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Friends That Invest
I retired at 29 through startups and investing: here is exactly how
Season 9, Ep. 18
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This week, Sim shares the deeply personal story of becoming financially retired at just 29 years old and reveals the exact strategies that helped her achieve FIRE (Financial Independence, Retire Early). She breaks down her FIRE number, the investing habits and side hustles that accelerated her wealth, plus the mistakes she wishes she avoided along the way. Sim also opens up about the surprising reality of “retirement,” why financial freedom didn’t look the way she expected, and how reaching FIRE changed her relationship with work, money, and purpose.
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15:58||Season 9, Ep. 32This week, Sim shares what happened when she broke one of investing’s biggest rules and tried to time the market by selling her NVIDIA shares. She breaks down why predicting market bubbles is almost impossible, the hidden costs of buying and selling, and why time in the market can matter more than getting the timing perfect. It’s a real-life investing lesson on overconfidence, market timing, and why a long-term strategy built around broad market index funds can be much simpler.
31. Why I’m Not Selling My S&P500 Funds
22:16||Season 9, Ep. 31This week, Sim breaks down why she’s not selling her S&P 500 investments or pulling her money out of the US stock market, despite growing fears about America’s future. She explores four key reasons she remains confident in US investing long term, including innovation, access to capital, market liquidity, and the global revenue generated by S&P 500 companies. Plus, Sim explains where emerging markets can fit into a diversified investment portfolio without making drastic decisions based on short-term fear.
30. 6 Ways People Pleasing Is Costing You Money
25:09||Season 9, Ep. 30This week, Sim breaks down the hidden ways people pleasing could be costing you thousands, from accepting extra work without recognition to underselling yourself, overspending, and struggling to set financial boundaries. She shares practical strategies to negotiate your salary with confidence, stop money leaks, and build healthier habits at work and at home. If you want to earn more, spend less, and stop letting guilt get in the way of your financial goals, this episode is for you.
29. I Retired Early, Then Went Back to Work
15:38||Season 9, Ep. 29This week, Sim reflects on what happened after reaching financial independence and why retiring early wasn't what she expected. She shares the reality of hitting her FIRE number, why she chose to keep building Friends That Invest, and the surprising lessons she learned about purpose, productivity, and finding a career you don't want to retire from. If you're working towards financial freedom, this episode will help you rethink what wealth really means once you've reached your goal.
28. Should You Save For Tomorrow or Spend Today? My Framework
17:54||Season 9, Ep. 28This week, Sim explores one of the biggest personal finance questions of all: should you spend money enjoying your life today, or save everything for the future? She shares how to find the balance between building wealth and creating meaningful experiences, why being too frugal can sometimes hold you back, and practical ways to spend with intention instead of guilt. If you've ever wondered whether you're saving too much or not enough, this episode will help you rethink your relationship with money.
27. The Best & Worst Performing Asset Classes Over 10 Years
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26. 6 Popular Financial Tips You Should Absolutely Ignore
24:57||Season 9, Ep. 26This week, Sim breaks down six of the most common money tips that sound smart but could actually cost you thousands over the long term. From trying to time the stock market and day trading to using debt to invest, relying on Bitcoin as an inflation hedge, and believing property prices always rise, she explains what the research really says. If you want to build wealth with fewer mistakes and more confidence, this episode will help you separate financial facts from popular myths.
25. 15 Little Splurges To Help You Be So Productive, it Feels Illegal
32:09||Season 9, Ep. 25This week, Sim shares the 15 purchases that have genuinely made her more productive, happier, and more intentional with her money. From a Kindle and a quality mattress to meal prep, travel upgrades, and the surprising $99 gadget that helped her reclaim over 1,000 hours from social media, she breaks down which splurges are actually worth the investment. If you're trying to spend smarter instead of simply spending less, this episode will help you decide where paying more can genuinely improve your life.
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