Most people spend their lives trying not to lose. The wealthy? They play to win.

In this solo episode, Tyler Gardner breaks down the asymmetry of opportunity—why one big win can outweigh dozens of small failures, and how our fear of loss keeps us from seeing the upside that could change everything.

Tyler takes you from Disney’s acquisition of Pixar to Jeff Bezos’ “regret minimization framework,” unpacks the psychology of loss aversion, and explains why Monte Carlo simulations, the Kelly Criterion, and even barbell investing can help you make better decisions in life and money.

You’ll also learn:

• Why we overweight risk and underweight opportunity
• How only 4% of public companies have driven all net market gains (ASU study)
• What venture capital teaches us about failure and power laws
• Why the S&P 500 has never lost money over any rolling 20-year period (Fama/French)
• The exact 3-question framework the wealthy use to evaluate high-stakes decisions

Whether you’re building a business, investing for your future, or just trying to get out of your own way, this episode will help you rewire your decision-making process and start playing for upside.

🧠 It’s not about taking reckless risks—it’s about taking the right ones.
📈 Learn how to structure your decisions like a builder, not a hedger.

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For more insights, visit tylergardner.com, and subscribe to Tyler’s weekly newsletter for 3 actionable financial ideas every Sunday.

Follow Tyler on all platforms @socialcapofficial (IG + YT) and @socialcap (TT)

This week on Your Money Guide on the Side, I’m joined by the incredible Jessica Inskip—one of the sharpest, most grounded voices in modern investing. Jessica was the first female on Fidelity’s active trader desk, and you may have seen her breaking down complex strategies alongside Jim Cramer, or offering sharp, accessible takes on CNBC, Fox Business, Schwab Network, and Yahoo Finance.

In this episode, we unpack her journey from nearly becoming an engineer to becoming a nationally recognized voice in financial education—and why she made the bold decision to give up her professional licenses in order to educate people where they’re actually learning: on TikTok, Instagram, and her #1-ranked personal finance podcast, Market MakeHer.

Jessica shares the powerful story of how she pivoted careers after realizing that the people who needed the most help—young investors learning from unverified sources—weren’t being reached due to compliance constraints. The tragic case of Alex Kearns, and the inability for licensed professionals to correct misinformation in real-time, was a tipping point. From that moment on, Jessica committed to bridging the gap between Wall Street and the everyday investor, even if it meant leaving behind the traditional career path.

We talk about how she built a media presence without compromising her authenticity, how she measures impact over virality, and why she believes good education, not flashy trends, is the antidote to financial misinformation online. She shares her approach to making complex topics like credit markets and macroeconomics accessible—and the surprising (and sometimes frustrating) viral moments that have shaped her platform.

We also dive into:

• How she transitioned from Merrill to full-time educator and creator
• The emotional and professional weight of giving up her Series licenses
• The difference between being a financial expert and simply playing one on social media
• Why compliance rules continue to keep great educators out of the creator economy
• How she balances family life, media work, and her growing personal brand
• Her podcast, Market MakeHer, and how it became a trusted resource for tens of thousands

Jessica also reflects on what success really means in a digital world that rewards metrics over meaning. Her answer? It’s not about the followers. It’s about the impact—the emails, the DMs, the women who now feel confident speaking about bonds, credit markets, and earnings reports because someone took the time to meet them where they are.

We wrap by talking about her work with Jim Cramer, the power of representation in finance, and how she’s planning a book that will finally explain the domino effect of markets—from interest rates to consumer behavior—in a way that actually makes sense.

Whether you’re an active investor, a new creator, or just someone trying to be smarter with your money, Jessica offers a masterclass in clarity, commitment, and courage. This conversation is packed with insights, humility, and heart.

🎙️ Take a listen—you won’t just learn about markets. You’ll learn why voice, vision, and values matter more than ever in today’s financial landscape.

Bonds have been a staple in portfolios for decades, often hailed as the “safe” investment that brings stability and protects wealth. But what if I told you that this belief is outdated, and in many cases, dangerously misleading?

In today’s episode, I take a hard look at why bonds are overrated, the risks most investors overlook, and whether they deserve a spot in your portfolio at all. While bonds can serve a purpose, blindly following the 60/40 portfolio mantra without questioning its effectiveness can be a costly mistake.

We’ll break down the three biggest risks of bonds and why they may not be as “safe” as you think:
✅ Interest Rate Risk – When rates go up, your bond values drop. It’s that simple, and 2022 proved it when the Bloomberg U.S. Aggregate Bond Index suffered its worst year in history.
✅ Inflation Risk – Your 3% return isn’t a real 3% return if inflation is running at 4-5%. That’s a recipe for losing purchasing power over time.
✅ Opportunity Cost – For every dollar you park in bonds, you’re missing out on investments with real growth potential—whether that’s stocks, real estate, or other wealth-building assets.

Many investors believe bonds guarantee stability, but I argue that true long-term financial security comes from growth, not just preservation. The reality? A well-diversified stock index fund has statistically near-zero risk of going to zero, while bonds can quietly eat away at your purchasing power.

So, do bonds ever make sense? Maybe—if you’re already financially set and just want to protect what you have. But for most investors, the classic advice to shift heavily into bonds at retirement may be one of the biggest financial missteps.

This episode isn’t about hating bonds—it’s about thinking critically before defaulting to outdated strategies. Are you actually protecting your wealth? Or are you unknowingly holding yourself back?

👉 Tune in now, challenge conventional wisdom, and decide for yourself.

Back in 2003, I met Mike Taormina at the London School of Economics, never expecting we'd stay in touch—let alone spend decades debating finance and traveling together. Fast forward, and Mike has become a powerhouse in fintech, co-founding Vault, CommonBond, and Alluvial, with a Wharton MBA and a CFA to back it up.

But credentials aside, what sets Mike apart is his ability to break down complex crypto and finance topics into something actually useful. In this episode, we dive into decentralized finance, separating the noise from real opportunities, and why blockchain tech is transforming financial transparency.

We also discuss personal investing, risk tolerance, debt, and why even a seasoned finance pro like Mike trusts a robo-advisor over DIY trading. Whether you're deep into crypto or just trying to make smarter financial moves, this conversation is packed with insights.

In this week's episode, we explore our common tendency to react emotionally to political elections and their perceived impact on the stock market. I argue that changing investing habits based on external "noise," and it is noise to me, is nonsense; I only change investing habits when my own life or financial needs have changed. Emphasizing and drawing upon historical data, the show explores the market's long term patterns of growth, regardless of who is in office. In short, the market transcends our politics (in a way). Additionally, we explore the pitfalls of trying to time the markets based on politics, business cycles, or consumer sentiment. Finally, as always, we remember that it's normal to feel this way, and the moment of empathy comes form knowing that we all feel this way at times and need to remind one another to take a breath and focus on the long term plan. 

My guest this week, Patrick Wetherille, shares a little bit about his experience with optimizing life, managing empathy through start-up culture, and taking advantage of every opportunity to learn from and alongside business minds at every level. As the episode progresses, Patrick shares his thoughts on the importance of being able to work from anywhere and how that very freedom can often bring teams together and create optimized work cultures and production.

In this episode, I explore the power of diversifying communication channels, income streams, and the irony of many people knowing they should diversify and yet their not quite being able to walk the same walk. When the TikTok "ban" occurred, I was left wondering why so many creators, all of whom discuss the power and importance of diversification on a daily basis, had not diversified their digital assets, as well, and considered their content as part of their overall portfolio. 

In this episode, I do my best to touch on the absolute musts of investing and controlling our emotions. Not only controlling our emotions, but knowing our emotions and our reactions to market volatility first-hand through experience. I attempt to highlight the importance of thinking slightly differently and distantly about the markets and taking a walk when we need to escape from the relentless noise that is encouraging us to panic and make choices that we will, ultimately, regret when the waters calm. 

I am thrilled to offer a brief glimpse into the "why" behind building out the podcast. The ability to add nuance, engage other minds, and learn from multiple voices intrigues me and hopefully will help add value to your life. This episode is primarily highlighting what this endeavor will aim to achieve and how each episode might help you move closer to where you need to be with your personal finances, your attitude towards money, and your ability to learn more each and every day and ultimately take control of your own finances.