Brian Gray made partner at a top 100 CPA firm, built a career advising billionaires and high net worth families on complex tax strategies, and then realized that none of it had made him any happier.
Brian is a tax partner, award-winning CPA, frequent speaker at the USC Tax Institute, and the author of Suck Less, Laugh More. He has had a front-row seat to some of the world’s most successful entrepreneurs and noticed a pattern: about 10% of them get the balance right and 90% are still searching. By his early forties, he recognized himself in that pattern. He was helping clients structure their legacies while his own family life was strained, and he had been telling himself that family came first when his actions said otherwise.
This conversation goes deeper than practice management. Brian shares the specific moment that shifted everything, the exercises he used to identify the beliefs running in the background, and how he rebuilt his personal values, his family values, and eventually his firm’s values from the ground up. His firm’s core value landed on caring, and he and his business partner made the financial commitments to back it up, hiring for capacity and reinvesting in their team even when it meant reducing the bottom line.
The conversation covers:
- Why making partner didn’t change anything and how that realization set off a deeper search
- How having a front-row seat to entrepreneurial clients revealed the pattern: financial success rarely equals fulfillment
- Why telling yourself family comes first when your actions say otherwise keeps you stuck
- How writing down seven days of negative and positive emotions reveals the patterns running in the background
- Why he moved “success” from his number one value to number six and replaced it with love
- How his firm landed on caring as its core value and then made the hiring decisions to actually live it
- The warrior and the wizard framework: why achieving eventually needs to give way to mastering your emotions
Brian’s core insight is one that lands differently depending on where you are in your career: growing is not the end game. Growing is the ability to continue making more of yourself so there is more of you to give. That shift, from growing for status to growing for contribution, changed everything about how he shows up for his family, his team, and his clients.
This episode is for firm owners wondering whether the next milestone will actually feel different, leaders curious about how to align personal values with firm culture, practitioners ready to examine whether their definition of success is still serving them, and anyone who has ever made it to the top of something and wondered what comes next.
BOOK RECOMMENDATIONS
Two books mentioned in this episode:
Suck Less, Laugh More by Brian Gray
Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins
TIMESTAMPS
00:00 – Brannon Poe intro and podcast welcome
00:13 – Introducing Brian Gray: tax partner, speaker, author of “Suck Less, Laugh More”
00:48 – The gap between financial success and fulfillment: what Brian observed in wealthy clients
01:39 – Asking the question: when is enough, enough?
02:05 – Making partner and realizing it did not solve anything
03:07 – The Olympic gold medal pattern: achieving the goal and wondering what it was all for
03:32 – What the astronauts who went to the moon felt when they came back
04:02 – How alcohol became a way to numb the gap between achievement and meaning
04:51 – What it looks like when high-achieving CPA clients are financially successful but not fulfilled
05:10 – Growing as a way to become more, not just accumulate more
06:12 – The midlife reset: when it arrives, how long it lasts, and what kind of clarity it takes
06:51 – Helping clients structure their legacies while his own life needed restructuring
07:17 – The specific moment of clarity: “my family deserves better than I’m being”
08:21 – Being honest about what really came first: business or family
09:03 – The lies high achievers tell themselves and how the ego protects against discomfort
09:49 – Humility and gratitude as the antidote to self-deception
10:13 – How a core belief like “success equals happiness” gets installed and how to question it
10:55 – Shifting the number one core value from success to love, and what changed
11:17 – The seven-day emotion-tracking exercise from “Suck Less, Laugh More”
11:58 – What the exercise reveals about the emotional patterns running in the background
12:22 – The warrior and the wizard: why the achiever eventually gets tired
12:45 – Why high achievers are especially at risk of the burnout that comes from the warrior pattern
13:07 – Tony Robbins on emotion: you have already felt what you are chasing
13:26 – Why the satisfaction from external achievements lasts days, not months
14:04 – Stated values vs. lived values: how Brian approached this for himself, his family, and his firm
14:39 – Writing down eight family values with his kids in middle school
15:29 – How the firm’s leadership team landed on “caring” as the number one company value
16:08 – What it actually means to live the value of caring: hiring for capacity and investing in the team
16:27 – Hiring and client decisions driven by values, not just targets
17:07 – Funny story: parenting teenagers and the wisdom of just saying yes
18:15 – Book recommendation: “Suck Less, Laugh More” by Brian Gray
18:42 – Additional recommendation: “Die with Zero” by Bill Perkins
19:03 – Where to connect with Brian: LinkedIn
TRANSCRIPT
Brannon: I’m Brannon Poe, and this is The Accountant’s Flight Plan podcast, where you can enjoy engaging conversations about mergers and acquisitions and accounting practice management. Listen in on strategies to build a more fun and valuable accounting firm.
Welcome to The Accountant’s Flight Plan. Today I’m talking with Brian Gray. Brian is a tax partner at a top 100 CPA firm and the author of a book called “Suck Less, Laugh More.” Brian has impressive credentials: an award-winning CPA, a frequent speaker at the USC Tax Institute, and a trusted advisor to entrepreneurs and high net worth families on complex tax strategies. By his early forties, he hit a wall that a lot of successful people encounter. He was helping clients structure their legacies while his own family life was strained, and his book documents the rebuilding of his definition of success. Welcome to the show, Brian.
Brian: Thanks for having me. I appreciate being here.
Brannon: First question: you have seen hundreds of wealth stories up close as an advisor to high net worth families. At what point did you start noticing a gap between people who are financially successful and how fulfilled they actually were?
Brian: To have financial success, you put a lot of focus into your business and your career, and with that focus, you get rewarded. The question becomes: when is enough, enough? Having a front-row seat to some of the world’s greatest entrepreneurs, including a few billionaire clients, you realize that no matter how much someone has, there always seems to be not enough. The chase never fully ends. And I think that can be unfulfilling.
For me personally, I was chasing making partner at a firm. I thought that was the ultimate success. When I got there, it didn’t feel any different. I was still just grinding, and the dream of making partner was not going to solve all my problems. It didn’t solve any problems, actually. I feel lucky that having these entrepreneurial clients, many of whom were also in that same chase, helped me see the pattern earlier. Maybe 10% of them get it right and 90% are still searching.
Brannon: You know, as of this recording the Olympics just happened, and it reminds me of a pattern with gold medalists. They train for years, they win, and sometimes what follows is a real low. Are you familiar with that?
Brian: They don’t advertise what happens after the goal. There is documented history of astronauts who went to the moon experiencing something similar when they came back. You’ve gone to the moon. What else is there? Getting the gold medal, making partner, making a million dollars, making a hundred million: you reach that goal and you realize nothing has changed. What was it all for?
That’s exactly where I was. And not fully understanding it at the time, alcohol became a way to numb the confusion. From the time I made partner to the time I figured things out, I was drinking more than I should have. I wasn’t as focused. I hadn’t been spending time with my family because I had been so focused on work, and then suddenly I had more space and didn’t quite know what to do with it.
Brannon: Having experienced this yourself, do you now see those patterns in clients? What are the signs that someone has a lot of money but is not actually happy?
Brian: You see it everywhere once you become aware of the pattern. The realization I came to was that I wasn’t growing for myself. I was growing to become more of a result, a number, a status. What I eventually understood is that growing is not the end game. Growing is the ability to continue to make more of yourself, so there is more of you to give. That was the turning point.
It took a long time to get there. I wrote the book and shared the examples so people could work through what actually fulfills them, because it is not the number in your bank account or the size of your house. You have to get to a certain point to really know that. Most people hear “more money, more problems” and think: let me try it. Let me deal with those problems. So you go get the money and the success, and then the question becomes how do you figure out what actually matters.
For men especially, this tends to land somewhere between 40 and 42, though it can come earlier or later. How long you stay in that place and what kind of clarity you need before you move forward depends on the person.
Brannon: During this time, you were helping clients structure their legacies while your own personal life was under strain. When did you realize something had to change?
Brian: I remember it as a specific moment. I had told my wife I would stop drinking. I was struggling to actually follow through because I had essentially wired myself to associate fun with drinking. But there was a moment of clarity after a difficult night when I said to myself: my family deserves better than I’m being. Not better than who I could be. Better than how I was actually showing up. That was the leverage I needed over myself.
Brannon: You’re very open about all of this. Was that hard to admit?
Brian: I put a lot of things before my family coming through the ranks of a firm. Long hours, going out with coworkers, going out with clients. Everything was business first and family second. I told myself family was first, because that is what you are supposed to say. But the honesty is more useful than the comfortable story. Lying to yourself doesn’t help you. Telling yourself family is number one when your actions say work is number one doesn’t move you forward.
Brannon: You mention in your book some of the things entrepreneurs lie about. What are some of the other common ones?
Brian: The ego does a number on you. It doesn’t want you to feel pain or be wrong. Humility and gratitude are the antidotes to self-deception. If you think you might be lying to yourself, it’s likely your ego trying to protect your feelings. But there is so much to be grateful for, so much to learn, so much to grow from, that the lie just keeps you stuck in the same pattern.
Some people don’t even realize they’re doing it. It’s a blind spot. You have to start questioning things you have never questioned before. For me, the core belief was: if I am successful, I will be happy. You could see it in the house, the cars, everything around me was about looking successful. That’s a belief society tends to install in high achievers. My number one core value now is love. That changes everything. Now I try to be a blessing. I try to give more than I take, to do things that light up other people. That brings me more joy than anything the old value ever did.
Brannon: We all have beliefs running in the background that we’re not even conscious of. How do you start to become aware of them?
Brian: There is an exercise I write about in the book. For the last seven days, write down every negative emotion you felt. Frustration, anger, anxiety, whatever came up. Then do the same exercise for the positive emotions: love, satisfaction, gratitude. What almost always happens is that the negative list comes much more easily than the positive one. Once you see that, you can start to ask: what patterns am I running? Why am I always frustrated? Why doesn’t gratitude show up more naturally?
I describe this in the book using the framework of the warrior and the wizard. The warrior in you wants to achieve and achieve and achieve. But the warrior gets tired eventually. The next step is the wizard, which is about mastering your emotions, understanding the patterns, and working from a different internal place. My mentor, Tony Robbins, puts it this way: every emotion you want to feel, you’ve already felt. So instead of saying “when I get the new job, when I get the new house, then I’ll be happy,” go back to a time when you already felt that. The satisfaction from external achievements lasts maybe five days at most. The real work is inside.
Brannon: I want to dig into your company values, because I have a feeling they reflect some of this inner work.
Brian: They do. I did the values work for myself first, recognizing that success as my number one value was taking me in the wrong direction. Success is still important to me, it’s just around number six now. Then I realized that as the dad in my family, we should write down what we were actually living at home. My kids were in middle school at the time. We came up with eight family values together, laminated them, put them up around the house. That was a powerful exercise. They got really into it.
After doing it personally and as a family, the last piece was doing it at work. Our management team worked through what our most important value actually was. We weren’t trying to be the biggest firm or break into the top 50. What we ultimately landed on was caring. We care. We want to create an environment of care, for our clients and for our team. That value really comes close to love when you sit with it. The feeling is similar even if the word is different.
But then came the real question: are we actually living it? If we say we care about our people and then we bring in new clients without adding capacity, or the tax laws change and workloads increase and we keep the same headcount, are we really showing up for the team? My business partner and I decided we needed to hire for capacity, to take some of our bottom line and reinvest it in our core value. Caring is easy to say. Making the hiring decisions and the financial commitments that back it up is what makes it real.
Brannon: You have to keep values top of mind so that you are actually living them, making hiring and client decisions that reflect them.
Brian: Exactly. It has to show up in the decisions.
Brannon: Before we close, do you have a funny story to share?
Brian: When you have kids in middle school, you are in the last stretch of real influence. With phones and rideshares and food delivery, kids have a kind of freedom now that used to wait until sixteen. It starts shifting around middle school. My advice to parents: just say yes to the kids. They are going to find a way to get what they want anyway, and you want to have family harmony. When you say yes to something you probably should say no to, you sometimes get the best reaction: they look at you and say, “are you sure?” And then you say, “no, actually I’m not.” It turns the whole thing into a dance instead of a fight. My wife is more of a fighter, so I have been working on coaching her on this approach.
Brannon: The book title is “Suck Less, Laugh More” by Brian Gray. That will be our book recommendation. Any others you’d like to suggest?
Brian: “Die with Zero” by Bill Perkins. I will say it is a little repetitive in places, but the core concept is strong. It is about actually enjoying what you have worked hard for, rather than endlessly deferring it. A good one that travels in the same direction as a lot of what we talked about today.
Brannon: Brian, thank you so much. What is the best way for people to connect with you?
Brian: LinkedIn is the best place to find me.
Brannon: We will put that in the show notes. Thank you, Brian.
Brian: You’re welcome.
