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Victoria here, Girlboss’ executive editor. 👋 |
Today’s How-To Thursday topic is all about money and taking financial risks! Who else’s palms just got all clammy? ✋ Look, I get it. Money talk can be uncomfortable—scary even—but there’s no better person to give you an honest, no-BS answer than Stephanie Guild, Robinhood’s Chief Investment Officer. |
Her advice boils down to this: you don't need to get rid of the fear, you just need to stop letting it make all your decisions. Scroll down to learn how she thinks about risk, timelines, and why $1 a day can turn into $55K down the line. 👀 |
Other stuff the Girlboss team is talking about on Slack: |
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💼 Job of the day: Fishwife (the cool-girl tinned fish company) is hiring a fully remote Senior Director of Brand Marketing to own brand strategy, campaigns, and partnerships. You'll work directly with the CEO and manage a real budget and a growing team. Don’t let this amazing opp swim away! 🐟🤪 |
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Strawberry.me |
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When Work Just Feels Off
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You have a job. A decent title. A regular paycheck. So why does it still feel like something's missing? 🤔 Sometimes it's hard to see clearly when you're this close to it. Let’s talk about it! |
Strawberry.me matches you with a real, vetted career coach to help you get clarity on what's actually bothering you and build a plan around it—whether that's an awkward conversation with your manager, the raise you've been putting off asking for, or a full-on career rebrand. |
Girlboss readers get an exclusive 50% OFF their first coaching session with code GIRLBOSS. Remember: "good on paper" was never the end goal. Being satisfied with where you're at and where you're going is. |
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Scared of Losing Money in the Market? Let’s Talk About It |
The dilemma: “I’m scared of losing money in the stock market. How do I get more comfortable with risk?” |
The answer: Stephanie Guild, the chief investment officer at Robinhood. With 20+ years of managing high-net-worth portfolios and a current C-suite role at an S&P 500 financial institution, Steph has thrived in a male-dominated industry. Now, she’s eager to share her hard-earned expertise to empower the next generation of women leaders. |
I get this question more than almost any other. The possibility of losing money, even on paper, can feel scary. You work hard for what you have. But what I’ve learned after 25+ years investing: a healthy respect for risk is crucial, but must be paired with an equal fear of not growing what you have. |
How to stay the course, even when the market gets bumpy: |
💹 Make sure you’re only risking what you can afford to ride out |
Much of the "fear of the market" is often fear of not having money if or when you need it. That's solvable: |
Start knocking out expensive debt first. Credit card debt especially—paying it down starts to look like savings quickly. Student loan debt is usually cheaper and can wait.
Then build an emergency fund. This can be three to six months' worth of expenses in a high-yield savings account. Once that exists, you know the emergency fund is what you tap in case you need it when the market is dipping.
Internalize that not investing limits the future value of your money. Inflation, or increases in the cost of living, has averaged 2.68% since 1990. So you want your money to grow at least as fast as that to stay at the same value. |
⌛ Know your timeline |
It closely relates to how much risk you can take. The more time you have, the more risk, like investing in stocks, you might be able to take on. Pairing a timeline with an intention for the money calibrates the fear that can come with taking risks with investing. |
🐌 Invest bit by bit |
You don't build tolerance for risk overnight. You build it in reps: |
Set up automatic transfers of even a small amount weekly or monthly. Small and consistent can beat big, but only once.
For example, $1 a day for 35 years adds up to $12K in contributions. If invested, at even a below-historical-average annual return of 7%, it becomes roughly $55K. Bump it to $3 a day, and you're looking at $165K. Not guaranteed, of course—you do have to take some risk to aim toward it.
Diversify by investing in a fund. One fund can spread your investment across a whole group of stocks, spreading your risk with it. |
💡 You already know more than you think |
You know about investing by doing life. You buy coffee, you grocery shop—you already have opinions on which companies have great service. That instinct counts for more than people give it credit for. |
☁️ Zoom out to get perspective |
Every week in my Investor's Guild column, I break down what's happening in markets and what I think could be next. More often than not, a dip is just noise, not a long-term trend. Zooming out on a chart almost always tells a calmer story than the headline does. |
If you take one thing from this: The goal is not to eliminate fear. It’s to make sure it’s not the only thing steering the ship. 🚢 |
Got a work problem you need help with? Drop it here, and the answer to your question could be featured in an upcoming newsletter. 📬 |
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When Did Moving Out Become Proof I'd “Made It”? |
Leaving home has become a milestone we associate with success. But for a generation balancing ambition, affordability, and family responsibility, adulthood is not as simple as having a place of your own. |
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What Team Girlboss has been loving lately. |
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🛋️ Venus Williams just dropped a home collection with Crate & Barrel, inspired by a design trip to Milan and, of course, tennis. You’ll find sculptural chairs with subtle tennis ball accents, artful light fixtures, and a coffee table so chic you'll forget it's furniture. |
🎧 Don’t know what to listen to on your next hot girl walk? We love this episode of the Entreprenista Podcast with Katie Austin, founder of KA App, where she shared how she turned a loyal audience on social media into a thriving digital fitness and nutrition business. Want more? Explore the Entreprenista League for access to like-minded founders, exclusive events, and resources to grow your network. |
✨ Want glowing skin on the go? These collagen stick packs from Great Lakes Wellness are TSA-friendly, dissolve in any drink hot or cold, and taste like nothing. BRB, adding them to our gym bag and carry-on, stat.* |
♨️ Content Marketing Manager Kamela swears by T3 curling irons. She's got both the 1.75" and 1.5" barrels, and says the Korean CeraGloss™ ceramic tech means less frizz, more shine, and an effortless glide through your hair. No more frying your precious strands off! |
🪩 Executive Editor Victoria has been playing Jamie Miller’s mega-viral hit “Babydoll” on repeat for the past few weeks and still hasn't gotten sick of it. The groovy beat is so damn infectious and his vocals make her swoon every time. Go listen now! |
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