The Lifestyle Investor - Investing, Passive Income, Wealth

Change is unavoidable, but how you respond to it can have a huge impact on the trajectory of your life. Whether you're navigating a career transition, facing rejection, or pursuing an ambitious goal, uncertainty often reveals who you become under pressure. That's why I'm excited to welcome Justin Forsett to the podcast. Justin had a nine year career in the NFL and played for seven different teams...

LIL #006: I Had Financial Freedom Before I Was a Millionaire The size of the pile was never the point - here's what actually matters. Episode Summary In this episode of The Lifestyle Investor Podcast , host Justin Donald breaks down why cash flow - not net worth - is the real path to financial freedom . You'll learn the three numbers that actually determine your freedom, why your net worth is prob...

Professional athletes earn more money than most people will see in a lifetime, but their wealth can vanish surprisingly fast without the right guidance, relationships, and mindset. Whether you're a professional athlete, entrepreneur, or investor, building wealth requires far more than simply earning a high income or a big payday. That's why I'm excited to welcome Devin McCourty to the podcast. Dev...

LIL #005: Your Advisor Collects Fees Whether You Win or Lose Your advisor gets paid every year. Less than 5% of them actually earn it. Episode Summary In this episode of The Lifestyle Investor Podcast , host Justin Donald breaks down why the traditional financial advisor model is broken and what the ultra-wealthy use instead. You'll learn why AUM fees create a structural conflict of interest, how...

Success has an interesting way of moving the goalposts. You land a book deal, the business starts to take off, money starts flowing, you sell the business for life-changing wealth, and yet somehow struggle to keep the calendar open for what matters most.  For many entrepreneurs, the pursuit of wealth and freedom slowly turns into a new set of obligations, responsibilities, and pressures that...

LIL #004: How the Ultra-Wealthy Actually Invest Their Money The stock market isn't their strategy. It's their holding tank. Here's what the data reveals. Episode Summary In this episode of The Lifestyle Investor Podcast , host Justin Donald breaks down how the wealthiest families in the world actually allocate their portfolios, using data from Goldman Sachs, JP Morgan, and UBS. You'll learn why th...

Financial success is often described as the finish line, but reaching it doesn't always bring the fulfillment people expect. For many entrepreneurs, that ambition in the pursuit of more often comes at the expense of the relationships, values, and sense of purpose that matter most. That's why I'm excited to welcome Rich Christiansen back on the podcast. Rich has founded or co-founded more than 50 c...

LIL #003: 1,000 Lunches Taught Me More Than My Finance Degree One weekly habit, 20 years, 1,000+ conversations - and a deal network no textbook could build. Episode Summary In this episode of The Lifestyle Investor Podcast , host Justin Donald breaks down the single habit that built his entire investment network - one lunch at a time, every week, for two decades. You'll learn how a hands-on financ...

Achieving success in real estate isn't about predicting the future. While many investors have spent the last few years waiting for certainty, some of the best operators in the industry, including today’s guests, have been quietly positioning themselves to acquire high-quality assets at significant discounts and prepare for the next market cycle. That's why I'm excited to welcome founding partners...

LIL #002: Why Doing "All the Right Things" Keeps You Broke The investing playbook you inherited was never designed to set you free. Here's what works instead. Episode Summary In this episode of The Lifestyle Investor Podcast , host Justin Donald breaks down why following conventional investing wisdom - save, max out the 401k, grow the pile - keeps most people stuck. You'll learn the critical diffe...

Running a successful business doesn’t automatically translate into success at home. In fact, many ambitious entrepreneurs and high performers slowly drift away from the people they care about most without even realizing it. And by the time they realize their ambition has come at the expense of their family, the resentment that’s been building can take years to heal. That’s why I’m excited to intro...

Lens #01: 3 Shifts the Ultra-Wealthy Already Made (And You Haven't) The wealthy rewrote the investment playbook years ago - here's how to catch up. Episode Summary In this episode of The Lifestyle Investor Podcast , host Justin Donald breaks down the three shifts separating the ultra-wealthy from everyone else . You'll learn why the stock market is the alternative investment (not the other way aro...

Jesse Flocken had what most people would consider a dream life: a stable career, a guaranteed pension, a great family, and retirement within reach before his 40th birthday. But after years of working 24-hour shifts and missing valuable time with his family, Jesse and his wife Courtney began reflecting on a question they often helped others answer: “What do we want to be known for at the end of our...

If your business is growing but your energy, focus, or quality of life is declining, something is out of alignment. And that disconnect is exactly what today’s episode is all about. I’m excited to introduce you to my friend Talor Zamir, an entrepreneur who has built and exited multiple 8-figure businesses while prioritizing his health, family, and freedom. From his early days on Wall Street to sca...

Building a business from scratch might seem like the obvious path to financial freedom, but it comes with a unique set of challenges. And in many cases, it can be one of the slowest and riskiest ways to create consistent cash flow and income, especially without the right systems, support, or experience in place. That’s why I’m excited to introduce you to one of our newest Lifestyle Investor Master...

Many investors mistakenly believe higher returns require higher risk. However, some of the most consistent investment outcomes are generated by strategies built on predictable cash flow and backed by real assets that are resilient to market volatility. That’s why I’m excited to introduce you to one of our Lifestyle Investor Mastermind members, Andrea Propp, who brings years of experience from Wall...

Staying focused and avoiding distractions has never been more difficult. We blame our phones, the constant notifications, and endless distractions, but the root cause of distraction isn’t your phone—it’s how you respond to it. Nir Eyal is a globally recognized behavioral design expert and NYT bestselling author of Hooked, Indistractable, and has just released his newest book, Beyond Belief: The Sc...

For many high achievers, success in business doesn’t always translate to success at home. I’ve seen many entrepreneurs build successful companies, generate life-changing wealth, and yet still struggle in their marriages and relationships. Often, it’s because the same drive that fuels success is the very thing creating distance in the relationships that matter most. This pattern is something Stefan...

Building wealth and keeping it requires different skills, and many entrepreneurs fail to realize it before it’s too late. The same instincts that create wealth can sabotage your ability to preserve or grow it after a big exit. Michael Sonnenfeldt is the founder of Tiger 21, a global peer network of ultra-high-net-worth entrepreneurs with over 1,800 members with more than $250 billion in combined a...

There’s a big difference between building wealth and being healthy enough to enjoy it. And too often, entrepreneurs focus so heavily on growing their businesses that they unintentionally sacrifice their health and overall well-being in the process. Regan Archibald is the founder of Ageless Future and a pioneer in functional and regenerative medicine. Over the past two decades, he has worked with h...

One of the most overlooked ways to build lasting business relationships isn’t a marketing tactic or networking event; it’s with thoughtful and intentional gifting.  When done well, the right gift can create memorable experiences and strengthen relationships in ways that a generic Christmas card or gift simply can’t. John Israel is the founder of Mr. Thank You. Despite building a very successf...

The best asset that most entrepreneurs overlook is relationships. It’s an investment that compounds over time, and when you surround yourself with curious, like-minded people who have your back, they help you take bigger swings, and shape your personal and business trajectory in meaningful ways. For over a decade, Jayson Gaignard has been building one of the most thoughtfully curated entrepreneuri...

Building a successful career in the corporate world and reaching the pinnacle isn’t easy. Walking away from that success, with four kids and looming college bills, to bet on yourself is even harder. Most people never make that leap. Fewer still build companies that exit for eight or nine figures while pursuing a life of freedom, faith, and long-term impact. That’s exactly what today’s guest did. A...

It’s crazy when you think about it, but less than 1% of entrepreneurs ever sell their companies. Even fewer do it intentionally, strategically, and on their terms. If you’re building a business without preparing for a future exit, you may be leaving millions on the table or worse, creating a company that can’t function without you. Stephen Scoggins knows this firsthand. He is a speaker, author, an...

One of the biggest reasons many entrepreneurs struggle to scale their businesses is that they focus on attracting more clients by casting a wide net and pouring money into marketing that doesn’t generate and convert enough leads. But everything changed when today’s guest did the opposite by narrowing his focus, niching down, which ultimately skyrocketed business growth and positioned his company f...