Earn & Invest

In this rewind episode we speak with Vicki Robin author of ⁠Your Money or Your Life⁠, and ⁠Douglas Tsoi⁠ writer of The Money and Meaning Newsletter about the promises that come with financial indepenence/retire early. Should FIRE have a warning label? Why money does and doesn't eventually end up meeting our expectations. Learn more about your ad choices. Visit megaphone.fm/adchoices

Join us in this rewind episode of Earn & Invest as we sit down with Jason from the Two Sides of FI podcast to explore the uncharted waters of life after early retirement. Together, we delve into the fascinating journey of financial independence and the vital question of how one fills their time, and whether boredom lurks in the shadows. Jason candidly shares his personal experiences, revealing the transformative impact of early retirement on his life. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of the Earn & Invest podcast, host Doc G explores the concept of abundance, arguing that it is entirely a mindset and a deliberate decision rather than a reflection of material wealth or bank account balances Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of the Earn and Invest podcast, host Doc G welcomes childhood friend and Brooklyn-based filmmaker Powell Brian. Brian, an executive producer best known for directing the critically acclaimed Netflix documentary Charles Bradley: Soul of America, joins the show to discuss the massive disruptions currently reshaping the entertainment industry. Throughout the episode, the two use the technological and AI-driven upheaval in Hollywood as a metaphor for the rapid changes threatening nearly every modern career Learn more about your ad choices. Visit megaphone.fm/adchoices

In this unique "Man on the Street" episode of the podcast, host Doc G steps away from interviewing professional authors and experts. Instead, he records the conversation from a pool in Cabos, Mexico, speaking with a random stranger named Mike about courage and trauma. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of the Earn and Invest podcast, host Doc G interviews Fritz Gilbert, founder of the Retirement Manifesto blog and author of Keys to a Successful Retirement, to discuss what life is actually like eight years into early retirement. Having retired from a high-level corporate career in 2018 at age 55, Gilbert shares profound insights into the emotional, financial, and relational realities that emerge once the initial honeymoon phase of leaving the workforce fades. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of the Earn and Invest podcast, host Doc G presents a solo "10 Things" episode reflecting on his first eight years of retirement. Recording at 5:00 AM from a beach in Cabo, Mexico, fresh off speaking about purpose at the EconoMe conference and death and dying at the White Coat Investor conference, Doc G shares how his life has evolved since scaling back his medical practice in 2018 to focus primarily on hospice work and his personal passions. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of the Earn and Invest podcast, host Doc G (Jordan) welcomes Dave Meyer, the Chief Investment Officer at BiggerPockets, host of the On the Market podcast, and author of Real Estate by the Numbers. The episode centers on the state of real estate investing in 2026, exploring whether average investors should double down, get out, or stay the course in the current economic climate Learn more about your ad choices. Visit megaphone.fm/adchoices

In this "Current Events Thursday" episode of the Earn & Invest podcast, host Doc G is joined by Carmel and Ian, members of his Wealth with Purpose mastermind group, to discuss a provocative article from The Independent titled "Financial Anorexia: I'm scared of spending money and I save obsessively. It's ruining my life". Learn more about your ad choices. Visit megaphone.fm/adchoices

What a death doula can teach us about money, meaning, and making time count Most of us approach financial planning as if it’s purely a math problem. We reduce it to formulas and timelines: save a certain percentage, invest in the right accounts, retire at a specific age. It feels structured, predictable—almost controllable. But that sense of control depends on one fragile assumption: that life will unfold according to plan. What happens when it doesn’t? That question sat at the center of a recent conversation I had on Earn & Invest with Rose Zealand, a Certified Financial Planner and end-of-life doula. Her work lives at a crossroads most people spend their lives avoiding—the intersection of money and mortality. And once you hear her perspective, it becomes very difficult to see financial planning the same way again. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this "10 Things Thursday" episode of the Earn and Invest podcast, host Doc G revisits themes from his book, The Purpose Code, to explore the profound impact of purpose on our lives. He structures the episode around ten core insights, aiming to demystify purpose and offer actionable advice for cultivating it without falling into common psychological traps. Doc G begins by emphasizing that purpose fundamentally matters because studies link it to better health, increased happiness, and greater longevity—acting much like a miracle pill without the side effects. He then defines the happiness equation as a combination of meaning and purpose. He clarifies that "meaning" is cognitive, relating to how we make peace with our past and the stories we tell ourselves. "Purpose," on the other hand, is entirely action-based; it is rooted in the present and future, consisting of the activities that actively light us up. A major theme of the episode is dismantling the myth that purpose is something you "find". Doc G argues that treating purpose like a hidden needle in a haystack leads to analysis paralysis and what researcher Lissa Rainey identified as "purpose anxiety"—a condition affecting up to 91% of people. This anxiety manifests as frustration, depression, and even job-hopping as people restlessly search for a singular calling. Instead of finding purpose, Doc G insists that we must actively build it by testing out activities and seeing what brings us joy. Doc G attributes much of our purpose anxiety to societal pressures from parents, social media, and advertising, which push us toward what he calls "Big P purpose". He declares that Big P purpose is "always bad" because it is strictly goal-oriented, relying on massive, scarce achievements like becoming an astronaut, running a seven-figure business, or having six-pack abs. This sets people up for failure, loss aversion, or an endless "achievement treadmill". Conversely, he heavily advocates for "Little P purpose," which is process-oriented. Little P purpose involves engaging in abundant, failure-proof activities that induce a "flow state" where you lose track of time simply because you love the process. While Big P purpose is bad, Doc G clarifies that having goals is not inherently wrong, provided they don't ruin the process. For example, aiming for a million podcast downloads is fine if you genuinely enjoy the daily work of recording and interviewing. However, if achieving that goal requires doing things you hate—like making TikTok videos—it morphs into toxic Big P purpose. Ultimately, there are no strict rules for purpose; it can be a lifelong global mission or a fleeting, selfish hobby. By focusing on the easy, joyful pursuit of Little P purpose, Doc G believes individuals will naturally attract others and create a lasting legacy that impacts generations far more effectively than striving for unattainable grandiosity. In the episode's closing community segment, Doc G reads an email from a listener named Ted N., who shares his own "10 keys" to building wealth and achieving financial independence. Ted's strategy highlights a steady path to financial independence, including consistent investing, limiting debt, earning a Master's degree to boost income, living simply, taking full advantage of a company 401(k) match over 33 years, and prioritizing experiences like family vacations over material goods. Ted also emphasizes relying on a company pension plan and, most importantly, maintaining an "attitude of gratitude". Doc G concludes the episode by encouraging listeners to share their own lists and directing them to his Substack for detailed show notes and his weekly blog posts Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of the Earn and Invest podcast, host Doc G interviews Tony Award-winning Broadway producer Ken Davenport about the mechanics and appeal of passion investing, specifically in Broadway shows. Davenport compares passion investing to buying a sports team: it is a way for individuals with financial security to add joy and potential profit to their portfolios. He emphasizes that investing in a Broadway show is essentially like investing in a startup company; it is a brand-new product trying to penetrate the market, which inherently makes it highly risky Learn more about your ad choices. Visit megaphone.fm/adchoices

In this Thursday “10 Things” episode of the Earn & Invest Podcast, Doc G shares his personal list of the ten biggest reasons he believes he successfully built wealth. Inspired by a recent conversation with financial historian Joseph Moore, Jordan begins by acknowledging the privileges that helped shape his path, including being born in the United States and growing up with professional parents. But he emphasizes that a series of specific habits and decisions—some simple and some unconventional—ultimately accelerated his financial journey. First, he credits relentless consistency. Inspired by Nick Maggiulli’s philosophy of “just keep buying,” Jordan invested throughout his entire career regardless of market conditions. Even when he made early mistakes—buying individual stocks or expensive mutual funds—the habit of consistently purchasing assets eventually led him to the simplicity and power of broad index fund investing. Second, he explains why he never relied on a traditional budget. Instead, he and his wife automated their finances by living off one income while sending the entirety of the second income directly into savings and investments. This approach allowed them to build wealth automatically while avoiding the stress of tracking every spending category. Jordan also discusses why he stopped worrying about financial minutiae. Rather than chasing small optimizations like credit card points or the highest-yield savings accounts, he focused on the big financial moves—saving large portions of income, investing consistently, and building a profitable business. Throughout the episode, he highlights several other mindset shifts that shaped his success: ignoring people who said something “couldn’t be done,” redesigning his medical practice into a low-overhead concierge model, and thinking in decades rather than weeks or months when pursuing long-term projects. He also shares the importance of embracing failure through experimentation, adopting an abundance mindset, losing interest in accumulating material possessions, and forgiving himself for inevitable financial mistakes along the way. Learn more about your ad choices. Visit megaphone.fm/adchoices

What if the best financial advice isn’t new—but simply forgotten? In this episode of Earn & Invest, Doc G sits down with historian Joseph S. Moore, author of How to Get Rich in American History: 300 Years of Financial Advice That Worked—and Didn’t. Moore spent a decade exploring centuries of advice aimed at everyday Americans, testing which strategies actually worked—and which didn’t. Remarkably, his research led him to build a seven-figure net worth using lessons from the past. Moore’s journey began with a personal financial scare: after taking a risky “NINJA loan” to buy a townhouse in 2005, he realized his vulnerability as the Global Financial Crisis of 2008 approached. Selling his home just in time sparked a curiosity that would consume the next decade. One of his most surprising findings? Optimism is a powerful predictor of financial success. Research from the Consumer Financial Protection Bureau shows that believing you can shape your financial future often outweighs inheritance or education. Moore argues that financial “gurus,” often dismissed for overhyping strategies, actually provide hope and practical frameworks that help people take action. We also explore how many “modern” wealth tactics are centuries old. House hacking—renting out spare rooms to pay a mortgage—was once a standard working-class strategy, frequently managed by women whose contributions rarely appeared in official statistics. Mobility was another forgotten tactic; in the 1800s, roughly one in three Americans moved annually to chase opportunity. Moore introduces the concepts of slow time and fast time: slow time is when we build skills, capital, and relationships; fast time is when booms, crashes, or major shifts create opportunities. Those prepared in slow time can seize advantage when fast time arrives. We also discuss concentration vs. diversification, the myth of effortless compound returns, and why financial independence isn’t the finish line—it’s the point when life becomes flexible enough to pursue meaningful goals. For anyone curious about wealth-building, historical financial strategies, or the patterns behind money and opportunity, this episode offers practical insights drawn from 300 years of experience. Learn more about your ad choices. Visit megaphone.fm/adchoices

Every parent wants to give their kids a financial head start. But I’m not convinced that means whiteboard lessons on compound interest at age eight. In this week’s Earn & Invest, I shared 10 things I’m teaching my children about wealth. Most of them push back against the mainstream narrative. First, kids learn about money in three ways: didactic teaching, modeling, and experiential learning. The worst of these? Lectures. You can explain mortgages and index funds all day long. But until a child feels the weight of a financial decision, it won’t stick. In medicine we say, “See one, do one, teach one.” Money works the same way. So instead of lecturing, we model. My kids overheard conversations about rental properties. They watched us set up LLCs. They saw investing as something normal, not mysterious. By college, buying and renting property didn’t feel radical—it felt logical. We also replaced weekly allowance with a $500 lump sum each January. That money had to last the year. My son ran out after breaking his phone. My daughter saved so much she skipped things she wanted. Both learned something no lecture could teach: money involves trade-offs. I’m also wary of monetizing childhood. Kids don’t need Roth IRAs before they need curiosity and kindness. I didn’t start investing seriously until my thirties. Wealth can wait. Character can’t. As for inheritance, I want to teach them how to fish. The ability to generate income matters more than a trust fund. The exception? College. I’ll pay for it. Crushing debt isn’t a safe learning experiment. Above all, I want them to know money is a tool. It buys time, flexibility, dignity. It is not happiness. Some of my best memories cost $2,000. Some expensive experiences felt empty. Joy comes from connection and meaning—not the price tag. If my kids understand that, they’ll be just fine. Learn more about your ad choices. Visit megaphone.fm/adchoices

Financial independence looks difference when you have kids. Yet, it can become a masterclass for how managing your finances well looks. We join Kristy Shen and Bryce Leung as they discuss their new book: Parent Like a Millionaire. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jesse Cramer from The Best Interest joins us today to talk about a study that has been circulating in financial independence circles that suggests that delaying retirement can be deadly. We breakdown the data and how not to fall for misinformation in the financial space. Learn more about your ad choices. Visit megaphone.fm/adchoices

Andrew Giancola is the host of The Personal Finance Podcast. Today, we discuss how to build wealth on a small salary. While this may not be you...it might be your child, friend, or family member. Do you truly need a high income to make it today? Learn more about your ad choices. Visit megaphone.fm/adchoices

There are so many reasons to spend more money today than you did five years ago. Whether gross economic inflation vs personal lifestyle inflation, it's important to keep track of your budget. On this rewind episode, Joel and Matt from ⁠How to Money⁠ join us as we delve into spending growth. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this rewind episode we talk with Brian Preston who is the author of ⁠Millionaire Mission⁠ and cohost of The Money Guy Show. We discuss the financial order of operations. How do you maximize your ability to both spend today as well as to save for tomorrow. Brian talks about what has been successful for his clients through decades of financial planning. Learn more about your ad choices. Visit megaphone.fm/adchoices