As the founder and managing partner of Chequers Financial Management, a female-owned high-net-worth tax and financial planning firm in San Francisco, Megan Gorman is no stranger to the complexities of personal finance.
In her upcoming book, All the Presidents’ Money, Gorman takes readers on a captivating journey to uncover the diverse money stories of the U.S. presidents. Challenging the perception that the nation’s highest office-holders are financially infallible, Gorman’s book delves deep into the grit, education, and risk-taking that have shaped the presidents’ personal financial journeys over the past 250 years.
Through meticulous research, she reveals how even the greatest leaders have struggled with money management, while some of the least-favored presidents have proven adept at building personal wealth. As a female pioneer in the financial planning industry, Gorman offers a unique perspective on the intersection of politics, leadership, and personal finance.
Check out our full interview with Megan Gorman below.
As a female entrepreneur in the financial planning industry, what inspired you to take the leap and start your own firm, Chequers Financial Management?
Megan Gorman: Over the course of the first 12 years of my career, I had always kept in the back of my mind that if I ever had a chance to create a firm, I would do things differently. I had always chafed in the corporate structure. I didn’t like always following the rules and playing all the required political games. But I loved working with clients and building great relationships.
As I got closer to 40, my husband turned to me one day and said, “you talk about this firm you want to set up one day, are you ever going to do it?” And that was likely the push I needed to make the jump.
It was absolutely terrifying at first. I only had myself to rely on. Yet I found I quickly got comfortable with that. Without the constraints of a big corporation framework, I could be nimble and service clients that way I felt was a better client experience.
What were some of the biggest challenges you faced in transitioning from a VP role at large firms like Ayco and BNY Mellon Wealth Management to launching your own boutique practice? How did you navigate those challenges?
Megan Gorman: When you are at a big firm, you don’t have to worry about payroll or HR and other corporate services. When you launch a boutique practice, you have to be a jack of all trades – and still deliver client service.
I saw building a boutique practice as a step-by-step process. As the firm grew, I was able to recruit the right talent at the right time to propel us forward. This allowed us to work with the right type of clients. We want to be deeply engaged in their personal finances. Ultimately the secret to our success are the people who work with me and the clients we service.
Your clientele ranges from entrepreneurs to corporate executives to inheritors of family wealth. What are the unique financial planning needs and considerations for each of these client segments, and how do you tailor your approach accordingly?
Megan Gorman: Regardless of background, there is no cookie-cutter approach. Everyone has their own emotional patterns related to money. What is important is to really develop a philosophy on wealth. Wealth isn’t just about money – its about choices and the ability to be in control of your destiny. I want to understand how my clients see wealth – and then what tools I can bring to the relationship to help them achieve it.
In many ways, I like to see myself as a financial dream maker—money has always been intuitive to me. Tell me what you want, and I can help make it happen.
You’ve been named to the Forbes lists of America’s Top Women Wealth Advisors – Best in State for 2022 and 2023. What do you attribute to your consistent recognition and success in this field?
Megan Gorman: It’s a nice accolade from the industry. But honestly the real recognition is when a client is happy and appreciative of what we were able to do for them. That being said, why this list is so important is that it helps give you the right gravitas you need to be managing a boutique practice. I’m very appreciative of the acknowledgement and it helps clients feel they made the right decision working with us.
In your upcoming book All the Presidents’ Money, you take readers on a journey to understand the personal money stories of US presidents. What inspired you to explore this topic, and what are some of the key insights that you discovered while writing the book?
Megan Gorman: First of all, I’ve loved reading and studying the presidents since I was six years old. Researching all the stories, I got to experience the presidents, not as the chief executives of the country, but as real people who had all the same stresses we have today. It really humanized them for me.
Second, I was really lucky to work with wealthy individuals and families early in my career. In many ways, I had a front-row seat to the skills and behaviors that the wealthy use to build their asset base. So, over the years, people have asked me what the secrets are.
The truth is there isn’t so much a ‘secret’ to building wealth as much as the fact that if you have the opportunity in this country, and you put discipline around it, you have a shot of creating wealth. That doesn’t mean it always happens, but you are really increasing your chances of financial stability.
However, one of the conclusions I made in writing the book is that some of the opportunity sets that previous generations had are not as easy to access today. The American Dream is still alive – but it’s a lot harder to achieve. And I think that is why many Americans are frustrated today.
How do the money management habits and financial decisions of US presidents, both good and bad, compare to the financial challenges faced by your clients?
Megan Gorman: Regardless of the time period, everyone struggles with financial decision-making. That being said, it was really interesting to see that the presidents who had extremely strong budgeting skills, like George Washington and Ronald Reagan, often were able to really propel their finances ahead. I see that with my clients as well. Budgeting may be boring or tedious, but it’s a tremendous skill.
But where things can go awry is when a person lets emotion control the situation. What do I mean by that? Well, let’s take James Monroe – now, he’s not a president most Americans think about. But he’s a pretty modern guy for a founding father. At times, when at a financial decision point, he would avoid tough decisions and make assumptions that might not have been reasonable. Today we would call it FOMO.
Let me give you a quick example: he gets sent to France by President George Washington. Now even in his day, Washington was quite the daunting individual and Monroe is thrilled to have been tapped by Washington to go. Monroe says yes to the appointment even though he has a substantial plantation at home that needs significant management to keep it going.
Monroe gets to France and realizes that to do the right diplomatic work, he needs gravitas. And in 1790s France, that means having the right home to entertain in. So he goes out and buys a house for the US with his own money. He doesn’t ask for permission and doesn’t think about the obligations he has back home. His salary doesn’t cover half of what he is spending. He keeps pushing his financial matters off to another day.
Of course it is eventually time to come home to the US, and Congress doesn’t understand why he bought the house so he sells it at a loss. Plus while he was gone, his plantation suffered. So when he gets back, he’s in a bit of a financial mess and tries to sort it out.
But Monroe keeps getting sucked back into the passion of creating a new country. He never fully focuses on his personal finances which is why he’s broke at the end of his life.
We hear this story and think he’s foolish – but honestly, it’s a common one today. Being present with our finances and learning to say no is incredibly hard. Money is emotion – and managing it is very hard for all of us.
As the chairwoman of the Investment Committee for the $200 million NEFE endowment, what are some of the key considerations and strategies you employ to manage such a large institutional portfolio?
Megan Gorman: One of the things to keep in mind is that when you deal with large endowments or even wealthy families, you are really dealing with an institutional approach. As a result, process is key to mitigating any risk in managing these types of assets.
As the chair, it is not my job to pick the underlying investments. We have an outside advisor to help with that. But investing at this level is complex as we are dealing with both the public and private markets. I believe my role is to help drive important conversations that the committee needs to have to make key decisions. That may include education about certain segments of the market.
But just because it is serious work, doesn’t mean that exploring the capital markets can’t be easy to understand and enjoyable. I try as best as possible to engage all committee members – even those who do not have an investment background – to learn more about why certain investments are worthy of consideration. That way, when they make decisions, they are meeting their fiduciary duties.
What advice would you give to young women who are interested in pursuing a career in financial planning or wealth management, especially in navigating a traditionally male-dominated industry?
Megan Gorman: Look, it is a male-dominated industry. Is it getting better? Sure, but there’s still a long way to go.
But a lot of the best parts of financial planning is really about reading emotions and understanding behaviors. While this may be a generalization, women tend to have strong skills in this area. So it’s a career path that can be extremely fulfilling.
So my advice is to look for where the women are – the ones who have climbed the ladder ahead of you. We understand what it’s like to be overlooked or not considered. We’ve found ways to make our own opportunities. And we will help the women behind us to progress.
How do you maintain a work-life balance while juggling the demands of running your own firm, previously writing for Forbes, and serving on the NEFE board?
Megan Gorman: I’m not a big fan of the term ‘work-life’ balance. It feels like a term created to make you feel bad about yourself. Anyone who is successful generally doesn’t follow the concept of ‘work-life’ balance.
In my case, I have a lot of different interests and ambitions. I’ve found that when an opportunity presents itself, you need to go for it and see where the adventure takes you. And I strive to be a renaissance woman and have a strong intellectual curiosity with the world.
In your experience, what are some of the most common financial planning mistakes or blind spots that you see among your clients, and how do you help them address those issues?
Megan Gorman: I would say that the biggest struggle we all have in our financial planning is maintaining a good understanding of what we spend. It’s the most important number in planning. Most people underestimate what their spending is. Getting them to the place where they have their arms around this number is one of the greatest challenges.
What are some of the most significant personal finance trends or developments you’ve observed in recent years, and how are they impacting your clients’ financial strategies?
Megan Gorman: Given the current political climate, acquiring property overseas has become the norm for high-net-worth individuals. From Italy to Costa Rica to Portugal, people are looking for places that are calmer politically and offer a more cost-effective lifestyle.
But, of course, this opens up a whole host of issues. There are numerous tax and estate planning considerations that need to be worked through. Depending on the country, it can be very complex. Further you also need to consider medical coverage. Ultimately you want to make sure they can live a life abroad with the same benefits of living inside the US.
Lastly, is there a specific mantra, quote, or affirmation that you hold close to your heart?
Megan Gorman: “Life is to be lived. If you have to support yourself, you had bloody well better find some way that is going to be interesting. And you don’t do that by sitting around.” – Katherine Hepburn
“Pour yourself a drink, put on some lipstick, and pull yourself together.” Elizabeth Taylor
Emily Sprinkle, also known as Emma Loggins, is a designer, marketer, blogger, and speaker. She is the Editor-In-Chief for Women's Business Daily where she pulls from her experience as the CEO and Director of Strategy for Excite Creative Studios, where she specializes in web development, UI/UX design, social media marketing, and overall strategy for her clients.
Emily has also written for CNN, Autotrader, The Guardian, and is also the Editor-In-Chief for the geek lifestyle site FanBolt.com
