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Women Leading The Finance Industry: Casey Halliley of Sqwire On The 5 Things You Should Do To Increase Your Financial Literacy

An Interview With Tyler Gallagher

Start early: Just start early, start early, start early! Start tackling your debt, start saving, start investing, start asking questions, start learning, just start. It doesn’t matter what your age is, the earliest you can start is today. But with that said, even if you haven’t started early, it doesn’t mean you’ve missed the boat! There is always hope.

As a part of our series about “Women Leading The Finance Industry”, I had the pleasure of interviewing Casey Halliley

Casey Halliley is the SVP of Financial Education at Sqwire, a financial wellness provider. Casey spent the first twelve years of her career trading and selling Currencies and Structured Credit Products to Hedge Funds at Citigroup and Barclays Bank PLC. Following that, she oversaw risk management and compliance for an Asset Manager, Cove Capital Management. After discovering her passion for financial wellness, she started Wealthology in 2014, where she has educated thousands of students and professionals at numerous companies and universities. In 2020, Wealthology was acquired by Sqwire.

Casey believes people deserve to be financially well. She is on a mission to empower people by providing them with the tools and knowledge they need so they can change the trajectory of their financial future.

Casey has taught courses at universities from Columbia Business School to Yale University and at corporations from Capital One to Weil Gotshal. She is currently the lead on a project to rewrite the financial literacy curriculum for the US Air Force and will be teaching as an adjunct professor at Baruch College in the fall.

Thank you so much for joining us in this interview series! Can you tell us the “backstory” about what brought you to the finance field?

Thanks for having me — I’m happy to be here!

I was very passionate about working in the not-for-profit sector in high school and college. I traveled the world doing community service in my teens and early twenties to Africa, Central America & India, minored in Public and Community Service in College, and got my Masters in Public Administration specializing in Finance from NYU with the hopes of working at a nonprofit. While I was in grad school, I interviewed endlessly for $8/hr jobs, and I could not get an offer anywhere. A friend of my father’s asked me what I liked about my grad school program, and I told her I loved economics, accounting & finance classes so she asked if I’d like to meet her friend who worked at Solomon Smith Barney. I hadn’t the first clue what they did but I took her up on her offer. I met her in her corner office on the Citigroup trading floor (a woman with a corner office on a trading floor in 2001!). I sat across from her in her shoulder-padded skirt suit and bright fuchsia lipstick as she flipped through the binder to find what they were paying interns and let me know it was $40/hour. Although it was far from what I had intended to do with my life, I took the internship thinking at the least I might learn something (or earn something). From that moment forward I never considered another career path. I was enamored with the furious pace, the challenge, and the unbridled enthusiasm for winning that permeated life on a trading floor.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

The story that comes to mind happened in my first 6 months on the Foreign Exchange desk at Citibank and, if I’m being honest, I still cringe when I think about it — even 20 years later — but the lessons I learned were so invaluable that they still shape my actions to this day.

Let me preface this by saying there is a LOT that can go wrong for a junior employee on a trading desk — you could buy when the customer wanted to sell, you could forget to ask an important question, forget to book a trade, or any number of other things that could go catastrophically wrong. Because of that, it was standard procedure for a senior employee to supervise all incoming calls.

On this particular day, the phone rang and there was no one in sight who could supervise the call, but I had been told that I’d be fired if I didn’t answer each call by the end of the first ring. I might have actually preferred getting fired to answering the phone alone at that point, but I answered it anyway. What could possibly go wrong? I found out all too quickly as I was immediately greeted by a man screaming into the phone that he needed a price on $250 million dollar yen — meaning he wanted to trade two hundred and fifty million American dollars against the Japanese yen. Now, this sort of request was just not done — nobody would ask for a two-way price on a trade of this size — but what choice did I have? I knew from my training that I was supposed to yell this number out to the trader who would yell some numbers back which I would relay to the customer, and he could decide if he wanted to buy or sell. I’d yell the final decision back to the trader and he would say “Done!” if the price was still good. The trade would be complete, and I’d book it. All of this would go down in approximately 15 seconds during which time I would never break eye contact with the trader and use a system of gestures to signify buy or sell (point a finger up for buy and point it down for sell). It could all be very exciting if not for the fact that it was also terrifying. So, I did what I was supposed to do and yelled over to the trader… and was completely ignored. I shouted again and he ignored me… again. Panic started to set in as the customer started screaming expletives into my ear about what a useless loser I was, and I imagined myself getting fired on the spot. But this is where Lesson Number One came in — SPEAK WITH CONFIDENCE! I found my trading floor voice that day and screamed to the trader so there was no way he could ignore me. He finally popped his head up and shouted the prices back to me, which I relayed to the customer. The customer made his choice to buy and then HUNG UP THE PHONE. Now, you must understand that in order for a trade to be completed, both sides of the trade must be confirmed. By the time I tried to confirm with the trader, he wiped his hand like an umpire and screamed, “Price out!” The price was no longer good, and I would need to refresh it. But of course, that was impossible since the customer had already hung up the phone thinking he had just bought $250m dollar yen at a price the trader was no longer willing to sell him! My newly found trading floor voice went right out the window as I tried to tell him that the customer wanted to buy to which he responded that the price was “OUT!” and that I was now short $250m dollar yen and I’d better figure out what to do about it! He screamed at me to call the customer back, but I couldn’t remember his name. He screamed at me to call the company back, but I couldn’t remember that either! Lesson Number 2 — LISTEN! The trader stopped yelling at me when I fell to my knees in the middle of the aisle and clutched my chest with the phone still in my hands. I heard some commotion from across the trading floor. I realized people were laughing and cheering and heading right towards me looking like they wanted to hug me. Before I knew it the guys who had been huddled in the office on the other side of the floor playing this horrendous prank on me were clapping me on the back and telling me how much they admired the way I handled the situation as everyone else who had deliberately abandoned their desks trickled back to their seats to answer the legitimate phone calls coming in. Later, one of the jokers bought me a soda and said, “You know, we only do that to the ones we like. You’ll thank us someday. You’re good at this.” He praised me for keeping my cool and remembering my training even while I was being berated on the phone. He laughed and said, “I thought you were going to crack when I called you a USELESS LOSER!” I think I blacked out most of the experience, so I’m not sure if he was just being kind but overall, the experience taught me so much. Most important was Lesson Number Three — TO BELIEVE IN MYSELF (I was more capable than I gave myself credit for).

Are you working on any exciting new projects now? How do you think that will help people?

I work for Sqwire, which helps people realize their financial promise by providing a comprehensive financial education. Right now, we’re currently working to update the financial literacy curriculum for the US Air Force with an incredible team of people who have dedicated their professional lives to teaching our Airmen and Guardians in the Air Force as well as an evaluation team at the University of Georgia. It’s hard to put into words just how proud I am of this work.

What do you think makes your company stand out? Can you share a story?

The Sqwire financial literacy curriculum is hopeful, respectful, and fun. We’re passionate about showing people how they can build their wealth in different ways as well as helping them work towards a future of financial freedom. Recently, we were doing a focus group survey to try to connect with our learners post-pandemic and provide education on how to move forward after what was a financially devastating experience for so many. I was speaking to a man in his 50s living out in Seattle with his husband. They were both hospitality workers who’d been furloughed but were making more on unemployment than they’d been making while they were working. Given the freedom of extra time and a bit of extra money, he was trying to figure out what he was going to do next. They had little savings, but no debt, so he felt open to new possibilities. A question about his dreams for his financial future sparked a heart-warming conversation about his hopes for himself and his husband. At the beginning of the call, he felt like he’d missed the boat. He’d struggled to keep his head above water, remain debt-free, and maintain an open and communicative relationship with his spouse, so he never envisioned the possibility that he would be able to feel financially secure. We talked for a long time about possibilities and options for him and when we ended our conversation, he had an entirely new perspective on his financial future. He had hope. That’s what we provide at Sqwire. We’ve built our entire curriculum with people like him in mind — people who are trying their hardest but who are limited and may feel stuck simply because they never got the tools, resources, or training to make confident, informed financial decisions.

Ok. Thank you for all that. Let’s now jump to the main core of our interview. Wall Street and Finance used to be an “all white boys club”. This has changed a lot recently. In your opinion, what caused this change?

  • An increase in minority business owners and leaders who expect to sit at the table with their bankers and see people that look like them and share their values. Smart financial institutions know that and have started prioritizing diversity in their hiring choices.
  • Speaking of hiring choices, I think the industry has changed a lot in the past 10 years as there have been more deliberate attempts to move women and folks with diverse and underserved backgrounds into positions of power. That, of course, is now being accelerated even more in the current push for diversity, equality, and inclusion, and has expanded into finance and non-finance industries broadly. I see firms large to small, finance to non-finance, prioritizing diversity by recruiting women and people of color into their training programs that I speak at. I know many female friends who have gone back to the big banks through their Returnship or Re-Entry programs and I’m pleased to see large investment banks inviting more women and people of color onto their boards or into positions of leadership so that everyone has a seat at the table.
  • There has also been a push to keep up with the Silicon Valley and FinTech “brain drain” as women and people of color are moving into these roles for the salaries, cultures, or ability to work on their passions while wearing jeans and working remotely (sounds pretty great to me!). I think that puts the pressure on traditional investment banks to keep up with the changing times.

This progress pleases me to no end to see as, although I was recruited onto a trading floor by a woman in a corner office, I had no idea at the outset how rare it was for a woman to be in a position of power in my industry. I encountered so few women along the way who managed to organize their careers and family lives in a way that jived with the way I wanted to be a working mother. When I got pregnant and looked around to find someone who was making it work in the way I would have liked, there was no one doing it, so it seemed like an improbability. I ended up leaving Wall Street at the peak of my career to prioritize my family. The culture didn’t work for me then, but my guess is it would be very different now because of all of these changes taking place. My hope is that this kind of progress is making it easier and more accessible for women to step into positions of power without having to sacrifice on the home front.

Of course, despite the progress, we still have a lot more work to do to achieve parity. According to this report in CNBC, less than 17 percent of senior positions in investment banks are held by women. In your opinion or experience, what 3 things can be done by a)individuals b)companies and/or c) society to support this movement going forward?

  • I think the returnship & return-to-work programs many of the banks use are very effective for bringing women who have left the business back in at different points in their working lives. Recruiting junior people at the bottom and selecting board members at the top with Diversity, Equality, and Inclusion in mind will help women see more people who look like them to model themselves against (half of JP Morgan’s board are now women, and other banks, too!).
  • Beyond ensuring that women are seeing other women in the workplace, the single most powerful tool I’ve always taken advantage of in my career has been mentorship. Senior leadership (men or women) mentoring younger people can be a major differentiating factor in their success and staying power when they hit a rough patch in their career.
  • And we can’t forget about culture — it is so important! As more and more women leave traditional businesses (law, finance, consulting) to go to FinTech, InsureTech, and other start-up type companies to work on passion projects in a more flexible way, with a broader mix of people across age, gender, color, ethnicity (even geography in this new remote world), Wall Street is taking notice (as it should).

Let’s now turn to a slightly new topic. According to this report in Fortune, nearly two-thirds of Americans can’t pass a basic test of financial literacy. In your opinion or experience what is the cause of these unfortunate numbers? If you had the power to make a change, what 3 things would you recommend to improve these numbers?

Honestly, the simplest answer I can give is that we as a society just haven’t made it a priority for our young people. Until recently, there really hasn’t been much discussion about including financial literacy in the curriculum throughout high school and college which leaves our graduates to enter the world without the tools needed to make smart financial decisions. As a financial educator, this is obviously a priority for me and I’m grateful to be in a position to impact change through what we’re doing at Sqwire.

If I could make sweeping changes in how our country handles financial literacy, I would make it a requirement in three parts:

  1. High school: Students should learn about banking, the cost of debt, different types of savings (emergency, short-term vs. long-term, retirement, etc.), education financing, and other basic money management skills.
  2. College: The next level of financial literacy should be geared towards college students who are preparing to enter the workforce and live independently. They should be required to learn about homeownership, investing, insurance (life, liability, home, and health), debt management, budgeting, and the decisions they will need to make when they enter the workforce like starting to save for retirement right away!
  3. The Workplace: Just because we leave school doesn’t mean there’s nothing left to learn. Employees who receive financial wellness training that covers topics like retirement savings, taxes, investing, inflation, estate planning, and more advanced topics will be better able to make the right decisions at the right times and secure their financial futures.

We’ve found at Sqwire that just giving people some basic information makes them feel more comfortable asking questions, asking for help, or thinking about their options. I believe that a basic understanding of a few critical topics could change people’s perspectives from being apprehensive to becoming active participants in their financial well-being.

You are a “finance insider”. If you had to advise your adult child about 5 non intuitive things one should do to become more financially literate, what would you say? Can you please give a story or example for each.

  1. Inflation: It’s important for people to understand how their money sitting in cash will depreciate in an inflationary environment. If inflation stays the way it is right now, (running at 7.5% as we speak), that means that money sitting in cash will be worth half its value in 9.5 years. That’s a really scary thought when people believe they’re saving because they see the numbers go up, but the value of their money is diminishing.
  2. Debt: Debt is expensive! One example we use in our courses is if someone has a $500k mortgage at 5% interest, they’d end up paying $466k in interest over 30 years. That’s almost the cost of another house! Debt is expensive, especially debt that is outstanding over long periods of time or with high-interest rates. Paying small amounts of principal back towards outstanding debt, particularly high-interest rate debt or debt that’s compounding, can make a big difference in the overall cost of the debt and the length of time it’s outstanding. Beyond how incredibly important it is to start investing if you want to build wealth for yourself, there are a few particulars I would teach my adult child:
  3. Management fees can be astonishingly expensive: For example, say you decide to save and invest $75/week, you may be able to accumulate $1m over time (assuming a 7% return). But, if you’re paying a 1.5% management fee, at that same return, you’d accumulate only $680k. That’s $320,000 shaved off of the value of your portfolio simply due to fees. YIKES.
  4. The reality of Your 401k: I’ve talked to so many people who diligently contribute to their 401k (or whichever type of tax-advantaged retirement plan they have access to) and expect that money to be growing for their future as they get on with the tasks of everyday life. The difference, however, between a portfolio of bonds and a portfolio of stocks can mean the difference of hundreds of thousands of dollars (or more) in their retirement accounts. I would recommend that you check on your fund choices every so often to make sure your asset allocation is appropriate for your risk tolerance and age. Most people I speak to let too much time go between checking their retirement account funds and are not growing their wealth as much as they could be.
  5. Start early: Just start early, start early, start early! Start tackling your debt, start saving, start investing, start asking questions, start learning, just start. It doesn’t matter what your age is, the earliest you can start is today. But with that said, even if you haven’t started early, it doesn’t mean you’ve missed the boat! There is always hope.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I have had a string of professional mentors along the way in my career that have dragged me along behind them and allowed me to learn things I never could have learned in a classroom or from a book. I’ve been challenged, trained, yanked out of my comfort zone, yelled at, been made a fool of (see above), been beaten down, and have been built up. I believe that mentors are one of the only shortcuts to hard work in this world (the irony being, however, you don’t get anything out of them without doing a ton of hard work, so maybe not a shortcut after all).

But, if I had to pick just one person, I can honestly say that I never would have done any of this without the love and support of my mother. The one story I can recall, which actually has nothing to do with me, was when my sister was deciding what to do with her life after college and she briefly considered nursing. My mom casually said, ‘Well, if you’re going to go back to school, why not just be a doctor?” and my sister shrugged her shoulders and said, “OK, good idea.” The lesson in our house was to just go for it. If you’re going to climb a mountain, find the highest one, prepare to the best of your ability, and then just go for it. I approach every aspect of my life that way and I think it all stems from that moment (and thousands of others that came before and after) where my mom didn’t question whether or not we had the chops. She didn’t blink when we both ended up pursuing careers in male-dominated industries. She didn’t flinch when there were questions of how we’d pay for it, what an incredible sacrifice it would be, or how extraordinarily difficult the path might be. She just encouraged us to GO FOR IT and without those subtle encouragements to just try, I don’t know if I’d have the confidence I do today.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Things turn out the best for the people who make the best of the way things turn out.” — John R. Wooden

I haven’t had a perfect life, but I have tried at every turn to make the best of my circumstances and that strategy has worked for me.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. :-)

My ultimate dream — and one I think has the most potential to impact real change — is to develop our financial literacy program and make it available in colleges and universities. I believe there are ten basic topics all people should be taught before getting launched out into the world. As I work through revamping the curriculum for the Air Force, my wheels are always turning and I’m starting to map out what a post-secondary financial literacy program might look like. In the Fall of 2022, I will be joining Baruch College in NYC as an Adjunct Professor and while I’m there I hope to create a basic financial literacy curriculum to propose to them or other schools for future semesters. As more and more states start to mandate financial literacy as a requirement for graduation, I hope other schools will consider the curriculum as well. Everyone deserves to realize their financial promise and I believe if we provide the tools, resources, and education needed, the benefits will be far-reaching — not just for each individual but for the world at large.

Thank you for the time you spent on this interview. We wish you only continued success.

In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

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Tyler Gallagher

Tyler Gallagher

CEO and Founder of Regal Assets

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