Guest: Megan Gorman, Founder and Managing Partner of Chequers Financial Management, a female-owned, high-net-worth tax and financial planning firm based in San Francisco.

In a Nutshell: High-net-worth clients have high-net-worth needs. Advisors who want to swim in the deep end of the pool have to scale the quality of their teams, their tech stacks, and the services they provide beyond basic wealth management.

On today’s show, Megan Gorman discusses how her firm meets the business challenges of serving high-net-worth families, including personalized services that address both the technical and emotional aspects of wealth, executing on client promises, tax and estate planning, and building a world-class team.

We also discuss insights from Megan’s new book, All the Presidents’ Money: How the Men Who Governed America Governed Their Money.

megan gorman

Megan Gorman: “The book and the story of the presidents are really a story about the challenges we all face. The issues today are the same as they were over different parts of American history.”

.Megan Gorman and I discuss:

  • How Megan draws on her background as an attorney and her passion for tax strategy when advising high-net-worth clients.
  • Common financial issues that high-net-worth individuals face and how Megan created a “one-stop shop” to meet her client’s needs.
  • Megan’s vision of the “perfect” client experience.
  • Why Megan likes hiring people who have experience in other service industries, like hospitality.
  • How Megan has delegated responsibilities so she can focus on the best uses of her time as the firm approaches $1 billion in AUM.
  • Using high-quality work to drive referrals.
  • The importance of strategic annual planning.
  • What researching the presidents taught Megan about universal money management challenges.
  • Which president Megan wishes she could have advised and which president she would have tapped to be the CEO of a new advisory firm.

. Quotes: 

Megan Gorman on delivering personalized solutions for common high-net-worth challenges:

“How we typically work with clients is very holistically. And so right now, like a lot of advisors, we’re dealing with the fact that the unified credit is scheduled to go down in 2026. So it’s a lot of really intricate estate planning. We’re talking about SLATs and all the fun things of moving things out of estates. In this interest rate environment, we’re talking more about irrevocable life insurance trusts to help mitigate taxation, and really just working to understand with clients, what is important to them? Is it the income tax consequences or the estate tax consequences? Because never the two shall meet. You really can’t get strategies that benefit both. The other thing that we’re focused on is working with different generations. I’ve worked with certain clients for 20 years, and so their kids are now adults. I often work with Generation 1 and my colleagues will work with Generation 2. I think the hardest group to work with right now is the $20 to $30 million space, because depending on what the law is, it will drive whether they need to do something. But a lot of them are starting to feel the pressure that they should act at some point. So again, it’s a lot of deep discussions, a lot of understanding what’s important, and also understanding the underlying assets. It’s a lot of fun, a lot of problem solving, but it’s not one-size-fits-all. And just because something works for one client doesn’t mean it works for another.”

Megan Gorman on growing along with her firm:

“I think in growing a firm — and we’re getting closer to a billion — I think what you’re focused on is always growing with the firm. So as much as I love a lot of the day-to-day aspects of running a firm, over the course of my career, I’ve had to also accept that my best skill set is with the client. That’s the best thing I can bring to the firm. And so as time goes on, you’re constantly evolving the firm and looking to your colleagues to take responsibility of different parts of the firm. There are key parts of the business that I feel very strongly about staying involved with. And there are other parts where I’ve learned that I have to staff it out. Because when I’m in front of the client, that’s the best thing that I do. And it’s not easy. When you’re in this industry, there is that fork in the road where you have to decide, are you going to remain client facing? And it’s hard, because anyone in a client-facing role knows you are working 24/7. It’s a very different lifestyle and mindset. But what I found was that my passion is spending time with the clients and the problem solving that comes with complex estate and tax planning.”

Megan Gorman on cultivating and growing her client base:

“I think the quality of the work is what gets people to refer us. But what’s interesting is I think it’s because we’re all very social with our clients. Not like taking them out golfing or anything like that. We spend a lot of time with them and I think we talk about a lot of things that don’t get spoken about so that makes it an easier entrée when someone wants to refer. And I think it’s really important to thank the clients when they refer you, but it also means the pressure’s on. I tell my team, ‘Okay, this client knows six of our other clients. So we have to be doing everything consistently.’ We have to be on the ball because they bring you the clients, but they can also move the clients.”

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