Wait, What? Yes, There Really is Life Beyond Wall Street

A candid look at what happens when top financial leaders step away from their C-suite and executive management roles to pursue other equally challenging business turns—from joining or launching start-ups to championing social causes to reshaping industries from the outside. This dynamic panel brings together executives who have successfully pivoted from traditional finance to new business ventures (of all sorts) where their finance capabilities are serving them well while allowing them to play to their desire to take on the next, new thing. They'll share personal stories about what drove their decisions, the skills that carried over, what it took to make the leap, and the lessons they learned in taking on new chapters in their careers.

Transcription:
Transcripts are generated using a combination of speech recognition software and human transcribers, and may contain errors. Please check the corresponding audio for the authoritative record.

Holly Sraeel (00:08):
How's everybody love their career in banking and financial services? Show of hands, who really loves it? That's all? If that's all, then you're ready for this next panel. All right, for those of you who have not met me yet today, I'm Holly Sraeel. I'm the founder of the Most Powerful Women in Banking, and I'm Senior Vice President of Live Media for American Banker. We have a terrific session now. We're going to talk about Life After Wall Street: the inside scoop on reinvention, risk, and reward. I have some fabulous people on stage who started their careers in various lengths on Wall Street and in banking. To my left, Joyce Phillips, who is now founder and CEO of Equal Future; she is a former WIB honoree. Round of applause.

(00:58):
To her left is Anne Clarke Wolff, founder and CEO of Independence Point Advisors, also a former Wall Street person. And finally, we have Brandon Snower—thank God we have another man in the room—who is founder, CEO, and creative director of Le Alfré. Sorry about that. So each of you has had a differing length of time in the financial industry. You've done different things. You've worked in different businesses. I'd like you to give the audience a taste of what you did, and don't be shy. Let's do some bragging. Tell everybody what you did. We'll start with you, Joyce.

Joyce Phillips (01:40):
Good afternoon, everyone. I'm delighted to be here. I've worked across the financial industry in various significant roles. I started at GE Capital, was helping them build a consumer franchise in Japan, moved to Citi where I was also the leader in Japan and then rose to looking after all of international retail banking. Moved into AIG and led one of their global insurance divisions, and then to Australia and New Zealand Banking Group, where I was the global CEO of wealth management, and also the group executive for innovation, marketing, and M&A. And now, as Holly mentioned, I've stepped out of the large roles to really focus on an industry problem which I am passionate about: helping the mass middle market make good financial decisions. My company's called Equal Future. I want everyone to have a shot at an equal future by making good financial decisions.

(02:36):
Today, there's a hundred million people in the US alone that weren't educated and aren't served by financial advisors. So this is what I'm working on now. Thank you.

Anne Clarke Wolff (02:45):
It's great to be back with everybody, and thank you for having me. I spent 33 years across Solomon Brothers, Citigroup, JP Morgan, and Bank of America. I was a really slow learner who thought that somehow I could change the face of these big organizations, but I had the privilege of seeing almost every part of wholesale banking, having started in investment banking, capital markets, and an important stint in transaction banking, which I still think is the most complicated part of any bank. My last role at Bank of America was running global corporate banking and leasing. I had that moment, like many in COVID, of saying, "I think there's another chapter and I don't think it's here." I felt very strongly that I could leave a legacy in a different way. We'll talk a little bit about that.

Brandon Snower (03:34):
I wasn't as esteemed and experienced as these women on stage. I worked at JP Morgan as an intern in compliance in college. Then I did a couple years in investment banking restructuring in New York right out of college. Now I own and started a men's clothing brand in the city. I've been doing that for about four years.

Holly Sraeel (04:00):
All right. Let's get into some of the details on what made you decide to make the move. My first question would be: did you have a motivating factor or a turning point in your career that was an "aha" moment—either a push factor or a pull factor—that made you look around and decide to take a different direction?

Anne Clarke Wolff (04:27):
I'll jump in. It was probably a little bit of both. I would say the gift, in air quotes, was that I had been "chairmanized," which took away the direct responsibility for a thousand people and an $8 billion P&L. If I was better at just smiling and saying nicer things, I would be making a lot more money now. But I knew in my heart that in some ways that was very freeing because I felt an obligation to the incredible teams who worked for me around the world. This was the first chance to say, "What did I actually really want to do?" I thought again, I did not want to be an entrepreneur, but I looked at the state of our industry and I saw a lot less women and a lot less different people providing investment banking and capital markets advice.

(05:15):
I knew from having hung out in this room for a long time that there were brilliant minds that I thought clients would benefit from. So I reluctantly jumped into founding a company at a time that, as Brandon mentioned, I don't think the three of us have had the benefit of a single wind behind our back in the past five years. It's been a very tough time to be an entrepreneur, but you have to believe ultimately that you want to create something different and create a legacy.

Brandon Snower (05:46):
For me, I felt like the trajectory of where my life was going—seeing your EDs and MDs—felt like there was a lot of work that was constrained and limited to your mind and your creativity as an analyst and an associate. You have to stay there for a long time. I just felt like my trajectory in my mind was a little different than being an associate for five, six, or seven plus years, depending on how much you worked or how many times you said yes to your ED and MD. I said no a lot. I didn't think my trajectory was going to be as quick, even though you work until 1:00 or 2:00 AM every day. It was a natural progression; I knew I wasn't going to do it and it was only a matter of when I was going to stop.

(06:54):
I think a lot of people get caught up because they're focused on the pay, the prestige, or the fear of not getting a job after. That's in a lot of people's heads—at least a lot of my friends—but I wanted to bite the bullet, quit while I was there, and just figure it out.

Holly Sraeel (07:22):
Everybody in this room knows that the banking and financial services industry has a certain cultural vibe and work ethic. There are expectations about what you do and how you do it; it's non-negotiable. What I'd like to talk about now is what it was like when you actually made the decision and told people in your orbit that you were moving on. What was their reaction? Joyce?

Joyce Phillips (07:53):
Most of the people who knew me thought this was a no-brainer. They could easily see that I was passionate about creating new things. I was always an entrepreneur, so it was a very logical step for most people that I knew in the industry.

Anne Clarke Wolff (08:09)
I was pleasantly surprised. One of the powers of COVID was that I reached out to probably 300 people to get their advice on what I was thinking about. Every single person took the call. Maybe people were at home sitting on Zoom and were generous, but I think everyone knew that I had been a fearless advocate for clients and they could see as clients it was getting harder and harder to achieve what they wanted to with some of the big banks. They also saw how I felt about building and nurturing talent, which they saw as an opportunity. I think clients are pretty open-minded to our industry being ready for change.

Brandon Snower (08:52):
Mine was pretty different.

(08:56):
If you're going into fashion and clothing, it taps a completely different brain and world. People in my team and everyone on my floor was like, "What the hell are you doing?" You just kind of believe in yourself. I actually didn't know I was going to start a clothing brand; I just knew it wasn't going to be something in banking or finance. I was looking at marketing jobs and applying to different roles. When my circle in banking and other financial institutions heard, it was hard for them to comprehend. Plus, you don't really have a community around you that are in clothing, fashion, or entrepreneurship—especially since I started this when I was 23. It's pretty difficult, and you just learn to figure it out on your own.

Holly Sraeel (10:02):
We talked about your decision to go off and start a new chapter, but what did it actually feel like leaving the stability of a full-time job behind? Did you struggle with fear, an identity crisis, or a status issue? Because all of that happens in financial services, particularly if you're a WIB honoree. Tell us, how did you manage through the fear and identity crisis, if you had one?

Joyce Phillips (10:36):
It's scary. It's giving up your network of really smart people. It's stepping out of the titles and still trying to get people to return your phone calls and join the mission. It takes a lot of courage. It's not for the faint-hearted to step out of a big role and lots of money to go out there on your own and build your own team. It hits on all of that—not getting invited to things you were always on the invitation list for—but you get access to new circles. You meet new smart people doing different things. It's a very different journey and requires resilience, but if you see it through, it leads you to a whole new realm.

Anne Clarke Wolff (11:30):
My husband still misses my Global Services status on United. I kind of miss it too. I did finally cross two million miles, although the last 50,000 took a lot longer than the 10 years leading up to that. As Joyce said, one of the things we shouldn't take for granted is that in this industry, we have the privilege of working with exceptionally smart people. Women in particular just get things done, and that's so much fun to be part of. As entrepreneurs, it's lonelier. I say every week, "I wish working more hours would make me less stressed," but it actually isn't about the number of hours you work anymore. I think back to the financial crisis in 2008; that was a lot less stressful than wondering now if we will make payroll.

(12:25):
Should we commit to more than a two-year lease? We all feel that sense of obligation to make these businesses financially sustainable before we can get to the real mission we're trying to accomplish.

Brandon Snower (12:42):
Going on what everyone said, I was extremely happy. It was just a new world and perspective that you don't really get to see or tap into as much. It's a process and a gradual learning curve of switching your brain from having so much structure and organization to literally, on the first day, asking, "What's my schedule? What am I doing?" You learn how to do it naturally on your own. Then you get to a point where you meet amazing people that inspire you or that you aspire to be within your industry.

(13:44):
That's not to say that that is the only world you're in. We're in menswear, so we still have to be in the corporate world because we make button-downs and cool corporate attire for guys. It's a process of being fully embraced in what you're doing. That's the hard part, but it gets a lot easier as you grow.

Holly Sraeel (14:18):
We're going to talk about the hours you log and the dedication required to start your own thing. But before we go there, let's share some tricks you've learned to manage through isolation and stress, because people in full-time corporate roles feel that too. How have you learned to cope?

Anne Clarke Wolff (14:55):
None of us can or should be defined by our day job. It's a big component of who we are, but the best compliment I was paid in the past 35 years was always, "Wow, I find it hard to believe you're a banker." That's actually a good thing. You have to figure out how to keep your identity in check. I wish I could say I make myself work out now, but I hate it every single day. So I'm not going to lie and say it's a great stress release. There is no magic bullet. Brandon said something yesterday: if you get up in the morning and consistently don't want to go to work, listen to that voice and do something about it.

(15:47):
We all have the economic privilege of probably a lot more choice than we think we do. I don't think anybody in our fortunate circumstances should have to do something that makes them unhappy.

Brandon Snower (16:02):
I agree. Part of the reason I left was I consistently woke up slogging out of bed saying, "I don't want to go to work." If you're doing that for weeks or months on end, then it's time to pivot. Yes, it's frightening. Everyone here has different responsibilities. I was fortunate enough to be very young with no kids and no real responsibility other than paying rent. But longer term, if you spend the same amount of time and effort on your career that you don't necessarily love, imagine what you could do if you absolutely love something you're passionate about. Never designed a clothing product in my life; didn't know anything about clothes. We just opened up a 6,000 square foot store on Madison Avenue in less than four years.

(17:04):
That kind of work ethic is something I give kudos to banking for. My time in finance gave me thick skin, the ability to work nonstop, and the mentality to power through things. If you love banking, that's awesome. My MD loved it; he could create models blindfolded. That passion is why you do what you do.

Holly Sraeel (17:43):
You just set me up perfectly for the next question: how do you translate your Wall Street, financial, and banking skills into what you do today so that people know these skills are portable?

Joyce Phillips (18:00):
For me, that was easy because I'm staying in the industry and I have deep vertical knowledge across the financial spectrum. I've taken jobs always because I wanted to learn more. I've been a hands-on manager. I could leverage that expertise to think about what the industry needs, marry my skills to that, and build something. I use every bit of my professional background every day, along with a range of new skills. I'm now the chief sales officer, so I'm pitching all day long, getting rejected, and pitching again. That's a new skill for me. I encourage you to make sure you're learning along your journey so you can leverage that later.

(19:03):
That network led to my bootstrap rounds of funding. It's critical as you're moving through your current roles to keep your network strong and keep learning; you will have many more options in the future.

Anne Clarke Wolff (19:17):
I wish I had been more deliberate about building a portable skill and brand. I was really good at running big parts of big banks, growing top-line revenues, and managing talent. None of that translated into what I do today. I tend to advise people: if you're at an earlier point and you're passionate about a particular industry, focus on that. I would have been better off in the long run had I focused on healthcare or technology 30 years ago. Clearly, there's a lot we've acquired, but don't confuse being good in a large financial institution with being immediately portable. I spend a lot of time helping people understand if they have built something portable that's truly theirs, which is trickier than it sounds.

Holly Sraeel (20:28):
And Brandon, you're all about work ethic. You have this 6,000 square foot store opening on Madison Avenue. Why don't you talk about that?

Brandon Snower (20:38):
Keep your mind very open to learning new skills. When I left and woke up the next day, the shift was sudden and rewired everything I had learned. It's okay to have things that aren't necessarily applicable. I would pick pieces of skill sets I learned or observed from others and build from that foundation. If you go into something thinking, "I'm really good at this, so I have to make it work in this box," you'll struggle, because there is no box.

(21:40):
If you're an entrepreneur or joining a startup, there's no structure. It's just your understanding that you have to be open to learning and open to not knowing stuff. By knowing that, you can do anything.

Holly Sraeel (22:07):
Were there things you had to unlearn from your prior careers?

Joyce Phillips (22:18):
I wouldn't say unlearn, but I focused on what I had to learn: setting up a company, new skills like UX design. I immersed myself in learning and tapping into people with expertise. "Unlearning" would mostly be about dealing with the isolation and pivoting away from the network, the titles, and the first-class travel. You have to be happy saying, "I'm starting a new life here; there are no minions to do the work, you've got to do it yourself." You can pass that hurdle quickly if you make your mind up.

Anne Clarke Wolff (23:28):
It's a big shift. In large organizations, I believed you couldn't change what you didn't measure, so I was a big believer in metrics and goals. In small companies, that doesn't really work and it annoys people. As a leader, it's about proving I do my own expense report and I don't have a secretary. When people ask for my assistant's name, I say, "That's me." I take the coffee cups back to the dishwasher. It's surprising how much you can strip down. Much of the reporting you do in large institutions doesn't translate to an early growth stage. It's a completely different brain, and as Brandon said, the fun part is making your brain do different things.

Holly Sraeel (24:52):
Brandon, how do you define success now compared to when you were in financial services?

Brandon Snower (25:05):
I have a different philosophy. Success as an individual is waking up genuinely enjoying what you do. That has nothing to do with money. By default of doing that, you're going to be successful. If you're genuinely trying to get better every single day and working at it, at some point it's going to hit—whether in year three, seven, or ten. Success now for me is how to build a team and inspire people to excel in what they genuinely enjoy doing. I just had a conversation with our head of partnerships about switching roles to head of events because I know she'll excel at that.

(26:18):
She's insanely excited now to do something she's passionate about, and that's overall going to help the company grow. There are always different levels of success every month.

Holly Sraeel (26:45):
Looking back, do you think Wall Street culture makes it hard for people to imagine taking up alternative paths?

Anne Clarke Wolff (27:07)
When I founded IPA, we were trying to address three pain points. Part of that was locational flexibility. The second point was comp transparency—understanding the cause and effect between hard work and compensation. And then, no "yucky" people. What was interesting was that I found four years into it, while women are eager to make a change, they're really risk-averse. I think they should bet on themselves. Wall Street compensation has been stagnant since 2008, but the cost of living in the city has not.

(28:03):
When I challenge people on economic risk, it's not as much as they think it is. But people have it ingrained in their heads that getting off the financial treadmill is scary. My message is: have faith in yourself. If you apply the same intentionality and passion, you can do amazing things. We need more people to believe that before they just opt out of the industry.

Joyce Phillips (28:54):
Completely agree. My advice is: live well within your means. If you don't like what's going on around you, you can pick up your bag and go without putting your family in financial peril. It also makes you a better leader because you can make clean decisions. I lived within my means throughout my career, which allowed me great flexibility and made me a good decision-maker because I wasn't worried about what would happen if the job disappeared tomorrow.

(29:45):
I knew we would be just fine.

Holly Sraeel (29:52):
If the industry truly wanted to retain creative, entrepreneurial talent, what would have to change?

Anne Clarke Wolff (30:07):
Early in your career, it's relatively straightforward how you're evaluated. As you become more senior, it becomes much more tilted toward political alliances. It took it out of the realm of what you could control. I had the naive view that if I just had great results and top talent, they would recognize that. Ladies, that is not how it works. Organizations that want to retain talent should be moving people around. We all benefited from being put into seats that were uncomfortable. In 2009, Jamie Dimon offered me roles in treasury services or wealth management. I told him, "I don't know anything about either." He said, "I don't care, I know you'll figure it out."

(31:17):
That's what the industry could do: pluck talented people out of seats where they are growing roots and let them learn something different. They are a lot less likely to quit when they feel that expansion of their brain.

Joyce Phillips (31:43):
Absolutely. Move around and learn as much as possible. Promote someone a little bit earlier than they deserve and give people autonomy. As an industry, let's face it: we reward incrementalism. We don't reward bold decisions to try something new. The current incentive is just to deliver incremental progress from what you did yesterday, and that's a big problem for the industry.

Holly Sraeel (32:22):
There are so many exciting things going on with innovation, AI, digital assets, and on-chain finance. Do you think more people will leave banking over the next few years, or will finance be forced to reinvent itself to keep talent?

Joyce Phillips (33:04):
I think both. Reinvention is already occurring. Banks are embracing AI to do things differently. This will create opportunities for those with deep vertical knowledge. I recently attended a meeting where leaders said, "AI can do the coding now; the engineer won't be at the pinnacle because AI can build it." It's that deep vertical knowledge that will be required to understand what is missing. Marrying cutting-edge technology with that knowledge is where the future careers are.

Anne Clarke Wolff (33:55):
I encourage every bank CEO to let their top talent serve on corporate boards that touch something in AI. You learn a ton and see the world differently. This is where banks get flummoxed in compliance and regulatory excuses, but you need a bridge to figure out what that change will be. I think all this talk about AI eliminating all these jobs is something we'll still be talking about in two years; I'm not sure how different it will be because we struggle as an industry to move from talk to actual deployment.

Brandon Snower (34:54):
AI is a tool. It's going to filter out people who aren't going above and beyond. At the end of the day, we're in a service industry. I'm not in the clothing business; I'm in the service business. People do business with people. AI and tools will help increase access to knowledge, but who's going to tell the story of the model or talk to the client? It's just going to filter out people who aren't going above and beyond to understand what is needed to communicate effectively.

Holly Sraeel (36:20):
How can people use the skills they have and the networks they've built to create freedom, and not just income and wealth?

Anne Clarke Wolff (36:52):
You have to build something portable that's your "secret sauce"—whether it's a product, clients who follow you, or people who listen. No matter what that is, that's your differentiator. Then you have the freedom to do that in a variety of settings.

Joyce Phillips (37:23):
I lived in Japan for a number of years and there's a concept called "Ikigai," or life path. It combines four things: what you love, what you're good at, what the world needs, and what you can get paid for. The more of those you can align, the happier you'll be. I feel like I'm in my Ikigai phase right now. I have great freedom, I can do what I like, and I'm focused on a big problem the world needs.

Brandon Snower (38:12):
Think about what you genuinely enjoy doing—your hobbies and things that excite you—and expand into that. Take time on Saturdays or Sundays to strategize and learn. If you don't take time to self-reflect and understand yourself as a person, it will be harder to have the freedom to do things you might otherwise not know you're capable of.

Holly Sraeel (39:08):
Final question: what have you learned about ambition and happiness that only life after Wall Street has taught you?

Anne Clarke Wolff (39:22):
Ambition is not a bad word. Our industry suffers from caricatures of the bad elements of ambition, but ambition can accomplish great things. It allows us to give back and be a role model for the next generation. I'm tired of people being embarrassed by the word ambition.

Brandon Snower (39:55):
Dream big. Who cares what other people think? It's your life. Do whatever the hell you want.

Joyce Phillips (40:08):
Go for it. I'm in my third chapter, and I'm focused on: "if I don't do it now, when am I going to do it?" I almost wish I did this 10 years ago. What have you got to lose? Even if you failed, you can go back and get a job. They will love you more for the risk you took and what you learned. There's not a lot of risk here; it's an opportunity. You've got a nice safety net, so give it a shot.

Brandon Snower (41:12):
Imagine what you would do if you couldn't fail. If you have that ultimate confidence, you don't have to worry about anything else.

Holly Sraeel (41:55):
All right, we're at time. Any questions? Does anyone have the courage to ask a question?

Joyce Phillips (42:27):
I'm using AI to create personalized journeys that were once reserved only for the wealthy. Now you can do retirement plans in minutes and bring life decisions together in one seamless platform. It ranges from educating a 17-year-old on college funding to creating retirement plans. I'd love to work with anyone interested in changing the dialogue from just selling products to helping people make good decisions.

Holly Sraeel (43:08):
Other questions?

Audience Member 1 (43:16):
Was the decision to leave Wall Street a planned launching pad, or did you not have a plan and just didn't know what your next steps were?

Anne Clarke Wolff (43:41):
I had no plan. You have incredible resources around you in your current jobs, and that's a great opportunity to learn or meet people, but I've never been the beneficiary of a life plan. Brandon, you had no plan either.

Holly Sraeel (44:07):
No plan, and he's very open about it. But look at him: he's opening a 6,000 square foot store on Madison Avenue. Before we thank our panelists, we're going to go to a break. Get some coffee, some water, and talk to each other. Networking is important. Connect on LinkedIn; it is the most powerful platform out there. LinkedIn is where you want to be. I am not kidding. Please join me in thanking Joyce, Anne, and Brandon.