Wealth Actually

Frazer Rice
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Covering the issues that affect business, entrepreneurship, wealth, trusteeship and culture.

  1. 3D AGO

    Bringing Simplicity Back to Investing

    In a world of noise and distraction, there is a trend in “Bringing Simplicity Back To Investing.” RICK FERRI and I talk about why it’s important for investments and why it’s important for individuals. You’re going to leave here understanding a new framework for looking at your investment portfolio and hopefully bring some peace of mind as you go forward. https://youtu.be/8EFnt_UTjEA Rick Ferri has been a good friend to the podcast. He shares his insights on simple investing, emphasizing the importance of clarity, discipline, and understanding the core principles of investing. He discusses the pitfalls of complexity, the value of index funds, and how to maintain a disciplined approach amidst market noise. https://open.spotify.com/episode/743dxOLLgZjUzKszZo4Owy?si=57mqK1ZmQ0a7LPdcwVoQ-g Keywords investing, index funds, simplicity, portfolio management, financial planning, discipline, asset allocation, tax efficiency, global growth, investment philosophy Key topics The philosophy of simple investing The stages of investor learning: darkness, enlightenment, and simplicity The importance of cash flow and intrinsic value in investments Asset allocation based on liabilities and time horizon Tax-efficient investing strategies for taxable and retirement accounts Risks of alternative investments and private equity in retirement plans Discipline and automation in maintaining investment strategies Chapters of “Bringing Simplicity Back to Investing” 00:00 The Philosophy of Simple Investing 07:03 Stages of Investment Understanding 11:19 Financial Planning and Purpose 17:57 Implementing a Simple Portfolio 23:01 Discipline in Investing 30:46 Navigating Complexity in Wealth Management resources Rick Ferri’s Website – https://rickferri.com Bogleheads.org – https://bogleheads.org Index Fund Book by Rick Ferri – https://www.amazon.com/s?k=Rick+Ferri&ref=nb_sb_noss_2 Website – https://rickferri.com Twitter – https://twitter.com/RickFerri Skeptic’s Guide to Investing Outline: “Bringing Simplicity Back To Investing” Introduction: Three parts to simple investing: Philosophy, Strategy, Discipline Part 1: Philosophy: Overview: Embrace Simplicity – the Education of an Index Investor – 4 stages 1: Born in Darkness (who you ask, chasing returns, naive research) 2: Finding Enlightenment (measure, compare, enlightened) 3: Complexity Traps (slice’n dice, factors, the fallacy of perfection) 4: Embrace Simplicity (global equity, specific fixed-income as needed) Part 2: Portfolio Strategy Overview: Making the Philosophy Work for You 5: Setting Goals (family – culture, career – taxes, risk tolerance) 6: Managing Risk (three ways to allocate assets: required return, risk avoidance, cash-flow) 7: Tax Management (three account types, asset class tax, tax avoidance) 8: Investment Selection (ETF vs fund, balanced funds & TDFs) Part 3: Discipline: Overview: Implement, automate, stay the course 9: Implement fully (consolidate, tax issues, lump sum vs DCA) 10: Maintain regulatory (automate new, rollovers, TLH) 11: Adjust as goals change (accumulation vs distribution, tax situations, legacy) 12: Stay the Course (recommit occasionally, continue ed., conferences) Transcript of “Bringing Simplicity Back to Investing” Frazer Rice (00:00.962) Welcome aboard, Rick. Rick Ferri (00:02.3) Well, thank you for having me. Frazer Rice (00:04.258) Well, thank you. First of all, want to thank you for a kindness you showed me way back in time and having me on the Boggleheads podcast. It was probably worth at least 25 % of my book sales and it was a lot of fun to do and never forgot it. So it took a while, but here we are back on my podcast. And what I want to do is go through a little bit about really the three parts to simple investing, which I think is something, especially now with the proliferation of alternatives, a lot of noise with crypto. That sometimes we kind of lose sort of the forest for the trees as far as what’s the right things to be thinking about in terms of an overall investing philosophy sort of embrace. And so maybe let’s start with that. How do you think about the parts to a good investing thesis and what is your overall worldview on that? Rick Ferri (00:55.804) So I’ve been in the investment advisory industry now for 40 years. And what I have learned is that the simpler you can make investing and the simpler you can make the portfolio, the better for you, the better for your family, the better for those who will inherit your portfolio. Don’t make it complicated. Complexity is just job security for those people who are selling you things and trying to manage your money. And in the end, you don’t benefit from that. They do in the form of fees. And if you just had a simple portfolio of a few good index funds and maybe some individual securities, you’ll be much better off and your family will be better off in the long term. And that’s the philosophy of simple investing. Frazer Rice (01:50.947) Mm-hmm. Rick Ferri (01:53.208) The second part is a strategy. How do you go about doing this, particularly if you’ve had a complex portfolio? And the third thing is discipline, which is how do you stick with simplicity as an investment philosophy? Frazer Rice (02:06.318) Sure. and without the second two, it’s great to have high-minded thoughts and so on, but if you can’t do it, it’s all for naught, and then if you can’t stick with it, then the best laid plans just kind of go asunder here. So let’s go back to the philosophy for a second here, and as you think about, it’s almost like the life cycle of discovery and learning about how these things work. How do you think about that from an ARC perspective? Rick Ferri (02:12.561) Ha ha. Rick Ferri (02:36.05) So generally when you’re new to investing, you’re going to ask other people for advice. I where you get that from, might be a friend or family member, maybe a professional advisor, might be coworkers, maybe you’ll just get on the internet and start searching. I don’t know, but 99.9 % of the time you’re gonna run into advice that is not very good. And the advice will be, you should put your money here, you should put your money there. Use these 10 different funds. It’s just a lot of confusion, quite frankly. I call this stage darkness because you don’t, you you’re just investing in the dark. You don’t know. And a lot of the advice is going to be very short based upon short-term performance. So recency biased people are going to be recommending, but you know, growth stocks because the Magnificent Seven has done well in the past. Or buy crypto because crypto went up a lot in the past and so therefore you should buy it now. And so most of the advice you’ll get in darkness is going to be recent based upon recent performance and rather than looking at it over say how should you be investing over 10, 20, 30 years and that will end up being quite different. So darkness is where we all begin. And most people stay in darkness. They never get out of darkness because they don’t put the brain cells to work to look at how am I doing? I mean, how has that done for me? What seems to be happening in my portfolio? Really? Do I really know what’s going on? And then the ones who are very fortunate start asking questions about, what if I just Frazer Rice (04:06.125) You Rick Ferri (04:31.334) bought the market and bought an index fund and just got the return of say the US stock market or the international stock market and that’s all I ever did. Would I be better off? And the answer to that 98 % of the time is yes, you would be better off if that’s all that you did. And if you come to this realization, I call it the second stage, which is enlightenment, where you now realize that, okay, all the stuff I’ve been doing may have been okay. I’ve been moving in and out of things, but now I need to start looking at just buying the market and holding it for the longterm. And that’s enlightenment. But for some people, it doesn’t stop there. And they start to dig into this idea of indexing. When you start doing that, it’s good that you’re learning, but you’ll start running into a whole lot of noise. That is alternative indexes, enhanced indexes uh… explore strategies all of these things that you’re going to take this nice simple concept called indexing and make it complicated again. So you start adding all these things to your portfolio because it has the word index in it or maybe the word passive in it and uh… advisors are notorious for doing this it’s called complexity for job security Frazer Rice (05:39.148) Right. Rick Ferri (05:54.066) Basically, are, you know, you take the idea of indexing and you just add a lot of things all around the edges of it and you make a simple portfolio complicated. So the third stage of this process of simplicity is complexity. In other words, you’ve made something simple complex. Okay, so the last stage is Frazer Rice (05:54.221) You Rick Ferri (06:18.544) Simplicity. That is that you realize this is going on. You realize that all the stuff that you’re adding to your portfolio is just making it all complicated again. And that the people who are benefiting from this are not you, but the people that are selling you all this stuff. And you say, that’s it, I’m done. I’m going back to my second epiphany, if you will, which is simplicity. I’m just going to go back to a simple portfolio of a few broad index funds, US stock market index fund. An international stock market index fund that covers the whole market and a couple of bond funds, municipal bond fund and maybe corporate bond funds or treasury bond funds. And you could use index funds for those as well. And it’s a really low cost, very tax efficient and very simple. Frazer Rice (07:05.953) A couple of quick asides here. The first one is for people who are co

    35 min

  2. APR 15

    DIGITAL ASSETS ESTATE PLANNING

    This interview explores the critical importance of managing digital assets in estate planning, highlighting the challenges of digital inheritance, account access, and cybersecurity risks. TATYANA THURSTON and NATALIA PARKER share insights on creating effective digital estate plans, tools, and best practices. https://youtu.be/2N56L51cD6Q https://open.spotify.com/episode/01ScInrdux6UOQ0G1kPzNF?si=uiCizZbOTEisa9PJ_D_S5g KEYWORDS: Digital assets, estate planning, digital inheritance, cybersecurity, online accounts, digital executor, wills, estate law, digital legacy, digital estate management KEY TOPICS Digital assets definition and scope Challenges in digital inheritance and estate planning Tools and strategies for digital asset management Legal and cybersecurity risks in digital estate planning Guest Name Tatiana Thurston and Natalia Parker Sound Bites “Biometric security doesn’t work after death.” “Planning ahead saves hundreds of hours and pain.” “Domain name issues can take months to resolve.” Chapters 00:00 Introduction to Digital Assets 01:28 Understanding Digital Assets and Their Importance 04:14 Challenges in Estate Planning for Digital Assets 09:17 Navigating Access and Security Risks 13:22 Creating an Inventory of Digital Assets 18:21 Preparing Executors for Digital Asset Management 24:40 Resources and Tools for Digital Asset Planning GUEST RESOURCES DEXITPLAN TRANSCRIPT Frazer Rice (00:01.146) Tatiana and Natalia, welcome aboard. Natalia Parker (00:04.206) Thank you. Tatyana Thurston I Dexit (00:04.211) Hi, thank you for having me. Frazer Rice (00:05.966) We are, this is a new frontier for wealth actually. You are the first two person interview I’ve done so far. So it looks like the technical issues seem to have gone away. That’s great. But we’re gonna talk about something that I think is the driver for your new company and something that’s important to me because when I’m advising people around a lot of different topics, either estate planning wise or wealth management wise, the digital asset question comes up and. You’ve formed this new company. Tell us a little bit about that and more importantly tell us the problem that you’re trying to solve around digital assets Tatyana Thurston I Dexit (00:40.83) Okay, so I’ll first start with what is a digital asset because there’s a lot of different definitions out there and a lot of people have different concepts of what it might mean. of all, because crypto is in the news quite a bit, it is not just about crypto. Everybody has digital assets because basically if you are logging into an account and it is storing data, you have an account that has assets online and it could be monetized. It could be social media, which means that the information that’s there is very personal to you. It could be that you have reward points you’ve accumulated. There’s all sorts of types of assets that are out there and there is a pain point problem. Let’s die down. Natalia Parker (01:28.462) Yes, and we started actually, it was interesting, Tatiana just went through the process of writing a will and she will tell about it. I went through a divorce where we had online business and it was really, really hard to trace all those online accounts because I had no understanding how many we had and what to do with them and how even to find them. And Tatiana wrote a will. Frazer Rice (01:54.67) Yeah, no. so just to put a finer point on that, it’s not only the monetary assets and the social media accounts and everything that basically requires a password to get into it probably in this day and age. Natalia Parker (02:10.252) Yes, and I can tell you more than I lost pictures of my family from my daughter’s birth to age seven because I didn’t think that the iCloud password and iCloud identity gone through a divorce. Yes. Tatyana Thurston I Dexit (02:10.336) That’s all. Tatyana Thurston I Dexit (02:26.88) So she can resell for it. Yeah. Frazer Rice (02:26.992) Yeah, and a very painful thing to go through. so, Tatiana, as we sort of look at that example and make the definition a little bit even more in depth, how else do you sort of think about that in terms of the roles that are played from a Will’s perspective? Tatyana Thurston I Dexit (02:49.366) So from a will perspective, you have two kinds of entities. You have things where business owners have created online accounts where their business is running off of certain platforms. And you also have a personal side aspect. And it may be an influencer, it may just be your personal account. The thing is that we’re dealing with a problem of immortality. And this means that these accounts remain open, active and online, ready for hackers and ready for now, today, AI to continue the trajectory of that account because they’re making money off of the data that we’ve put online. So we actually have two things to look at. One is from the business perspective and how do you transfer a business over? Because maybe you’ve built a platform for 10 years on Facebook, right? You have a following which is important to your base. Maybe you’re just a mom and you’ve put all your baby pictures on there, like Natalia, and then what is the loss? What is the impact of that loss? And both are really difficult on families. So estate planning means that we actually need to be looking at these accounts, we actually need to be planning for these accounts, because down the line, it’s gonna be a heavy impact, whether it’s sociological, emotional, or monetary. Frazer Rice (04:14.552) So as we think about this little bit further, the concept that these accounts are going to live on beyond the life of someone who created them. Maybe dive into that a little bit, because I imagine you not only have points of risk, certainly during the lifetime, and someone hacking in and pillaging your bank account or otherwise maybe blocking access or something like that, but what happens when someone passes away? How do those risks translate to the people who are inheriting these properties? Natalia Parker (04:45.258) Okay, let’s talk about it. We have those certain pain points. The first one, when somebody dies, the executor or administrator, they don’t know what is existence. They don’t know what kind of accounts the person had, what they wanted to do with those accounts. That’s a first problem because they don’t know even what banking, where the life insurance, did they have Venmo because they don’t have access to phone. The second one, didn’t know what the person wanted to do with that account. Did they want to close, transfer, memorize it? They have no clue. The other one is authority as an executor doesn’t mean that you will get automatic access to the account. Many people think that yes, it is. No, for Google it doesn’t matter. Unless you were appointed as inactive account manager. The same for Apple. Frazer Rice (05:48.68) I was going to say those annoying terms of services agreements that no one reads and you click so that you get, you move on with life and get into your accounts, that’s where some of these details are buried. And the intersection between that and maybe what we call estate law and how an executor works, that’s where the friction takes place. Natalia Parker (06:09.43) Yes, I agree and many people don’t even know that that feature exists like legacy contact for Meta and Apple or inactive account manager. Otherwise, when you look at the hierarchy online tool, we call it Castonian tool, outweighs everything what you have in wheel. If the online tool wasn’t enabled, then it goes what kind of language you had in wheel. if you appointed some digital executor and if that executor was authorized to have access to all your accounts. The third one, it always default to terms of service. Terms of service for basically 99 % of each company says do not give access. Frazer Rice (06:56.09) So if you were stuck and you didn’t do anything and you relied on the terms of service, you could be in a really deep set of troubles. They might delete your account, they may not allow access, or they may make it otherwise very difficult in order to access and do it. You think that the person who died with it wanted to have done. Tatyana Thurston I Dexit (07:16.246) That’s right. Natalia Parker (07:16.598) Absolutely. Tatyana Thurston I Dexit (07:17.504) That’s why some of these really large companies have a custodial tool. You do have to go to certain settings within the device or within the account. And you can enable these tools so that you can either add what could be a legacy contact. It may not have the term beneficiary on it, but it’s important to be able to enact that so that these settings will allow certain access down the line. A lot of the companies are very particular about that the larger ones have it and then a lot of them don’t so Knowing which company has the most value to you and those terms of service is really important Frazer Rice (08:01.84). For someone who has an account that lives beyond them, there are identity and financial risks to having that. I can imagine, you know, when you put a credit card on file and, it’s auto-debated or you have information lurking out there that that’s a problem. Maybe talk a little bit about how bad that can get. Tatyana Thurston I Dexit (08:21.517). So I think there’s a few issues on that. We all know that there are scammers and hackers. The really important stories that have come out in the past is where AI is enabling recopying your name, image, and likeness posing as you live on a video stream or live on a phone call asking for money or data or information. And this is becoming really prevalent. This is where families, if they want to save and secure their reputational legacy. But also perhaps crypto, perhaps their banking accounts, it’s really important that they underst

    29 min

  3. APR 7

    QSBS ROLLOVERS

    BRADY WELLER discusses the intricacies of QSBS rollovers, including eligibility, timing, and strategic planning for founders and investors. The goal is to help the listener maximize tax benefits and navigate the legal complexities of this powerful tool. https://youtu.be/gvQ0ZskvWVI QSBS, tax exemption, startup founders, rollover, legal structuring, investment strategy, tax planning, startup exit, C corporation, Key Topics QSBS eligibility and benefits Challenges in executing rollovers Legal and tax considerations for founders Timing and risk management in rollovers Strategic structuring for maximum benefit “QSBS ROLLOVERS” Sound Bites “60 days is a very short window for founders.” “Rollover continues your holding period clock.” “Partial rollovers are common for founders.” Chapters 00:00 Understanding QSBS and Its Benefits 03:07 Challenges for Founders in QSBS Compliance 05:54 Advising Founders on QSBS Rollovers 08:57 Structuring New Ventures for QSBS Eligibility 12:00 Navigating QSBS for Tech and Non-Tech Founders 14:54 Investor Considerations in QSBS Transactions 17:46 State-Specific QSBS Regulations and Planning 20:57 Future of QSBS and Strategic Planning Resources Brady Weller on LinkedIn qsbsrollover.com qsbsreference.com Frazer Rice and Michael Arlein discuss the nuts and bolts of 1202 QSBS Features for Founders Guest links LinkedIn Transcript Frazer Rice (00:01.314) Welcome aboard, Brady. Brady Weller (QSBS Rollover) (00:03.043) Hey, Frazer, thanks for having me. Frazer Rice (00:04.738) Well, you are the nice compliment to a piece I just did with Michael Arlene on QSBS. We covered some of the nuts and bolts around 1202. You come at it from a little bit different angle. It’s usually where people, founders especially, have issues sort of complying with things like the three and five year rule. And otherwise really maximizing the capability of the rollover and the tax significance for it. Tell us a little bit about who benefits and what you do here. Brady Weller (QSBS Rollover) (00:35.107) Yeah, QSBS is. by far the biggest tax exemption available to individual taxpayers in the U.S. So it’s been something that hasn’t been up. I should say there’s not a massive advisory network around it. So it’s not something that’s been taken advantage of, I think, to its full scope. Michael, who you had on recently, is a top trust and estate planner for founders of companies around QSBS. The specific problem that QSBS rollover solve is for a shareholder of an early stage company. Most often founders or very early investors, say, maybe series A or earlier shareholders. It’s an incentive to basically hold your stock for a quote unquote long time. In this sense, that means, you know, now under some new rules, basically three to five plus years. It’s a tax exemption available to folks who hold their stock for at least five years. Then they can exclude from federal income tax now up to $15 million of gains when they sell that stock. So you have to be a shareholder in an early stage C corporation, early stage company. Frazer Rice (01:50.616). Those founders before three to five years are trying to figure out how to use this tool. What are the challenges in making sure they don’t blow up the transaction by transferring something poorly. Or having their company grow too large or have too much cash or those types of things? Maybe list out a little bit some of the challenges that are out there that that a founder needs to be aware of. Brady Weller (QSBS Rollover) (02:22.509). Yeah. So we don’t have to constantly caveat. I’ll mainly talk as though we’re speaking about the pre July 5th, 2025 rules for QSPS. Anything, any stock issued after that date, middle of last year. is under a slightly different set of rules. They are more expanded rules, but I’ll speak to this sort of from those old rules. And so the old rules state that you have to hold your stock for at least five years. And if you do, you can exclude a large portion from federal income tax, usually $10 million for founders. But if you don’t hold the stock for five years, your only option is to take the cash from that sale. For example, say you sell stock at year three or year four, and purchase new QSBS eligible stock with that cash within 60 days. So it’s sort of like the 1031 exchange. Folks maybe are more familiar with real estate property exchanges. Its sort of like a 1031 exchange for stock. So you take the cash and you purchase a like kind quote unquote asset with it. Now the challenge with that is 60 days is not a very long time. And when you’re a founder of a company who just went through liquidity. You just got your deal done and the whirlwind that that is. Now you’re dealing maybe in a post liquidity world. You’re maybe running another team at the acquirer or you’re otherwise involved. 60 days is not a long time to be able to find and diligence a new opportunity. . It’s just not feasible. Especially for founders to use that cash to say buy stock in someone else’s company. It just doesn’t make sense. Like risk adjusted, I suppose. Frazer Rice (04:05.579) No, it’s a miracle that your company did great. Now you have to go and find another miracle and make it work within 60 days. It’s crazy. Brady Weller (QSBS Rollover) (04:10.143). That that’s the biggest that’s probably the biggest barrier to executing them. For the longest time there just weren’t a lot of people. They hadn’t come alongside founders to help advise them on structured ways that they could do these rollovers. Yeah, the options are risky. It’s like take your money and invest it in Dave’s startup in San Francisco. He’s going to lose your money. So that may be what you want to do with that money. To keep your risk profile sort of moving. But that’s not tax planning in any way. Right. To make that decision just to save on federal income tax might not be the best way to use your rollover. So we’ve seen it much more for angel investors, something that they might use. People who want to maybe have a lot of deal flow. A lot of investment opportunities in front of them. But they want to keep that risk profile moving. I’d say timing and risk are the two biggest challenges when you’re trying to execute a rollover. Frazer Rice (05:13.805). As a detail on that, you’ve got your company. You’ve got $10 million coming to you. Hopefully tax free, similar to a 1031. You don’t have to go into one company, you could go into a basket of companies. Brady Weller (QSBS Rollover) (05:28.579). Yeah, you could take the cash, say you make $10 million from a sale. You could pay taxes on $3 million of it, assuming you haven’t hit your five year requirement. Then, you could roll over the other seven in various other deals. You could put it all into one new company. What the rollover actually does is it continues your holding period clock from the last stock. So if you held for three years in your original company stock, You sell. You’re able to reinvest those proceeds within 60 days. It continues your holding period. Once you’re beyond a combined five the next liquidity event in the second company. Now you have proper seasoning on your shares, for lack of a better word, and then you can sell them under the QSPS exemption. Frazer Rice (06:17.143) So, this gets to what you do on a day-to-day basis. So a founder comes to you and says, all right, I’ve got this situation I think that’s coming. And I need some advice. You’re sort of letting them know what’s happening here. How do you advise them, in a sense, whether it’s through your company or even as a general matter? Do you have a suite of other founders and companies that are out there? And then… Maybe also similar to a 1031, is there sort of an intermediary function that needs to happen in order for the asset or the cash to go into sort of a, for lack of word, like an escrow account to then be deployed correctly into the eligible next company so that you keep that period going. Brady Weller (QSBS Rollover) (06:50.713) Boom. Brady Weller (QSBS Rollover) (07:05.839) That’s a good question. It’s not as formalized as the, you know, in terms of the 1031 world where there’s sort of a designated intermediary and that’s sort of required step in the process. This is very much the wire goes into your checking account for the sale of company A stock. Frazer Rice (07:11.703) Mm-hmm. Brady Weller (QSBS Rollover) (07:22.281) You send a wire back out to purchase stock in company B. When someone comes to us and is looking for guidance on how to do a rollover, sometimes they’ve talked to tax or trust in state attorneys already, or maybe they’re CPA. And there are maybe 50 folks in the US who have, I’d say, Frazer Rice (07:37.463) Sure. Brady Weller (QSBS Rollover) (07:45.07) I call it advanced QSPS planning knowledge, which is they have the trust planning strategies, rollover knowledge, all of these things that sort of at their disposal that they can speak to, but it’s a very small network. so our firm is actually the only non-CPA non-law firm in the country that deals directly with founders on these. And so we ended up kind of playing quarterback, connecting them with the right attorneys, maybe the right CPA, if they don’t have one to make sure that the team is sort of assembled. You know, because the risk profile of taking your money and investing in someone else’s company typically doesn’t align with most founders’ interests at that time, the service that we provide is helping them to roll that money into a new startup of their own. We think these founder-led rollovers where the founder or the shareholder who sold their original stock can now direct the proceeds into a new entity that they own and control. It’s a really great way to execute this. It gives the shareholder, the founder the optimal amount

    30 min

  4. MAR 25

    Health as an Asset Class

    https://youtu.be/FU5IvtBbtCY JOHN SAMUELS from WELLWORTH ADVISORS discusses “HEALTH AS AN ASSET CLASS” and the nuances of personalized healthcare management for high-net-worth individuals. We contrast concierge medicine with comprehensive health advisory services. Learn about his book “WEALTHCARE” which lays out the frameworks of his practice. Finally, John goes into how expert navigation, team-based care, and strategic planning can significantly improve health outcomes and client relationships. Finally we hear a little bit about what his favorite medical shows are on TV! Key Topics Differences between concierge medicine and health advisory services Team-based care and specialist involvement Integrating healthcare with wealth management Debunking myths about healthcare access and VIP treatment Strategies for managing mental health and complex conditions Key Frameworks of Health as an Asset Class Team-based healthcare approach Evidence-based treatment decision-making Action Items Review your healthcare risk factors and create a plan. Organize your medical records and update legal documents. Engage a healthcare advisor to understand your coverage and treatment options. Chapters in “Health as an Asset Class” 00:00 Understanding Concierge Medicine vs. Health Advisory 02:11 The Importance of Team-Based Care 03:49 Collaborating with Client Advisors 06:23 Navigating Complex Healthcare Needs 08:07 Addressing Client Misinformation 09:40 Challenges in Mental Health Treatment 12:24 The Purpose Behind the Book 14:26 Debunking Myths in Healthcare 16:31 Preparing for Healthcare Interactions 20:56 Managing Healthcare Risks 23:05 Finding Resources and Support Resources Wellworth Advisors – https://wellworthadvisors.com John Samuels’ Book on Healthcare Management – https://www.amazon.com/Healthcare-Management-Advisor-Guide/dp/B09XYZ1234 More From John on “Wealth Actually”: https://frazerrice.com/ep-126-john-samuels/ Guest links Website – https://wellworthadvisors.com Email – mailto:john@wellworthadvisors.com https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/ Keywords healthcare, concierge medicine, health advisory, high-net-worth individuals, patient navigation, mental health, healthcare risk, medical research, healthcare myths, health insurance Titles Beyond Concierge: The Future of Personalized Healthcare for Wealthy Clients How Expert Care Navigation Transforms High-Net-Worth Healthcare Sound Bites “We map out the cost of treatment for clients.” “We focus on evidence-based treatment options.” “VIP care often doesn’t mean better care.”

    23 min

  5. MAR 13

    THE FIGHT AGAINST GASLIGHTING IN THE WORKPLACE

    “Breaking the Glass Ceiling: Julia Carreon’s Fight Against Corporate Gaslighting” In this episode, Frazer Rice sits down with Julia Carreon to explore her recent high-profile litigation against a major financial institution and her powerful insights on women in leadership, corporate culture, and overcoming systemic barriers. YOUTUBE https://youtu.be/e05k7SVQ2xI We discuss: Julia’s experience with workplace gaslighting and her litigation journey with Wells Fargo The importance of transparency, accountability, and protecting yourself in corporate environments How societal and corporate cultures disadvantage women, especially around motherhood and leadership The themes and motivations behind Julia’s book, Walking on Broken Glass Practical strategies women can use to build political capital and safeguard their careers The significance of external networks and understanding your personal strengths The evolving landscape of equity, ownership, and governance in corporations How to proactively prepare for and respond to systemic workplace challenges SPOTIFY https://open.spotify.com/episode/5c546gs6Qctx4bGOvalgXj?si=1dDyJxnwSyu4tnhXxpzVxg Timestamps: 00:00 – Introduction: Julia’s litigation and book overview 02:03 – Gaslighting in corporate culture and early experiences 04:14 – Dealing with systemic backstage politics and fighting for justice 05:10 – Motivations for writing Walking on Broken Glass 08:08 – Diagnosing workplace culture and gender dynamics 09:33 – The weaponized HR department and accountability 11:38 – Protecting yourself: cultural awareness and bias 13:12 – Demographics, gender disparities, and moving forward 15:12 – Institutional misogyny and societal shifts 16:05 – Motherhood, work-life balance, and corporate support 18:28 – Questions of corporate culture change post-COVID 22:21 – The fear factor and change in workplace loyalty 27:12 – Tactical career strategies and building political capital 28:15 – Always Be Executing (ABE) and tracking success 30:53 – The ownership mentality and equity’s role in career resilience 34:45 – Building internal and external networks for support 36:49 – Understanding personal aptitudes through testing and reflection 40:12 – Leveraging political capital and seizing opportunities 43:31 – How to follow Julia and stay updated on her journey Transcript Frazer Rice (00:01.004) Welcome aboard, Julia. Julia (00:03.32) Thanks for having me. Frazer Rice (00:04.652) Well, as I said in the opening, the concept of gaslighting in the boardroom is something that certainly isn’t new, but it doesn’t make it any more comfortable for the people who deal with it on a day-to-day basis or as part of their career. And you’re in the midst of litigation right now with a major financial services company. Maybe talk a little bit about what’s going on there. Julia (00:24.801) Yeah, so I am in a high profile lawsuit with my former employer. I would say this is not a path that anyone chooses on purpose. In my particular case, Frazer, I spent 20 years at Wells Fargo, 15 of which were pretty spectacular. I have come to realize almost maybe fairy tale like in terms of my experience. I want to talk about some of the things later on that made it a fairy tale. So yeah, I wouldn’t have chosen this. I did not see the culture at my former employer coming for me. I was blindsided by it and it got ugly quickly. One of the things that I think I am doing here. Or at least trying to do is not be shy about it. Not hide from it. Try to show women a different way for how to deal with these situations. Because I have very strong feelings about the fact. With the rollback of DEI and the current administration’s point of view on women, that we’re going backwards. If women don’t start fighting for ourselves in a more public way and without fear, then I don’t know where we’re going to be in the next five to 10 years. I am soldiering on and it’s not easy to your point. But it is what it is and it’s a fight that I believe is worthy. Frazer Rice (02:03.608) So it’s a daunting task taking on a big bank. Big financial services firm, whether it’s in this situation or frankly any. It’s just these well-resourced big behemoths. What has been the experience been like so far? As far as gathering information? Of getting the walls built that you need to in order to live your life while you go through this conflict with this bank? Julia (02:29.822) It’s hat that is the million dollar question. Right? I will say that in my case i got really fortunate and came across a quote. It’s going to sound really strange. But i came across a quote that said fear is fake and danger is real but fear is fake. I believe that the patriarchy wants women to be afraid. So it tells us these bad things are going to happen if you take on a big firm like this. It is grueling. The days are long sometimes. But once I internalize the reality that it is all fake in terms of all of the bad things that you think could happen really can’t happen. Worst case scenario, there’s nothing Like I’m not going to die. They’re not going to, you know, take away my family. Like all of these things, right? We tell ourselves that it could get really nasty. And in my case, I have to stay really grounded in the fact that what I’m doing is worthy. We tried my lawyer and I tried for 14 months to come to a different answer. And so in a way, not just telling myself fear is fake. But in another way, I kind of feel like it’s my destiny. Because, I just want to say this real quick, I had 20 years at a place that was not toxic. And so I know what good looks like, and this is not good. So in that way, I really feel like it’s my destiny. And so that’s what you do, and you have to have a good support network. I have a great husband, so that really helps. Frazer Rice (04:14.21) The, as I’ve told people, sometimes doing the right thing or going after something that upholds justice. It can be expensive and hard. I give you kudos for standing up. Not only for yourself, but others who are going through a difficult situation. Where you’ve had a significant wrong done to you. You’ve written a book about this experience as well. We can take some time to think, to talk about what the book tries to do. First of all, writing one in tandem with the process here, I think is a bit unusual. Some people do it after the fact. To go through a catharsis after going through a difficult process. Talk about first the why of the book.thhen we’ll talk a little bit about what you talk about in it. Julia (05:17.241) The book is called Walking on Broken Glass: Navigating the Aftermath of the Glass Ceiling.” It was co-written with a fabulous woman named Shannon Nutter. I hope people follow on LinkedIn. The book is not squarely about what happened to me the book came together. With Shannon and I meeting on LinkedIn. Then discovering that we had a lot of the same shared experiences as we are Gen X. in hindsight. Our generation has had the opportunity to have the most benefit of the Gloria Steinem Women’s Movement. Think about the fact that we got the advantage of the birth control and all of the DEI efforts that have been in the last 15, 20 years. And we really felt like there was still a long way to go. Then all of that is starting to go backwards. So last year when we met or the year before, we’re like, my God, the idea that we got the best of the best is shocking to us. And so what are we going to do about it? We really wanted the book to speak to women of all ages in their career. But it was written from a lens of two then 53 year old women who had seen a lot. We wanted to give the book as a love letter or a gift to our 35 year old self. To say, this is what we should have or wish we had known 20 years ago. Because we would have done things differently if we had really faced kind of what the challenges were that women are facing at work. In a real way right not in a way that sugarcoats it or pretends to throw it under the rug. And or always makes it the woman’s fault like the woman always has to be changing and evolving in order to adapt to the systems and i you know it’s exhausting right so the book was written for that reason and it does tap into a lot of the things that we both experienced. Julia (07:35.17) But it isn’t a kind of a personal journal of what happened to me with my former employer. Frazer Rice (07:39.82) Right, one of the things that I found useful about the book is you divided it into three sections. I think it brings us sort of clarity into what you’re trying to achieve here. The first one is just diagnosing the situation that you’re in. Maybe talk a little bit about that. Part one the understanding of your surroundings. What’s happening around you. The conditions that women are facing as they embark on these big situations in the workplace. Julia (08:08.982) Yeah. So the first part of the book does give a primer on kind of the history of feminism and how did we get here and what are some of the big open questions that are still left to answer. We also want to set the stage that makes it very clear that women are accountable for our actions in the workplace. Like this is not in any way a book that seeks to make someone who’s failing feel good about the fact that they’re failing, right? Shannon and I both reached really high levels of corporate success at major global firm. There is a lot of work to do. So we really try to dimension how, what are some effective ways for you to approach that work? What are some of the pitfalls and how are some of the ways that you can handle that? In a way that’s kind of clear-eyed, but never about putting the blame or the onus on the company. And if you don’t mind, I want to say something about that because it relates to my lawsuit. One of the things that I’ve heard criticisms ab

    44 min

  6. MAR 9

    THE TRUSTEE CRISIS: Navigating the Challenges

    There is a storm coming with the challenges of navigating the TRUSTEE CRISIS. It is one of the biggest blind spots in the “GREAT WEALTH TRANSFER” and will be the source of mountains of litigation for the unwary, https://youtu.be/hwQev88A03M Summary In this conversation, Frazer Rice and Jennifer Zelvin McCloskey discuss the current crisis in trusteeship, highlighting the shortage of qualified trustees amidst a significant wealth transfer. They explore the importance of modern trust planning, the challenges faced by individual trustees, and the need for better education and training in the field. The discussion also covers the emotional and interpersonal aspects of trusteeship, the functions and responsibilities of trustees, and the necessity of managing risk effectively. They emphasize the importance of building a pipeline for future trustees and improving the perception of the profession, while also identifying opportunities within the trust industry. https://open.spotify.com/episode/4qpkrVdaUa2AfDxgl7j3yN?si=XVgG3jE_Qpqq2JTqi8XLXQ Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠) Takeaways The coming crisis in trusteeship is already here. There is a significant shortage of qualified trustees. Trusteeship requires strong interpersonal skills and emotional intelligence. Managing risk is a fundamental aspect of trusteeship. Trustees critically need education and training. The role of a trustee is evolving with increasing complexity. Beneficiaries need to understand their rights and the trustee’s role. Custodial responsibilities are essential for asset protection. There are many opportunities for growth in the trust industry. Trust law and investment management are distinct fields. This Episode is for . . . Anyone that has an estate plan with a trust in it and doesn’t know what a trustee does Any advisor who works w/ multi-generational situations (that’s everybody in wealth management) Any RIA looking to sell Financial types worried about compliance world Fiduciary litigators Chapters of “THE TRUSTEE CRISIS: Navigating the Challenges” 00:00 The Coming Crisis in Trusteeship 02:06 Importance of Modern Trust Planning 04:11 Challenges with Individual Trustees 08:03 The Dwindling Pool of Qualified Trustees 10:06 Functions and Responsibilities of a Trustee 12:20 The Emotional and Interpersonal Aspects of Trusteeship 16:05 Managing Risk in Trusteeship 19:07 Building a Pipeline for Future Trustees 22:10 The Role of Education in Trusteeship 25:07 Improving the Perception of Trusteeship 28:19 The Need for Better Trust Education 30:39 Bifurcation of Trustee Functions 33:26 Distribution Functions and Beneficiary Relations 36:52 Custodial Responsibilities in Trusteeship 40:19 Consequences of Poor Asset Management 46:41 Curriculum for Trustee Education 52:13 Opportunities in the Trust Industry Transcript of “THE TRUSTEE CRISIS: Navigating the Challenges” Frazer Rice (00:01.068) Welcome aboard, Jennifer. Jennifer Zelvin McCloskey (00:02.723) Thanks Frazer, how are you today? Frazer Rice (00:04.782) I am doing great. We’re going to dive into a topic that is near and dear to both of our hearts. And that is what I’m describing as the coming crisis in trusteeship, but I think it’s already here. Which is the concept of qualified trustees being in short supply, right in the face of a gigantic wealth transfer. And first of all, before we get into that, just describe what you do on a day to day basis first. Jennifer Zelvin McCloskey (00:33.445) Sure, I actually wear a bunch of hats. Day to day, right now, I’m a full-time practicing trust and estate attorney. I’m also an individual trustee for a variety of trusts that need either somebody here physically located in Delaware for a short period of time or even a successor trustee. But I’ve also spent many, many years building programs in trust management and trust administration. Because there is this crisis of human capital that just does not exist. I built multiple programs. They’re housed out of the University of Delaware. So I act as a trust and estate attorney, do planning, administration, I teach in the area, I build programs in the area, and I serve as a trustee. PEAK TRUST MANAGEMENT CERTIFICATE Frazer Rice (01:23.182) A full plate to be sure. To me, I came out of Wilmington Trust and another trust company served an individual trustee too. I’ve seen all these different flavors of trusteeship. My general sort of bon mot around that is that the individual trustees. I’d say 95 % or higher don’t really have an appreciation of the risk and responsibility that they’re taking on. And then the corporates have their own issues, which we’ll get into in a little bit. If we pull back even further, modern trust planning in wealth management, why is this so important? Jennifer Zelvin McCloskey (02:06.275) That’s massively important. It’s not just for the mass affluent or the ultra high net worth. It’s for everybody. We have all of these assets that we have this hyperfocus on building and increasing our wealth. Making sure that we have the ability to sustain ourselves throughout our entire lives. But if we don’t do this type of planning, if we don’t have structures and implementation for when we die, then our assets that we’ve planned so diligently for will fall off of a cliff. We lose the ability to control ultimately what happens to those assets. Layered on top of that, of course, is the tax component for ultra high net worth folks who are trying to really focus and direct their assets to make and create generational wealth transfers. Without this type of functionality and wealth planning and estate planning long-term, people lose control of what they’ve spent so much time building. Frazer Rice (03:13.338) One of the things I tell people as far as trusts are concerned is that, you know, we’re putting these structures together. They’re durable enough to withstand taxation or creditors or other asset protection features, create some guidelines around distributing the assets to the next generation or other constituencies. But also have some flexibility to be able to deal with the things we can’t look into the crystal ball and figure out over time. And that those three things just putting a document together that tries to do all that is hard enough, but then to put it in the hands of somebody or something to administer and to exercise discretion around it. That’s where the real art and science kind of stitched together and create this issue. You know, as we think about that too, the idea, the history of these types of scenarios kind of goes back to, you know, you’d put a structure in place and then you’d go hire a bank and they’d take care of everything. How do you look at that and say, all right, we’ve gone well past banks to individuals and then to dedicated institutions. What is the problem there? Jennifer Zelvin McCloskey (04:22.956) Now the problem, there’s two problems. In my opinion, what I see is that, you know, your individual trustee by and large is Uncle Joe, right? He’s the guy that everybody goes to in the family. The responsible one. He’s the smart one. The wealthy one who, great, doesn’t know what the fiduciary duties are. He doesn’t know that he has a duty of impartiality. He doesn’t know that… Frazer Rice (04:32.419) Right. Jennifer Zelvin McCloskey (04:48.475) He can’t self deal unless the instrument says so. Doesn’t understand how the instrument works. He doesn’t understand the nuance and the legalese written into the instrument. But he’s flying by the seat of his pants and everybody looks to him as the respected one in the family. No one knows that they have the ability to challenge him. So with your individual run of the mill trustee named in the instrument, they just don’t have the expertise, they don’t have the technical knowledge. Don’t know what they don’t know. They can get into trouble in that way. The other problem that you have with professional individual trustees oftentimes is that they are not formally trained. They may be an attorney who is working in that area, who’s doing plans for people who may or may not know what the full scope of being a trustee is. They may not realize, I have to get a special insurance policy because my malpractice insurance policy doesn’t actually cover this type of fiduciary engagement. There’s a lot of landmines that individuals can run into when they’re doing this type of work. On the corporate side, the problems that we run into is that there’s just a complete and utter lack. Frazer Rice (05:50.061) Hmm. Jennifer Zelvin McCloskey (06:12.059) Of available educational programs to teach people the proper way to be able to understand trusteeship. It has always been, and it just has developed over time through, you know, oh, we’ll give it to the bank, the bank will do it. This apprenticeship model, and that just does not scale well because if you learn improperly at the edge of a desk from somebody that learned improperly at the edge of the desk. Then the person that you’re teaching now at the edge of the desk is learning what you learned improperly. So anecdotally, I did karate for a long, long time. And the man who taught me karate, I’m almost a secondary black belt to like, was serious in karate. And the man who taught me karate said, you practice, it makes permanent. Don’t practice wrong. Because when you’re practicing wrong, you’re making permanent wrong things. And that’s what the apprenticeship model has the risk of lending itself to. It’s not that every trustee that learns at the edge of the desk learns wrong, but the risk is too high because the fiduciary responsibilities and the duties are too high to run that risk. The other problem is that we have

    59 min

  7. FEB 27

    SPORTS MEDIA FOR ENTREPRENEURS

    Frazer Rice and Bram Weinstein, the “Voice of the Washington Commanders,” discuss the shift in sports media for entrepreneurs. The current state of sports journalism is in flux, especially with the decline of the Washington Post’s sports section and its implications for local coverage. We explore the opportunities that come from this void. (Including the potential for new media ventures and the challenges of monetizing content in a fractured media landscape). The discussion also touches on the future of the Washington Commanders, the importance of audience engagement, and the evolving nature of podcasting and digital media. https://youtu.be/O0syDGcSkvU https://open.spotify.com/episode/3Ut9QRj7X9QD1pGEA6y6qt?si=39nLO2reQ8SK_nj0zenzDA Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠) Takeaways The Washington Post’s sports section closure is seen as a significant loss. There is a growing opportunity for new media companies to fill the coverage void. Monetizing media ventures requires innovative strategies and diverse revenue streams. Podcasters face challenges in gaining audience traction and monetization. The Commanders’ future depends on effective roster changes and health improvements. Engagement with the audience is crucial for media success. Digital platforms like YouTube provide exposure but limited revenue. The media landscape is rapidly changing, requiring adaptability. Local sports coverage is essential for community engagement. The importance of maintaining journalistic integrity in a changing media environment. SPORTS MEDIA FOR ENTREPRENEURS CHAPTERS 00:00 The State of Sports Journalism 02:59 Opportunities in Media 06:07 Monetizing Media Ventures 09:05 Navigating Podcasting Challenges 11:59 The Future of the Commanders 15:06 Engaging with the Audience DISCOVERING BRAM, THE COMMANDERS, AND AMPIRE MEDIA BRAM on SPOTIFY AMPIRE MEDIA ON YOUTUBE AMPIRE MEDIA WEBSITE Transcript of “SPORTS MEDIA FOR ENTREPRENEURS” Frazer Rice (00:00.686) Welcome aboard, Bram. Bram N Weinstein (00:02.551) Hey, Frazer, how are you? Frazer Rice (00:03.736) Doing great. The last time we spoke it was about three days before the Chicago Hail Mary, so I’m viewing that as good luck. That must have been something having to call that game. Bram N Weinstein (00:14.071) That was part of the most magical season I’ve ever been a part of. Not only first ever for the franchise, but 12 and five, NFC championship game, hadn’t done that in a generation. It was pretty incredible, yeah. Frazer Rice (00:28.652) No, as a skins fan, now commander’s fan, it’s been a long time, but it was a wild ride. One of the things that’s happened recently, which I know strikes near and dear to your heart, and frankly, for people who grew up sort of following it, has been, I guess, kind of the evisceration of the Washington Post sports section. And it’s got all sorts of impacts. But from your perspective, How do you make sense of that and what does it look like going forward for a city essentially that has all the major sports and the major paper not really covering it? Bram N Weinstein (01:09.719) I don’t make sense of it. I don’t understand it. I think at its core, The Washington Post is two things. It’s one of the most important publications in the world as the paper of record in the most powerful city in the world and the democratic center of the world. But it also is a local newspaper for one of the top 10 markets, top five markets in the country. And the idea that it would not cover its sports teams, or Metro desk, which, I know, you know, for our purposes, we focused a lot on the sports desk being shuttered. The Metro desk is too. So the Washington Post not covering the mayor’s office, city council meetings like in especially in these political times where, you know, the district budget is held by the federal government. To me, it doesn’t even it doesn’t compute that that wouldn’t exist. as far as like the sports section goes, which I think is like the lesser of the two real problems with this, but obviously is a real problem is, you I think for me, it feels like a death. I grew up reading the Washington Post. A lot of the reasons why I wanted to do what I wanted to do was through osmosis of reading Tony Kornheiser and Michael Wilbon and Tom Boswell and all of the great writers that came through the Washington Post. And I just don’t really understand how it’s not within the business model to be part of this. At the same time, you know, it does open opportunities for entrepreneurs like myself who have media companies and are always looking for new talent and always looking for openings. And I can tell you that void is going to get filled. But I do think it is sad that the Washington Post could not figure out a way to modernize itself to allow its coverage to continue for its loyal readership. This is a local paper that isn’t covering local news. That is astoundingly terrible in terms of a business practice to me. Frazer Rice (03:14.317) It’s weird because from my perch here in New York, I work across the street from the New York Times building and there’s a little bit of sort of guffawing that the New York Times has turned into a gaming company and sort of a media company second, which has helped to subsidize its continued commitment to long form journalism. But even then, I mean, it’s really focusing on arts and leisure and cookbooks and wordel and all sorts of things like that. And it’s a shame that the Washington Post either couldn’t pivot in that direction or otherwise make sense of things. Bram N Weinstein (03:48.727) Is the business model of media the same that was no. so there are a few things that play here to be fair. I’m not asking Jeff Bezos to lose money. You know, like, or just be the beneficiary to subsidize something, but you do bring up a point, which is. And I read this quote recently from, the old ownership group, the Graham family, who basically said. “You know, the newspaper is a grocery store. Like you are supposed to go in there and pick all the different things that you want. And hopefully there’s something for everybody or hopefully a number of things for everybody. And in modern times, the New York Times has done a very good job of putting together a new modern grocery store for people. So there’s a variety of different things that does subsidize the important work that it does. And in the end, like to me, the New York Times and the Washington Post and maybe the Wall Street Journal. Are the three most important newspaper entities, if you can call them that, in the United States of America. And for one of them to not understand their role in protecting democracy, in covering our world, in informing the readership, whether it’s locally or nationally, to me is an absconding responsibility. So I don’t know what the answer is. Again, I’m not like demanding Jeff Bezos just…money to keep things subsidized. Like it is a business and I understand that, but there must have been better ways to go about it or maybe, you know, sell it to someone who does have ideas because it’s important for its foundations to remain intact. And so I just, you know, for me, it’s, been hard to digest, honestly. And like to your original question of like, like, how do you make sense of it? I really don’t. I don’t make any sense of it. Frazer Rice (05:39.692) Well, you also now have a fledgling media company and I’m a devourer of yours and Kim’s and Standix podcasts and I learned something from it each time. I see an opportunity there if major component of the media establishment in the area is abdicating its role, not only to the major sports that aren’t getting covered as much. There’s an opportunity there. But even like the local hotbed sports like lacrosse, they’re completely ignored, I would imagine. And that might be a way to sort of get some grassroots component going. Bram N Weinstein (06:17.195) Yeah, we also here with my company Empire see the opportunity, unfortunately, but we do. And there’s a lot of talent that is available. There is a void in coverage. We know, you know, the size of our community, the appetite for sports. And so, you know, I don’t want to say too much, but we are actively seeking partners to expand in a pretty large way if possible. So Frazer Rice (06:24.045) Right. Bram N Weinstein (06:46.067) We’re working towards that and I’ve been working towards that and moving very fast in the hopes that we’re not the only ones thinking this like you. There’s a lot of people thinking there’s an opportunity here. I wish it wasn’t the opportunity that it is, but it has presented itself and it’s an opportunity that we intend to see through. So we are actively speaking to a number of different interested parties about funding a major expansion of what we’re doing. Frazer Rice (07:11.379) Really cool. Well, I’ll be sure to keep an eye on that as it develops. When you’re thinking about sort of the money making aspect of it, we don’t do things for free and it’d be lovely if we all had time and disposable income to do that without giving away the playbook because you’re raising money and you don’t want to give that up necessarily. But how do you think about that in terms of delivering value for sponsors or advertisers or the general audience? Have you made any…sort of commitment strategy-wise there. Bram N Weinstein (07:42.197) Yes, digital audio video forward. You know, I also believe in enterprise journalism. I also very much believe in long form journalism, but the audience appetite for it is limited. And so you do have to subsidize it. And that comes in the form of a number of different properties repurposed for different platforms in various ways, podcasts, video shows, YouTube. All offer o

    23 min

  8. FEB 3

    QSBS for FOUNDERS

    This conversation delves into the intricacies of Qualified Small Business Stock (QSBS) and its significant tax benefits for founders. MICHAEL ARLEIN, Partner at Patterson Belknap, explains the eligibility criteria, the importance of strategic planning, and the potential pitfalls that can arise. The discussion also covers the implications of state taxes and the advantages of gifting strategies. We cover innovative approaches like the “GOAT” trust to maximize tax-free gains. Founders are encouraged to engage with legal experts early in their business journey to fully leverage QSBS opportunities. https://youtu.be/lfBt0j7BlW0?si=LufZ8j2YtgdspLMJ Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠) Takeaways from “QSBS For Founders” QSBS is a powerful tax benefit for founders. The maximum exclusion amount has increased to $15 million. Careful planning is essential to avoid QSBS pitfalls. Gifting QSBS stock can multiply tax exemptions. State tax implications vary; California does not recognize QSBS. Discounting shares can aid in estate planning. Converting from an S-Corp to a C-Corp can preserve QSBS benefits. Early engagement with legal counsel is crucial for founders. Innovative strategies like the GOAT trust can maximize benefits. Almost all businesses should consider QSBS eligibility. Chapters 00:00 Understanding QSBS: A Founder’s Guide. 02:56 Navigating the QSBS Landscape: Common Pitfalls. 06:07 Maximizing QSBS Benefits: Stacking Strategies. 08:42 The Importance of Timing: Gifting and Valuation. 12:03 State Tax Implications: The QSBS Challenge. 14:52 Entity Structures and QSBS: What Founders Need to Know. 17:37 Transitioning to C-Corp: Strategies for S-Corps and LLCs. 20:29 Who Should Pay Attention to QSBS? 23:44 Innovative Business Structures: Technology and QSBS- 26:36 Early Stage Strategies: Cloning Yourself on the Cap Table- Transcript of “QSBS for Founders” Frazer Rice (00:01.109) Welcome aboard, Michael. Michael Arlein (00:03.096) Thank you. Good to be here. Frazer Rice (00:04.617) So let’s get started here. QSBS, Qualified Small Business Stock, is something that certainly all founders should be aware of. It’s a tax feature. It’s probably one of the nicest goodies that the federal government gives to people who are starting businesses. Take us through a little bit about what happens there. For founders, you’re going to hear the numbers 1202, which is the section that is quoted here. Take us through a little bit about what happens at QSBS and why it’s a powerful feature. Michael Arlein (00:37.496) Sure, that sounds good. To your point, the New York Times called QSBS a lavish tax dodge that is easily multiplied. And I happen to. I’m not aware of any other provision of the tax code that can save anyone as much money as QSBS. It’s really incredible. I think the policy reasons behind the provisions are that they’re designed to encourage entrepreneurship. Everyone on both sides of the political aisle is in favor of. The basic premise of it is that if you create a company.You own the stock for five years. The company’s in the form of a C corporation, It’s not in one of a series of restricted industries. Mainly service industries, that when you sell the stock, you can exclude from paying tax $10 million, the first $10 million of your gain. That’s the old rule, which I’m still dealing with, that that’s for stock that was issued before July 4th, 2025. And now QSBS has gotten even better. So if you get stock after that date. You hold it for actually now three years, you can exclude ultimately up to $15 million from tax. So we’re now dealing with two different regimes. I’m still stuck in the old regime. Most of the people I’m dealing with got their stock before last July. But I’ll try and point out the differences as we go along. Frazer Rice (02:29.066) Sure, as you said, there are a bunch of things you have to jump through. To make sure that you can sort of apply and then to further comply with the rules associated with it. Things like services. Making sure that maybe you don’t have too much cash and that it’s deployed correctly. Making sure that the original stock issuance persists throughout. What are some of the things that you tell your clients? How do you walk them through the process so that they don’t trip on themselves and lose this nice tax advantage? Michael Arlein (03:09.676) Yeah, there are some landmines, things that you can step on and blow it. There’s some weird rules around redemptions. Like if you have redemptions. Let’s say you create a company and then there’s three co-founders. Then very early on, one of the co-founders wants out or you want to kick them out. And then the mechanism for that is the company kind of buys back their stock. You know, there’s complicated rules that can, you know, blow up QSBS for the entire company. I think some people start their businesses as LLCs or S-Corps or things like that, and then later convert them. And that has to be done very, very carefully with good tax advice. Otherwise that can also blow things up. When I talk to founders, it’s pretty clear their business qualifies. They didn’t screw anything up. Frazer Rice (04:19.626) So the OBBBA in a sense turbocharged a little bit the tax savings. That five year requirement that you talked about. You can now get some of the benefits even as early as three years. And then the dollar amounts got expanded. In addition, and this was not necessarily OBBBA related. The ability to take one exemption and maybe multiply it via stacking continues to be a powerful tool. For those people who are walking into your office now. How do you get them when they sit down situated so that they do that planning upfront? Michael Arlein (05:08.598) Yeah, that’s, you we kind of buried the lead. The benefit of QSBS: it would be incredible if you could just pay no tax on 10 or $15 million. But what’s even more incredible is that you can stack or multiply the number of exemptions. You have using a provision of the code. It says that if you gift QSBS stock to some other person or entity. That that person or entity can take their own up to 10 or 15, their own QSBS exemption. I’m just gonna say it’s 15. We understand that’s for newly stocked. So, classic move for a founder would be to set up trusts for children. There’s a special kind of a trust for a spouse. You can do this with sometimes people make trust for their parents, their siblings. There are certain states where you can actually make a trust for yourself. Usually when people come to my office, the conversation is around creating entities. Typically trusts, and then gifting shares to those trusts. that As a family, you could go from 15 million tax free to 30 or 45 or 60 million tax free. The record I had one guy who had a very large family. He married, he had kids and was very close not only with his parents. With his siblings, his nieces, his nephews, even his aunts, uncles, and cousins. He created 23 trusts, which on paper at least would save up to $230 million. Wow. Yeah. Frazer Rice (07:08.896) There’s a danger with that though, with those 23 trusts had to be different. I imagine the IRS would say, wait a minute, we see what you’re doing. Stacking all of these different things is theoretically nice and all, but is there a way to create differences within those trusts so that the IRS doesn’t view them as one big pot? Michael Arlein (07:39.692) Yeah, great question. So you can’t create multiple identical trusts. Meaning I can’t create five trusts for my child. The IRS has rules that consider those trusts as one trust and would have only one exemptions. So, one of the limiting factors on creating trust is often, who are the people you’re willing to gift to? You know, so this guy with the 23, he actually was willing to create trust for his cousins, his aunts, uncles. Now, those individuals were the beneficiaries of the trusts, which means that they were eligible to receive money from the trust. But those trusts were designed so that when those people passed away, the money would circulate back to his children. So, you we never talked about it, but it’s possible that in his head, his plan was that he would maybe provide some benefit to his cousin. Maybe he’d say to his cousin, hey, if there’s $5 million in this trust and you need a little money, I’ll make some distributions to you, but I’m going to request that the trustee kind of withhold most of the money. And then when you die, it’ll come back and benefit my kids. So there are nuances there. But generally speaking, most people aren’t willing to do that. They’re not close enough with their cousins and their aunts and their uncles. So they end up maybe creating trusts, you know, for their kids, for their parents, sometimes, you know, for their spouse and maybe sometimes they go a little beyond that, but not that far. One thing that’s important is that the U.S. Frazer Rice (09:33.472) One thing that’s important is that the the QSBS is a capital gains tax Concept meaning you’re you’re saving on the tax. From a QSBS for Founders standpoint when the the founder sells the business, and you have to pay capital gains tax on that front. Part of the reason I’m skewing this toward founders is that there’s an gift in a state exemption of 15 million dollars. So it’s important to get these assets into these trusts as early as possible and with as low evaluation as possible. That in many ways is where the real leverage is. Does that square with your thinking? Michael Arlein (10:11.019) Yeah, absolutely. We have a permanent $15 million lifetime gifting limit. $30 million for spouses. And when you gift stock into these trusts, you’re typically gifting at a common stock valuation. People are familiar,

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Covering the issues that affect business, entrepreneurship, wealth, trusteeship and culture.

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  • Creator
    Frazer Rice
  • Years Active
    2015 - 2026
  • Episodes
    204
  • Rating
    Clean
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    © 2025 Wealth Actually LLC
  • Show Website
    Wealth Actually

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