Chapter 1

But Are You Ready to Start Investing?

THERE I SAT, staring at my phone, willing it to light up with a text message. It was fall 2011 and, shockingly, I wasn’t a young woman hoping a boy would follow up about setting another date. Oh, no. It felt much worse than that. I was a financially desperate twenty-three-year-old trying to make ends meet in New York City, one who was hoping that, through sheer force of will, I could make one of the parents for whom I babysat respond to the feelers I’d just sent out.

“Are you free on Friday or Saturday evening?” the mother of my favorite babysitting charge texted.

“Yes, either one works for me,” I wrote back within a few seconds, suppressing the urge to end with the colon-plus-parenthesis smiley face. It would have added desperation.

“Great, let’s do Friday at six p.m.,” she responded an agonizing twenty minutes later.

Friday at six p.m. meant I’d probably earn $120. This mom paid $20 an hour, and usually stayed out until at least midnight on her ladies’ nights out.

I logged in to my bank account and assessed the rather pitiful state of affairs. At the time, I worked three jobs. My main job was as a page for the Late Show with David Letterman. The job, while fun, certainly didn’t cover even my most basic living expenses: food, MetroCard, rent, cell phone bill. So, I had to subsidize it by babysitting and working as a barista. These three jobs usually resulted in me working from around 5:00 a.m. to 11:00 p.m. six or seven days a week. All those hours, and I still barely grossed $23,000 my first year out of college.

The brief story of how I made this work without sinking into debt involves finding ample free (or frugal) entertainment and living off of a lot of coffee shop leftovers (products that had passed their sell-by date but weren’t expired), rice and vegetables, and the snacks fed to the little kids I babysat. That, and I’d stashed away a $10,000 buffer in college because of my obsessive pursuit to live in New York City after graduation. That buffer never ended up getting touched (after I raided it for the security deposit on my first apartment), but it was a significant emergency fund to have during a financially stressful time. I also knew I had the privilege of being able to call my parents if anything went truly, truly wrong. The parental safety net isn’t one I ever used, but even its existence enabled me to take more career risks than peers who were not in a similar situation.

Worrying each month about making enough to be able to pay all my bills without dipping into my cash reserves didn’t exactly put me in a prime position to start investing. Even though I’d learned some basics about investing already from my dad, I knew it wouldn’t be wise to put anything in the market quite yet. Every penny I earned needed to go toward other, short-term financial goals. I needed to be able to put on my financial oxygen mask before taking any risks with my money.


GETTING YOUR FINANCIAL LIFE together is step one on the journey to becoming an investor. You also need to shake the common misconception that investing is just for the wealthy.

INVESTING ISN’T JUST FOR WEALTHY PEOPLE

“[T]here’s this misconception that you need to be in a certain place before you can start investing,” explains Jennifer Barrett, chief education officer for Acorns, the saving and investing app. “That was true when I was in my twenties, too. I sort of had this idea that investing was for the wealthy or investing was for the financially successful, which meant I had to get my stuff together before I could really go in big. I think a lot of people feel that way because it’s intimidating and, at least in the past, you had to have $500 to $5,000 to open an account, so you really did need to have some money set aside outside of savings that could be used for investing.”

Barrett touches on a real concern for most rookie investors: how much does it take to start? In some cases, you will be faced with a minimum amount to buy into a fund. For example, you may need as much as $3,000 to open an S&P 500 index fund with certain brokerages. Saving up $3,000 just to gain entry to investing can be a ludicrous scenario for some.

Fortunately, technology really has changed the game, and now the average rookie and seasoned investor alike have more choices and can start with much lower thresholds than available to previous generations. The much-touted index fund wasn’t even created until 1976.1 That may sound like a long time ago to your average Millennial, but consider that the New York Stock Exchange has existed as a formal organization since the 1800s. Chapter 8 will take a deeper dive into how technology allows you to get into the game without hefty minimum initial investments.

INVESTING ISN’T JUST FOR OLDER PEOPLE

As you continue on your journey to learn more about investing, there will be one common mistake that gets mentioned time and time again. “I’d say the biggest mistake is not starting early,” explains Julie Virta, senior financial advisor with Vanguard Personal Advisor Services®. “The earlier you start, the better.”

There are plenty of other mistakes you can make as a rookie investor, and we’ll address those throughout this book, but believing you’re too young to start is the simplest one to fix when you’re young. In theory.

PUTTING ON YOUR FINANCIAL OXYGEN MASK

In reality, it can take years to get your financial life together, and while it’s a mistake to wait too long to start investing, it’s also a big mistake to throw your money into the market before you’ve taken the time to put your financial oxygen mask on first.

“You have to earn the right to invest,” says Douglas A. Boneparth, CFP®, New York City’s financial advisor for Millennials, and president of Bone Fide Wealth. “Investments are the sexiest part of personal finance, but it’s just one piece.” He adds, “There are a number of boxes you should be checking off before you find yourself putting risk on your money.”

Ready to Start Investing Checklist

Once You’re Ready to Start . . .

AM I TOO MUCH OF A BROKE MILLENNIAL TO START INVESTING?

You picked up this book excited to learn more about investing so you could get started, but after reading the checklist, you have a few unmarked boxes. Does that mean you can’t invest yet?

Unfortunately, outside of contributing to retirement accounts, it does. It’s important to lay the foundation first before you begin putting money in the market. Without the proper foundation, you can put yourself at greater risk in what is already a somewhat risky situation. Investing is a critical part of building wealth, but as Boneparth says, you must earn the right to start.

When You’re Not Ready to Start Investing

If any of these boxes get a checkmark, then you need to press Pause on investing. Take the time to put your financial oxygen mask on first. At the risk of being too self-serving, I suggest you start by reading Broke Millennial: Stop Scraping By and Get Your Financial Life Together. It will help you lay that necessary foundation in order to start investing. That’s why this is the second book in the series!

That being said, I’m not telling you to stop reading this book. You can learn about investing before you’ve built your emergency fund, paid off your credit cards, or set all your financial goals.

HOW THIS BOOK IS ORGANIZED

The introduction has explained why it’s important to invest your money and not just stash it in savings, and now you’ve figured out whether now is the right time to actually begin investing. In the words of Douglas Boneparth, you’ve “earned the right to invest.” Or you’ve realized it isn’t time for you to be putting money into the stock market (outside of retirement plans), but you still want to learn.

Akin to the style of the first book in the Broke Millennial series, this book does not have to be read cover to cover. Each chapter stands on its own, but I do advise you to read chapter 2 before progressing so we’re speaking the same language.

However, just because you can skip around doesn’t mean you should. I’ve created three categories of potential readers and recommended chapters based on your level.

The True Rookie

You’ve never dabbled in investing but are eager to learn more. Well, maybe not so much eager, but you’ve been told it’s important, and this book seems like a way to ease in. You probably don’t contribute to an employer-matched retirement plan yet or an IRA, and it’s also totally okay if you don’t know what either of those terms mean.

For the true rookie investor, it would be best to read this book in chronological order, chapters 2 through 9. (I’m assuming you’ve already read the introduction and this chapter, but if you randomly opened up to this page, go back and start at the beginning!) After that, you’ll have a solid foundation and can begin to jump around based on your personal interests or where you are in your investing journey.

Chapter 2: Let’s Establish a Common Language

Chapter 3: Grabbing the Bull by the Horns When You’re Risk Averse

Chapter 4: I Have a 401(k)—Do I Need to Do More Investing?

Chapter 5: Should I Invest When I Have Student Loans?

Chapter 6: I Want to Put Money in the Market—How Do I Start?

Chapter 7: I Like Gambling—Isn’t That Like Individual Stock Picking?

Chapter 8: Investing—Of Course There’s an App for That

Chapter 9: Robo-Advisor or Human Advisor—Which Is Better?

Got Some Game, but Looking to Level Up

You’ve started contributing to your employer-matched retirement plan (or you contribute to an IRA), and maybe you’ve downloaded an app or two that’re helping you dabble in investing. But you know you can do more and want to level up your current investing strategy. For you, I recommend:

Chapter 4: I Have a 401(k)—Do I Need to Do More Investing?

Chapter 8: Investing—Of Course There’s an App for That

Chapter 11: Riding Out the Panic of a Market Crash

Chapter 12: Sniffing Out a Scam

Chapter 14: Tactics the Wealthy Use to Make and Preserve Money

Chapter 15: Where Can I Get More Investing Advice (Because I’ve Been on Reddit . . .)?

Want to Keep Learning (and Maybe Feel a Little Smug About Being Ahead of the Curve)

As mentioned in the preface, this book is designed for beginners. I won’t be taking you on a deep dive into cryptocurrency or providing a blueprint for individual stock picking (granted, the concept is addressed in chapter 7). Also, I won’t make it easier for you to understand “hedgies” (the colloquial term for people who work at hedge funds) or any other term you may overhear at happy hour. There are well-written books available for you to learn about all those things.

Have you already opened your own brokerage account and contribute to your 401(k) and dabble a bit in investing apps and are thinking about hiring a financial advisor? Don’t worry, there is still some value for you in this book.

Chapters that will interest you include:

Chapter 9: Robo-Advisor or Human Advisor—Which Is Better?

Chapter 10: Impact Investing—Making Money Without Compromising Your Ethics or Religious Beliefs

Chapter 12: Sniffing Out a Scam

Chapter 14: Tactics the Wealthy Use to Make and Preserve Money

Buckle up, it’s time to move on to deciphering investing jargon. I promise to make this as painless as possible.