Perennial Pride

Tax season just wrapped, and the next one is closer than most of us want to admit. In this Perennial Pride Podcast episode, I borrow a simple idea from Stoic philosophy, focus on what you can control and let go of what you can't, and apply it to your tax situation. There's still time before the year ends to change what your next tax bill looks like. Key Takeaways Let go of the tax code, law change...

In Part 1, I walked you through how I evaluated a multifamily syndication from the investor's chair. This time I sat down with Jeremy Dyer, VP of Capital Formation at Rise48 Equity, who's been on both sides of the table, to talk about what operators wish more investors would ask. If you're weighing a private real estate deal, this conversation gives you the questions, the red flags, and the honest...

I get asked "where should I invest?" all the time, and I can't answer that without knowing your situation. What I can do is walk you through how I actually decided on a real estate syndication, from the introduction to the site visit to the call with my CPA. The numbers matter, but the people behind the deal are what I'm really underwriting. Key Takeaways A referral from someone you trust is where...

When someone tells Tom they want to pay less in taxes, he's learned that's rarely the real question. In this episode, he breaks down what's actually going on beneath that statement, and why the strategies that move the needle, like entity structuring, Roth conversion timing, and cash balance plans, take years of lead time to set up. The real shift is trading a number-focused mindset for a plan-foc...

Charitable giving sounds simple until you get into the details, and most people never make it past the first question: where do I even start? In this episode, Tom walks through the giving landscape from cash donations and donor-advised funds to charitable trusts and leveraged giving, and why the reason behind your giving has to come before the structure. He also covers where the IRS has tightened...

Executive Summary If you're a business owner maxing out your 401(k), SEP, or IRA and still facing a growing tax bill, there's a whole category of retirement planning you're probably not hearing about. In this episode, Tom breaks down cash balance and defined benefit plans, tools originally built for large corporations that business owners can now design, own, and control for themselves. It's not a...

Summary Tom opens this episode with a question most successful business owners avoid: what happens to everything you've built after you're no longer here to manage it. He explains that a trust isn't really a legal document, it's a structure, a set of intentional decisions about who receives your assets, when they receive them, and how much control they have. He breaks down the basic split between...

Summary For most business owners, the company they built is their biggest asset, yet so few of them spend real time thinking about how they'll eventually exit it. In this episode, I walk through why taxes are often the largest cost of a sale, and why planning ahead, sometimes five to ten years ahead, can be the difference between keeping the bulk of what you built or losing a significant chunk of...

Summary Most of the financial world is obsessed with investment alpha, chasing better returns, better allocations, better timing. Tom argues there's a bigger, quieter opportunity sitting right next to it: tax alpha. Taxes are the number one expense most successful business owners and professionals face, and a huge amount of that expense happens invisibly, through withholding you never see land in...

Summary I recently talked with someone who'd just finished their tax return and found out they owed over sixty thousand dollars they hadn't planned for. Not their total tax bill, just what wasn't withheld, plus penalties on top of it. When I asked when their CPA knew about this, the answer was simple: when they did the return. That's the moment I want every Perennial Pride listener to avoid, and i...

Summary Every time you solve a financial challenge, a new one takes its place. Make more money and you face a growing tax bill. Reduce those taxes and you need a smarter investment strategy. Build real wealth and now you're thinking about retirement. Reach retirement and legacy planning moves to the front. Most people spend their lives chasing a state where problems disappear. That state doesn't e...

SUMMARY True wealth planning goes beyond spreadsheets and tax returns. That's the premise behind Heidi Olson's work at Pathfinder Legacy, and it's what drew Tom to have her on the show. In this conversation, Heidi shares how she helps families, farmers, and business owners move past the discomfort of estate and succession planning to get to what really matters: making sure the right people know th...

Summary This episode is part two of a series covering Tom's due diligence trip to Raleigh, North Carolina, where he evaluated a multifamily real estate syndication opportunity. This time, Tom is joined by his son Aidan, a college student who came along for the trip and got a firsthand look at how private real estate investing actually works. Aidan shares his honest first impressions, what surprise...

Summary Every advisor, every CPA, every financial professional has heard it: "I'm paying way too much in taxes." And while that pain is real, I've noticed something important when I dig a little deeper with clients. The taxes themselves are often the most visible and most painful part of a much larger problem. Just like a fever tells you something's off without telling you what, a high tax bill is...

Summary There's a certain kind of financial education that never shows up in a classroom or on a balance sheet, and that's what Tom set out to give his son on a recent trip to the Raleigh, North Carolina area. Alongside touring a multifamily syndication investment, Tom used the experience to open the door on how real investors evaluate operators, read markets, and make decisions with significant c...

Summary There's a version of financial success that looks good on paper but feels off in practice. You've got money coming in, multiple advisors in your corner, and accounts growing in the background — but you can't shake the sense that something isn't quite working. That unease, Tom argues, is almost always a design problem, not a money problem. In this episode, Tom walks through exactly how fina...

Summary Tom opens this episode by flagging one of the most expensive planning gaps he sees among business owners: the assumption that there is always more time to figure out the exit. His guest, Steve DeTray, CEPA and founder of Freedom Path Planning, brings a sharp framework to the conversation built on years of working directly with CPA firm owners who come to him too late, or just in time. They...

Executive Summary A college tour with his son gave Tom Suvansri an unexpected lens for examining some of the most important principles in personal finance. In this episode, he draws five lessons from the trip—on exposure, cost vs. return, legacy, comfort zones, and life design, and connects each one back to the wealth decisions his listeners face every day. The episode's central idea: most people...

Episode Summary Balancing "offense vs. defense" in your financial life to build resilient, optimized wealth It uses a sports analogy (especially basketball/March Madness) to explain how: Offense = wealth-building activities (investments, income, growth, assets) Defense = protection and structure (tax strategy, insurance, liquidity, risk management, debt strategy) Key ideas include: Most people ove...

Episode Summary In this episode of the Perennial Pride Podcast, Tom Suvansri sits down with philanthropic advisor Barron Damon to explore a topic often overlooked in financial conversations: how we use our wealth for good. With over 20 years of experience in the nonprofit and philanthropic space, Barron shares his personal journey into philanthropy, sparked by a life-altering event that reshaped h...

Summary In this episode of the Perennial Pride Podcast, Tom Suvansri dives into the realities of tax season and the growing risks taxpayers face from fraudulent schemes. Using the IRS "Dirty Dozen" list as a foundation, Tom breaks down common tax scams—from phishing attempts to misleading social media advice—and explains how easily individuals can fall into costly traps. More importantly, he shift...

Summary Real estate investing often seems complicated for those who are busy running businesses or managing their careers. In this episode, host Tom sits down with Neil Timmins, founder of Little Guy Loans, to unpack two major paths into real estate: becoming an operator (fixing and flipping properties) or becoming the lender behind those deals. Neil shares insights from more than 20 years in the...

Episode Summary In this reflective episode of Perennial Pride, Tom Suvansri shares lessons sparked by a college visit trip with his son — and how that experience became a powerful metaphor for life, finances, and long-term fulfillment. Tom explores the idea that life is a compounding journey shaped by daily decisions. Whether in finances, health, relationships, or personal growth, the choices we m...

Episode Summary In this episode, host Tom Suvansri sits down with Josh Gilmore, SVP at SDIRA Wealth, to explore how real estate investing can serve as a long-term pathway toward financial independence. Drawing from personal experience and over a decade working with investors, Josh explains how direct ownership of rental properties can create predictable income, tax efficiency, and protection again...

EPISODE SUMMARY Taxes are not a once-a-year inconvenience. They are a system that quietly influences nearly every financial decision you make — how you earn, how you save, how you invest, how you use your money, and how you transfer wealth to the next generation. In this episode, we break down the five stages of wealth where taxes play a critical role: How you earn How you save How you invest How...