The Lifestyle Investor - Investing, Passive Income, Wealth

Today, as a part of the Lifestyle Investor member spotlight series, I’m speaking with Ryan Williamson.In our conversation, Ryan shares his incredible journey from being a NAVY vet and board-certified neurologist to a prolific entrepreneur and investor who’s disrupting the healthcare staffing field.Ryan details his tax and investment strategies that have not only weathered economic downturns but have also produced remarkable returns, the lessons he took from other Lifestyle Investor Mastermind members, and how all these experiences helped him create his dream life. In this episode, you’ll learn: ✅ The tax strategies that Ryan uses to add an additional 6-figures to his annual income.✅ Ryan’s recession-proof investing strategies that consistently yield high returns.✅ The story of how serving in the NAVY and working in medicine motivated Ryan to build a locum tenens healthcare staffing agency.Free GiftGet Ryan's Healthy Brain Cheat Sheet! Visit LifestyleInvestor.com/169Show Notes: LifestyleInvestor.com/169Free 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today, I’m talking with Chris Board. Chris is an NFL linebacker who plays for the New England Patriots. But his talents aren’t limited to football. Off the field, Chris channels the same intensity and commitment to his financial planning. As a proud member of The Lifestyle Investor Mastermind, he stands out from the traditional professional athlete mold. During our conversation, he opens up about how he manages his NFL earnings, which often come with complex structures, and how he smartly invests in single-family homes and index funds. He also shares fascinating details on what it’s like to be coached by the legendary Bill Belichick and his appreciation for the lessons and opportunities he’s gained from being a part of the TLI Mastermind. In this episode, you’ll learn: ✅ Why so many professional athletes go broke, and the strategies that allow Chris to steer clear from their mistakes.✅ Chris’s personal journey of going into real estate investing as an NFL athlete and the financial lessons he picked up from mentors and the TLI Mastermind.✅ An inside look into the unique payment structures NFL athletes are facing.Show Notes: LifestyleInvestor.com/168Free 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Jeff Socha is a financial consultant and Founder of Socha Capital who has helped many entrepreneurs and executives, especially those who earn $1 million annually, navigate the complexities of wealth management and grow and protect their wealth using unique tax strategies.During our conversation, Jeff shares his perspectives on how vital it is for high-earners to protect their wealth from excessive taxation without going against regulation. He emphasizes the significance of having a robust and effective tax strategy, which is often overlooked but crucial for long-term financial security. He also gives valuable advice for those tempted by seemingly attractive yet risky tax strategies and the warning signs to watch out for when consulting financial advisors.  In this episode, you’ll learn:  ✅ Unique strategies to generate significant tax returns - whether it's on your income, capital gains sale, investment portfolio, or estate planning. ✅ The critical differences between CPAs and tax strategists and why people often get them confused. ✅ The most common tax-saving mistakes Jeff sees all the time and the most overlooked tax strategies you should be considering.Free GiftGet Jeff's free PDF titled 23 Overlooked Tax Strategies for Entrepreneurs. Visit LifestyleInvestor.com/167Show Notes: LifestyleInvestor.com/167Free 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Jhana Li is the founder of Spyglass Ops, a digital startup COO and operations consultant with an impressive track record, including being the COO of two 7-figure startups and serving as an operations consultant to over thirty 7 & 8-figure online businesses.Today, we take a hard look at the greatest bottlenecks founders face in their businesses that prevent them from scaling effectively. Jhana offers her perspective on why operators are crucial to business growth and why founders often struggle to hire the right person for this role. Plus, she's got some great tips for picking the right operator for any business and the warning signs to watch for when bringing one on board.In this episode, you’ll learn:✅ The distinction between an ops manager, CEO, and COO and how to determine the right role for your business.✅ Common pitfalls to avoid when hiring an operator and the most widespread misconceptions about the role of operators.✅ Strategies for pinpointing operational bottlenecks that are hindering your business’s ability to scale effectively.Free GiftGet Jhana's Bottleneck Breakthrough Detector resource. Visit LifestyleInvestor.com/166Show Notes: LifestyleInvestor.com/166Free 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today, I have the pleasure of speaking with Mark W. Yusko, the visionary Founder, CEO, and Chief Investment Officer of Morgan Creek Capital Management, renowned for his forward-thinking investment strategies and sharp eye for identifying emerging trends.Mark is confident about the big shift toward a blockchain-centric future. You'll hear his thoughts on the future of cryptocurrency and how it's reshaping our views on banking, investments, and personal privacy. Plus, he's got some really insightful tips on navigating the often confusing and fast-paced world of digital asset investments like crypto.  In this episode, you’ll learn: ✅ Strategies for future-proofing your investment portfolio, especially against the weakening dollar and fluctuating market conditions. ✅ Mark’s take on why Web3 will generate an astonishing $15-20 trillion in value and what that means for investors.✅ A deep dive into the incredible world of cryptocurrency – why it might just eclipse traditional assets like the dollar and gold, and how it's set to shake up the financial world.Free GiftGet Mark's free research paper "The Quantitative Investment Case for Blockchain Technology in Institutional Portfolios." Visit LifestyleInvestor.com/165Show Notes: LifestyleInvestor.com/165Free 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today, as a part of the Lifestyle Investor member spotlight series, I’m speaking with Ryan Thacker. In this episode, we're taking a deep dive into Ryan's journey, particularly his impressive rebound after a huge setback during the pandemic. Since joining the Lifestyle Investor Mastermind, Ryan's strategies have really taken off, and we're going to unpack all of that – including structuring deals to maximize tax benefits and his clever use of life insurance, 1031 exchanges, and Roth IRAs to boost investment returns. We're also going to touch on a critical issue: why so many people find themselves absolutely unprepared for retirement and how Ryan addresses that problem through his INC. 5000 company, B.O.S.S. Retirement Solutions.  In today’s episode, you’ll learn: ✅ The major problems with 401k plans – and why 1 in 10 Americans will not have enough money to survive their retirement. ✅ The secret tool the rich use to build tax-free wealth.✅ The major benefits Ryan’s gotten from being a part of the Lifestyle Investor Mastermind community.  Show Notes: LifestyleInvestor.com/164Free 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today, I’m talking with Kamal Ravikant – a serial tech entrepreneur and Managing Partner at Evolve VC, an early stage Silicon Valley Venture Capital fund. He’s also the author of the bestselling books, “Love Yourself Like Your Life Depends On It”, “Rebirth”, and “Live Your Truth”.Kamal has been building companies in Silicon Valley since the late 90's. And his experience and relationships over the years have given him access to some of the very best deal flow in tech.In this episode, Kamal’s shares his incredible story, marked by both triumphs and setbacks. He opens up about the failed entrepreneurial venture that left him deeply depressed – and the silver lining of developing remarkable mental resilience, which later fueled his success. You’ll also learn… ✅ The biggest mistakes angel investors should avoid.✅ The specific attributes that set legendary founders apart from the rest.✅ What it was like growing up with his brother Naval Ravikant, who is recognized as one of the most legendary figures in the investing world – and the best lessons he’s learned from him. Free GiftGet Kamal's book Live Your Truth for free! (limited time only). Visit LifestyleInvestor.com/163Show Notes: LifestyleInvestor.com/163Free 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today, as a part of the Lifestyle Investor member spotlight series, I’m speaking with Pasha Esfandiary.Pasha has been a part of our mastermind group for a few years now and has brought a ton of wisdom, experience, and opportunities to our community of investors.In this episode, I wanted to chat with him about his investing journey. You’ll hear how he transitioned from playing professional poker to building a real estate empire with over $250M in transactions across multiple asset classes. These include residential homes, boutique motels, large multifamily properties, mobile home parks, and more.You’re going to hear why he decided to double down on mobile home parks, how he syndicates deals for investors, his process for managing operations for his real estate business, and the benefits he’s gotten from being a part of our mastermind group.Show Notes: LifestyleInvestor.com/162Free 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today’s guest is my dear friend Brooke Nichol. Brooke is the heart and brains behind Saving Face in Austin, Texas – a full service aesthetics practice specializing in anti-aging injectables and lasers.Brooke went from being an overworked ICU and OR nurse to building Austin's premier spot for feeling and looking fantastic.Trained by world-famous plastic surgeons, Brooke set the bar high in the industry and was named a top 100 Injector by The Best Aesthetic Injectors in America in 2018. In today’s episode, you’ll learn: ✅ Brooke's path from an overworked ICU nurse on the verge of bankruptcy to a leading aesthetic expert with a team of 23.✅ Strategies for building a business that not only succeeds but makes a real difference in people's lives.✅ How couples can leverage their unique strengths to build a thriving business together without sacrificing intimacy.Free GiftGet 10% off your first treatment at Saving Face. Visit LifestyleInvestor.com/161Show Notes: LifestyleInvestor.com/161Free 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Today, I’m talking with Joe Stolte. Joe is a former Inc 500 entrepreneur and 5-time technology founder with three successful exits, including Lottery.com, which went public for $526M, and GrowFlow, which sold for $62.5M. Joe is now the CEO of Daily.ai, an AI company that helps brands and thought leaders publish AI automated email newsletters in less than 5 minutes per week, all without writing a single piece of content. Daily.ai produces AI newsletters for thought leaders such as Peter Diamandis, Joe Polish, JJ Virgin, Cameron Herold, Chris Voss, and 70+ other small brands in 20 different industries.In this episode, you’ll learn:✅ Joe’s entrepreneurial journey to starting, scaling, and exiting multiple 7, 8, and 9-figure businesses. ✅ How to get 40%-60% open rates with AI-powered newsletters.✅ How I use Daily.ai to power my own newsletter – it’s amazing how this tool scours over 350,000 different sources to find the content that resonates the most with my audience – all on autopilot!Free GiftGet Joe's Webinar, Audience Engagement on Autopilot with AI. Visit LifestyleInvestor.com/160Show Notes: LifestyleInvestor.com/160Free 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.