So I know what I'm thinking, and I'm guessing my listeners are thinking, what about adults? Do you have classes for adults?
I do. I call it Wall Street 101 for Adults because we didn't learn this when we went to school. I wish I had someone to teach me when I was much younger. So I've had many parents that had kids in the class and then they joined me. So in the adult program, we do that on a weekend, like a Saturday and a Sunday, and it's a combination of Wall Street 101 and the investing, but just at a much faster pace.
Outstanding. Well, you know, this crypto thing is a common topic with my students. I have students right from 7th, 8th, 9th, 10th, 11th, and 12th, and they're all very forward-thinking. They want to be an influencer, they're, they're going to buy a house with crypto. And I want to learn crypto because I want to speak their language.
Yeah, right.
It's a whole nother world. They describe it to me as like the first time the cell phone was introduced and we're all like, there's no way you can walk around with a phone that's not connected. And we're panicking. And students say, that's exactly what this is. Just learn it, embrace it. Can you share maybe with some parents who are a little fearful of their teaching their child to invest and then opening up the world of crypto?
Okay, so there I caution, I don't invest in crypto. In Wall Street speak, when you invest, you kind of, you buy something and it has the potential to go higher. So commodities is, um, A crypto is classified as a commodity and you trade a commodity, you speculate in that. So people don't invest in crypto, they speculate. But the technology of crypto is where you need to invest. The companies that is working on the crypto technology. Because I don't know how familiar you are with crypto, but it is amazing technology. So it started in 2009. In the aftermath of the financial crisis. Many people were fed up with the banks, similar to what's happening now. My money is in the bank, guys.
Sounds a little familiar.
Exactly. So people wanted to— in those days, the banks were a little more sort of rude towards their customers, taking the customers' deposits and then paying themselves bonuses. It's not that way today. There are different problems. But anyway, in 2008, there was a big outcry against the banks, and people wanted to do business, pay each other without the banks. So that— the technology of blockchain, which is the foundation of crypto, made that possible. And then you need electronic money. So Bitcoin, meaning computers, and coins, meaning money, that lives in cyberspace. So the technology evolved a lot over the past 12 years, and there's big investment from Wall Street in this because everyone's saying, we missed out on Amazon, we're not going to miss out on the next Bitcoin or the crypto technology. So there's been a huge influx of money into this technology, and it can solve a lot of problems in the bank. So Bitcoin, actually, in all the problems with the banks, have gone significantly higher over the past 2-3 weeks because in Bitcoin there can be no interference by the government. Like, you see the government stepping into the banks now. Bitcoin doesn't have that interference, and there's much more transparency in Bitcoin where where's the transactions, who has access to it, that is not in the current system. And from that perspective, Bitcoin and the crypto technologies is fantastic.
What a great way to link that together. You are truly gifted teacher because I've heard so much information on AI, Bitcoin, NFTs, crypto. Like, my job is to make sure this next generation is looking forward. We can even tell our students if a robot will be doing their job in 5 years. We have that ability now, and that's wonderful. So I love what you're doing. Um, on it— on a— and on another note, how did you decide that you wanted to teach this, or what's your why? I mean, you probably don't need to do this.
You know, I, when I left my Wall Street job, I actually worked with a career counselor to figure out what, because I was just frustrated. And she told me, you could be a teacher, I swore it, like an actor. I said to myself, this is not true, I am not that, I come from Wall Street. But once I started giving tours, I realized I'm a gifted teacher. I can entertain people and take Wall Street, which is difficult, and explain it that people can understand it. And for me, the beauty is like when I take— I have a new intake of students, I can see they're uncertain. By Friday, you should see them, like they're amazing how much they can learn. And that is my why. Like money can't buy that joy of seeing people learning. And taking that knowledge and then doing something with it.
So I have to ask, when you were younger, did you dream of being a Wall Street trader? How did you get there? What was your path? Because I have so many students who are frustrated, they don't know what they want to do, and I encourage them to try this internship, research, all of the, the stuff that's needed. But for somebody who went through Wall Street And you, when you did it, I'm sure women were not the norm. So how did you end up in Wall Street?
A circuitous way. So I always tell my students, I have a degree in political science. I have no Wall Street degree. But what I learned on Wall Street, you can teach anyone how to do a spreadsheet. You can teach them to read a stock chart, but you can't teach common sense and people skills, the things that really make the difference. So I actually, in the 1990s, I realized I was in a dead-end job, and the internet had just started. So I quit my job and I took a job as an admin assistant in a computer company to learn about technology and the computers. And that's how I went to Wall Street. When we moved here from South Africa, I sent out my resume and they looked at my technology skills and they said, That's what we need because you've done in South Africa what we are implementing right now. Because countries around the world sometimes are a little bit ahead of the US because big companies here like Facebook now is doing testing in Australia and New Zealand. It's a small isolated population. So I came from South Africa with skills that was needed here. That's how I went to work on Wall Street and I learned a tremendous amount there.
Yeah, I mean, of course you did. You didn't have the, you know, the foundation, but you were able to learn it. What was the best part about working on Wall Street?
The people and the opportunity. I worked with really smart people, and at Morgan Stanley, we would analyze problems and work out the best solution. Like, not just like quick band-aid fixes, we would work through it. And like the smart people that I worked with, when I first worked there, in the beginning I was intimidated. The guy sitting next to me was from Harvard, the guy was from Yale, this one dropped out of Stanford. Here am I from South Africa. I was so intimidated. And then I realized they're just like me. They, um, And they could use big words, which I always caution Wall Street people, speak the language of the students because students don't have that sophisticated vocabulary. They will develop that. Hmm. But it was the people and then the opportunities because I worked in projects and technology like crypto, which were you trailblazing the whole time. But that keeps you on your toes.
Sure, yeah. And then I think you had alluded to that the hardest part were the long hours. So maybe for students who are considering a Wall Street, uh, career, what would be some advice or some things you wish you would have known before you did it?
You know, I think it's just to be mindful of the time. And technology made— now, when I first worked there, we didn't outsource as much as what we do now. But now cell phones made that you work much longer. You sit in bed, you check your email. Before you go to bed, you check your email. So self-management to just put down boundaries and say, from say 6 PM until 6 AM, I'm not going to touch my phone. I turn my phone to silent mode. That is one of the most important skills. And then surprisingly, it's like when you, like, for students, like, to say sorry when you're wrong. Like, so you can't be right about everything, but I've learned, like, to just say I'm sorry or I don't know. I learned on Wall Street people have respect if you say I don't know, but don't try and BS your way around the topic. That is going to get you nowhere.
Hmm, such wise advice. I like to ask my guests, have you ever failed? Have you ever failed at something?
I've had my setbacks.
Okay, and did you learn?
I learned. Yeah, sometimes your biggest setbacks are your biggest assets. You just don't realize it at the time. Or when things go wrong, for me, like, they were— I was like, over the past like 12 years, I look back and I think the financial crisis was so terrible, but it put my previous business on the map because everyone was interested to learn about Wall Street. And then the pandemic was another opportunity And in that first class that I taught online, I will never forget. As an adult, all you look at is, these are my failures. I didn't understand Zoom to understand, tick the box to turn on the sound. I'm playing the video. I'm like, this is me giving a tour. Let me show you Wall Street. There was no sound. And I said to the students, I will send you the video. For homework, like, to watch it. And during that week, I could see how many mistakes I did. But on Friday, I asked the students to do a little survey about the class, and they said to me, "We loved it. We had so much fun." And I realized it's the two perspectives. You look at it as an adult just seeing your failures. But if I didn't do those and have those little failures, I would not be where I am now. And that is sometimes people are too scared to fail. I'm not scared of failing because I know I'm gonna learn or I'm gonna go up.
Thank you for sharing that. I'm really encouraging students to step out of their comfort zone, to really lean into the unknown, and sometimes they're just scared they're gonna fail, like failing's a bad thing. I say, have I told you how many times I've failed and learned huge lessons. So that is so important for them to learn. Now, if our families are like, gosh, I— that I want to do that, how may they reach out to you?
The easiest is to go to my website, teachmewallstreet.com, and then I have a direct link to the summer programs just, yeah, from the main page.
So I'm going to repeat that: teachmewallstreet.com, correct?
Yes, that's all I do, all things Wall Street.
It's fantastic. Well, I can't thank you enough for being on our show, and I'm hoping that students out there who are looking into this world will reach out to you as a wonderful resource. So thank you for being on the podcast.
Thank you for having me.
Oh, my pleasure.
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