Is the industry due for a reckoning after years of eroding trust with the public? Megan Gorman thinks so. The founding partner of Chequers Financial Management, a female-owned high-net worth tax and financial planning firm in San Francisco, says it’s up to firms and advisors to band together and become more transparent.

 

“I would love to see the industry have a point of reflection,” she said. “One of the biggest struggles I’ve always had is we are not a transparent industry. We need to give clients — our consumers — a better way to come into the industry and have transparency. Because, what’s happened over the years is we have eroded trust with the public.” 

 

Trust, says The Current State of Consumer Trust In Financial Services, plays a major role in consumers’ use of different financial services providers. It’s definitely not an attribute the public readily gives away — it needs to be earned. 

 

How? A recent E&Y study reveals consumers want personalized experiences. More than 86% rank their primary financial relationship’s ability to provide seamless cross-channel experiences as important.

 

Gorman’s approach with her clients is similar; she sees herself as a consultant or counselor: “I think we need transparency to make it easier for individuals and families to work with the advising community …  the industry would be best served if we could figure out a way to provide potential and existing clients a way to transparently look in, almost as a report card … [that] we actually execute and here’s proof in the pudding.” 

 

New Viewpoints That Matter

 

Gorman, who spent the first part of her career as a vice president at Ayco, a Goldman Sachs Company and BNY Mellon Wealth Management, will take the stage this September at Future Proof Festival to start this conversion and share her experiences as the industry has evolved.  

 

“We’ve done a really good job as a community in creating conferences, creating groups, and creating networks,” she said. “But what we really need to do to take it to the next level.” The path, said Gorman, gives clients the transparency they need. “Because that will allow people to trust us more, and find that the work that we do really matters.” 

 

This customer-centric approach to advising is a concept near and dear to the attendees of Future Proof, who are registering for the event to be exposed to a broader perspective. Breakthrough, said conference organizers, requires commitment to new frontiers and questioning traditional ways of thinking.

 

Gorman agrees: “You can’t be afraid to learn — and continue learning. The advisor I was 15 years ago … is very different from the advisor I am today. Because the longer you’re in the industry and the more open you are to different planning ideas, the more value you can provide to a client.”

Christine Benz is bringing her unique approach to personal finance to Huntington Beach, California. Christine is the director of personal finance and retirement planning at Morningstar. She also co-hosts The Long View podcast, where she serves up a mix of practical financial advice and portfolio reviews, while interviewing notable figures like best-selling author Ramit Sethi, columnist Jason Zweig and FIRE (Financial Independence, Retire Early) blogger JL Collins.  

 

Christine took a circuitous path to podcasting and writing about personal finance. Raised in a family of political junkies, she studied political science and the Russian language. After a stint in publishing, she started working at Morningstar in the early 1990s, where she continues to work today.

 

I sat down with Christine to talk about the state of financial literacy in the U.S. (spoiler: “not great”), the recent human-centric transformations of the wealth management industry and how a broken foot led to a new approach to taking time off of work. 

 

Future Proof: The career path you took is going to surprise some of the attendees at the Future Proof Festival. How did you arrive at the intersection of personal finance and investment analysis? 

 

Christine Benz: I can’t even make it seem intentional in hindsight; it was very circuitous. 

 

I grew up in a family of political junkies and was always interested in politics, current events and international relations, so I studied political science. I also majored in Russian, because I had been studying the language for quite a bit of time. When I emerged from college I was not super marketable.

 

My dad had always been an avid investor and knew of Morningstar. It was a rapidly growing company, so he suggested I apply there. 

 

From the beginning I loved that it was an intellectual place. It was an intellectually curious, vibrant place—which I’m happy to say it remains so. 

 

I eventually led our U.S. fund analysis team, but I realized we weren’t talking about broader issues of asset allocation and some of the other things that we know make or break someone’s financial success. 

 

So I went through the certified financial planner program and began to research and work on some of the broader topics of personal finance and financial planning that I focus on today.

 

FP: Speaking of allocation, you remind advisors to pay attention to clients’ “time on earth” allocations. What do you mean by that? 

 

Christine: I like it when advisors think about the resources that their clients have, broadly speaking. A “time on earth allocation” is one’s allocation of personal time and energy.

 

Historically, advisors spent the bulk of their time on allocating household cash flows, allocating savings and apportioning their clients’ investment mix.

 

Time on earth is different. A client might have a job that’s super remunerative, but it’s detracting from their quality of life. Maybe it’s detracting from the time that they can spend with their family. 

 

Advisors can add value in situations like that. They can help their client take a step back and say, “You seem to be on this hellish treadmill where you are at peak earnings, but if this isn’t delivering you satisfaction, can we figure out a way to get you to a place where you’re happier with your balance.” 

 

FP: You’re also an advocate of improving financial literacy. How would you assess the general levels of financial literacy in America? 

 

Christine: Not great. Studies have shown that the general population only gets about half of very basic financial literacy questions right. This cuts across populations; it cuts across the globe. 

 

One thing I worry about is the lower levels of financial literacy among lower income segments of our population. It’s troubling. The less money you have, the fewer opportunities you have to learn and to improve your financial decision making.

 

FP: What can the wealth management industry do to improve that discourse? 

 

Christine: Counseling consumers definitely helps. We need to teach people the importance of being skeptical and bringing skepticism to financial relationships and financial arrangements.

 

FP: You work with survivors of domestic abuse to provide them with financial education. What lessons do you focus on in that setting? 

 

Christine: It’s a broad ranging personal finance curriculum, supplied by an organization called W!SE, which stands for Working In Support of Education. 

 

It starts with very basic budgeting, but gets into investing and saving for college. One thing I’ve found working with these groups is even though most of their questions are about the here and now—like getting out of debt or getting into a home of one’s own—people still aspire to save money for their kids or to have a better life or buy a home at some point down the line.

 

In my time volunteering, I’ve gotten better at familiarizing myself with very basic financial information, like how to deal with credit card debt and how to budget. Those are areas that I probably had an average knowledge about, but volunteering helped me hone my skills. 

 

FP: In your articles and podcasts, you strive to balance the theoretical elements of finance with the human factors of money; money is a tool to achieve something. What are your observations of the financial service industry’s ability to address the human factor? 

 

Christine: Over the past decade or two I’ve noticed a change. We have all become more attuned to the importance of behavioral finance and psychology, in terms of helping people reach their goals. 

 

The wealth management industry, as a professional class, has become much more receptive to human-centered advice. It’s really encouraging. 

 

Concepts like mental accounting and bucket investing for retirement seem to be more accepted by professionals. What matters isn’t necessarily the efficient frontier. What matters is whether someone can achieve their goals and find peace of mind with their plan. 

 

There’s more alignment with individuals and the professional community, which I think is for the better. 

 

FP: Travel is really important for you, whether that’s a trip to Huntington Beach or elsewhere. What is your most memorable travel experience?

 

Christine: I have so many. One trip that really stands out was a trip that my husband and I took to Barcelona. We were renovating our old house and I had broken my foot that summer. I was also working on a book at the time. It was just kind of a hellish summer. 

 

So we went to Barcelona, and just went to that one place for a whole week. 

 

It taught us the importance of going deep on a place and not moving around too much. You don’t have to go everywhere on a particular trip. We know that if we like a place, we’ll come back.

 

I’m also a foodie. Whenever I decide I’m going somewhere, I almost always book my restaurant reservations first. That’s the first thing I look at. 

 

Sometimes I even overdo it. I’ll plan days in advance, look at the menus, sort of hint what I think my husband should have. I make a point of trying to make reservations, because I am not a happy camper if I’m figuring something out on the fly. So I can go overboard, but it’s a fun part of travel for me. 

 

FP: You’re a big music fan, too?

 

Christine: I’m a huge music fan, so I’m excited about the opportunity to hear live music at Future Proof. 

 

I like to stay current on my music and one person who I’m really loving right now is Steve Lacy. He’s just come out with a new record. I really love everything I’ve heard from him.

 

My musical tastes are really broad ranging. I love jazz. I love blues. But mainly I love contemporary music. 

 

FP: We’re excited about the music that will be at Future Proof! At the beginning of our conversation you described your love of intellectual curiosity. What opportunities for intellectual curiosity are you looking forward to at the Future Proof Festival?

 

Christine: I love how interdisciplinary the agenda is. I’m excited to hear from speakers who I might not run into at typical financial planning conventions, and with so many different people I’m hoping I’ll come away with some new guest ideas for our podcast. 

 

Future Proof gets beyond the typical conference that we all go to. It’s bringing in people from different areas—beyond our financial services sector. 

There’s a cultural rebirth underway in wealth management, and you can find it all over TikTok. Finfluencers — financial influencers — offer the ordinary investor information and advice on stock market trading, personal finance, mutual funds, and more.

 

This advice is often dismissed by the industry as bad or biased because it’s not coming from professionals or experts. That’s why writer, investor, researcher, and financial influencer Kyla Scanlon stands out. Her approach to finfluence isn’t advice-based. Her TikToks are educational and often dive into topics that are deeper than some of her finfluencer counterparts. 

 

“TikTok is such an opportunity, right? It’s the audience that you really want to talk to,” said Scanlon. “You have people in their 20s and 30s who watch TikTok, and the reason that they watch it is to be entertained and engaged. For me, I did see a lot of misinformation being spread on TikTok, but I also saw an opportunity to help people learn about finance.”

 

It’s the perfect audience to help educate, she said, to bridge the gap about topics such as the Fed, inflation, portfolio management, and investing. Scanlon, who covers everything from macroeconomic policy to crypto regulation, wants to make the financial services market more accessible and easier to understand ​​for the ordinary investor. 

 

Mass Appeal 

 

Often trivialized as silly entertainment, TikTok is a platform that young audiences truly use to educate themselves. They’re attracted to the short, accessible video content, which provides an entry point into topics that are otherwise intimidating. 

 

“There’s so much more that can be done to make people understand this stuff,” she said. “A lot of the response to my videos has been from beginners who are just like, ‘Wow, I never thought Econ could be this way’ or ‘I never thought about the market that way.’” 

 

Making high-quality financial information more accessible is a good thing. And FinTok, the financial TikTok space, is growing fast. Content tagged with #PersonalFinance has garnered more than 4.4 billion views and #economics, which Scanlon frequently uses, has more than  623.9 million views.

 

The platform itself has  over 1 billion monthly active users. Almost half are between ages 10-29 and 42% are 30-49. For many, TikTok is their first source of education on money matters.

 

“This is the next generation,” said Scanlon. “You could ignore them right now, but I don’t think that’s a good idea. They’re the future. I think a lot of people are really dismissive of younger people … So it’s really about getting as many people as possible to understand the big economic world that we all live in. And part of that is recognizing that there are good people to talk to you.”

 

Bridging the Gap

 

Remember, a lot of the FinTok content is lacking in substance or just too promotional. Scanlon’s content — financial education — is straightforward and accessible. 

 

“I just tried to really make it simple. And I think people crave simplicity at the end of the day,” she said. “I make it very clear that it’s not financial advice. It’s purely education.”

As Scanlon works to bridge the gap between mainstream entertainment and financial education, she’s excited her content is resonating. She’ll take the stage at Future Proof Festival in Huntington Beach this September, to share her approach with the hopes the audience is able to make financial content accessible to all.

According to Morgan Stanley, 85% of individual investors in the United States are interested in sustainable investing – but only 10% are actually doing it.

 

Why?

 

Gabe Rissman, the President and Co-Founder of YourStake, which helps advisors align client portfolios with their values, believes there are a few reasons.

 

One: The industry is making a mistake and assuming ESG means the same thing to everyone.

 

Not all ESG investors are created equal, and one ESG portfolio isn’t going to be a match for all ESG investors. There are so many different variations of ESG and values-based investing, and it’s impossible to correctly assume which issues every individual client cares about without asking them.

 

“There are people who are hunters that really care about the environment and forced labor and gender equality,” explained Rissman. “So figure out what your client actually cares about, not what you’re assuming.”

 

Two: Advisors are thinking about ESG investing in terms of ESG scores, while clients think about it in terms of real, tangible values.

 

Most clients aren’t saying to their advisors, “I want a superior ESG portfolio.” What they’re saying when their advisors actually ask is: I don’t want to invest in prisons. I don’t want to invest in fossil fuel companies. I want to invest in clean energy companies and companies with good gender diversity.

 

“And that’s how advisors should talk about it,” said Rissman. They should be asking clients, what do you care about? What are the issues that matter to you? How can we create a portfolio that’s better on gender diversity, rather than focusing on the best methodology for conducting an ideal score? 

 

Three: Greenwashing is the biggest thing working against the growth of ESG.

 

Greenwashing, a term that refers to inaccurate or misleading representations about a company’s environmental friendliness, is used in ESG investing to describe strategies or initiatives that don’t align to an investment product’s sustainable label.

 

“Marketing language is outpacing actual practices, causing people to lose trust,” said Rissman, who believes our industry is moving in a “prove it” direction. 

 

Catch Gabe Rissman Live at Future Proof

 

Rissman will take the stage at Future Proof Festival in Huntington Beach this September to share his vision for the future of ESG, values-based investing and personalization.  

 

“You’ll be able to walk your client through all of the aspects of their life, their values, how they want to retire, and capture all the preferences the client has, and what they need to have a successful experience with you. Advisors will have the ability and the tools to create personalized solutions to be able to serve that. So that means personalized portfolios, and better advice,” said Rissman.

 

“And I see the industry going to a place where advisors will have to prove exactly what they’re doing. So if you capture my values as a client, you’re putting a portfolio together, then show me with full transparency that it’s actually accomplishing the job that I want it to do. That’s where I see the field moving.”

Soraya Darabi is co-founder and general partner of TMV, formerly Trail Mix Ventures, a New York City-based, founder-first early stage venture capital firm launched in 2016. Soraya leads a team that believes good people can create extraordinary outcomes. 

 

As recently as January, Soraya and her co-founder, Marina Hadjipateras, launched a $64 million fund—their second institutional venture fund—to back startups focused on people, purpose and profit. Investor demand reflected the firm’s success: it was oversubscribed by roughly $5 million and is backed by some of the world’s largest family businesses. 

 

TMV’s success comes from finding businesses overlooked by others, many times simply because of biases. Ahead of the Future Proof Festival, Soraya shared the blindspots she sees in wealth management, including the circumstances that led her to fire her own financial advisor, what she looks for when investing and how she uses her love of food and travel to connect with others.

 

Future Proof: You’ve had your progress in finance seemingly blocked by biases favoring men over women, yet you’ve found ways to capitalize on these obstacles. For example, you started an investing organization called Transact Global that’s now the envy of your peers. Tell me more about Transact Global and what it’s taught you about networking. 

 

Soraya Darabi: We started Transact Global in 2018, two years after launching TMV’s first fund. It’s a worldwide group of almost 400 fund managers who happen to identify as, or be, a woman. 

 

There aren’t enough women fund managers out there and this was a group born of necessity. My business partner and I had started investing in funds founded by women, not thinking about pioneering anything. It just felt like the right thing to do because the female fund managers I know are so careful with capital and access such interesting deals; ones our male peers don’t see. 

 

I was an LP [limited partner] in a couple of funds started by women and they were asking me questions as if I was the foremost expert—just because my fund was two years older than theirs. 

 

We knew that we had done a good job of angel investing, but we didn’t feel as if we had the right wealth knowledge to share with them. Raising money for my first fund had felt pretty darn hard for me, too.

 

We decided to meet weekly, over a video call, and to operate with an abundance mentality. We had to share information that had been kept from us, and to introduce one another to LPs, with warm, positive notes. 

 

We’re peer-led, which is exciting and novel. We decided to operate with a wolf pack mentality: if we can do this together, we’ll grow further and faster. That is exactly what happened. 

 

Today, we’re in 18 countries. What sets us apart is that we refuse to charge our women fund managers a penny. TMV pays for the organization. 

 

TMV pays for it because we think that this information should not come at a cost to the—quite honestly—to the disadvantaged. Rather it should be accessible and universal, so that we can play on the same playing field as everyone else. 

 

FP: Transact Global’s origin story is a great example of how TMV finds opportunities to capitalize on obstacles created by others. What similar opportunities for capitalizing on obstacles exist in the wealth management industry?

 

Soraya: If you look at the data, startups and large organizations with diverse boards perform better. They generate more capital. If you’re really seeking alpha, then it’s smart investing to invest for the triple bottom line: people, purpose and profit. 

 

TMV has seen 700% growth in assets under management since 2017. We’ve been a Series A investor in companies like [mattress firm] Casper and [healthcare provider] Cityblock Health. We invested in [podcast studio] Gimlet before it was acquired by Spotify.

 

Search out mission-driven founders. They’re the best founders. Mission-driven founders tend to stay at companies longer—beyond the IPO. It’s the mission holding them accountable. 

 

FP: What’s been your own experience with the wealth management industry and financial advice? 

 

Soraya: When we closed the sale on the first startup I co-founded, wealth managers read about it in the news. I started receiving an email a week from wealth managers, whereas I was of little interest to them before. 

 

A friend introduced me to a wealth manager at a bigger bank. The wealth manager asked what was important to me, and I told him I wanted to invest in something along the lines of the S&P 500, but without oil and gas stocks. I let him do his thing, so I could focus on angel investing–the asset class I knew best.

 

As my angel portfolio was blossoming and growing, the capital I had turned over to the outside wealth manager was underperforming the S&P 500. 

 

By the time five years had passed and I turned 32, I said, “Enough is enough. You’re in finance. It’s time to take matters into your own hands.” 

 

I decided I would manage my capital myself, so I don’t have a wealth manager. 

 

A lot of times women are raised to hand their capital over to men to manage. That wasn’t working for me. 

 

FP: Why was there such a disconnect between your values and your experience with a wealth manager?

 

Soraya: It’s a generational problem. I was very young when I came into money for the first time. I assumed that the person with the most years under—in this case—his belt would be the right person to steer me in the right direction. 

 

I was raised in a middle-class household where we didn’t talk about money. We threw away the business section of the newspaper every day. It wasn’t of interest. 

 

It’s also a discovery problem. Finding a wealth manager, if you wish to go down that path, is one part values fit and one part cultural fit. Are you going to get along? It’s also a literacy fit. Can they assess how much you know, how much you want to learn, and be along on that journey with you? 

 

It’s common to hear, “I don’t want to invest the way my parents did. I don’t want to invest my capital the way my grandparents earned theirs.”

 

For the next generation of capitalists, it’s important to hone into their values on day one. Modern wealth managers, attuned to those changes, may find a new generation of clients very willing to take a leap with them.

 

FP: The Future Proof Festival is designed to celebrate the convergence of values and the emergence of new ideas. You’ve been to a lot of conferences over the years. What stands out to you about this event?

 

Soraya: First and foremost, it just looks like a whole lot of fun. Getting to know humans on a human level is so refreshing. 

 

I want to know what motivated people to get into the line of work that they’re in, or have a conversation with someone where what they do doesn’t even come up at all.

 

FP: If someone runs into you at Future Proof and wants to talk about something other than venture capital, what’s a good conversation starter?

 

Soraya: Ask me what the best movie was that I saw recently. Or the most interesting book I’ve read lately—although with a toddler I’m not reading as much as I’d like to. 

 

We can talk about food and travel. My grandmother was a chef and I’m always trying to become a better chef. I’ve been to over 65 countries and I hope to reach 100 in the next decade. 

 

I’ve been lucky enough to take cooking classes in Oaxaca, Mexico, so I like to make mole. I took a cooking class in Thailand, so I really like to make pad see ew. I took a cooking class in China and learned how to make drunken fish—which is one of my favorite dishes of all time. 

 

This conference is going to bring together world class individuals in one place. There’s music and entertainment, and we’re not just talking about money all day. It’s going to be a treat.

When you think about wealth management and the advisor-client relationship, mental health may not be what immediately comes to mind.

 

But according to Courtney Ranstrom, Co-Founder and Financial Life Planner at Trailhead Partners, mental health can have a lot to do with the way we earn and manage money.

 

“Financial advisors are not therapists,”  Ranstrom explained. “But there is a lot of overlap in how we talk to people and how we empathize with them. And money tends to be one of the biggest sources of stress for a lot of people.”

 

Throughout history, wealth management has been centered around investment vehicles and retirement planning – transactional, data-focused interactions. But that’s not good enough anymore. 

 

“You really have to look at the whole person, and what their hurdles are to getting to where they want to be, to building the life they want to build,” she said. And to develop more comprehensive financial plans that incorporate client goals and account for client behavior, empathy is key.

 

Here are three things to keep in mind when approaching client conversations:

 

Mental illness is more common than we think. In fact, one in every four adults suffers from some kind of mental disorder in a given year, meaning advisors may face these challenges themselves, and are likely to encounter clients who do. Money-related issues like debt can trigger or worsen anxiety, depression and stress, and they’re also a major cause of stress in relationships.

 

Stress about money is the highest it’s been in years. Speaking of stress, the March 2022 “Stress in America” survey from the American Psychological Association found that 65% of respondents reported being stressed about money (the highest level recorded since 2015), and 65% also indicated they’re stressed about the economy, also an increase from previous years.

 

Shame has no place in an advisor-client conversation. Understanding client circumstances is critical for being able to approach their financial situation from a place of empathy and guidance, not shame. 

 

“A big thing in our practice is that it’s a shame-free zone. So whatever financial problems you have when you come to see us, you’re not allowed to feel ashamed when you’re in our office. We’re not going to make you feel that way,” said Ranstrom.

 

Catch Courtney Ranstrom Live at Future Proof

 

Ranstorm will take the stage at Future Proof Festival in Huntington Beach this September to share her perspective on the role of mental health in the investment management experience. 

 

“What I’m looking forward to the most is just being able to have these conversations. Not everyone is dealing with a mental health struggle at the moment, but most of us will deal with mental health issues at some point in our lives. And I think if we talk about it, if we know that there are resources out there and tools available, that’s huge,” Ranstrom said.

Shirl Penney’s entrepreneurial journey could very well be a movie or a best-seller. He grew up in “the sticks of Maine,” was raised by his step-grandfather, experienced several years of homelessness as a child but never missed a day of school and eventually became the first in his family to attend and graduate from college. His career in finance began with a 16-hour bus trip from Maine to Manhattan, where he interviewed in a suit he bought from the Salvation Army store.

 

By 2010, he had started his own firm, Dynasty Financial Partners. Seeing an opportunity to provide breakaway advisors with proprietary technology, financing and a step-by-step process for becoming an independent firm, Shirl launched his company as a service provider for registered investment advisors (RIAs). Earlier this year the firm filed to go public. 

 

Ahead of the Future Proof Festival, I sat with Shirl to discuss his business philosophy, his passion for horse racing and how he started Dynasty Financial from an office in his garage. 

 

Future Proof: Most Future Proof attendees will know you as the CEO and President of Dynasty Financial Partners, but you describe your wife as the co-founder of your business. What lessons have you learned about business from your wife?

 

Shirl Penney: This is a little bit of a secret I’ll share. My family and I were living in Saratoga Springs, New York, while I was trying to build Dynasty. My two girls were still very little and I was constantly on the phone, trying to raise capital. This was after the 2008 financial crisis, so I was even making trips down to New York City to raise funds. 

 

I came home on one of those trips and my wife took me to the garage. In the corner of the garage she had built this walled-off area that took up about third of the space. It looked like a giant box in the corner of the garage. Even today it gives me goosebumps to think about.

 

I walked over to the box and opened the door. Inside was an office. It had hardwood floors, crown molding, a fireplace and air conditioning. There was a TV above the fireplace. It was gorgeous. 

 

My wife, Mary Ann, built it with her own hands and the help of my father-in-law. She said, “A big-time CEO is going to sit in this office, so we had to make sure it looked nice.” 

 

She read my business plan, helped design the Dynasty logo, the marketing materials and approved all of our first hires. She is the best judge of character of anyone I’ve ever met. She has been more right about talent, in particular, over the course of my career than I’ve been. 

 

Entrepreneurs thinking about starting a new business need to overcommunicate, not just with their partners in the business—but start by overcommunicating at home. The real co-founder of your business is your spouse and sometimes entrepreneurs don’t realize that.

 

Mary Ann teaches me the importance of prioritization and to focus on what’s most important in life. She is also the CEO of Team Penney Racing. 

 

FP: What is Team Penney Racing? 

 

Shirl: Team Penney is a term that we use in our family when my two daughters, my wife and I are doing something together as a family. Team Penney Racing is our own horse racing stable. 

 

FP: What attracted you to horse racing?

 

Shirl: I was captain of the baseball team when I was at Bates College. One of the things we loved to do as a team was go to the horse track. We spent so much time at the horse track we started calling ourselves the track team.

 

I fell in love with horses and decided that I would like to own one if I could afford it. If you’ve ever been close to race horses, they’re absolutely beautiful. And unbelievable athletes. Most of them—but not all of them—are friendly. 

 

Team Penney Racing had some early success about 15 years ago, when we won the Black-Eyed Susan Stakes, and over the years we’ve owned about 125 horses. 

 

Team Penney Racing is also about camaraderie. 

 

We might get 50 to 100 friends and family at a race. For someone who is as busy as I am with work and traveling, to have so many people that you care about—together—for the excitement of the race, is absolutely special. I always say that I’ve won before the gate even opens. 

 

FP: As you advance in your career, are there any lessons that you wish you had unlearned or graduated from more quickly? 

 

Shirl: I was a young man in a hurry. I would tell young Shirl that you don’t have to be in such a hurry. It will all come to you in due course. Truly successful people in life, and in business, are the ones who empower the team.

 

You can be an All-Star individual contributor—and that’s what you are: an individual contributor. It’s better to be a world class leader and to have all the All-Stars on the team.

 

FP: You experienced homelessness from the ages of 11 to 13. Did that experience factor into your need to move quickly as a young professional?

 

Shirl: Absolutely. There’s no greater motivator. I can tell you, firsthand, that being cold and hungry is a heck of a motivator. 

The reality is I’ve been broke twice. Once as a kid, and again when I went all-in on Dynasty. I was not homeless, nor was I hungry, so it was a better form of broke. But there’s no question that adversity builds character. I had a fair amount of it, as a lot of people do growing up.

 

Even so, I always felt loved by my step-grandfather. I always had one person in my life that believed in me. That was huge. 

 

He taught me that your word is your bond. He was old-school and I like to think that I am, too. You don’t need a handshake or a contract. If you say you’re going to do something, you’re going to do it. 

 

It also takes a community to raise a child and I had a great community.

 

FP: You talk about the idea of “staying close to the field” as key to success. What do you mean by that?

 

Shirl: That’s another element I learned from my step-granddad. He was always present. He made sure that I was present. I actually got an award before I left for college: I never missed a day of school from kindergarten to grade 12. 

 

Proximity to a client is critical in any business, but particularly in ours. Most of the innovation and positive changes come from advisors interacting with clients. That’s where the consumer—if you’re listening and not talking—is telling you about what’s most important. 

 

When I meet with clients it energizes me. We have this really cool wall of plaques that celebrates all of the clients we support. It’s right in the lobby. The receptionist chair is across from the plaques, and one of my favorite things to do is sit in the chair, late at night when there’s no one around, and just go across all those plaques and use that time as a way to connect with our clients.

 

I look at my calendar and make sure I’m moving around the country over the course of the year in a way that allows me to meet with each of our clients.

 

There’s nothing like going out in the field; it’s unfiltered.

 

FP: Future Proof is positioned to be an incredible opportunity to connect with others. What are you most excited about for Future Proof?

 

Shirl: I’m excited about the lifestyle perspective that is going to be present. Future Proof is about humanizing our profession. 

 

I think everyone will have a great time, but I hope that the people who aren’t there will see it—and that it encourages them to think differently about this profession. We need more people in financial services. 

 

Whether you’re retiring from the military, are a retiring school teacher or are transitioning careers, we need more people in this profession. It’s an incredible profession where you can make a huge impact on someone’s life. My hope is that Future Proof inspires younger professionals, as well as people in other professions, to consider entering the financial services industry.

David Canter is trading his laptop for a guitar—at least for part of the inaugural Future Proof Festival in Huntington Beach, California. The executive vice president and head of the registered investment advisor (RIA) segment at Fidelity Institutional’s Clearing & Custody Solutions is slated to join his bandmates onstage, where they will perform as the group Hi-Fidelity. 

 

The group, started in 2011, covers a range of rock, reggae and jam band hits. I sat down with David and between riffs of some of his favorite tunes (yes, he was playing guitar and singing during the interview), he shared how to connect with an audience, what he’s learned from blending his personal and professional pursuits and how the Grateful Dead inspires better leadership.

 

Future Proof: Most attendees at Future Proof will know you from your work at Fidelity, but you’re really making your appearance at the festival as a musician.

 

David Canter: It’s funny you say that. I haven’t been quiet about my musicality. I love music. 

 

Live music provides such a great chance to commune with people. It’s really a way of bringing people together. 

 

That’s why I’m so excited about Future Proof. This event is about more than just the function of wealth management. It’s about bringing community to it all. Offering live music and other creative outlets fosters a sense of community and culture.

 

FP: You’ve been playing music since you picked up a clarinet at age 9, which you later swapped for a guitar when you were a teenager. What are the risks and rewards of performing at Future Proof?

 

David: I deeply appreciate the team aspect of playing in a band and other members of the band have all achieved a level of mastery. I view myself as a credible musician, but I’d say that what I bring to the band is a sense of cohesion. A band is a collection of individuals, just like any team, any business, any company. What I love about our band is that we all gel. 

 

The easy risk to cite is that you worry you aren’t very good. You always worry that you’re not going to satisfy the audience. But I think we’ve gotten to a place where we feel that we’re a credible act. We probably have at least 50 songs we could just pull out of a hat, immediately.  

 

[At this point David broke into a few bars of the song “867-5309 / Jenny” by Tommy Tutone.]

 

We also want to be good participants at the broader festival. We love the feeling of helping to make events more successful. 

 

FP: If you need a vote of confidence, you’re booked to perform at a four-day festival in Huntington Beach, California, that’s already drawing comparisons to SXSW. Would you say you’re booked more for music than for speaking?

 

David: Not quite. They’re almost equal, with the edge going to speaking. I’ve done a heck of a lot of speaking, because people want to hear about our business perspective. But it seems like they really get more enjoyment out of hearing the music.

 

By the way, you should know we play all original songs—made famous by other artists.

 

[David laughed and played a few bars of the song “Deal” by the Grateful Dead.]

 

I’m excited about the chance to surprise and delight the audience and stretch creatively. I’m also excited about seeing these Wall Street-type, wealth management people rock out.

 

FP: One of the aspects I see advisors continually trying to balance is the intersection of their personal and professional personalities. Do you see Hi-Fidelity blurring the lines between who you are professionally and who you are personally? How do you navigate that intersection?

 

David: It goes right back to traveling up the value stack. It goes back to authenticity. 

 

If you can find a way to connect with others that’s broader and more emotional than just the functional elements of your profession, you’ll have better outcomes. The best advisors, the best business professionals, can carefully integrate their personal life and their charitable life into their professional life.

 

FP: You’re a huge fan of the Grateful Dead. What do you think the band’s guitarist and singer, Jerry Garcia, would like about Future Proof? 

 

David: Jerry wasn’t exactly a perfect person, but he had this mindset that you shouldn’t strive to just be the best at what you’re doing; you should strive to be the only ones that do what you do. 

 

I think that’s what he would like about Future Proof. It’s about creativity. It’s about imagination, specialization, doing something no one else is really doing. 

 

To my knowledge, no one else is doing a wealth management event that infuses creativity, the arts and music. It’s a crossover event and I think that’s awesome.

 

You know what else I think he would love? Even though the Grateful Dead was not a surf band, he’d love that it is happening in Surf City, USA. 

 

FP: What album does every advisor need on their playlist? And what’s your favorite song?

 

David: This is an easy one. The Beatles’ album “Revolver” is perhaps one of the greatest albums ever made. 

 

My favorite song of all time and one that inspires me is the Grateful Dead’s “Ripple.” It’s such a beautiful song with so many instructive lyrics. It’s a leadership ballad: not everyone’s going to follow you, because the path might be yours alone. 

 

FP: I can’t wait for more later this year! What should attendees expect to hear when you hit the stage in September? 

 

David: The rock hits are fun. I love crowd pleasers. We’ll probably play some Prince and Red Hot Chili Peppers. We might do some reggae. We’ve been known to play some Bob Marley. And you know, it wouldn’t surprise me if you heard a song from The Beach Boys, too. 

With more than 1,000 attendees already signed up to attend, the Future Proof Festival is easily the most anticipated event on this year’s wealth management calendar. Over the coming weeks we will be sharing a preview of what’s to come, featuring interviews with entertainers, advisors and executives who will be in Huntington Beach, California, from September 11-14, 2022.

Our first interview is with “Downtown” Josh Brown, CEO of Ritholtz Wealth Management and author of The Reformed Broker blog. He is an on-air contributor at CNBC and has more than 100,000 subscribers on his YouTube channel, The Compound. 

Here’s what he had to say about the four-day Future Proof Festival, his deep hatred of branded thumb drives and why this is the wealth management event the industry needs.

Future Proof: What is the Future Proof Festival? 

Downtown Josh Brown: The Future Proof Festival is a wealth management festival that feels like your favorite live event. 

We asked ourselves, “What are the things that can’t be replicated online? What are the things that people actually really care about and look forward to—and look back and remember?”

“Where is the real impact?” 

It’s almost entirely about the personal connections people make. Networking is the number one reason you should go to an event. The connections formed at a great event are the number one thing you take with you. 

We want to put great people on stage and we want to have an atmosphere that’s fun and engaging. Most importantly, we want to facilitate people meeting with each other and exchanging ideas with a drop dead gorgeous backdrop and experiences that will be like nothing that they’ve ever had at any other wealth management event. 

You can’t do this on LinkedIn. You can’t do this on Twitter. The relationships you create online will never be as meaningful as those formed in-person.

FP: I’ve heard you draw comparisons between SXSW and Future Proof. What’s going to surprise attendees at this conference?

 

Downtown: The boardwalk’s not going to look like your typical exhibitor hall, for starters. The whole thing will be outdoors. The booths are going to be more like brand activations—something you would see at a concert. 

The types of companies that are going to be exhibiting and sending people are going to be a little bit livelier. The types of companies that have agreed to sign on to something like this, in its first year, are going to be a little bit more on the adventurous side. And quite frankly, the brands that want to make an impact at Future Proof are going to have to adapt to us. 

FP: What do you mean by that? 

Downtown: We’re going to have the younger end of the spectrum of advisors at this event. The young advisors who are coming probably are not interested in collecting pens and stress balls.

This is the new live event environment that financial services companies and software companies that cater to our space are going to have to get accustomed to. They’re going to have to do things that are high impact, memorable and visually appealing. 

It’s a new era. We’re past the pandemic. We’re past the exhibit halls and the dreary hotel ballrooms. All of that is over. The future is about experiences. 

FP: Okay. But there’s still going to be swag?

Downtown: I hope so, but by God, it better not be branded thumb drives. I will take a table full of branded thumb drives and dump them into the ocean. 

I’m just kidding. I will not pollute the ocean. 

FP: A lot of advisors enjoy going to conferences in their niche, some even more than attending actual advisor conferences. How is Future Proof addressing all the niches of finance?

Downtown: It’ll be a mass-attended event, but with a lot of niche events happening within it. 

This was Advisor Circle CEO Matt Middleton’s vision from the beginning: There are all these groups that cater to advisors, like trade organizations, custodians and tech firms. Why not just carve out a space for all of these groups at our own event? That way they can have their own onsite mini events. 

It’s also not strictly advisors in attendance.

High net worth investors will be there, plus a lot of people from asset management and fintech. Some people attending just want to be on the cutting edge of what to do with their wealth. 

FP: What’s got you most excited about Future Proof? 

Downtown: It’s got a crossover feel to it. When you get a group of advisors in a room, there’s a lot of groupthink that goes on. We want to shatter that.

It’s high time advisors went out and actually met with their public. 

Future Proof is not just a room with 500 financial advisors in it. We’re encouraging advisors to walk out—literally into the sunshine—and interact with people from technology, people from art and culture and fashion, music and software. 

FP: What types of communities will be created at Future Proof?

Downtown: Let’s say you’re a younger advisor, or a newer advisor. Let’s say you work for a team or you started your own thing or you recently went out on your own. Whatever stage you’re at, you’re going to interact with 10 or 20 people just like you. They’ll be from different parts of the country and different walks of life. They will have been trained at maybe a different type of firm. But you are going to meet people who are in the same situation, facing the same decisions about software and compliance and custodians. 

You’re going to have substantive one-on-one, two-on-one, five-on-one conversations with your peers. They’re all going to be there. They’ll be from all over the country. That’s game changing for a lot of young advisors, especially.

Then the layer above that is a whole group of very experienced, very talented RIA executives, brokerage firm teams and wirehouse teams. They are people that have done this already, successfully, and have a lot of knowledge to impart. 

The layer above that is this opportunity to see what the cutting edge looks like. All of the exhibitors are leaning into the Future Proof theme. Whatever they’re bringing out to show the crowd is whatever their newest stuff is. 

I really want people to go home feeling like they’re going to be a part of the future and they’ve gotten a sneak preview of it. 

FP: It’s hard to imagine, but for advisors who are asking themselves, “Is this conference for me?” How would you answer that question? Why is attending Future Proof going to be worthwhile? 

Downtown: If you see what we’re saying about this event and you’re on the fence, it’s probably not for you. If you want to drink lukewarm stale coffee and sit through another ESG panel sponsored by an ESG mutual fund, you could do that. 

But what we’re going to do is going to change people’s lives. I don’t say that flippantly. Literally my life has been changed by the events I attended.

I was a failed stock broker trying to become a financial advisor. I went to a series of events that were life changing. They changed my life because of the people I met and the inspiration I got from listening to what those people had to say. 

That’s what we’re doing. We’re giving the next generation an opportunity to have their lives changed by in-person experiences and networking. 

So if you’re on the fence, maybe we’ll see you next year. This isn’t for you. But if you see what we’re doing and what we’re talking about and you are immediately excited, then you’re coming. I think that the people who belong there will be there. 

Technology is transformative, disruptive and impacts our lives in countless ways. Perhaps no other industry is embracing the drive to update and upgrade the tools and technologies evolving our industry more than the wealth management ecosystem. 

 

From the early days of crunching numbers on a giant IBM machine, investors have been obsessed with using technology to improve investment outcomes. That same desire still exists, but through a much wider lens. 

 

Today, fintech has revolutionized its presence by creating digital solutions, improving inefficiencies and reshaping the way financial advisors interact with and provide services to their clients. But with countless products and providers in the marketplace, how do you keep pace?    

 

The answer is simple … at Future Proof’s FintechX Demo Drop! 

 

Future Proof is looking to showcase the newest and latest innovations that will shape the future of the wealth industry. To ensure we can cover the entire spectrum, complete our open application form. We want to see and hear what you’ve been working on, what problems you’re looking to solve and how it will help push our collective industry forward. 

 

The deadline for applications is July 8, 2022. There is no cost to apply and no cost to demo your tool at Future Proof should you be selected.* 

 

Our judging committee, a panel of industry experts, will hand-select 10 tech providers from the applications we receive to demo their latest solutions, based on creativity, outside-the-box thinking, and the ability to create a real impact for the Future Proof audience. 

 

Join us in Huntington Beach, California, Sept. 11-14 as we explore the intersection of money, tech, culture and impact. 

 

*Future Proof does not cover the cost of travel and accommodation for those participating in the FintechX Demos.