Ep 26 - Tess Waresmith - 3 Silent Wealth Killers Hiding in Plain Sight (Or Small Print)
Tess Waresmith is a financial educator, speaker, and investor known for helping people reach financial independence with simple investing. She’s the founder of Wealth With Tess, where she helps women build wealth and confidence through investing. Tess has been featured by CNBC, Business Insider, and Fox 5 NY, and is a self-made millionaire focused on helping others avoid the mistakes that cost her… well let’s not go there.📚 What We Discuss with Tess Waresmith:🔍 03:15 — Early mistakes and financial wake-up calls — who should handle your money? 💸 06:40 — Millions lost in fees — how hidden costs quietly eat your future 📈 08:15 — “It’s not that hard” — building confidence by learning the basics 🧠 10:00 — Asset allocation 101 — understanding fiduciary duty and financial jargon 🧾 13:00 — Learned money scripts and access to real financial literacy ⚖️ 15:00 — Avoiding absolutes — why personal finance isn’t one-size-fits-all ⏳ 17:20 — The time investment of investing — and why it’s worth it 🚫 20:00 — Breaking up with your advisor — navigating the money manager minefield 🚩 25:55 — Red flags in your fees — questions to ask and answers to expect 🤫 29:00 — Your ignorance is someone’s profit — staying sharp in a noisy market 🎓 30:30 — $50K of financial education in 4 minutes — a crash course curriculum ⚡ 35:30 — Lightning round! — quickfire investing truths and final thoughts💡 What You’ll Walk Away WithHow to spot hidden fees that quietly drain your portfolioThe confidence to make financial decisions without outsourcing everythingWhat to ask before trusting someone with your moneyA basic framework for asset allocation and fiduciary responsibilityWhy there's no single “right” way to investTools for becoming an informed investor, even if you’re starting from scratch🧾 ResourcesTess’s website: www.wealthwithtess.comFinancial independence mini-course: www.wealthwithtess.com/fiFollow Tess on Instagram: @wealthwithtessFeatured on:CNBCBusiness InsiderFox 5 NYIf you're still game to support the show, leaving a quick review really helps — even one sentence goes a long way.You can also join thousands of other investing-minded folks by subscribing to the newsletter: one practical idea, once a week, zero fluff — www.tylergardner.com/newsletters.Check out episode 23 with Bill Perkins — a hedge fund manager and author of Die With Zero, who explains why the best return on investment might be spending your money now on experiences that matter.
--------
42:29
--------
42:29
Ep 25 - The ONLY 6 Accounts You Will Ever Need (And How to Use Each of Them Strategically)
In this solo episode, Tyler breaks down the only six financial accounts you’ll ever truly need—and more importantly, how to actually use them. Whether you’re just getting started or managing a more complex portfolio, this is your streamlined, nonsense-free guide to designing a system that works.No more chasing every new fintech app or wondering if you’re missing something. If you’ve ever felt overwhelmed by the alphabet soup of financial tools, Tyler’s here to cut through the noise and give you a clear path forward. These six accounts are enough to build wealth, protect your downside, and create long-term flexibility. And anything beyond them? Likely just extra complexity disguised as “optimization.”What You’ll Learn:Why a regular checking account should be boring—and how to keep it that wayHow to think about a High-Yield Savings Account (HYSA): the “glovebox” for your cash—not your investment engineThe power of a Roth IRA—and how it’s often misunderstoodWhy a pre-tax IRA or 401(k) still matters, even if retirement feels far awayThe secret weapon of the wealthy: the HSA (Health Savings Account) and how to use it for more than doctor’s visitsHow a taxable brokerage account unlocks true flexibility—and why you might want to use it before maxing everything elsePlus:A better metaphor than “bucket strategy”Why most emergencies aren’t emergencies at all (and what that means for where your cash lives)The order Tyler recommends for prioritizing contributionsWhen not to use these accounts (because yes, even the Roth IRA can be misused)Whether you're 25 and just opening your first Roth, or 55 and wondering how to consolidate accounts, this episode gives you a timeless roadmap to simplify your finances without oversimplifying your life. As always, Tyler brings the clarity, the nuance, and just enough humor to make talking about tax-advantaged accounts… well, weirdly fun.
--------
33:30
--------
33:30
Ep 24 - Bill Perkins - How to Die With Zero (and Actually Live First)
Is Future Planning Ruining Your Future?What if your financial advisor told you to spend your money now? To give away your inheritance early? To go on more vacations? To prioritize experience over investment?What if they told you the only inflation-protected asset is experience?Bill Perkins is a hedge fund manager, poker player, and author of the bestseller Die With Zero. On this week’s episode, he breaks down why money is just a means — and experience is the end.📚 What We Discuss with Bill Perkins:🛤️ 02:40 — Early revelations and going the non-traditional route 💡 05:10 — Borrowing from your poor self to give to your rich self 📆 07:35 — “What experiences belong when?” — and why delayed gratification can go too far 🤔 10:25 — What money can really buy — fulfillment vs. accumulation 🎢 12:22 — Staple experiences worth the cost — collecting memories that stick 🧠 13:35 — Memory dividends — the one return no market crash can erase 👵 15:40 — Retirement planning — running out of money vs. running out of time 🧘 17:50 — Letting go — why overplanning for the future can wreck the present 🕰️ 20:25 — “Life is now, life is urgent” — estate planning and missed chances 🏛️ 23:20 — When should inheritance be inherited? Challenging default thinking 🎯 26:15 — Hindsight and financial regret — is gold-plated better than good enough? 📖 28:20 — Learning from the past to make the most of what’s next 💸 29:20 — What is your time worth? The hidden cost of chasing more income💡 What You’ll Walk Away WithWhy deferring joy is often just fear in disguiseA new way to think about saving, giving, and legacyHow to measure value through memory, not moneyA framework for spending intentionally at different life stagesHow to plan for the end of life without missing the middle🧾 Resources MentionedDie With Zero by Bill Perkins → https://a.co/d/9KKHOzTYour Money or Your Life by Vicki Robin and Joe Dominguez → https://yourmoneyoryourlife.comIf you're still game to support the show, leaving a quick review really helps — even one sentence goes a long way to help others find the show.You can also join thousands of other investing-minded folks by subscribing to the newsletter: www.tylergardner.comIf you enjoyed this, check out episode 22 with Wendy Li — a former endowment CIO who managed billions for New York’s top institutions and shared how institutional investors evaluate risk, choose fund managers, and build resilient portfolios.
--------
33:57
--------
33:57
Ep 23 - The 3 Reasons You’ll Never Beat the Market (And Why That’s Okay)
Let’s be honest: you’re not going to beat the stock market. And that’s not an insult — it’s a liberation. In this episode of Your Money Guide on the Side, Tyler Gardner unpacks one of the most misunderstood goals in investing: trying to “win” against the market.Drawing on decades of investing experience (and more than a few Peloton mistakes), Tyler explains why comparing yourself to the S&P 500 is often irrelevant, how hedge funds and high-frequency traders have rigged the game against retail investors, and most importantly, why even when you do win, you often lose.We explore:The real origin of the “beat the market” mindset — and why it was never about helping youWhy the S&P 500 isn’t a fair benchmark for most peopleMarket efficiency theory explained without Greek letters (but with plenty of sarcasm)Behavioral biases that will ruin your returns: overconfidence, recency bias, loss aversion, confirmation bias, and moreHow even the pros struggle — and why surviving your own brain is the real edgeWhen paying a 1% advisor fee might actually be a bargainWhy boring, automated, diversified investing is the best strategy no one wants to hear aboutWhether you're new to investing or already deep in the weeds of candlestick charts and YouTube stock tips, this episode will reframe what success really looks like. Because real wealth isn’t built by outsmarting others — it’s built by staying in the game. 📬 Subscribe to the newsletter for 3 financial insights every Sunday 📲 Follow Tyler on IG/TikTok: @socialcapofficial 📈 Want to support the show? A quick review or share goes a long way.
--------
31:28
--------
31:28
Ep 22 - Wendy Li - The Secret Strategies of Billion-Dollar Portfolios
Wendy Li managed billions for New York’s top institutions — here’s what she thinks individual investors can (and should) steal from the pros.After leading portfolios for the Met Museum, UJA-Federation, and the Mother Cabrini Health Foundation, Wendy now serves as CIO at Ivy Invest. She’s spent decades on the inside — and in this episode she’s walking us through how institutional investors actually make decisions, where regular people go wrong, and what it means to manage risk.📚What We Discuss with Wendy: 🧠 02:17 — Institutions vs. individuals: why the ultra-wealthy play a different investing game 📉 06:28 — Risk vs. return: are you really being paid for the risk you’re taking? 📚 08:34 — Invest in what you know: learning by doing (and surviving your mistakes) 🪤 11:48 — Career course-corrections: mistakes, pivots, and staying in the game 🤝 15:28 — Trust but verify: what good investor relationships actually look like 💰 18:00 — The luxury of investing: identifying the how and the when to invest 🧾 20:32 — Portfolio allocation: managing your capital with intention 🚪 25:46 — Alternatives and access: knowing your place in a complex market 🕵️ 30:06 — Fund managers: who and how to choose 🛠️ 33:32 — Investing skills: humility, curiosity, and flexibility in the face of risk 🔍 36:58 — Where to learn: insider investment resources 🧰 42:18 — Practical takeaways: frameworks and tools you can use today💡 What you’ll walk away withHow institutions manage risk — and how to apply it to your own investingWhy most retail investors misunderstand returnsHow to think long-term when markets are volatileWhat to ask before trusting a fund manager with your moneyHow to approach alternatives without insider accessThe core skills every smart investor needsIf you're game to support the show, leaving a quick review really helps — even one sentence goes a long way!You can also join thousands of others investment minded individuals in subscribing to my newsletter here.If this episode resonated with you, be sure to check out Episode 15, where Tyler breaks down the 7 steps to identifying your needs for a financial advisor.
Your go-to podcast for mastering money and investing. Hosted by Tyler Gardner, a trusted influencer with over 2.5M followers, Your Money Guide on the Side simplifies the complex, adds nuance to what seems simple, and connects you with the brightest minds in finance, investing, and business. Whether you’re just starting or leveling up, this is your one-stop resource to navigate your own finances with clarity, confidence, and a bit of fun. Let’s get you one step closer to where you need to be.
Ireland