Ep 8 - Jessica Inskip - On Leaving Wall Street, Fighting Misinformation, and Redefining Financial Education

Hello, friends. This is Tyler Gardner welcoming you to another episode of your Money Guide on the Side, where it is my job to simplify what seems complex, add nuance to what seems simple, and learn from and alongside some of the brightest minds in money, finance, and investing.
So let's get started and get you one step closer to where you need to be. I am thrilled to welcome my guest this week, Jessica Inskip, the first female on Fidelity's Active Trader Desk, and who you might just see from time to time working alongside Jim Cramer.
Known for her expertise explaining advanced trading strategies and technical analysis, she has appeared on CNBC, Fox Business, Yahoo Finance, and the Schwab Network. Honestly, I'm surprised she doesn't have her own show at this point because she is quite simply a rock star and she knows how to take a complex topic and break it down for all to understand in an easy, engaging, and digestible way.
But what really drew me to inviting Jessica on the show is her ability to prioritize and promote financial literacy across all of her platforms, including her award-winning podcast, which is currently ranked number one for personal finance, well-deserved, and it is called Market Make Her. You can find her on Instagram and TikTok, where she does her best to teach you how to be fin-fluent, and I am honored that she spent the time helping me learn more about the fine balance between working in finance and teaching finance.
My only apology for this episode is, once again, my own audio is all over the place, and please trust that like all else in life, I will learn quickly, I will correct mistakes, and this too will get better. Good news is I did not create a podcast to have you hear me speak, but rather to highlight voices that deserve to be amplified, like Jessica's.
So, without further ado, a conversation with Jessica Inskip about your financial priorities, why she gave up her licenses to create content, and how we can think about markets in a more level-headed and thoughtful way. As you know, finance has a lot of different jobs, and I originally actually wanted to be an engineer.
I was in this magnet program in high school, and I thought I was going to do something with engineering. I actually knew AutoCAD really, really well.
And I was one of those people that would solve the mechanical engineering puzzles where you didn't know it was there. You had to figure it out.
I didn't know how my brain worked, but somehow did it. When I went to college, I just chose business.
So the engineering wasn't happening, but I knew the first two years was the same nonetheless. And I just went to my community college and I got an internship at that time.
And then that's when I shifted my entire career to the stock market because I found that internship. It was paid and I got a college credit at the same time.
And so I thought I was just being clever. And was that the first time you considered a career in finance rather than in engineering? Absolutely.
I was talking to my son about this the other day. He's 13, so he's very sarcastic right now.
And I was saying how I went to school for business because I wasn't sure what I wanted to do. And in all reality, the stock market is a bunch of businesses.
I still ended up doing the same thing. One of the first things that drew me to your content, Jess, was your transparency about having given up your financial licenses in order to create social media content.
And though I'm sure you've explained this at length on other channels, I'm wondering if you could help our listeners learn more about why you A, wanted to give up the licenses to do this, and B, had to give up the licenses to do this. I've explained some of it to a lot of people, but not all of it to a handful, actually.
I feel like I should give you the whole story to get the context. My career, I went from Scottrade to Fidelity.
Fidelity is where we came the first female at the active trader desk that I was plucked because I needed a female when I was on the track to be a financial advisor. I was the person that would come into the office and talk about covered call writing and the advanced platform that was there.
And they needed a female in Jacksonville. They didn't have one.
They said, hey, are you interested? I took my whole life and I moved up. That's the first time I took a huge risk in my life.
From there, I ended up moving to Merrill. Merrill and Jacksonville, Merrill and Fidelity are across the street from each other.
Not even a big, busy road, just a small side road. And I ended up getting plucked over to Merrill, went up to be in charge of all of the advanced trader strategies.
I was in charge of what was on the platform education-wise. That's an important component.
During that time was when COVID happened. And that's when investing became a trend.
And everyone, especially the younger generation, was learning from TikTok. Every aspect of my career had an educational component to it.
That's always something I've been drawn to. And during COVID, that's when we had these FINRA sweeps where everyone was saying, oh my goodness, options education, what does everyone have? For compliance-wise, there was a lot of work to do.
And that's when Alex Kearns ended up unaliving himself or taking his life. If you know that story with Robin Hood where they got the really big fine.
Could you go a little bit further about the specifics of what happened there just for the listeners who are not as familiar with that story?

He had a bull call spread, which is a limited risk options trade, very limited defined risk.

He lost maybe $400.

But because of the way the positions were booked into the system, it looks like he lost something like $700,000. That is pure misinformation.
That was learned from TikTok University. And as somebody who is licensed, and as you know, because you were, I couldn't go on TikTok and explain how these concepts worked.
That was one of my moments where I remember walking into my husband's office and saying, this just happened. I can't do anything about it.
I know how to, but I can't go post a TikTok. And it gut-wrenched me.
I was asked to be on CNBC's Options Action at that time. One of the best days of my life was going there.
Now I've done it multiple times, but I wasn't allowed to do that because of my licenses. And then I was asked to join SIBO and their adjunct faculty program.
I wasn't allowed to do that either because of compliance. And I realized that all of these things were happening where I wanted to make a difference.
I wanted to pursue this education. That was my job at Merrill, was making sure that we had the best education.
And I couldn't go to where Gen Z needed us. Alex Kearns was the tipping point for me because something just pulled in me and I said, I am over this.
You've mentioned you had direct oversight regarding education at Merrill. So what were you allowed to do and how could you help educate people if not via social media? So if you pull up their options education center right now, I worked behind the scenes and did that.
From the self-directed investors lens, my job was to make sure that they had all the tools and resources that they need for the advanced extended trade. And you still felt as if there was no way that you could possibly get this information into the hands of Gen Z? I couldn't post on social media at all.
I would put on Merrill's website. And as we know, if Gen Z wants to learn about even what a stock is, they're not going to go to a brokerage firm's website.
They're going to start on TikTok. It's like trying to get people to play football in a baseball field.
And even though it's clear you obviously wanted to reach this new generation of investors and meet them on their own turf, was it difficult to take this leap of faith? It was an extremely hard decision because I've been doing this at that point 13 years. And I was terrified because I felt like I didn't know how to do anything else.
I actually was going to work at Deloitte and I called up one of my vendors that I worked with at Merrill and I ended up signing a contract to work with them two days later. And that really was a great move because then I started writing all the education for all the brokerage firms and ended up working on the other side.
But that gave me the freedom because I didn't have the compliance constraints to post on TikTok. And then that led to my podcast and all these other things where we are today.
One thing I've wrestled with frequently since creating content myself

is where do I want to spend most of my time creating?

And I create now on TikTok, Instagram, YouTube, and this podcast.

For you specifically, why did you want to start on TikTok?

What was it that drew you there as opposed to some of the other platforms?

As each of these platforms obviously has its own type of personality

and its own advantages and disadvantages. The people that I worked with at Merrill was not there and my husband's not even on there so I could feel comfortable getting in front of the camera because I've been behind the scenes my whole life and I needed to figure this out.
I would go through phases. My son called me cringe one time.

And when you started this, did you have a specific strategy or an idea of how you wanted to create or

for what you wanted to be known? Or were you largely experimental in the early days of your

creating? The first thing I ever posted was when I worked at my previous company and we were at a convention and we just filmed it, which was fun because like all the NASDAQ and stuff was there. But that was just for fun to figure it out.
And then I moved to, okay, if I'm starting from the basics, what would I do? I started with what is a stock and then what is the stock market? Just the congruent order that you have to learn things. I videos that way and you can see just progression from consistency and practice then I had my spreadsheet where every so often I would go in I had the title of my video I gave it a category and then just some of the engagement metrics to understand what worked or what people liked or where interest was.
Because I'm sure, as you know, the algorithm changes, things adjust. You have viral moments.
I want to understand what makes them viral. Until this day, I'm very frustrated at my viral moments because it's what it is.
But it is. I would love to hear more about your experience with viral moments.
As one of the very first things I was ever told as a creator was be careful with what you go viral for, because that's forever and always what your audience will want going forward. Every time I go crazy viral, and I recently did on Instagram because I just started that journey a couple weeks ago, is when I say I gave up my licenses every time.

And I don't like putting down other creators.

That's why I say it's frustrating.

I am inherently a positive person.

I like bringing up everyone around me.

But the reality of the situation is there are a lot of bad content creators that exist.

And that's because they lack the experience. Because you and I are one of the few that have experience, and you can see that lack of information has some detrimental effects.
And every time I shed light to that, I go viral, but I hate going viral for a negative reason. And when you say negative reason, do you mean bringing down other creators, or can you unpack that a little bit more? I get very frustrated when certain creators call themselves experts or they're selling a course and that's how they made their money.
And then they're telling you that they're a money expert. I think it's a slap in the face to you and I who have spent hours mastering our craft and learning this and understanding it.
And I even attend some of their sessions. I've attended a course just for curiosity and some of the things that people say.
It's insane. So I made a rule for 2025.
I actually have a list behind me of creators whose content I will never comment on because there's no way I'd be able to say anything nice. And my mother taught me well, but I am curious if you found any ways to help such an endeavor because it's so hard to bite my tongue when I see these self-proclaimed experts genuinely share misinformation in an authoritative way.
What do I do? What do people do? Well, I believe in the buddy system. I do have a business partner.
And anytime I get frustrated with certain things, I will vent to them first. But thankfully, there's nothing to comment on because usually there's not even education.
The best way to battle it is by providing good education. And that's something I want to advocate for is there needs to be more people like you and I posting this content because then it can adequately compete with the flood of misinformation.

So what keeps other people, perhaps former financial professionals or others who just have a keen sense of good investing theory and knowledge, from entering this type of space?

It's free to enter. It's pretty darn low bar.
And it's an incredible opportunity for people to establish their own personal brands. So why don't we see more people here who, for lack of a better way to phrase it, know what they're talking about? It's definitely a younger generation that is in this space and that's charging the way.
Now on my professional life, I talk to people like Maddie Mills on Yahoo Finance. She is a phenomenal creator.
Great creator. She's great.
And she, I feel very similar about a lot of things, but then I speak to other people at Yahoo Finance. I say, yeah, I should really get there.
And so it's just spreading the word and showing that that's okay. Who was I talking to the other day? Her handle is smarter than a finance bro.
It's Victoria. She has a CFP.
She also gave up her licenses. And she told me there's this new wave of content creators coming.
Like that idea of what being a female in a male-dominated space just simply means that you can show the younger generation that you exist. And they could simply picture themselves.
That's all. So representation is important from that aspect.
I see more people trying to learn or trying to do the right way. But then I also see a bigger issue where, do you remember stock queen, Kirsten Crum? I became really great friends with her.
She had, was part of that first investor wave, had great content, even though she wasn't licensed, had 250,000 followers. Have you noticed you haven't seen her content on your platform anymore? I have noticed that.
That's because she decided to pursue a career in finance and is her financial licenses and therefore can't post anymore. And because of compliance, she had to remove all of her content.
So how do you balance the art of creating educational content, but still making it as engaging as it needs to be for people who have very, very short attention spans, even on TikTok University? A Trojan horse method is you want to do that. Cool.
Let me explain how they work. But actually, you should probably look at covered call writing.
And let me explain to you why that's better in a longer term conservative strategy. So meaning something that's clickbaity because it's trending, you're going to give them what they want.
But oftentimes, they don't know what they need. I think about the stop the scroll, but I definitely have way more education on my platform than I do the virality piece.
I have way more engagement with the educational stuff anyways. And were you ever surprised by what people did or didn't engage with in regards to your content? I don't know if you experienced this, Tyler.
If you ever have those videos where you feel like you put so much time and effort into it, hours and hours, and you're like, this is the best thing ever. And it doesn't do really well.
But one of my most viral videos I filmed in five minutes. And then that makes me realize that at least for TikTok, they like authenticity.
If you make something in five minutes, it seems very authentic. I think we're all seeing more and more, and studies are showing, that Gen Z, well, and certainly the millennials I know and hang out with, crave authentic marketing and authenticity in general from brands.

So how do you, Jess, incorporate that into your work?

What does it mean for you to create authentic content?

I love that question.

And I'm going to expand on it a little bit as well.

Thank you. for you to create authentic content? I love that question and I'm going to expand on it a little bit as well.
Authenticity to me is who I am as a person. I'm not trying to mirror someone else.
I'm not trying to be what I think what people want me to be. I'm being me.
So bringing that to an educational lens, I started with, okay, this is a stock. A stock is a piece of a company.
Authenticity is me stepping out of my comfort zone and saying, all right, you guys want to learn about the business cycle? It's like a menstrual cycle. And that's the way I talk to people.
And it's actually the best analogy. That to me is authentic because one, it's my analogy.

But two, it's still that educational piece, which I've been drawn to my whole life. I am utilizing the knowledge that I have and curated and marrying it with my personality.

I'm envious that you seem to have found that authenticity so early as it took me probably about a year of creating before my wife could even watch a video of mine without wondering what type of cringe nonsense I was doing with my free time. But were there any creators or are there any people beyond social media you know who you looked to early in your creative pursuits as role models because they were able to educate and engage and entertain and do it all with a positive and curious spirit.
This is the hard question. And I answer questions on live TV, Tyler.
You have stumped me. Tom Sosnoff, he's not a content creator per se, but I think he's the original financial influencer if you think about it back when i was on the active trader desk i would have tasty trade live running all the time it's before tiktok was a thing and youtube streaming was and he took that to a whole another level so tom sosnoff created thinkorswim which is or was td amerit's active trader platform.
Now is Charles Schwab's after the acquisition. He sold it and he built TastyTrade.
TastyTrade is an amazing options platform. And he just sits there live and trades all day and is very authentically himself.
Brings almost like a Saturday Night Live feel to trading. And that's super fun.
I find that authentic and creative. And as he's been someone that I've looked up to for quite a long time.
And did anything ever surprise you about the audience that gravitated towards you once you started seeing who was drawn to your content? I do have a lot of analytics on my podcast and a lot of people or the audience that I did attract that I didn't know I was going to attract was women who are working in finance for the first time and they feel confident talking about the bond market because they're so scared of it. And they're like, actually, it's not that hard.
And that has to do with bringing in the humor component. And it's not entirely humorous.
It's that's just my personality. I'm sarcastic.
Like, I'm married to a British person. Yeah, that'll usually do it.
And what about the challenges? Were there any times when you just thought you had had it and you just wanted to throw in the towel? Absolutely. I want to throw in the towel all the time.
I am overwhelmed and I'm fully aware of it. When I started my podcast market maker., I had no idea how much work it was going to be.
Very taxing, took my weekends, still takes my weekends. But it is something I'm passionate about and that certainly helps.
I like talking about the market. I like educating on the market.
I can't make content every day. I've gone in lulls where I haven't made any for a month.
I think you need to share your secrets with me there because I still haven't let myself off the hook to produce daily content and I'm slowly going insane, Jess. And do those breaks take a toll on your engagement? Do they take a toll on your capacity to keep an audience involved? every time that happens views go down and then i've got to recover from it which i'm I'm doing with TikTok right now because I got a new phone and TikTok is no longer on there.
So I only have it on my iPad, which has been very frustrating. I have a full-time job too, and I'm on the media every week.
That's a lot. And not to mention, I am also a mom and a wife and my son is 13.
At least he's self-sufficient. But seriously though, where do you find the time to create the amount that you do create? I marry everything together.
I realize that when I'm on CNBC or I'm on Fox Business or Schwab Network, I'm talking about the market. That's content for a TikTok or a short form video.
I don't need to reinvent the wheel. I need to marry everything together.
My job is literally

talking to every brokerage firm and understanding their tools and resources and telling them who's the best. So I researched the self-directed investor.
That is my day job. And media has a part of that job as well.
So that alleviated some of that pressure because media felt separate. So that all is also content.

So I've brought everything together and that has really helped. There is a harmony that is together.
Now, if I get sick or my son gets suspended from school, that is very difficult. But I have to time block.
I am a perfectionist.

I have learned that my mantra last year was accept 80%. My old boss told me that my bare minimum is someone else's maximum and I just need to quit.
I'm working on that. But I do want to quit a lot.
But every time, every time that happens, somebody sends me an email. Somebody sends me a message.
somebody leaves me a review on my podcast that says i don't know what i would do if i didn't listen to this i cannot use words to express how much that means to me when people say that that's the way i did this because i wanted to stop the misinformation and when somebody tells me that they understood it i'm like great i did it and then other things happen and fall into place. I work with Jim Cramer.
That is so cool. And when he sends me a message that says, I literally have one that says, Jessica, hey, genius, will you do that? And I'm just like, I think you could have even paused there just after saying that Jim Cramer sends you an email to begin with.
That in of itself is amazing. And I think it's pretty safe to say that you've obviously made it in a number of ways.
One of them, as we touched on briefly, is the podcast. And I do want to get back to that.
But I want to shift briefly, as this is a question I ask as many people as I can. And I always find people's answers useful.
What does success look like for you? Because by creating content, you've entered a world that prides itself on vanity metrics of likes and follower counts and shares and blue check marks. But I have a sense that's not why you're in the game.
So tell me what success looks like for you. I have learned to never compare myself to anyone else.
I think that is your detriment. I definitely compare myself to me.
I want to be better than where I was yesterday. It's impact.
I don't think success is achieving a certain amount of followers. I don't think it's videos going viral.
I think it's impact, but I don't know what that looks like. I know that I want to educate.
I know that I want to talk about the stock market. I don't know how that will transform because I also don't know how the world will transform.
Like we were talking about AI a couple years ago, and now it's all we're talking about. But I think success is also a feeling.
I'm successful when I see a lot of women or a lot of people, doesn't have to be women, that understand the stock market. That to me is successful.
What are some of the ways that you have seen this impact? Obviously, I know you touched on reviews and comments and notes,

but are there any other ways that you've seen this impact come to life? I think you can see it in other people. When I met with Victoria the other day, she was so kind.
She's a new creator. She gave up her licenses as starting this content career journey.
And she told me I was making an impact. So perhaps I personally have to hear it from other people i don't know but i set out on this mission to battle the misinformation and the more people who are making good content that makes me successful one of my friends told me our sons were doing karate together and i used to work with her at meryl and she said jessica is enough going to be enough for you? You need to stop sometimes and just realize this is what you're doing.
And I try to practice that. And there's this book I was listening to because I don't like reading them that stated, we constantly say, if I do this, I'll be successful.
Or if I do this, I'm going to be happy. And we're chasing a feeling that we've never actually had.
When all reality, happiness is, I'm here with Tyler, who has a million followers, and we're both educating in a space that makes me happy. I feel happy right now.
This is a successful moment for both of us. Well, and for what it's worth, I know I asked you who you've looked up to in the past when it comes to content, especially when you were first starting to create.
But please know, Jess, that you were and continue to be one of the few finance creators, scratch finance creators, one of the few creators in general, who I truly look up to as an emblem of responsibility, positivity, and genuinely producing outstanding content. See, that was a moment there.
That I define as success. That was a moment.
I agree. Completely agree.
And speaking of moments, I think you've had some great ones recently on your podcast, your number one ranked financial literacy podcast, Market Make Her. Can you share a little bit about what prompted you to branch out to that space? So that credit goes to Jessie, my business partner.
Her name is also Jessica, so not confusing at all. But we have been friends for 10 years and she would always ask me how the stock market works and things like that.
And she's in marketing and she has tried to tell me forever to make a YouTube channel, to have a podcast, to do all these things. And I've told her, no, Jessie, I work in finance.
I have licenses. I

am not allowed to do that. And so finally, when I gave it up, she was there.
She's like, Jessie,

Jess, let's do this. Let's do this.
Let's do this. So she convinced me and we did it together.

She's my partner in crime. We're literally yin and and yang she is gothic and she is learning and the complete opposite of me look wise but we're very similar otherwise and i'm literally teaching her and that was a key differentiator i guess that we had between every other podcast besides the fact that i did actually work in But what she taught me, and I didn't know this, is that I spoke this complete foreign language.
I did not realize how jargony I was. And she stops me.
And it's also very funny. Now that we're on episode 76, she now all of a sudden is starting to speak the language.
It was definitely her. And then we went on that journey

together. And I literally taught her and that created this perfect format.
And then it turned

into our three pillars, which is educate and explain, which is every episode. We keep it

current. So we talk about what Fed Chairman Powell said.
So we talk about AI. And then we tell you what to do with your brokerage firm.
A great example of that. And we had to do it over time.
And I love how she was my is so fulfilling to see her have light bulb moments. Like we didn't even talk about how to invest until episode 12 because we needed to build a foundation first.
And it's just beautiful to see her put the puzzle together, but then also be able to pay attention to what's happening. And now she realizes, oh, OK, well, the Fed, when the Fed was lowering rates, she's like, I need to lock this in because the yield curve is inverted and that's going to go down.
And my high yield savings account isn't going to stay this way. It's astronomically high for a reason.
And that's not going to stick. And I love that she knows that understanding the stock market to apply to your finances.
It's not that you need to know that you have to have an emergency fund in a high yield savings account. That's amazing.
And I love that every financial influencer that exists is going to tell you that. However, if you want to take a step further, you understand how the credit market works and better ways to put your liquid assets if you have the ability to lock them up for a period of time or how to ladder them.
Or if you're thinking about buying a home, looking at the 10 year, I just paid off my car. And then like, am I going to do this or not? And then I was thinking about the interest rate environment.
And you look at the three to five year and it's still elevated. I'm like, this is not a good time.
But that's the correlation that I know is missing. And I give that to Jesse.
And then that helps bring everything back to, I say the same thing on TikTok as I do on my podcast a lot. So that's how I bring it all together.

One of the bigger comments that I get on different content that I put up is, I don't understand a word you just said. I get that a lot.
How do you balance that mix of returning to beginner's mind, but also presenting an example of someone who does speak the language? That's why I started that credit market series. Before TikTok was banned, that's what I made sure I put out.
Because I knew it's important right now because we haven't thought about it since the great financial crisis. anything that is adjusting, fiscal policy, everything has to do with the credit market.
And not a lot of people talk about it. So the way that I battled that, because that will get jargony.
That's where I was methodical. And there were six videos in that series.
And they were three minutes apiece. You can't teach that concept in 90 seconds you can't you cannot and even then there are the episodes that we have on the podcast about that it took three or four for jesse to get that to click and those are 30 minutes a piece so you're talking two hours of of learning at minimum to grasp at least the basics of the credit market that you need to click.
And those are 30 minutes a piece. So you're talking two hours of learning at minimum

to grasp at least the basics of the credit market that you need to know. And I think everyone needs

to know, to be honest. And as an educator yourself, what are the two or three biggest things that

you'd say, look, primarily, these are the things that everybody needs to know about financial

markets right now? If you want to understand the stock market, what you need to focus on, I would say is the credit market. That's a piece of it.
But what moves the market is earnings potential. And if you can wrap your brain around the stock market as measured by the S&P 500 is 500 companies.
We are trying to understand if those companies are worth more. That's why the stock market moves in price constantly because it's constantly evaluating what is this actually worth? Think about Zillow.
If that was constantly, houses were constantly being appraised, same type of thing. If we're trying to understand those earnings, you have to understand what determines earnings potential besides buyers and sellers.
There are analysts that decide how much a company's price target will be and what their earnings per quarter is going to be. They're the ones looking at the balance sheets, free cash flow statements, things like that.
How do they determine the earnings? Well, they'll use discounted cash flow and PE ratios. What goes into discounted cash flow calculations? The risk-free rate.
What do they use for that? Usually it's the 10-year. So that's why you need to know the credit market.
There is a creator I love, math teacher guy.

I was one of the lucky students in math, and I am so thankful for my math teachers that taught me how to look at the problem rather than an algorithm.

And that's what I'm trying to portray is understand the why rather than just the output.

And how should what you just said help inform how somebody invests their own money? If you're picking stocks, and I'm just an overly analytical person, that's who I am. And that's going to reflect with everything I say and everything in my life.
And you don't have to know the details. But it does help to know the why, because it's a confidence thing.
Whereas I know, I know what's happening with the 10 year, the market's selling off. I know why.
And then I know that it's all back to earnings potential. I think AI is great.
And there are a handful of companies that contribute to that. But that's the biggest market cap on the S&P 500 and can drive it and can be a narrow rally and was for all of 2023.
And it carried the market. And I know that.
So therefore, I'm not going to panic sell because I understand why it's going up, why it's going down, and how to find investment opportunities because I get the impairment. I think it gives you an edge in picking stocks if you want to pick stocks, but it's also a confidence thing, especially with women.
I find women, for some reason, will not buy a stock, will not touch something unless they understand it inside and out. You don't have to know any of this.
You can just go read an analyst report. You can pull a curated stock list.
I teach the hard way, but just like on the podcast, when we do analyze a stock, we'll go through that. And then I'll say, you know what? You could also just pull Morningstar.
You don't have to do this. Do you work with people ever to help them figure out how to analyze stocks? Because from the sound of it, it seems like you are a proponent then of active management to an extent, right? And not necessarily.
So can you talk a little bit more about what are some of the benefits of actively picking your portfolio versus the age old Bogle guidance of set it and forget it in your two or three index funds and call it a day? You should have a combination of both. And I have worked with some very, very wealthy people in my career and they always have a combination of both.
They have their play accounts and I am a proponent of that as well. You should have your passive portfolio.
I have a passive portfolio. But you can have limitations on yourself to understand it.
For example, one of my best performing accounts is my son's account. I let him choose any stock in the S&P 500.
So it has to be in the S&P 500. You understand concentration risk.
That account's been growing since he was three years old. He's been picking stocks since he could talk.
Is it riskier? Yeah, but it's in the S&P 500, so it doesn't bother me whatsoever. And he is a great portfolio, but it's also a higher beta.
It moves up in way, way more than the market because it's not spread out between 500 stocks, and that's okay. I would never say to anyone, start picking stocks.
No way. Have your passive account first.
Have your emergency fund before you start investing. Like we definitely talk about that in the order of events of investing, but I definitely concentrate way more on understanding the stock market and have more of a 2.0 podcast, I suppose.
And I know I asked you about creators who you look up to, but are there any just voices in finance that you look up to right now? I will say Jim Cramer. If you watch the first 10 minutes of Bad Money, you will understand exactly what's happening with the market.
Jim does not have to be doing his job. He found oil on his property.
He loves it. He eats, sleeps, drinks, and breathes it.
And he will sit down and talk about what's happening. And he will do it even if you don't like it.
And there's something beautiful about that. The first time I met him, I will never forget that.
I was terrified. And I didn't know what was going to happen.
A, someone will hit on me. Happens.
Female. Finance.
Or B, they're a really nice person. Or C, they're crazy.
He was the really nice person. And then Jim took my work, not my face.
And that really helped my career. So when I met him, he sat me down and he said, all right, I've been doing this for a long time.
There is this group that is older.

He's like, I have them.

I understand them.

They're a great group.

There's this other generation where they invested during the great financial crisis.

They're into real estate.

I don't think there's any way of getting them back in the market.

And I agree with that.

He said, there's this younger generation. And then he looked at me and goes, all right, let's plan.

What do we do? And I was just like, I'm sorry. You want to, you, ask me what to do? I kept this email.
It's, that was the one that said, hey, genius. He said, I got this great idea.
I'm writing a book for the investing club. And you've had some really great calls.
And your process, I would love it if you wanted a chapter.

It's like you can write whatever you want,

you know, represent yourself however you do.

It's like, but that chapter is yours.

It's like the credit is to you.

If you don't have to do that. I pulled it all together, took me a while,

sent it to him and then had a couple of rewrites

and then sent it back.

He's so easy to work with, to be honest.

And is there a book in your future? Are you starting to put pen to paper yet? So I actually got asked to write one. I just haven't sent my proposal.
So I get on that. Got some work to do.
Yeah, it was completely my fault for that one. They asked me six months ago, so hopefully they'll still have it.
And what would it be about? I would explain how the stock market works. Keep it so basic, but by the end of it, just like I was saying how you understand that job.
I want people to understand the domino effect, to understand the impact of the U.S. Like the little inputs, the fiscal policy, monetary policy, strengthen the U.S.
dollar and people go to commodities. What does that all mean? The dominoes that just could flow back into the stock market and how it's all centralized around the consumer.
That's what I would do. And the market changes.
So that's always the fun part. You'll always have something to talk about.
Like tariffs now. And I won't go there because the one vow I actually have made on my platform is I won't be timely.
I commend you for that. There is a saying that we have on the podcast.
We have lots of them. But one of them is you cannot time the market, but you can prepare.
And being prepared means being financially literate and understanding things. And I do not believe in timing.
I am a long-term investor. Even my options trading is so long-term because you can be long-term with that.
You can even dollar cost average into QQQ or SPY with options trading if you know what you're doing. I think it's just understanding and there's just different ways to achieve the goal.
Well, Jess, thank you so much for being here, for exploring your journey with us, for helping us learn a little bit more about the foreign language that is finance. And honestly, I am truly looking forward to continuing to see your voice become one of the absolute dominant voices in finance going forward.
You are doing great work. So are you, Tyler.
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