You have probably heard that you should open an HSA. But has anyone actually walked you through what to do after you open it? That is what today is about.

This is Episode 18 of What the Wealthy Do and the first episode of the Logistics Series, breaking down the exact mechanics of how these wealth building strategies actually work in real life.

The health savings account is the only account with a triple tax advantage: tax deductible contributions, tax-free growth, and tax-free withdrawals for medical expenses. Most people open one, get the debit card, and spend it on copays. That is the wrong move.

Stephanie Dorsey walks through every step: how to check eligibility, employer HSA versus opening your own, how to invest the contributions, and how the wealthy use the HSA as a stealth retirement account worth hundreds of thousands of dollars by paying medical expenses out of pocket, saving every receipt, and reimbursing themselves tax-free decades later.

A real example: maxing out your HSA at 40 for 25 years at 7% annual growth gives you $290,000 tax free at 65 from $107,500 in contributions.

The HSA Quick Start Checklist is in the show notes below.

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HSA QUICK START CHECKLISTWeek 1:- Check if you have an HDHP (ask HR or check benefits portal)- If yes, check if your employer offers an HSA- If yes, enroll during next open enrollment- If no, open one with Fidelity

Week 2:- Max out contributions ($4,300 individual / $8,550 family)- Set payroll deduction or automatic monthly bank transfer

Week 3:- Log into your HSA provider- Move funds to investments (keep $1,000 to $2,000 in cash)- Invest in low-cost index funds

Week 4:- Set up a system to track medical expenses- Pay all medical expenses out of pocket- Save every receipt

Every Year:- Max out contributions- Rebalance investments- Keep saving receipts- Watch it grow tax-free

This podcast provides financial education and not financial advice.

This is the episode where everything comes together.

This is Episode 17 of What the Wealthy Do, Part 3 and the finale of the Bonds Series. In Part 1 we covered what bonds are and why smart money never ignores them. In Part 2 we broke down how interest rates and the yield curve affect bond prices. Today Stephanie Dorsey builds the actual strategy.

How much should you allocate to bonds? The old school rule of investing your age in bonds is outdated. The wealthy allocate based on where they are in life, what is happening in the market, and what their goals are. This episode walks through a framework by life stage, from investors in their 20s through 40s holding 5 to 15% in bonds, all the way to investors 60 and beyond thinking about 40 to 60% bond allocation and using bond ladders to create predictable retirement income without selling stocks during a downturn.

Which bonds should you buy? This episode covers US Treasury bonds, TIPS, I-bonds, municipal bonds for high earners, investment grade corporate bonds, and bond ETFs for investors with less than $50,000 to put into bonds.

The bond ladder strategy is explained in full, including how to reduce interest rate risk, create regular cash flow, and control when and how you reinvest as bonds mature. Stephanie also covers when to increase or pull back bond exposure and the most common mistakes to avoid.

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If this series changed how you think about your portfolio, share it with someone who needs to hear it. Leave us a five-star review and follow the podcast so you never miss an episode. See you next week.

BACKDOOR ROTH IRA QUICK START CHECKLIST

Here is your action plan:

Step 1:

• Open accounts if you do not have them
• Open a traditional IRA
• Open a Roth IRAUse the same brokerage (Fidelity, Vanguard, or Schwab)

Step 2:

• Clear out any existing traditional IRAs
• Roll old traditional IRAs into your 401k to avoid the pro-rata rule

Step 3:

• Contribute to your traditional IRATransfer $7,000 (or $8,000 if 50 or older) from your bank to your traditional IRAKeep it in cash, do not invest it yet

Step 4:

• Convert to Roth IRA (1 to 2 days later)
• Log into your brokerage
• Convert the entire traditional IRA balance to your Roth IRA

Step 5:

• Invest your Roth IRA
• Buy index funds or target date funds

Step 6:

• File Form 8606 with your taxes
• Use tax software or work with a CPA

Step 7:

• Repeat every January

HSA QUICK START CHECKLIST

Here is your action plan:

Week 1:

• Check if you have an HDHP (ask HR or check benefits portal)
• If yes, check if your employer offers an HSAIf your employer offers an HSA, enroll during next open enrollmentIf your employer does not offer an HSA, open one with Fidelity

Week 2:

• Set up automatic contributions to max out the HSA ($4,300 individual / $8,550 family)
• If employer HSA: set payroll deductionIf self-directed: set automatic monthly transfer from bank

Week 3:

• Log into your HSA providerMove funds from cash to investments (leave $1,000 to $2,000 in cash)
• Invest in low-cost index funds (80% stocks, 20% bonds or target date fund)

Week 4:

• Set up a system to track medical expenses (spreadsheet or app)
• Commit to paying medical expenses out of pocket, do not touch the HSA
• Save all medical receipts
• Every Year:Max out contributions
• Rebalance investments if neededContinue saving receipts
• Watch it grow tax-free

This podcast provides financial education and not financial advice.

Bonds do not exist in a vacuum. They respond to what is happening in the economy, what the Federal Reserve is doing, and what risks are present in the market. And if you understand those relationships, you can predict how bonds will perform, how stocks will perform, and how to protect your portfolio when things get volatile.

This is Episode 16 of What the Wealthy Do, Part 2 of the Bonds Series. Last week we covered the basics of what bonds are and how they work. Today Stephanie Dorsey goes deeper into two of the most powerful concepts in finance: the relationship between interest rates and bond prices, and the yield curve.

The single most important rule in bond investing is that bond prices and interest rates move in opposite directions. When rates go up, bond prices go down. When rates go down, bond prices go up. Stephanie walks through exactly why using a real example, and what it meant for everyday investors when the Federal Reserve raised interest rates from near zero to 5% in just 18 months in 2022. Some bond funds lost 15 to 20% of their value that year. Investors who understood this relationship either held to maturity or bought bonds at a discount to lock in higher yields. The ones who did not understand it got crushed.

The second concept is the yield curve, which Stephanie calls the bond market's crystal ball. The yield curve shows what return you would earn today if you lent money for different lengths of time. A normal yield curve slopes upward because longer term bonds pay more than shorter term ones. But when it inverts, meaning short term bonds start paying more than long term ones, it has predicted every major recession in the last 50 years, typically six to 18 months before it happens. It happened in 2006 before the Great Recession. It happened in 2019 before the COVID crash.

Sophisticated investors watch the yield curve obsessively. And now you will too.

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This podcast provides financial education and not financial advice.

Nobody is making TikToks about bonds. Nobody is talking about treasuries going to the moon. But the bond market is two to three times bigger than the stock market. It is the foundation of the global financial system. And if you do not understand bonds, you really do not understand how money works.

This is Episode 15 of What the Wealthy Do and the first episode of the Bonds Series. Today Stephanie Dorsey breaks down everything you need to know about bonds starting from scratch, in plain language, no finance degree required.

A bond is simply an IOU. Instead of borrowing money from the bank, you are the bank. You lend money to a government or a corporation. They pay you interest every six months and return your full principal at maturity. It is predictable, stable income that the wealthy have always used to preserve capital, generate cashflow, and balance the risk in their portfolios alongside stocks and alternatives.

This episode covers what a bond is and how it actually works, the key vocabulary you need to know including face value, coupon rate, maturity date, yield, and credit ratings, the different types of bonds including Treasury bonds, municipal bonds, corporate bonds, international bonds, and savings bonds, the two ways to make money from bonds, why the wealthy never ignore bonds even when the stock market is performing well, and the most common myths about bonds that keep most everyday investors from ever using them.

Next week we go deeper into how interest rates and geopolitics affect bond prices. In the coming weeks we will also cover what a potential dollar devaluation could mean and how to start incorporating bonds into your own portfolio.

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This podcast provides financial education and not financial advice.

Last week was the problem. This week is the solution.

This is Episode 14 of What the Wealthy Do, Part 2 of the Retirement Strategy Series. In Part 1 we covered why relying solely on your 401k is risky, how the retirement tax trap works, and what required minimum distributions will do to your money at 73 if you have not planned for them. Today Stephanie Dorsey builds the actual blueprint.

The framework covers three pillars. The first is tax diversification, which means spreading your retirement money across four buckets: tax deferred accounts like your traditional 401k and IRA, tax free accounts like your Roth IRA and Roth 401k, a regular brokerage account, and alternative investments like real estate, private equity, and venture capital. Each bucket has different tax treatment, different rules, and different advantages depending on where you are in your career and what tax bracket you expect to be in at retirement.

The second pillar is asset diversification across stocks, bonds, real estate, and alternative assets. The third pillar is income stream diversification so that no single account or market crash can wipe out your retirement income.

This episode also breaks down how your retirement strategy should shift by age, from aggressive wealth building in your late 30s and early 40s, to tax optimization in your late 40s and early 50s, to preservation and income planning in your late 50s and early 60s, to tax smart withdrawals and legacy planning in retirement. The backdoor Roth IRA strategy for high earners is covered, along with how the wealthy use portfolio loans to avoid selling their investments, how to think about Social Security timing at 62 versus 70, and the specific action steps you need to take right now to audit and rebalance your accounts.

This is one of the most practical episodes in the series. By the end you will have a clear picture of what your retirement strategy should look like and exactly what to do next.

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This podcast provides financial education and not financial advice.

Most of us think we know what retirement is going to look like. But here is the truth that nobody really says out loud. For most people, a 401k alone will not be enough to fund the retirement they actually envision for themselves.

This is Episode 13 of What the Wealthy Do, Part 1 of a two-part series on retirement strategy. If you are between 38 and 55, this episode is for you.

Stephanie Dorsey, CEO and Co-Founder of Margins Capital, breaks down why relying solely on your 401k puts your retirement at serious risk and what the wealthy do differently to protect their money from taxes before and after they retire.

The 401k was introduced in 1978 as a supplement to pensions, not a replacement. Corporations eventually shifted the entire weight of retirement planning onto employees, and now millions of Americans are trying to retire on a savings vehicle that was never designed to carry 20, 30, or 40 years of retirement on its own.

Three core problems get covered in this episode. The first is that contribution limits are simply too low to build the retirement wealth most people need. The second is zero tax diversification, meaning every dollar in a traditional 401k will be taxed at ordinary income rates when you withdraw it, and the IRS will force you to start withdrawing at age 73 whether you need the money or not. The third is limited investment options that keep most 401k savers locked out of the asset classes where the wealthy actually build wealth.

Stephanie also walks through what required minimum distributions really mean for your finances, how the retirement tax trap works in practice, and how the wealthy spread their money across tax deferred, tax free, and taxable accounts to control their taxable income in retirement.

Next week in Part 2, we build an actual retirement portfolio strategy. But today is about making sure you understand what is at stake and what needs to change right now while you still have time.

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This podcast provides financial education and not financial advice.

There are people out here with fancy websites, impressive titles, and slick pitch decks who have no business managing anybody's money. This episode is your protection against all of them.

This is Episode 12 of What the Wealthy Do and the finale of the Due Diligence Series. Over the past three episodes we broke down how to evaluate stocks and how to assess private equity and venture capital deals. Now we go one level deeper. Today is about vetting the people who are asking you to trust them with your hard earned money.

Here is the brutal truth most investors don't realize until it's too late. The fund manager matters more than the fund. A great manager can turn a mediocre strategy into outsized returns. A bad manager can destroy even the best one.

Stephanie Dorsey, CEO and Co-Founder of Margins Capital, walks you through the exact four-pillar framework that sophisticated investors use to evaluate any fund manager, wealth advisor, or investment firm. She even applies it to herself. Because anyone who gets an attitude when you ask hard questions about their track record, their fees, or their process is telling you everything you need to know.

The four pillars are track record and performance, investment philosophy and process, team and organizational structure, and integrity and alignment of interests. You will also learn how to run a background check on any fund manager, how to use AI to review a Limited Partner Agreement without paying a lawyer, and what questions to ask reference investors before you commit a single dollar.

A note on emerging managers is also included, including why the data shows they often outperform more established funds, and what to reasonably expect when evaluating a newer firm.

Margins Capital has a minimum investment of $25,000 and invests 20% of its own capital in Fund 1 alongside its investors.

Just 20 seats for high-earning Black women ready to stop second-guessing and start building real generational wealth. Learn more at joinsovereign.co.

This podcast provides financial education and not financial advice.

That is a wrap on the Due Diligence Series. You now have the complete framework the wealthy use to evaluate stocks, private equity deals, venture capital opportunities, and the people managing it all.

Share this episode with someone in your circle who needs to hear it, leave us a five-star review on Apple Podcasts or Spotify, and if you are ready to invest in a diversified portfolio of institutional quality alternatives starting at just $25,000 with a team that has skin in the game right alongside you, visit Margins Capital at https://www.marginscapital.com/

See you next week.

The stock market is just the beginning. The truly wealthy, the ones building generational, life-changing wealth are doing it through private equity and venture capital. And in this episode, Stephanie Dorsey is giving you the exact playbook.

This is Episode 11 of What the Wealthy Do, and it's part three of our Due Diligence Series. In Episodes 9 and 10, we broke down how to evaluate public stocks: qualitatively and quantitatively. Now we're going into private markets, where the real wealth is built, and where most people are locked out.

Until now.

Here's what we cover:

Private Equity vs. Venture Capital: What's the difference, what's the risk, and what are the returns? PE targets 15–25% annually. VC targets 3x–10x your money (with the understanding that most will fail, which is why Margins Capital focuses on late-stage VC).

The 2-Question Framework: The same questions Margins Capital asks for every deal: Does this make sense? And can they win?

Team Evaluation: In private markets, there's no analyst coverage, no public scrutiny. It's all on the founders. Stephanie breaks down exactly what she looks for and what makes her walk away.

Key Metrics for PE & VC: Revenue growth rate (50%+ for VC, 10–20% for PE), EBITDA margins, LTV to CAC ratio, burn rate, and total addressable market.

Red Flags: Lack of transparency, unrealistic projections, no exit strategy, and founders who aren't coachable.

The Fizz Story: A real example of why Margins Capital invested in a Gen Z fintech company backed by Kleiner Perkins, and what the "secret sauce" looked like in practice.

How to Access These Deals: Whether you're an accredited investor ($200K+ income or $1M+ net worth) or not yet, Stephanie breaks down the exact platforms and pathways: AngelList, Republic, SeedInvest, Fundrise, and more.

Margins Capital's minimum investment is $25,000: significantly lower than the traditional PE fund minimum of $250,000.

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This podcast provides financial education, not financial advice.

Most people give up on analyzing stocks because they try to learn 20 metrics at once. The wealthy don't do that. They focus on the numbers that actually matter — and that's exactly what this episode is about.

This is Part 2 of our Stock Due Diligence Series. In Part 1, we covered how to think qualitatively about a company — does the strategy make sense and can they win? Now, in Part 2, Stephanie Dorsey (CEO & Co-Founder of Margins Capital) breaks down the 5 essential metrics you need to evaluate any stock, in plain language, no finance degree required.

What you'll learn in this episode:

1. PE Ratio — Are you overpaying for the stock? How to compare it to the company's history, its industry, and the S&P 500 average.

2. Profit Margin — How much of each dollar in revenue does the company actually keep? What's healthy vs. a major red flag depending on the industry.

3. Revenue Growth — Is the business growing or dying? Because one of those two things is always happening.

4. Debt-to-Equity Ratio — Can the company handle its debt obligations? Too much debt is dangerous, especially when interest rates shift.

5. Free Cash Flow — Is the profit real, or just accounting magic? This is the metric the wealthy swear by.

Master these 5 and you'll know more than 90% of retail investors. Combine them with the qualitative framework from Part 1 and you'll know more than 97%.

Where to find these numbers for FREE: Yahoo Finance, Google Finance, your brokerage app (Fidelity, Schwab, Robinhood), or the company's investor relations page (look for the 10-K or 10-Q).

Join The Sovereign Collective — a judgment-free space for high-earning Black women ready to build generational wealth. Founding cohort launches April 14th. Just 20 seats. Learn more at joinsovereign.co

Margins Capital provides women and people of color access to an institutional quality portfolio of alternative investments.

This podcast provides financial education, not financial advice.

Are you buying stocks based on your cousin's advice or a finance bro on TikTok? Let's fix that.

In this episode of What the Wealthy Do, Stephanie Dorsey — CEO & Co-founder of Margins Capital — breaks down the exact due diligence framework she uses to evaluate stocks the same way she evaluates private equity and venture capital deals.

Here's what you'll learn:

✅ The 2-part framework: Does it make sense? Can they win?

✅ How to evaluate a company's strategy in ONE sentence

✅ Why macroeconomic trends can make or break your investment

✅ How to assess leadership, competition, and competitive moats

✅ Red flags that should make you walk away immediately

✅ How to use AI (like Claude) as your investing thought partner

Whether you're just starting your wealth-building journey or you're a seasoned investor, this episode will change how you look at every stock you consider.

📌 NEXT WEEK: Part 2 — The quantitative metrics (PE ratios, alpha, beta, profit margins & more)

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Margins Capital provides women and people of color access to an institutional quality portfolio of alternative investments.

⏱ Chapters:

00:00 Introduction

02:00 Why buying stocks = buying a business

04:30 The 2-part due diligence framework

07:00 Does the strategy make sense?

10:00 Macroeconomic indicators explained

14:00 Unit economics basics

17:00 Can they win? — Leadership

21:00 Competition & competitive moats

25:00 Secret sauce & red flags

29:00 Where to find this information

32:00 How to use AI as an investing partner