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Hey, what is up?
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Welcome to this episode of the Wantrepreneur to Entrepreneur podcast.
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As always, I'm your host, brian LoFermento, and I'll tell you what being a podcast host is a little bit like being a parent in the fact that you're not supposed to choose favorites.
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But I will say at the very top of today's episode that this is probably one of my favorite business owners that I'll ever get to interview here on the show, because I love her business, I love what she's built, I love her mission.
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I love how she's taken her past experiences and rolled it into her business.
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I love how adaptable and flexible she was when COVID hit and when the whole world is changing.
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I'm so excited to introduce you to today's guest.
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Her name is Anna Lynn Dinkelman.
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Anna Lynn is the owner and founder of a company called Teach Me Wall Street, which focuses on teaching how Wall Street works, who the players are and what they do.
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Now, why can Anna Lynn talk about Wall Street so in deep?
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Because for 15 years she has been an educator, teaching all ages about the stock market and finance.
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She spent a decade at Morgan Stanley in banking and compliance and then she moved to day trading, which was very lonely and led her to start Wall Street Walks in 2008.
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Different than her current company name.
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Why?
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Because she offered tours, lectures and conferences that blended history, business and education.
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But when the pandemic hit, annalyn took her business online and founded Teach Me Wall Street.
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Her online programs bring Wall Street's energy to virtual classrooms where they teach investing, trading, financial literacy and the scandals that have shaped the financial world.
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Her programs have been featured on CNN International and in the Daily Telegraph Newsday, usa Today.
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She is incredible at all the things that she does.
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I didn't tell her this just yet, but I was an economics and finance major myself in undergrad, and so I have so much appreciation for the institutions that have built the modern day financial markets.
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So this is going to be a fun one to explore Annalyn's business and entrepreneurial journey.
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So I'm not going to say anything else.
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Let's dive straight into my interview with Annalyn Dinkelman.
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All right, annalyn, I am so very excited to have you here with us today.
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First things first.
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Welcome to the show, thank you very much for having me.
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Heck.
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Yes, you heard in the intro to this episode just how excited I am that you're here, so I want to hear the whole story from your perspective.
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Though Take us beyond the bio.
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Who's Annalyn?
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How'd you start doing all these cool things?
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Originally I'm from South Africa and my husband and I moved to New York during the 1990s and then I went to work on Wall Street and I learned a tremendous amount when I worked there, but the hours eventually got to me and I decided to leave and become a day trader and then I realized how lonely that was.
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So I decided to do tours about Wall Street and the stock market and my very first client was a high school student group and I realized you have to do business with the business that finds you and that led me to build my business and teach a lot of students and university groups over the years and in the pandemic I took all my lectures online because pre-pandemic I had classroom space on Wall Street.
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So that's my story.
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I love that, annalyn, especially because I feel like so often within the entrepreneurial world we hear that advice of follow your passions, and it's interesting you and I have that very much shared in common in that my first business I loved soccer, so I just started a soccer blog and it took off.
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I didn't anticipate the growth from there and I'm sure for you.
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You have so much passion for Wall Street and all things finance and in that entire world.
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You, of course, live in one of the most significant cities on planet earth, in New York city, and you're at the epicenter of all these big things.
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Talk to me about that passion, or what was that drive after working in Wall Street, after being a day trader, that made you say you know what?
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I'm going to start offering tours.
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You know, I was just really lonely as a day trader.
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I had a virtual group that we met every day, but in those days Zoom wasn't as in use as it is today, so I would never see people.
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And I also learned I love currency.
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So I got up early and then, 6 am to 8 am, I'm done and I have the whole day ahead of me.
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What do I do?
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So that led me to just think what can I do that won't interfere with my trading schedule and tours have flexibility?
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And I thought I love Wall Street.
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I'm going to teach people about that.
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So when people come to New York, you come on a food tour or anything.
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I took my clients with the Federal Reserve, the stock market, the investment bank, like the financial district, just explaining what everyone does.
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I love that, andnalyn, take us back to that, because obviously it's been so pivotal and it's the foundation of what has transformed into your online business.
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What did your first tour look like?
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You talk about the high school student who found you.
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I don't know if I should picture, annalyn, you just standing on Wall Street with a flag saying I offer tours.
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What did that first tour look like?
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You know, first of all I got my first client, my website.
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In those days you could put up a sign that say website under construction.
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So based on that, I got the student group and it was the first time I heard the word.
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FBLA the Future Business Leaders of America.
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They actually I learned to study some Wall Street programs and business and they came on a field trip and after that I went to school in a different country.
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So this was like a new learning experience for me, but I loved it and after that many more school groups found me and the financial crisis eventually put my business really on the map.
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Yeah, I love that, especially because that was such a pivotal moment in time.
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I was in college, like I said, majoring in economics and finance during 2008.
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And so we're all very much aware of that time and I would imagine it drew increased interest in all things Wall Street With that in mind.
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Obviously, you did something with that interest.
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You started those tours.
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You also had lectures, you also had conferences that talked about the history, the business, the education side of it.
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How did all of that evolve?
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Because I always talk about the importance of understanding offers in businesses, it seems to me from the outside, looking in, I'm excited to hear your perspective on it.
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How did that evolve over time as far as what did you offer and what were the things that you were providing in the marketplace?
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So when I started in 2008, I had two main tours One tour, just like, focusing on Wall Street and finance, focusing on the history, and I had one tour specifically about the stock market crashes, because stock market crashes is really what shaped Wall Street.
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The crash of 1929 created the SEC, the FDIC and a lot of the regulators of Wall Street, so and then it has evolved over time.
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So I had this Wall Street tour and one of my stops on that tour was the bankruptcy court where many famous companies, including Lehman Brothers, filed for their bankruptcy and Time Out Magazine.
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Every year in those days, twice a year, they reviewed Walking Tour in New York and they chose my Panics and Crashes tour.
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And after that, I had a lot of journalists on my tour and it just sort of it organically grew.
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Yeah, I love that organic growth and I know that it's something that has followed throughout your career, and rightly so, because you work on something that's so cool and it's so impactful.
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I wish, as a teenager, that I got to see your passion for Wall Street, annalyn, because there are so many questions.
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It's something growing up in Boston.
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I know where the Federal Reserve Building is in Boston.
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I've seen it in New York City, but we don't know what goes on inside of those buildings.
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But it allows us to dream, to picture career paths, to picture networking opportunities and really deepen our knowledge and passion for the financial markets.
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So, with all of that in mind, it doesn't surprise me about that organic growth.
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Talk to me about the trajectory of it, though, because what was your mindset like in 2008 when you first started, and then when, all of a sudden, you started being featured as one of the best tours in New York City and you started to see that growth?
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Where along the journey did you say I'm on to something and this is what I want to invest in and double down in and continue this as a service?
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You know, brian, this may sound strange, but in the beginning I was completely green.
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I worked on Wall Street and nothing can really prepare you for what comes on your entrepreneurial path.
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So I remember in January I had a group of financial journalists January 2009, on my tour, and this one journalist kept talking to me while I was giving the tour and I wish he would just shush.
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And then three days later I was featured in his newspaper with my tours and I noticed that when I got a lot of traffic from that country, this journalist was actually from Turkey.
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And after that more journalists found me and it was just organic.
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I never set out and said this is my mission.
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It has just sort of evolved and for me, pivotal moments was those moments when you want to pull your hair out and say to the client I don't want to do this, I don't know what to do.
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But that has really catapulted me forward over the years and looking back, I realized that was organic growth.
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Those moments of frustration are your greatest moments to embrace and when things come on right back today, that is not so fun.
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I will often get excited and say what is in store for me now?
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What am I missing?
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What am I not seeing?
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Because I've learned those moments, hard moments or your best moments yes, I love those insights and those reflections from you, annalyn.
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I'm so appreciative of you sharing that with our worldwide audience, because that's the entrepreneurial journey right there.
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I remind myself in those low moments of most other people would quit here or most other people wouldn't continue.
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That's where I persist and it's something that has always driven me, so it's really cool to hear your reflections in that regard.
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I want to ask you about scalability, just because, knowing that you've worked within the world of finance and in all entrepreneurial circles, people love to talk about scalable businesses, and what I did up front and what you did up front maybe not the most scalable solutions, however, it was driven by passion.
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It was a huge proof of concept for both of us in our beginning businesses.
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What was your attitude towards scale at that time, knowing that your finite resource of time is something that that business relied on?
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I worked in the early days with the Actors Work Program and many actors were actually Wall Street professionals that lived and pursued their passion.
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So one of the people on my team was actually a broker and he worked on the floor of the stock exchange.
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Another one of my team worked with investor relations.
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So they were my first hires and together I was able to scale my business and over time I've hired several more guides and then many groups that travel come to New York as an entire school bus or two school buses, meaning it's a hundred person group.
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So we just got used to like dealing with us starting.
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I had a system of each tour guide would start in a different place on Wall Street so we would cover all the stops, but just in a different sequence so we could handle large groups of several hundred people all touring at the same time.
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Yeah, I really love those strategic insights, Annalyn.
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It makes me want to ask you about strategic partnerships.
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Obviously, you're so well aware of all these different student groups and organizations and associations.
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Was that part of your growth journey from there that led to that organic growth?
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Were you in direct contact and partnership with those types of groups and associations?
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Yes, I eventually became a sponsor of the FPLA and I went to many of their conferences and I also worked a lot with Virtual Enterprises, another student organization, and every year they would have a competition of students where they bring their products together and they run a store, and I was a judge in that competition.
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It was one of the highlights of my year to go there and then new york city also have a program where you can get student interns for the summer and they actually pay the interns.
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So it's a win-win for businesses and several years I got interns from that program and it is so fun for me to watch the careers of all those interns that I've had over the years and we still stay in touch.
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I have coffee sometimes with some of them because they are now all working on Wall Street and one is a doctor.
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That is so cool, annalyn.
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That, to me, shows it's why I've been so excited about your business and our conversation today, because of those downstream effects.
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Sure, even if we're talking about a walking tour, for example, that could follow someone through all of their life as inspiration, as an eye-opening moment.
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So huge kudos to you in the work that you've been doing and the work that you are doing.
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I want to transition to 2020 because obviously, the pandemic comes around and you're doing all of these in-person things.
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What did 2020 look like for you?
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What went through your mind when you said how can we transition this stuff to online?
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So when I first started my business, someone gave me a book about questions and I will never forget the three most important questions.
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I always ask myself when does disaster strike?
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What is good about this?
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And it's amazing how your brain can think of solutions In 2020,.
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I couldn't think of a solution, but one of my clients asked me to do an online presentation instead of the walking tour.
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And I told the client I've never done this, I may screw it up.
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And she said to me we know you, you will make something good of it.
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And I remember how energized I was.
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And the following day, I registered a new domain.
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Remember how energized I was?
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And the following day, I registered a new domain Teach Me Wall Street and I started to promote my summer program and I never looked back.
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I learned a tremendous amount.
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It's like drinking from the fire hose the first two years in learning all the online business, but, looking back, my team stuck with me some of them and we just made success with what we've got.
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It is the fun years of the business.
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Yes, I love that, Annalyn, especially because you've taken us on this journey with you here in this conversation today.
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So, transition what was the difference?
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Wall Street Walks all of a sudden becoming.
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Teach Me Wall Street what stayed the same, what changed?
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How did it evolve?
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I want to hear that story.
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So I took my tour content and I turned it into Wall Street 101, because you really need to understand who the players are and what they do.
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And some of that I had already presented as part of my lectures on Wall Street, so I already had some slides, and then it just evolved.
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When I first started, I taught a class all about fintech, because a lot of my background is in financial technology, and that eventually evolved.
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And in my second year online, I added the budget program.
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Many parents loved what their students learned and they asked me what else do I have to teach?
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And thus the budget program evolved and I also added the crypto program later.
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Yeah, anna Lynn, it's that constant evolution.
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That's what is so clear to me about your entire journey.
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Talk to us about that.
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I mean, you showcase that, even with your offers of adding crypto.
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These are things that you're not just staying the way that you used to offer things in 2008.
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You're evolving with the market as well as with your own entrepreneurial skills and explorations in the digital era.
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So, annalyn, with that in mind, what do your offers look like these days?
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I love your website because I can see all the different types of people that you serve, from high school programs as young as middle school programs adults.
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Talk to us about that service offering that's evolved to where it is today.
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So I started my main student groups for high school and middle school students, but to teach, I thought I'm going to start with the high school students and then many of my students especially in 2020 and 2021, were 12 and 13 year olds.
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But I tried in 2022 with a middle school program and I learned middle school students need a full-time in-person event or a class.
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So I failed on that, but I kept getting emails from parents and last year I started and I ran an after-school middle school program one hour a week over five weeks, and I continued to do that, and this year I also added the personal finance for middle school students.
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So the two programs are running back to back now over the winter, and then for high school students I have my three staple programs Wall Street 101, investing and Budgeting, and those I'm running over the winter, on Saturdays, and then in the summer it will run as one week virtual program, and the crypto program is one standalone that I run as an after school program, one hour a week over six weeks.
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Or I have a couple of master classes, three days, six hours in total for the class.
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So those are my offerings yeah, I love that.
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Annalyn, it feels silly for me to ask you this, but I am curious your answer on it because it's clear to me that you love the stuff that you do.
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So I want to reflect back.
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Being a day trader, obviously you felt that loneliness of just working from your house and being behind a computer screen.
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Well, here you are now with an incredible online business.
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Are those interactions with your students that you're working with, is that enough for you, or how are you keeping it fresh?
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So, even though you have an online business now, you don't feel that same loneliness again.
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You know, now I try, I have a virtual team so I have a lot of my meetings on Zoom and I also I'm much more alert of like getting out going places that I don't have that same loneliness.
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So from time to time I watch myself that I feel lonely.
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But I now have much better systems in place than what I had in 2006 and 2007.
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Yeah, I love that, especially because systems it's a core part of every single entrepreneur's journey.
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I want to ask you about that because your career has so many really interesting twists and turns obviously working on Wall Street to day trading, to being an entrepreneur what are some of those systems that have served you along the way?
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Because I would imagine that your professional career, even before your entrepreneurial journey, shaped the way that you think, the way that you view yourself you clearly have a high level of self-awareness and the way that you operate.
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How did those things play into the way that you operate as an entrepreneur?
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The longer I've been an entrepreneur, the more I understood the value, because I realized like there are certain things that I'm really an entrepreneur.
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The more I understood the value because I realized like there are certain things that I'm really good at, but certain things I don't like.
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So when I hire people, I actually have them do several like personality tests that I can identify that I hire complementary to my own skills and I also work a lot more like I learned on Wall Street proper systems in place, project management to track it and like proper procedures and certain of my processes.
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I can hire any person because it's well documented.
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I have like a standard operating procedure, things that I had in my corporate career and I said to myself I'm so glad to get away from all that admin.
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And then I turned around and I did exactly the same in my corporate career and I said to myself I'm so glad to get away from all that admin.
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And then I turned around and I did exactly the same in my business, because if you don't have systems, your business can't run.
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Yeah, Annalyn, now you're giving us some insights into that executive mind of yours as well.
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You talk about personality differences and hiring for things that complement your own personality.
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Give us some of those insights.
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I found in my 16-year entrepreneurial journey that this is one of the hardest things to get right in business is hiring the right team.
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I'd love to hear the way you navigate that.
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So one of the things that I have learned a lot in 2012, I learned about the Colby test and that sort of categorized people in like four broad categories of skills.
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So I'm a quick start and I'm a fire starter.
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I can start a project, but it's sometimes hard for me to finish a project.
00:20:29.547 --> 00:20:43.339
But people that are like good in their follow through, they cannot start a project because they keep asking questions, and sometimes I have people in that team I want to say stop asking questions, you are driving me crazy.
00:20:43.339 --> 00:20:46.924
But those are the questions that you need.
00:20:46.924 --> 00:20:48.981
So our skills are complementary.
00:20:48.981 --> 00:20:56.454
They will say to me stop, Not anymore on the project and I want to tell them stop asking me questions.
00:20:56.454 --> 00:21:01.742
But in that way it's a healthy relationship and we get a lot of stuff done.
00:21:01.742 --> 00:21:04.160
Yeah, my husband is the opposite.
00:21:04.160 --> 00:21:09.900
He's like an inventor, so he helps me with a lot of like technical stuff.
00:21:09.900 --> 00:21:13.991
I'm not good at all of that yeah, I love that, annalyn.
00:21:14.051 --> 00:21:19.911
Honestly, we've all heard about the very simple concept of yin and yang, and it's so important to have that balance, whether it's in marital relationships or business relationships.
00:21:19.911 --> 00:21:23.279
It's so important to have that balance, whether it's in marital relationships or business relationships.
00:21:23.279 --> 00:21:24.403
It's really important.
00:21:24.403 --> 00:21:33.700
And again, it starts with that level of self-awareness I want to ask you about when it comes to the future and when you look at where you want your company to go.
00:21:33.700 --> 00:21:35.884
Everyone wants to talk about AI.
00:21:35.884 --> 00:21:37.188
Everyone wants to talk about.
00:21:37.188 --> 00:21:46.230
Information is at our fingertips in a million different ways and, alin, it seems like you're so clear on what it is that you are and what it is that you want to be.
00:21:46.230 --> 00:21:48.683
Talk to me about how you view the future of your company.
00:21:49.836 --> 00:22:05.398
You know, growing my company and scaling it, and I actually have a lot of like game and learning tools that I use in my classes and I want to turn that into something that I can reach more students.
00:22:05.398 --> 00:22:11.778
So that has been sort of something that I'm working on and it's my one of my projects for this year.
00:22:12.579 --> 00:22:20.016
Yeah, and speaking of reaching more students, it's so clear to us when we hear about Wall Street Walks how much those partnerships, those associations, were clear to you.
00:22:20.016 --> 00:22:21.219
Do partnerships?
00:22:21.219 --> 00:22:26.079
Is that still one of your biggest sources of business of finding new people and reaching more students?
00:22:26.079 --> 00:22:29.796
Or what does that marketing mix look like today, since you're in the digital world now?
00:22:31.259 --> 00:22:48.636
I have found new partners, so I work a lot with college counselors now working to help students find the right extracurriculars and help them shape their careers, Because a lot of students, when they take my programs, they tell me at the end of the program we are going to pursue a business career.
00:22:48.636 --> 00:22:59.499
And it's so fun when I talk to parents and they will tell me my child, son or daughter is studying Wall Street or like a business career because of your class.
00:22:59.499 --> 00:23:00.384
So.
00:23:00.384 --> 00:23:20.369
But there are also a lot of learning tools and I can see from the feedback from my students I could make this easier for them, that they could review some of the lessons or work with some of their friends in ways that is accessible to many more people who don't have the time or the money to come on one of my programs.
00:23:20.911 --> 00:23:22.474
Yeah, annalyn, it is so cool.
00:23:22.474 --> 00:23:26.452
Again, I just want to stress it because it really is life-changing work.
00:23:26.452 --> 00:23:44.196
I know that myself, having been an avid and very eager student, but also I was a tour guide at school and nothing made me happier than, the next year, seeing an incoming freshman say you are my tour guide, you are part of why I chose this school and, again, these are decisions that follow these students through for their entire lives.
00:23:44.196 --> 00:23:47.996
So, annalyn, I can't stress it enough how much I admire the work that you're doing.
00:23:47.996 --> 00:23:57.470
I do want to pick on that executive mind a little bit more, because you so clearly called out there are things that you don't like doing in your business, and you've got a lot of responsibilities for your business.
00:23:57.470 --> 00:24:02.078
Now You've got your website, you are creating and launching online courses.
00:24:02.078 --> 00:24:06.028
You're servicing students in person and online.
00:24:06.028 --> 00:24:08.556
With all of that said, what are some of those things you don't like?
00:24:08.556 --> 00:24:14.730
And then, what is Annalyn doing on a daily or weekly basis as the CEO of your business that you do enjoy?
00:24:16.326 --> 00:24:20.176
So admin stuff and routine work drive me crazy.
00:24:20.176 --> 00:24:23.473
So I try to get rid of that as much as I can.
00:24:23.473 --> 00:24:34.674
In my previous business, as well as now, I'm the teacher and I find people to do all the admin work around me and I manage my time really carefully.
00:24:34.674 --> 00:24:38.241
Every year I do a time assessment and then I look where did I spend 80% of my time and which 20% of my time really carefully.
00:24:38.241 --> 00:24:53.199
Every year I do a time assessment and then I look where did I spend 80% of my time and which 20% of my time really drove the business forward and helped me pay the bills, and I try to focus just on that and every year taking more and more stuff off my plate.
00:24:53.199 --> 00:25:00.307
I once read a book from Elon Musk and he said when we developed the rocket, we saw in many things we did.
00:25:00.307 --> 00:25:02.132
What paths can we take out?
00:25:02.132 --> 00:25:08.814
So in my own business I will often stop doing something and if no one notices within a month, I take it off.
