Start Now with Greg M. Ostroff

Greg M. Ostroff
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  • Investing

Start Now: Your Direct Path to Lasting Wealth and Financial Freedom. This is the audio edition of the plain-language book on building your own tax-free pension — using nothing more than a Roth IRA and one low-cost index fund. Written and read by Greg M. Ostroff, a CFA who spent nearly two decades on Wall Street, each short episode walks you step by step through how anyone, on an ordinary salary, can build lasting wealth and retire on their own terms. No jargon, no hot tips, no market timing — just the few simple principles that actually work, and the discipline to use them. Free to listen, free to share. Start now. startnowbook.substack.com

Episodes

  1. 8h ago

    Key Terms

    This is part of Start Now — a complete guide to building your own tax-free pension, published free, one piece at a time. New here? Start Here → You'll usually find a glossary like this at the very back of a book. I've put it up front, on purpose. Start Now is being published a little unconventionally, one short piece at a time, each also read aloud as a podcast, so it helps to meet the key terms used early. There are almost fifty terms here, drawn from investing, finance, tax, and accounting, each with a plain-language definition. You don't need to memorize them, and you certainly don't need to read them straight through. Skim them now to get the lay of the land, and come back whenever a word trips you up. Even if all of this is brand new to you, with these at hand you'll be able to follow every step of the reasoning ahead. The terms are listed alphabetically: 1099 — The tax form an independent contractor receives. A 1099 worker is self-employed for tax and retirement purposes and uses accounts like the solo 401(k) rather than an employer plan. 401(k) — An employer-sponsored defined-contribution retirement account. The employee contributes from their paycheck (often with an employer match), chooses investments, and bears the investment risk. Similar in spirit to an IRA but offered through a workplace. 403(b) — A retirement account much like a 401(k), but offered by nonprofits, public schools, and government employers. Contributions come from your paycheck and grow tax-advantaged. 529 plan — A tax-advantaged account for education. After-tax money grows and is withdrawn tax-free when spent on qualified education such as tuition; spent on anything else, the earnings are taxed and penalized. Leftover funds can now be rolled into the beneficiary’s Roth IRA, within limits. 530A account (Trump account) — A federal account for children created by the 2025 tax law (also called a Trump account). The government seeds eligible children born 2025–2028 with $1,000; family may add up to $5,000 a year, invested in a low-cost U.S. stock index fund. It becomes a Traditional IRA at adulthood. Annual gift tax exclusion — The amount you can give any one person in a year without using your lifetime gift and estate tax exemption or filing a gift tax return, $19,000 per recipient in 2026 ($38,000 for a married couple who split the gift). Annuity — A contract, usually with an insurance company, in which you hand over a lump sum in exchange for a guaranteed stream of income, often for life. Backdoor Roth — A legal technique that lets high earners who exceed the Roth income limits still fund a Roth: they contribute to a Traditional IRA and then convert it to a Roth. CAPE (cyclically adjusted P/E) — The cyclically adjusted price-to-earnings ratio, popularized by Robert Shiller: stock prices measured against average inflation-adjusted earnings over the prior ten years. A high CAPE has historically signaled lower returns over the following decade. Capital gain — The profit when you sell an investment for more than you paid. A long-term capital gain (asset held over a year) is taxed at lower rates than ordinary income at the federal level. Catch-up contribution — An extra amount that savers aged 50 and older may contribute above the standard annual limit. Compounding — Earning returns on your past returns, not just on your original contribution. Over decades the effect becomes exponential rather than linear, the central idea of this book. Custodial Roth IRA — A Roth IRA opened and managed by a parent or guardian for a minor who has earned income; control transfers to the child at the age of majority. Defined-benefit (DB) pension — A traditional pension that pays a guaranteed income for life in retirement, with the employer bearing the investment risk. Now rare in the U.S. private sector. Defined-contribution (DC) plan — A retirement account (such as a 401(k) or IRA) funded by contributions, where the final balance depends on investment performance and the individual bears the risk. There is no guaranteed payout. Dividend — A cash payment a company makes to shareholders out of profits. In a taxable account, dividends are taxed in the year received; inside an IRA they are not. Dollar-cost averaging — Investing a fixed amount at regular intervals regardless of price, so you automatically buy more shares when the market is low and fewer when it is high, a natural byproduct of steady, scheduled saving rather than a strategy you have to time. Earned income (compensation), Money from work, wages, salary, or self-employment income, as opposed to gifts, allowances, or investment income. Only earned income qualifies a person to contribute to a Roth IRA. Exchange-traded fund (ETF) — An index fund that trades like a stock, with rock-bottom fees and no minimum investment. The most convenient way to own a broad-market index fund. Index fund — A fund that holds every stock in a market index (such as the S&P 500), in proportion, rather than trying to pick winners. It captures the whole market’s return at very low cost. Inflation — The gradual rise in prices over time, which erodes the purchasing power of money. This book uses 2% per year to express future dollars in today’s purchasing power. IRA (Individual Retirement Account) — A tax-advantaged account an individual opens to save for retirement, independent of an employer. Comes in Traditional and Roth varieties. Modified adjusted gross income (MAGI) — Your adjusted gross income with certain deductions added back. The IRS uses it to decide who can contribute directly to a Roth IRA, and to set other income thresholds. Net investment income tax (NIIT) — An extra 3.8% federal tax on investment income (such as capital gains and dividends) for higher earners, generally above about $200,000 of income for a single filer. Nominal vs. real return — A nominal return is the raw percentage gain; a real return subtracts inflation to show the gain in true purchasing power. A 10% nominal return is roughly a 7% real return after ~3% inflation. Ordinary income, Income taxed at the regular rate schedule, wages, interest, and Traditional IRA withdrawals. These rates are higher than long-term capital-gains rates. Present value (“today’s dollars”) — What a future sum is worth in today’s purchasing power, found by discounting it back at an assumed inflation rate. It answers “what would that future amount feel like if I had it now?” Pro-rata rule — A tax rule that treats all of your Traditional, SEP, and SIMPLE IRA balances as one pool when you convert money to a Roth. It means a backdoor Roth is only fully tax-free if you hold no other pre-tax IRA money, since each converted dollar is taxed in proportion to the pre-tax share of the total. Qualified dividend — A dividend that meets IRS holding-period rules and is therefore taxed at the lower long-term capital-gains rate rather than as ordinary income. Replacement rate — The share of your pre-retirement income that a source (such as Social Security or a pension) provides in retirement. Planners often target a total of 70–85%. Required minimum distribution (RMD) — The amount the IRS forces you to withdraw each year from a Traditional IRA starting at age 73 (rising to 75 for those born in 1960 or later), whether you need it or not. Roth IRAs have no RMDs during the owner’s lifetime. Return — What your money earns in a year, stated as a percentage of what you put in. Put in $100, finish the year with $108, and the return was 8%. It includes both price growth and any dividends the investment paid. Roth 401(k) — The Roth version of a 401(k), offered through many employers. You contribute after-tax dollars, and qualified withdrawals, including all growth, are entirely tax-free, at the much higher 401(k) limit. Roth IRA — An IRA funded with after-tax dollars; it grows tax-free and qualified withdrawals in retirement, including all growth, are entirely tax-free. Rule of 72 — A shortcut: divide 72 by the annual return to estimate how many years it takes money to double. At 10%, roughly every 7.2 years. SEP-IRA — A Simplified Employee Pension IRA: a straightforward retirement account for the self-employed and small businesses. The owner contributes a percentage of income, with far higher limits than a standard IRA. Solo 401(k) — A 401(k) for a self-employed person with no employees. It lets you contribute as both employee and employer, reaching much higher limits than an IRA, the go-to account for independent workers who want to save aggressively. Spousal IRA — A rule that lets a working spouse fund an IRA for a non-working or low-earning spouse, so a married couple filing jointly can contribute to two IRAs on a single income. Tax-deferred (Growth that is not taxed year to year, but will be taxed later on withdrawal) the Traditional IRA model. (A Roth, by contrast, is tax-free, not merely tax-deferred.) Taxable account — An ordinary, non-retirement brokerage account. You invest after-tax money; dividends are taxed each year and gains are taxed when you sell. No contribution limits or withdrawal rules, but no tax shelter either. The 4% rule — A rule of thumb that withdrawing about 4% of a portfolio in the first year of retirement (then adjusting for inflation) historically lasted a 30-year retirement. See Section 1.5. Traditional IRA — An IRA funded with pre-tax dollars (a deduction today); it grows untaxed, but every withdrawal in retirement is taxed as ordinary income. W-2 employee — A traditional employee on a company’s payroll, with taxes withheld and reported on a W-2 form. W-2 employees can join their employer’s 401(k). Withdrawal rate — The percentage of a retirement portfolio taken out as income in a given year. A lower rate is safer; a higher rate risks depleting the portfolio. Yield on cost — The annual income an investment produces measured against what you o

  2. 1d ago

    The Whole Plan On One Page and How to Read the Book

    Start Now This is part of Start Now — a complete guide to building your own tax-free pension, published free, one piece at a time. New here? Start Here → Thanks for reading Start Now! Subscribe for free to receive new posts and support my work. Greg M. Ostroff, CFA START HERE The Whole Plan - On One Page If you read nothing else, read this. Everything after it is why it works and why you can trust it. The five moves DO THIS FIRST If your job offers a 401(k) with a match, contribute enough to get the full match: that’s free money, and it beats everything below. * 1. Open a Roth IRA. The one retirement account you can open yourself, no employer needed. Fidelity, Vanguard, or Schwab: about 15 minutes, no cost. * 2. Put the money in one low-cost index fund that owns the whole U.S. market. * 3. Contribute what you can every year, ideally the max ($7,500 in 2026), automatically. * 4. Don’t sell. Ignore the headlines. Leave it alone for decades. * 5. Start now. The earliest dollars are worth the most. What it becomes You’ll put into your Roth IRA about $322,000 of your own money. By age 70, entirely tax-free, that grows to roughly $2.2 million even in the worst 30-year stretch on record, and about $3.7 million in a typical one, an income of $86,000 to $149,000 a year. But the number that really counts is what those dollars are worth in today’s money: about $975,000 to $1.7 million, tax-free. That’s the whole idea. Not a lottery ticket, not a fortune, a private pension you build yourself, tax-free, that makes work a choice instead of a necessity. Add that to your Social Security and you have your freedom. ✦ BEFORE YOU BEGIN How to Read This Book This book comes in two halves. First, the Chapters are the book. Ten of them, an hour or two’s read, end to end, depending on how long you linger over the charts and tables. These Chapters hold the entire argument and everything you need in order to act on it: what compounding does, why the Roth beats the alternatives, what a lifetime of maxing one out actually produces, what could go wrong, and the simple routine for starting. If you read only this half, you have not read an abridgement. You have read the book, and you may stop with a clear conscience. * 1. The Magic of Compounding: why growth crawls for two decades, then goes vertical. * 2. Why Hold Investments in a Tax-Advantaged Account: tax-free growth that, for most savers, outdoes both taxable and traditional accounts over a lifetime. * 3. Case Studies: A Lifetime of Maxing Out an IRA. The full range of results, from the 8% floor to the 13.6% ceiling, in both nominal and today’s-dollar (inflation-adjusted) terms. * 4. It Pays to Start Early: the measurable price of every year you delay, and why it’s never too late to start. * 5. A Middle-Income Investor in a High-Tax State: The California Example. The plan run for a typical ~$100K earner, where state tax makes the Roth’s edge larger still. * 6. Why This Falls to You: how retirement landed on the individual in America, and how Social Security and a Roth combine in retirement. * 7. A Family Strategy: Gift-Funding a Young American’s Roth. How to give someone just starting out a head start. * 8. What Could Go Wrong? A clear-eyed look at the risks to this plan. * 9. What Could Go Right? The upside we deliberately left out of every number, so the surprises run in your favor. * 10. Putting It Into Practice: the final chapter turns all of this into one simple routine: open a Roth, fund it as early as you can each year, invest it in a single low-cost broad-market index fund (we offer ideas later in the book), and leave it alone. Second, the Deep Dives are the evidence. Ten of those. Read straight through, they take a little less time than the Chapters do. This is where the work is shown. Every number gets its arithmetic, and every serious objection gets a chapter of its own rather than a sentence. Can a century of market history be trusted at all, the floor as much as the average? Were Japan’s “lost decades” really lost, and who actually lost them? Why did America win, and can it keep winning? And what is the one real decision all of this leaves you with? And one word about the numbers. The large dollar figures throughout are an illustration of a financial principle, not a savings target. You do not have to start young or contribute the maximum, though it helps, and the same forces work on any amount, begun at any age. The figures come from historical market returns. Markets, taxes, and inflation all change, and the next 30 years will not look exactly like the last. But those returns have held remarkably consistently for a very long time, which is a real source of comfort. Read them as a demonstration of why starting early matters, and scale them to your own life. A note about the vocabulary. Where a financial term earns its place, the Key Terms section in the very next post in this series defines it in plain English, so you never have to leave a page confused. One thing worth saying plainly: the Deep Dives assume you have read the Chapters. They are the defense of an argument, not a restatement of it, and they will not make much sense on their own. So read the Chapters first. That is the book. Then, if you want to know whether all of this survives contact with a skeptic, the second half is waiting, best read in order, though each Deep Dive also stands on its own. One thing to carry through all of it: every conclusion here is built on the worst long-term performance the U.S. stock market has delivered on record. The deck is quietly stacked in your favor, because every other outcome on record is better than the one we planned for. You do not need a financial advisor, a windfall, or a big salary. Open an account, contribute what you can, invest it, and leave it alone. Every year you wait is a year of compounding you can never recover.The tools are sitting in front of you. Start Now. A NOTE FROM THE AUTHOR Start Now is free to read and free to share. If it helped you, the kindest thing you can do is subscribe and pass it to one person who needs it. Questions, comments, or a story of your own? Leave one below, or just reply to this email; I read every one. If you’d like to give back, pay it forward: donate any amount to a cause you believe in. I don’t collect a penny of it; it goes straight to the charity you choose, not to me. If you’d like a suggestion, I support the Zach Moses Music, Love & Light Fund at the Sweet Relief Musicians Fund, which feeds musicians in need. sweetrelief.org/zachmoses → Coming next: Key Terms Thanks for reading Start Now! Subscribe for free to receive new posts and support my work. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit startnowbook.substack.com

  3. 2d ago

    How Anyone Can Build a Tax-Free Pension on an Ordinary Salary

    Start Now This is part of Start Now — a complete guide to building your own tax-free pension, published free, one piece at a time. New here? Start Here → Thanks for reading Start Now! Subscribe for free to receive new posts and support my work. Greg M. Ostroff, CFA THE OPENING How Anyone Can Build a Tax-Free Pension on an Ordinary Salary Greg M. Ostroff, CFA You may be here because you want to be a millionaire, and I’m going to show you how you can be, in today’s spendable dollars and entirely tax-free. It doesn’t take a complicated strategy or a hot tip, a lottery ticket, or outsized risk. What it takes is discipline, patience, a little knowledge I’ll share as we go, and about $20 a day. But nobody actually sets aside $20 a day, so in practice it’s a little under $300 out of each biweekly paycheck. Set it up once, automatically, and you’ll barely notice it’s gone. You’re probably also a young American just starting out in the workforce, or a few years further along, with your financial footing but no plan yet for retirement. Plenty of your peers are kicking that can down the road, heads down, living for today. This book makes the opposite case, and an optimistic one: the freedom to retire on your own terms is far more achievable than it looks, and the principles that get you there are few and simple. What you do with that freedom later is your business. My job is just to get you to it. And to start now. And if you’re further along, say in your forties or fifties with a 401(k) you set up years ago and quietly left on autopilot, this is a wake-up for you, too. You have less runway, so I won’t pretend the compounding is as dramatic as it is at twenty-five. For you, the bigger lever is often structure, not time: making sure your money sits in the right kind of account, so that when you spend it, more of it is yours and less goes to taxes. It is genuinely never too late, the rules have changed a lot since you signed up, and there’s a good chance you’re leaving real money on the table in accounts you already own. This book will show you where to look. It all comes down to this: when you start saving early and keep the money invested in a broad-market index fund inside a Roth, where it grows tax-free, you build your own pension, and with it your freedom, because in America, no one else will. And you’re not just saving. You’re becoming an owner: a small piece of the world’s best businesses, the giants of today and the fastest-growing innovators shaping tomorrow, all working for you while you sleep. “Retirement” is a terrible word for what this book is about. It sounds like an ending: a beige waiting room at the far end of a long career, if you ever get there at all. Forget that picture. What you’re really building here isn’t a retirement. It’s freedom: to walk away from a job that’s become a grind, to take a risk you couldn’t otherwise afford, or to keep doing what you love because you choose to, not because you have to. For earlier generations, a house did much of this quietly, a mortgage was a savings plan in disguise, and the equity was the nest egg. If that door feels closed at today’s prices, this path does the same job without the down payment. And that’s why this book asks one simple thing of you from the start. It’s written for the person with a self-reliant streak, someone ambitious, who prizes independence and would rather build the tools to run their own life than wait for anyone to hand them one. If that’s you, what follows is about the closest thing there is to an algorithm: start early, own broadly, keep going, and let time do the work. Do that, and hitting your financial retirement goals stops being an ending. Instead, it becomes the moment you start really living for yourself. Now the good news, folded inside a sobering statistic. Nearly half of U.S. households have no retirement account at all, according to Federal Reserve data. Not because the tools are exclusive or complicated, but because almost no one is ever taught to use them. What’s missing is rarely access; it’s knowledge. And that gap is the whole opportunity, because it is so fixable. This book exists to close it: to teach you the simplest, most powerful tools for building retirement wealth, and the concrete steps to use them. The Roth IRA and a low-cost index fund are open to virtually every working American; give an ordinary person an understanding of how they work and the discipline to use them, and a secure retirement stops being a distant worry and becomes a realistic goal. This gap is yours to close. You can do this yourself. Who this book is for. The plan works at any income and any age, but the earlier you start, the more it rewards you. So it is aimed first at people with decades still ahead of them to build a saving habit and let it compound. And it applies no matter how you earn a living, whether you’re a corporate employee, an independent contractor, or working for a small business, a public company, or a nonprofit. The tax-advantaged account may change: a Roth IRA, a traditional IRA, a 401(k), a Roth 401(k), a solo 401(k), a 403(b). But the idea behind it never does: own low-cost index funds, start early, and let them compound untaxed. These pages illustrate maxing a Roth IRA each year because that shows the mechanics most clearly, not because it is a requirement. If your job offers a 401(k) with an employer match, that match comes first, free money, before the Roth even begins; the short note right after Chapter 2 spells out the order. And a very high earner trying to replace a large salary will need more than a Roth alone: a 401(k), a backdoor Roth, taxable accounts. “Deep Dive I”, later in the book, walks through each of them in plain English, so you’ll have them when you need them (it’s subtitled “Beyond the Roth IRA: Your Other Options”). And if maxing is out of reach, the same forces work on whatever you can set aside. As you read, you’ll meet ordinary earners from many walks of life, among them Maya, a physical therapist; Carlos, an electrician; and Emma, a working musician. You’ll follow a normal paycheck all the way into a retirement they fund themselves. As you follow this plan, keep three things top of mind: * 1. Time is the most powerful force in investing. Money compounds: growth earns its own growth. Over thirty to forty years that turns steady, ordinary saving into extraordinary sums. Starting early matters more than how much you earn or how clever you are. * 2. Where you hold the money is almost as important as the money itself. Inside a Roth IRA, a lifetime of growth and every dollar you later withdraw are completely tax-free. That shelter is enormously valuable and highly advantageous next to an ordinary taxable account, and even a traditional IRA. * 3. In America, this is your job, but you’re also given the means to do it. The U.S. leaves retirement largely to the individual, yet it taxes you far less than most wealthy countries do, leaving more of your income in your hands. The opportunity is to take that cash flow from the relative tax savings and deliberately convert it into your own private pension. The tool is simple; the only hard parts are starting and staying the course. The headline result Contribute the annual maximum into a Roth IRA (about $7,500 today) every year from age 30 to retirement, roughly $322,000 of total contributions over a career. Then build every conclusion in this book up from the very bottom of the range of historical outcomes: the floor, about 8 percent a year, the worst thirty-year stretch in nearly a century. Even there it grows to about $2.15 million, entirely tax-free. That is enough to support about $86,000 a year at a sustainable 4% withdrawal. Everything above that floor is upside. The full range is in the chapters that follow. The amount you put in is ordinary. What time and tax-free compounding do with it is extraordinary. And because we planned on the floor, nearly every surprise runs in your favor. Put that in perspective. To simply buy $86,000 a year of income at retirement, you’d hand an insurance company well over a million dollars for an annuity, or hold more than two million dollars in dividend stocks, and either way, that income would be taxed. You reach the same $86,000 a year for about $322,000 of contributions, because you started early and let it compound, and every dollar of it is tax-free, with the balance still yours rather than an insurance company’s. ✦ A NOTE FROM THE AUTHOR Start Now is free to read and free to share. If it helped you, the kindest thing you can do is subscribe and pass it to one person who needs it. Questions, comments, or a story of your own? Leave one below, or just reply to this email; I read every one. If you’d like to give back, pay it forward: donate any amount to a cause you believe in. I don’t collect a penny of it; it goes straight to the charity you choose, not to me. If you’d like a suggestion, I support the Zach Moses Music, Love & Light Fund at the Sweet Relief Musicians Fund, which feeds musicians in need. sweetrelief.org/zachmoses → Coming next: The Whole Plan: On One Page Thanks for reading Start Now! Subscribe for free to receive new posts and support my work. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit startnowbook.substack.com

  4. 4d ago

    The Story Behind Start Now

    This is part of Start Now — a complete guide to building your own tax-free pension, published free, one piece at a time. New here? Start Here → About six weeks ago I got to talking with a thoughtful young man who was doing some contracting work at our house. It was right after SpaceX went public, and the headlines were full of a fresh wave of enormous new fortunes. He said something I haven’t been able to shake, as close as I can remember it: “When I was a kid, everyone talked about wanting to be a millionaire. Then we had billionaires. Now there’s a trillionaire. What’s going on? How am I supposed to build wealth? Where should I begin?” I responded, “Let’s go out for coffee and talk about it.” That evening I started writing this book. Because here’s what I wanted him to hear, and what I’ll tell you: you can start right now. I’ve been having some version of that conversation for decades: with our own kids, with their friends, with lots of young people just out of school starting their careers or ones a decade or so later, starting families. Years ago, I even tried to distill what I thought were the secrets to a wealthy life onto a single page, and I meant wealthy in the fullest sense: not just money, but meaning, happiness, and purpose. This book is the DNA of that page, narrowed to one piece, then expanded in depth: a simple algorithm for building a secure pension of your own. Thanks for reading Start Now! Subscribe for free to receive new posts and support my work. That afternoon, this young man’s question landed differently. It reminded me of NVIDIA. About ten years ago, when I was starting a virtual reality business, I went to a conference in San Jose, speakers in one hall and a room full of VR demos in another. I went there to learn, to network, and to look for investment opportunities among the demos. I walked that floor thinking like the Wall Street analyst I’d been for decades. Forget the gadgets: who’s the “Intel inside” here, the Levi Strauss of this gold rush? (Levi Strauss got rich selling supplies to the gold miners, profiting from the rush without ever digging for gold.) I had a long talk with a senior executive from NVIDIA and left certain that every idea in that building would run on their chips (as would later happen with crypto and AI, on a far larger scale). Then I went home, ran the numbers through my overly sophisticated investor lens, decided the stock which had just had a big run was overpriced, and placed a careful limit order to buy it lower. It never came down. I cancelled the order. I missed one of the greatest runs in market history. Here’s the thing, though, and it’s the whole reason for this book. It didn’t matter. In my own retirement accounts I had done the boring, disciplined thing this book teaches: I owned the entire U.S. market through a low-cost index fund. So I didn’t need to be right about NVIDIA. When it soared, I already owned it anyway, along with every other winner I never saw coming. The index quietly captured the whole explosion of wealth and creativity of the last decade, without my having to pick a single stock correctly. That’s not luck. It’s by design. A recent, well-respected study found that nearly all of the market’s long-run gains come from just a tiny handful of companies*, which sounds terrifying until you see the solution: own them all. Buy the whole market, hold it for decades, reinvest the dividends, let compounding double your money again and again, and even the worst 30-year return in the S&P 500’s history builds real wealth. You don’t have to find the next NVIDIA. You just have to own the haystack it’s hiding in. That alone would be reason enough to become an owner. But there’s a bigger one now: more and more of the world’s wealth flows to the people who own things (companies, technology, whatever AI becomes), and less to those who only earn a wage. That’s really what this young man’s insightful question was about: a way onto the ownership side, which on an ordinary salary is as close as a Roth and an index fund, all of it tax-free. I wish someone had sat me down at 25 and told me all of this plainly, not just how markets work, but the traps: how much chasing the next hot thing costs you, how quietly taxes and fees drain away your gains, and how much is won simply by starting early and staying put. I'm writing this book, first, for our children — Zachary, Isabel, Samuel, and Luc — and their friends: a way to continue, in detail, a conversation I've been having with them for decades. And I'm writing it because I see too many bright young people who've decided the game is rigged and there's no point, and who then go looking for a shortcut: meme stocks, crypto, prediction markets, the next big IPO, a lottery ticket dressed up as investing. Others just punt the decision a decade or two down the road. I understand the impulse. But there's an answer, and it isn't a secret, nor is it a gamble. It's patient, disciplined ownership of the whole market inside a tax-advantaged account. It's available to you, today, on an ordinary salary, and I'll show you how. So this book is my coffee with you. The plan is simple. It’s proven. Now it’s up to you. Start now. Northern California, July 15, 2026 * Hendrik Bessembinder, “One Hundred Years in the U.S. Stock Markets” (2026): the study finding that a small percentage of all listed companies account for essentially all of the U.S. stock market’s net wealth creation. And within that small group, just 46 firms produced half of it, from 1926 to 2025. ✦ How to read this Start Now is a book, published here one part at a time, free. A short chapter arrives each week. Read them in order or skip around; by the end you’ll have the whole plan, and you could open the account in an afternoon. The whole book, free, is coming. Once the chapters are out, I'll open the complete book to read free online. If you're subscribed, you'll get an email the moment it's ready…. Nothing to buy and nothing to ask for; it just arrives in your inbox. A glossary to keep. Early on you’ll find a short list of the terms you’ll meet in the chapters ahead, from compounding to the Roth IRA to the 4% rule. You don’t need to study it; it’s there to glance at whenever a word comes up that you’d like pinned down. That’s the whole map. Start now. A NOTE FROM THE AUTHOR Start Now is free to read and free to share. If it helped you, the kindest thing you can do is subscribe and pass it to one person who needs it. Questions, comments, or a story of your own? Leave one below, or just reply to this email; I read every one. If you’d like to give back, pay it forward: donate any amount to a cause you believe in. I don’t collect a penny of it; it goes straight to the charity you choose, not to me. If you’d like a suggestion, I support the Zach Moses Music, Love & Light Fund at the Sweet Relief Musicians Fund, which feeds musicians in need. sweetrelief.org/zachmoses → Coming next: The Opening Thanks for reading Start Now! Subscribe for free to receive new posts and support my work. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit startnowbook.substack.com

  • 4 Episodes

About

Start Now: Your Direct Path to Lasting Wealth and Financial Freedom. This is the audio edition of the plain-language book on building your own tax-free pension — using nothing more than a Roth IRA and one low-cost index fund. Written and read by Greg M. Ostroff, a CFA who spent nearly two decades on Wall Street, each short episode walks you step by step through how anyone, on an ordinary salary, can build lasting wealth and retire on their own terms. No jargon, no hot tips, no market timing — just the few simple principles that actually work, and the discipline to use them. Free to listen, free to share. Start now. startnowbook.substack.com

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