The Lifestyle Investor - Investing, Passive Income, Wealth

Hosted by Justin Donald

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Aug 2026

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Entrepreneur Magazine calls Justin Donald “The Warren Buffett of Lifestyle Investing.” Imagine being able to earn passive income, long-term equity, and achieve financial freedom while gaining total freedom from your business or a job. That’s what Lifestyle Investing is all about. Justin Donald has mastered the low-risk cash flow investment principles he shares with entrepreneurs around the world. His alternative investing principles center on creating passive income and significant wealth while liberating yourself from a day-to-day job so you never run out of money. His innovative mindset principles and 10 commandments of Lifestyle Investing have released scores of entrepreneurs from the “golden handcuffs” that came with running life-consuming enterprises. This show focuses on showing today’s entrepreneurs and business executives how to think and invest to limit risk, maximize repeatable returns, and achieve retirement goals through his proven passive income cash flow strategies. Justin’s principles enable you to move from an “earned income” career to support your lifestyle with passive cash flow investments including real estate, operating companies, debt, equity, and franchises that give you the absolute freedom to live the life you truly desire. Interviews with top thought leaders, such as, John Lee Dumas, Ryan Levesque, Hal Elrod, Jon Vroman, Mike Koenigs, Phillip Stutts, Rob Dial, John Ruhlin, Brad Johnson, Robert Glazer, Mike Michalowicz, Geoff Woods, Steve Sims, and many more! For more information, visit https://justindonald.com ]]>

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September 10, 202644 min

307: Why Asking for Help Is a Superpower for Success with Nathan Thomas

One of the biggest stumbling blocks many entrepreneurs and high-achievers face is believing they can figure almost anything out on their own. Asking for help often feels like admitting weakness. But sometimes, the very thing standing between you and the next level of your life is your willingness to admit you don't have all the answers. Today's guest, Nathan Thomas, knows firsthand how powerful that realization can be. After years of struggling with addiction and nearly destroying his life, Nate got sober, embraced humility working as a barista, and eventually worked his way up to become VP at Goldman Sachs. But he soon realized that the corporate world wasn’t his calling and went on to become co-founder and CEO of Shmoody, a mental health and wellness platform that has reached millions of users. Fast forward to today, and he’s now in the final steps of releasing his first book, Ask for Help, using his own story to show people how they can change their lives by asking for help, both spiritually and practically. In our conversation, Nate shares his remarkable journey from addiction and rock bottom to sobriety, entrepreneurship, and a life centered around serving others. We also discuss how those experiences reshaped his definition of success, the lessons he's carried into building Shmoody, and why some of life's greatest breakthroughs can come from being willing to admit you don't have all the answers. In this episode, you’ll learn: ✅ Why asking for help isn't a sign of weakness and how putting your ego aside can unlock relationships, mentorship, and opportunities you couldn't create alone. ✅ Why the best mentors, peer groups, and relationships often require you to step outside your comfort zone and ask people you admire for their help. ✅ Why taking action matters more than controlling the outcome and how reframing rejection can give you the courage to pursue bigger opportunities. Show Notes: LifestyleInvestor.com/307 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts , Spotify , or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review . Connect with Justin Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

September 3, 202641 min

306: How Wealthy Families Use Whole Life Insurance as a Family Bank with Brock Fortner

Have you ever wondered what makes the wealthiest families, like the Rockefellers, so successful? They don't try to maximize the return on every dollar. Instead, they build diversified portfolios with different assets serving different purposes to provide liquidity, stability, and access to capital when opportunities arise. That's why I'm excited to welcome Brock Fortner back to the podcast. Brock is a wealth strategist at Stone Century Financial and a longtime member of the Lifestyle Investor Mastermind who has become one of my most trusted resources on dividend-paying whole life insurance. I've personally used whole life policies for nearly 25 years to store cash, fund investments, and create greater flexibility with my capital. In our conversation, Brock and I challenge some of the conventional thinking around asset allocation, the traditional 60/40 portfolio, and the idea that every dollar needs to earn the highest possible return. We also talked about teaching the next generation to think differently about money and some of the costly mistakes people make when choosing and structuring life insurance. In this episode, you’ll learn: ✅ The incredible benefits and flexibility of using whole life insurance in your cash and fixed-income portion of your portfolio. ✅ How borrowing against your policy creates liquidity to quickly capitalize on new investment opportunities. ✅ How wealthy families use whole life insurance to build a family banking system and transfer wealth for multiple generations. Show Notes: LifestyleInvestor.com/306 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts , Spotify , or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review . Connect with Justin Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

August 27, 202641 min

305: The 3 Health Metrics Everyone Should Be Tracking To Improve Longevity with Dr. Ryan Williamson, M.D.

True wealth is about more than money. It's about having the freedom to buy your time back and live life on your terms. But none of it matters if you don't have the health and energy to enjoy the life you've worked so hard to create. With traditional healthcare falling short in helping people prevent disease before it starts, many high-achieving entrepreneurs are looking for better ways to take control of their health. Today's guest, Dr. Ryan Williamson, is a physician, entrepreneur, former Navy lieutenant commander, and longtime member of the Lifestyle Investor Mastermind. He's also the founder of Transcend Health, where he's combining advanced diagnostics, personalized medicine, and cutting-edge technology to help people take a more proactive approach to their health. In our conversation, Ryan explains why an annual physical isn't enough, which health metrics you should be tracking today, and how simple habits can dramatically improve metabolic health. We also explore how AI and emerging medical technologies are changing healthcare, why more high performers are turning to concierge medicine, and how Ryan's entrepreneurial journey transformed his definition of wealth and success. In this episode, you’ll learn: ✅ Why proactive healthcare starts long before symptoms appear and how regularly tracking your health data can uncover risks while you still have time to address them. ✅ How regular blood work, wearables, blood pressure monitoring, movement, sleep can help you build a more complete picture of your health. ✅ How AI, advanced diagnostics, and concierge medicine are creating a more personalized approach to health that can help entrepreneurs perform better and protect their longevity. Show Notes: LifestyleInvestor.com/305 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts , Spotify , or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review . Connect with Justin Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

August 23, 20263 min

Lens #013 - Never Trust a Skinny Chef With Your Money

Lens #013 - Never Trust a Skinny Chef With Your Money An old expression about eating your own cooking exposes a blind spot almost every investor has. Episode Summary In this episode of The Lifestyle Investor Podcast , host Justin Donald breaks down why "skin in the game" matters more than brand reputation . You'll learn the stat on mutual fund managers with zero personal money invested, the 30-second due diligence question that filters out bad advisors, and the mistake Justin made trusting a fund he never checked. Question of the Day 🗣️ Have you ever asked your financial advisor or fund manager how much of their own money is in the same investments they recommended to you? What happened when you asked? Drop your answer in the comments. Key Take-aways Nearly half of U.S. mutual fund managers have zero personal dollars in the funds they manage Private market operators get asked "how much of your own money is in it?" - public fund managers almost never do Brand reputation creates "cover" that lets the skin-in-the-game question go unasked A 30-second due diligence check filters out bad operators, bad funds, and bad advice If they hesitate when you ask, you already have your answer Timestamped Outline ⏱️ 00:00 – Introduction 00:08 – The "never trust a skinny chef" principle 00:25 – The stat: 47% of fund managers have $0 invested 00:56 – The DUSLX example: three managers, zero personal dollars 01:13 – Why this question gets asked in private markets but not public 01:37 – How brand reputation provides cover 01:55 – The lesson beyond mutual funds 02:31 – Justin's personal mistake with a financial advisor 02:59 – The question to carry with you 03:14 – Closing thoughts Links & Resources 🔗 Subscribe to The Lifestyle Investor Lens → https://lifestyleinvestor.com/lens Connect & CTA 🎯 👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts . 🎁 Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today: https://lifestyleinvestor.com/lens Credits Host: Justin Donald © 2026 Lifestyle Investor. All rights reserved. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

August 20, 202643 min

304: How to Escape From Living Paycheck-to-Paycheck and Build Lasting Wealth with Anthony O'Neal

A bigger paycheck isn't always the solution to financial stress. Despite rising incomes, millions of people—including high-income earners—continue living paycheck to paycheck because they never build the financial habits needed to create lasting wealth. That's why I'm excited to have Anthony O'Neal on the podcast. Anthony is a bestselling author, financial educator, and host of one of the fastest-growing personal finance platforms, The Table with AO . After overcoming homelessness and financial hardship himself, Anthony has helped millions of people eliminate debt and build healthier money habits to achieve financial freedom. His latest book, Stop Living Paycheck to Paycheck , outlines a proven framework for breaking free from financial stress and building wealth that lasts. In this conversation, we discuss why lifestyle inflation quietly keeps people trapped regardless of income, how eliminating consumer debt creates the margin needed to begin investing, and why true wealth comes from owning assets instead of keeping up with appearances. In this episode, you’ll learn: ✅ Why increasing your income won't solve your financial problems if your spending grows just as quickly. ✅ How getting financially stable creates the foundation for every other wealth-building decision. ✅ Why Anthony believes teaching financial literacy early could change the trajectory of an entire generation. Show Notes: LifestyleInvestor.com/304 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts , Spotify , or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review . Connect with Justin Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

August 16, 20267 min

Lens #012 - 40 Entrepreneurs, 1 Skill Everyone Was Missing

Lens #012 - 40 Entrepreneurs, 1 Skill Everyone Was Missing One question every entrepreneur can answer. One question almost none of them can. Episode Summary In this episode of The Lifestyle Investor Podcast , host Justin Donald breaks down the Four Wealth Quadrants and why most entrepreneurs are great at making money but never learn to manage, multiply, or direct it. You'll learn Kiyosaki's test for whether you actually own your business, why "can I afford this?" is the wrong question, and how financial freedom outside the business makes you sharper inside it. Question of the Day 🗣️ Which of the four quadrants - Make, Manage, Multiply, or Make It Matter - is the one you've been avoiding? Drop it in the comments. Justin reads every response. Key Take-aways Most entrepreneurs are A+ at making money and C- at managing, multiplying, and directing it Kiyosaki's business test reveals whether you actually own your business or it owns you "Can I afford this?" is the wrong question - ask what's right for your family and business instead Quadrant 4 (Make It Matter) sharpens your management and multiplication skills, not just your legacy Financial freedom outside the business makes you a better operator inside it Timestamped Outline ⏱️ 00:00 – Introduction 00:26 – The question that silenced the room 00:51 – The four quadrants of wealth 01:04 – Quadrant 1: Make Money 02:03 – Quadrant 4: Make Money Matter 03:00 – The Kiyosaki realization: "the business owned me" 03:56 – "Can I afford this?" - the wrong question 06:12 – Quadrant 4 exemplars: Maxwell, Weekley, Looper, Green 06:57 – The challenge: which quadrant are you avoiding? Links & Resources 🔗 The Lifestyle Investor by Justin Donald → https://lifestyleinvestor.com/ Subscribe to The Lifestyle Investor Lens → https://lifestyleinvestor.com/lens Connect & CTA 🎯 👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts . 🎁 Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today: https://lifestyleinvestor.com/lens Credits Host: Justin Donald © 2026 Lifestyle Investor. All rights reserved. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

August 13, 202659 min

303: The Venture Capital Strategy That The Wealthiest Investors Use with Yotis Tonnelier

Investing in private markets has become one of the most sought-after opportunities for sophisticated investors. But while venture capital has created extraordinary wealth for some investors, success isn't simply about finding the next great startup. That’s why I'm excited to have Yotis Tonnelier on the podcast. Yotis is the co-founder and managing partner of YXS Capital, a venture capital firm focused on later-stage technology companies where he has delivered a 14.6x gross TVPI with zero losses across 14+ companies, and backed five unicorns including Mercury, Canva, and Wise. After exiting multiple businesses of his own, Yotis has developed a unique investment approach that combines the discipline of private equity with the growth potential of venture capital by helping identify high-quality companies long before they become household names. In this conversation, we discuss the growing role of secondary markets, the sectors Yotis believes offer the greatest long-term opportunities, and the principles that have shaped his investment philosophy throughout his career. In this episode, you’ll learn: ✅ Why Yotis believes investing after product-market fit can dramatically improve your odds of success while still capturing venture-level returns. ✅ How relationships, reputation, and trust helped him create access to some of the world's most sought-after private investments ✅ Why aligning incentives between fund managers and investors may be one of the biggest competitive advantages in venture capital today. Show Notes: LifestyleInvestor.com/303 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts , Spotify , or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review . Connect with Justin Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

August 9, 20266 min

Lens #011 - 1,000 Lunches Built My Entire Investing Career

LIL #011: 1,000 Lunches Built My Entire Investing Career What if your most valuable asset isn't in your portfolio - it's in your phone? Episode Summary In this episode of The Lifestyle Investor Podcast , host Justin Donald breaks down why your network is the highest-returning investment you'll ever make . You'll learn the 1,000-lunch habit that built his entire deal flow, a four-category framework for auditing your network, and why the cost of staying out of the right rooms far exceeds the cost of getting in. Question of the Day Who are the 3-5 people in your life right now who are actively elevating how you think about wealth and investing? If you can name them easily, you're ahead of most people. If you can't - that might be your biggest area of opportunity. Drop your answer in the comments. Key Take-aways Your network is more valuable than any single investment, property, or business you own 52 lunches a year for 20+ years compounds into deal flow money can't buy Audit your network across four categories to find the gaps holding you back Being in a room with 50 people beats 50 individual conversations every time The cost of NOT being in the right rooms is always higher than the cost of entry Timestamped Outline 00:00 - Introduction 00:09 - What would you say your network is worth? 00:52 - 1,000 lunches: the most valuable habit 01:49 - Four categories of people you need in your network 02:43 - The practical approach to building relationships 03:41 - Why Justin is in 14 masterminds right now 04:24 - The liberating shift: paying for the right rooms 04:44 - The compound effect of networks 05:48 - You don't need a billion dollar portfolio 06:32 - Your challenge: name your 3-5 people Links & Resources The Lifestyle Investor Lens (weekly newsletter) - https://lifestyleinvestor.com/lens Connect & CTA Subscribe and leave a review on Apple Podcasts . Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today. Subscribe so you don't miss the next issue: https://lifestyleinvestor.com/ Credits Host: Justin Donald © 2026 Lifestyle Investor. All rights reserved. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

August 6, 202640 min

302: Why Creativity Is the Ultimate Wealth-Building Skill with Nick Nanton

Creativity is usually associated with artists, musicians, and filmmakers, not entrepreneurs and investors. People either have it or they don't... or at least that's what most of us have been led to believe. But today's guest expertly challenges that assumption and explains why creativity may be one of the most valuable wealth-building skills you can develop. Nick Nanton is a 24-time Emmy Award-winning director, producer, songwriter, and entrepreneur who has directed more than 75 documentaries featuring some of the world's most influential leaders, entertainers, and innovators. Through decades of storytelling and business building, he's developed a unique perspective on creativity, resilience, and success. In our conversation, we discussed the surprising lessons Nick learned from producing documentaries featuring world-class performers and entrepreneurs, the behind-the-scenes experiences that shaped his perspective while documenting anti-human trafficking missions, and why curiosity may be one of the greatest predictors of long-term success. In this episode, you’ll learn: ✅ Why Nick believes creativity is simply the ability to see options where others see obstacles and why that mindset can transform your investing, business, and personal life. ✅ How embracing the traits that make you different can become your greatest competitive advantage instead of something you feel pressured to hide or change. ✅ Why serving others creates new opportunities, unlocks creativity, and helps you overcome scarcity by shifting your focus toward creating value for those around you. Show Notes: LifestyleInvestor.com/302 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts , Spotify , or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review . Connect with Justin Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

August 3, 20265 min

Lens #010 - $100 Trillion Is Changing Hands - Here's How to Catch It

Lens #010 - $100 Trillion Is Changing Hands - Here's How to Catch It $80 to $105 trillion is about to move between generations. Most will watch it happen. A few will catch it. Episode Summary In this episode of The Lifestyle Investor Podcast , host Justin Donald breaks down the largest wealth transfer in history and how to position yourself for it. You'll learn why retiring boomers create unprecedented deal flow, how seller financing lets you acquire cash-flowing businesses with little or no money down, and why following millennial spending points straight to the next decade of opportunity. Question of the Day 🗣️ If $100 trillion is changing hands over the next decade, what's the one move you'd make right now to position yourself for it? Drop it in the comments. Key Take-aways Boomers own more businesses, real estate, and investable assets than any generation - and they're retiring without succession plans Buying from a retiring boomer beats buying from an institution that's out to gouge you Seller financing turns the seller into the bank - often with far better terms than traditional lending Where millennials shop, work, and live points to the next decade of opportunity The boomer-millennial mismatch - who owns assets vs. who spends - is where the money is U.S. households worth $100M+ jumped from about 30,000 to 74,000 in just five years Timestamped Outline ⏱️ 00:00 - Introduction 00:23 - The largest wealth transfer in history 00:37 - The numbers: $80 to $105 trillion changing hands 00:50 - Boomers are retiring with no succession plan 01:17 - Buying from retiring boomers vs. institutions 02:12 - Seller financing - when the seller becomes the bank 03:02 - Follow the millennials to find opportunities 03:30 - The boomer-millennial mismatch 03:42 - Ultra-wealthy growth - 30,000 to 74,000 households 04:21 - The takeaway - this is happening now, not someday 04:48 - Next week - how to actually get access 05:08 - Closing thoughts Links & Resources 🔗 The Lifestyle Investor Lens (weekly newsletter) → https://lifestyleinvestor.com/lens Connect & CTA 🎯 👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts . 🎁 Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today. Subscribe so you don't miss the next issue: https://lifestyleinvestor.com/lens Credits Host: Justin Donald © 2026 Lifestyle Investor. All rights reserved. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .