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Leading with Communication & Mitigating Risk as a CEO w/Brittany Burns Ep.169

By Anthony Taylor - November 21, 2022

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Brittany burns communicationBrittany Burns Communication


Anthony Taylor
: Hey there, folks. Welcome to today's episode of the strategy and leadership podcast. My guest today, Brittany Burns, who is the CEO of simpler trading Brittany, how's it going today?

Brittany Burns: Good, good. Thanks for having me, Anthony.

Anthony: I'm excited to chat. I love your background. I love what your company does, why don't you tell our listeners a little bit about who you are? And what simpler trading does?

Brittany: Sure. So, simpler trading is a retail education platform. And so our focus is to help the individual investor participate in the financial markets. We're currently heavily focused on the options in future space. That's a bit of a result of just our founder and his experience and past, but we are very quickly diversifying and moving into new asset classes, like equities and into new markets, such as foreign markets and exchanges.

Anthony: Cool. I got that. And so what I'm curious about is, you know, your background is as an attorney by trade, I believe, and then moving into an industry that can be dicey at times, that's not going to be my nice way of explaining it. How has the transition from a practitioner to corporate development, to leading this organization? And what are you hoping to bring to your organization and kind of like the world as a whole?

Brittany: Sure, yeah. So did start out as a licensed attorney in Virginia, I'm no longer practicing, initially following law school. And actually, while I was in law school, I focused on financial regulation. So I previously worked with a fin tech startup in Richmond, Virginia, that was in the BD space. And then I moved over to a investment advisory firm, and then came to simpler, had a period between my post law school career and coming to simpler where I was consulting for about two years, and really found a lot of enjoyment in helping companies to identify their response and understand how to navigate through the complexities of being either a regulated company or oftentimes a regulated adjacent company. So for simpler, we are focused in the education space, we fall into the publishers exemption of the 40 Act. But being next to regulated industries, like investment advisors, and being regulated by the FTC, like any consumer facing company, we just face different challenges. And I kind of did was simpler in 2017. And initially was helping them to navigate the implications of GDPR on their organization, and helping them to understand really where their risks live, given that they were only marketing in the United States and had very, very minimal customers in contact with people in the European Union. And so helping them to understand what the absolute best practice of no risk and no exposure would look like. And then also moving into, okay, what is what your business need to do to protect yourself in the best way that's still feasible for the size of the company. And as I was doing that, I really got to know the founder, and really just saw a lot of opportunity within the organization. But there's also a lot of challenges on the horizon. I couldn't have predicted 2020 and everything that we sort of went through that year. But where I think we're uniquely positioned and where the legal background is, serves our company really well is the absolute hyperbolic growth in the retail trading space that was really initially ignited by a move to 0% commissions, and then amplified by COVID, has drawn more scrutiny from regulators. And so we're really well positioned to be a thought leader in this space, and to really help regulators to find regulation that both supports individual investors so they can still have access to the markets, but also protects consumers who may have been exposed to some predatory practices in the past. And so being able to tie that legal experience and with the actual application from a business perspective has been really fun and challenging. And I think that provides a lot of opportunity for us, as well as anybody else in a space where regulation is starting to come into their space and it can become a business burden, but it can also become a huge opportunity for a lot of companies.


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Anthony: Yeah, absolutely. So if we take continue down that path and think of you as an individual, like kind of outside us employer, if we think of I heard a couple key things kind of like really that that risk mitigation, risk management, the complexities of regulation, and a lot of our listeners are either there's nonprofits, there's municipalities, there's government, there's education, where they don't control everything. And then I think one of the areas that I believe you're good at is that communication piece, like how do you navigate that both from a personal piece, but also like communicating that? So imagine, you know, we're at a party, and I say, tell me about the coolest thing about your job? Where do you have the most fun? Where does your problem solving brain go? You're in your flow state? What is that? And what do you want our listeners to know about going to being able to manage that world successfully?

Brittany: I think it is really a lot like a puzzle. You know, whether you're regulators or not, you have a risk thoughts as a, as a company and as a leader in a company, and understanding the goals of whoever's placing that risk on you. So it could be a regulator, it could be a, you might have a dependency on a vendor, or a lot of people are impacted by the, you know, ability to get materials and in 2020, and 2021. And so I think that it's understanding sort of where your risks are coming from, and understanding how to navigate the company in a way that is covering as much exposure as possible. But understanding that covering all exposure is not always in the best interest of the business. And so there's always my legal background, I think always has led me to go first to what is the, quote, perfect way to cover all exposure, and many times the cost can outweigh you really what their risk is, I think that regulators can be most times reasonable when you are working with when you're willing to collaborate and understand what they're trying to achieve. And there's, like I mentioned, a lot of opportunity to and that can be fun, when you're looking at competitors who, you know, maybe wouldn't be able to navigate this regulatory challenge. And so that that puzzle piece, and you're figuring out like, Okay, where's the most exposure? What, from a business perspective, is feasible to cover that exposure? And where do we feel like we maybe don't need as much coverage, because if it were, if that exposure were to be further exposed, the impact would not be worth the cost of coverage. And so that's always fine, I wouldn't say it's necessarily the most fun part of my job, or what I get most excited about. I think it's what my background and skill set lends me to help our company grow, we're most what what really gets me out of bed in the morning is the ability to help educate our customers with a skill, like a life skill that can really help them to have the competence to take control of their financial future. And it's something that has intimidated me in the past, being I have always leaned more towards a legal and political career paths. So find this has always been the one of those things that I think a lot of people back away from, and to be able to open up those outlets or open up that opportunity for customers. That's what really excites me and to keep expanding into new areas we can meet traders and investors, wherever they're at on their journey. It's just a really great opportunity.

Anthony: Oh, I actually see it quite as a parallel. Because on one hand, what I heard is like, you know that bringing to organizations and that there's no perfect way. So it's managing your risk, hedging your risk, and looking at what is feasible, what is possible, and, you know, making sure that the investment that you put in matches the kind of return and doing your best without being overkill. And then I hear on the education side, you're doing the same thing, you're helping traders mitigate their risk, you're giving them more confidence by understanding what they're getting into. And by being a good AI by understanding the levers of the financial markets, you de risk yourself, and then you're not gambling, you're actually saying, Hey, I'm making a calculated risk, a calculated investment in this organization, because I see the upside potential. And I find in my experience, when I'm totally out of my depth, that's when I'm scared when I at least have enough knowledge. I say, Okay, I'm confident understanding what I'm getting into, that helps me be more prepared. And I also find the same thing in people in leadership development is that it's scary to lead people, it's scary to be able to support and, and you know, especially as you move from an unknown, you're KCMO to sea eel. It's a step but if you're educated, you have the support, you have the resources. It's all just risk management granting you, the upside generally outweighs the downside. Thoughts on the parallel? And then how does that apply to your specific journey?


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Brittany: No, I love it. Anthony, you said it way more articulately than I did. And so I've been good. I never thought about it in that exact way. But yeah, the risk management really is, like I said, not not limited to whether you have a regulatory risk or any sort of outside, you know, risk of reliance, it's internal, as well, it's meant mitigating the risk of putting in place a new policy and how that's going to impact your employees and how they're going to react. And we're not as employers in an environment where recruiting is easy, and retaining talent is easy. And so you really have to stand out from, you know, other organizations that are looking for the strong talent that you've developed within your organization, or that you've been able to recruit. And so every decision that we make, we have always had a really hard, large focus on our employee culture. And communication is one of my personal core values, but also one of our core values as a company, I place a heavy emphasis on communication and trying to be as transparent as possible, while of course, mitigating risk of transparency to to employees, because as I'm sure all the leaders on your that, listen to your show know, too much transparency can also be a risk if it's not well understood within the organization. But I think that risk mitigation does carry through to our personal, you know, offering as a company, but really, as a leader, it's what you're constantly balancing both internally, with your employees and then externally with any sort of external threats to the organization.

Anthony: Yeah, absolutely. I really liked that piece. I am pro-communication. And I find that again, if we talk about de risking, it's the uncertainty like you'd rather it's the devil, you know, rather than the devil, you don't, so being able to do that, but then also managing that, so you don't kind of give away the farm speak too early, I sometimes have a bad habit of dropping ideas that might not be fully baked. And that like it, that can cause more confusion. So for leaders to make sure that if you are communicating, it is fully complete, and that you close the loop around that, I find that super important. So Brittany, if we look back at your career, and you've had a very cool experience of things, what was a big like, aha moment for you that kind of shaped how you view things like maybe you got your butt kicked, proverbially. And you're like, oh, man, that was like a huge lesson that I learned that helps guide you in your role as the CEO. Now, if you have one of those moments, or probably a couple …

Brittany: I'll probably choose one from more recently, and around what you touched on previously, in terms of what, what and how you communicate to the organization. The company was founded about 20 years ago. And I was, of course, not the founder. And I joined in 2018. And our founders were phenomenal, he was way ahead of the times in terms of having a live content offering. And that's like fun to join that type of organization, but maybe about three months. And I think he, he him and I laughed about the story before mad I pull him aside and say, Hey, John, you're coming into meetings with ideas that you have, but you're dropping them and not realizing that when you drop them as CEO and founder of the company, like I'll be having a meeting about like, you know, a plan that we're going to implement over six months. And everyone just turns to what that idea is because you hold the power in that room. And I think that and he's like, Oh, I got it, he immediately starts to stop, you're kind of doing what I told him is like, you kind of dropped these tornadoes into like the meeting. And all of a sudden, it's like, we're all moving on a path. And everyone starts pivoting towards this, like an idea, bright, shiny idea. And even though I recognize that, when I was in my position, I realized when I moved into CEO, like I did the same thing. And I would, you know, announce something to the team and be like, Oh, wouldn't it be cool if we did this or couldn't be cool if like, we went after like this new cohort. And then three weeks later, I would hear that, like, we really ran down this path in a direction that like, maybe it wasn't what I was thinking. And I was like, Oh, guys, I was just like, saying, that would be cool. And, and so I had to realize and take that step back and say, you know, I think it's very obvious and we can recognize it. If we're honest with ourselves as leaders like that. We know that the team wants to, really, I think if you're a good leader who wants to please wants to overperform for, you know, for their team, for the company and for their leader. And so it's recognizing that amount of power you have and it In conversations and, you know, presenting those ideas before, maybe they're fully, fully baked, are closing the loop. And so that's been a bit of a learning lesson. And it continues to be. I think communication is something that you can never perfect and it's constant work. But I had something that over time, I've gotten better X, I've seen myself run the team, you know, into the ground, like proverbially in terms of just being very tired and exhausted chasing after something that I was like, Oh, I didn't think that was hilarious. That was kind of a cool idea. So it's a, it's a bit of a hard lesson, but it's definitely something that I commented on myself before I, you know, shoot a Slack or say something in a meeting, it's like, how's this going to be interpreted? How much of a, you know, how do we communicate that this could be an opportunity in the future, but it's not a pivot of the ship now. And I think it's, uh, especially in an organization our size, we're right at about 100 employees. And we scaled that from 30, and 20. Teams. So I know, like most of the team has, like been scaled directly and hired directly by me. There, it's so much easier for the team to get off track and pivot quickly, which can be a blessing, but it can also be a curse if you're not communicating correctly. And so that's been something that I continue to learn, but definitely has been a big learning lesson. Since stepping into this role.

Anthony: Oh, that's awesome. I appreciate you kind of putting yourself out there. Because it's not easy to look back. There's some real gold there, I heard. So once again, just like recognizing, I don't want to start recognizing for you, as the CEO, what behaviors can have an impact? We talked earlier about risks and communication and transparency. I think also, if we think of both internal and external communication, when you signal something, the market will follow a signal. So that's a signal and people are following it. But the other thing I really heard out of that is that as a team member, there was the trust and the structure for you to say, hey, I don't know if you realize that you're doing this, and this is the impact. And so for your CEO at the time to have the foresight or the understanding, say, Whoa, okay, cool, I thank you for that feedback and adjust it was I imagined able to keep you moving forward. A lot of people I talked to have meetings that spin around in circles. And it's often because people drop ideas, and they go down the rabbit hole versus staying focused. And then using like a strategic planning session or something like that, to take a step back and make sure that those potentially great ideas are executed in the right way. Did I capture what you meant to share?

Brittany: Yeah, yeah, I think that perfectly captured it. Perfect.

Anthony: Cool. So as we finish up here, what is the last thing you'd like to leave with our listeners to help them both be successful in their life, in their businesses and potentially with their finances?

Brittany: Yeah, yeah, I think that well, for life and business, I think I can have a bit more of a takeaway, that I know we've talked a lot during this about communication. I can't because my background prior to law school was in corporate communication. So I've really a heart and a huge belief in the importance of communication. Whether it's in business or in life, the importance of having those crucial communications communicating earlier and clearly is so important. And it's it, you can see when you look back, I mean, hindsight is 2020. But typically, when a project internally goes off the rails or in personal life, if my husband doesn't do something that I, you know, in the way that I want it to be done, I can almost point back to like, where the communication broke down, like where there was not, expectations weren't clearly set, where there wasn't buy in and agreement on what we wanted the outcome to be in defining success. And so that's something that I'm extremely blessed from an organization standpoint to be surrounded by people that are significantly smarter than me. And that was extremely purposeful on our executive team. I wanted a group of people that were significantly smarter and experienced than I am as a young CEO. And it's something that I bring to the table and keep reinforcing with organization is when we leave with the decision we need, how are we going to measure whether this was successful or not? I'm extremely competitive. So I can joke with my team like, how am I gonna know if I won guys like, I need a number or I need something that's specific. How do I know that I won? And then how are we checking in on that 30 days from now? Does that something we did not use still we would launch something we'd say we won or lost. And then it would almost go to this ether of like didn't want to go check on like that still running. And so I think that communication setting expectations from the beginning sometimes can be very uncomfortable. I highly recommend the book crucial to communicate critical conversations. It has helped me a lot to have tools to you know, bookmark other conversations they start coming up and more setting expectations but communicate Communicate, communicate, you can't do it enough, you can't do it too often, and you really can't set expectations, you know, to clearly so heavily lean on that as a tool in my toolbox. Very

Anthony: cool. I love that I think everybody can benefit from those things. One more question before people can connect with you. What is supportable?

Brittany: Yes, this affordable is a nonprofit organization that I was involved in in Richmond, Virginia, an amazing organization, I played division one sport in college. So I played lacrosse at Old Dominion and have always looked for ways to stay involved in the athletic community. So I coached for a while and then got involved with splittable. It helps to serve disabled, physically disabled and visually impaired athletes. And so there's different sports that the organization supports. I did a lot with our visually impaired runners, where you could run together to a visually impaired runner and run races. But we also had basketball tournaments and larger races in Richmond. So it was a phenomenal organization. Unfortunately, since I'm not in that area anymore, I haven't gone to participate in a few years, but I highly recommend anybody that's in the Richmond area should look at getting involved.

Anthony: Cool. I thought I'd take the opportunity to give it a plug because I just thought it looked really cool. And I was like, Oh, cool. I figured

Brittany: I appreciate that. Yeah, it's a phenomenal organization.

Anthony: Awesome. Check it out. It's portable in Virginia. Brittany, where can people connect with you? And where can they learn more about your company?

Brittany: You can find me on LinkedIn. That's where I'm most active. And then the company where you can find us at simplertrading.com. So it's very easy to remember.

Anthony: Awesome. Brittany, thanks for being here today. It's been a blast. I wish you all the best in all of your future endeavors, including whenever you get back into lacrosse, but it's been a real pleasure chatting with you today.

Awesome. Thank you, Anthony. You too.

Anthony: Thank you again to my guest, Brittany Burns as you move forward with your organization, especially in what we'll call an uncertain time. Being aware of your risks, risks, risk boxes, being aware of your communication, how to manage all of that set expectations will only help you become a better leader as you move forward. So I hope you got a lot out of today's podcast, be sure to connect with Brittany, and be sure to subscribe if you haven't yet. So my name is Anthony Taylor. This has been the strategy and leadership podcast. I appreciate you being here. And I'll see you next time.


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