023: Achieving the Yield of Dreams with Charlie Epstein

Today, I’m speaking with Bobby Castro. Bobby started his entrepreneurial journey with a modest ninth-grade education and a small but significant $1,700 gift from his mother-in-law. This initial capital became the seed for founding Bankers Healthcare Group (BHG) in 2001, a venture that would grow his net worth to over $500 million.

Under his guidance, BHG flourished to achieve a billion-dollar exit and sale. Beyond BHG, Castro, alongside his wife Sofi, founded Ortsac Capital Group, LLC. This family office oversees a multifamily real estate portfolio valued at over $700 million, encompassing more than 2,500 units that generate over $500,000 in positive cash flow monthly. 

In this episode, you’ll learn:

✅ Bobby's transformation from a waiter grappling with financial difficulties to the architect of a billion-dollar business empire. 

✅ How Bobby shifted from a quitters mindset to an unstoppable force fueled by focus and dedication.

✅ How the super-rich think about money – and why most people NEVER achieve true wealth and freedom.

Free Gift

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Show Notes: LifestyleInvestor.com/176

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

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Alex Day is a real estate tech entrepreneur and Founder & CEO of Modus, a venture capital-backed, tech-enabled title insurance and escrow business, which he successfully sold to Compass in October 2020.

In today's conversation, Alex shares his vast experience scaling startups. Between 2014 to 2018 he played a pivotal role at Peach – an SMS-based lunch delivery service that predated the mainstream emergence of industry giants like Doordash and Uber Eats.

He then leveraged that experience to build Modus. After bringing the idea to a startup hackathon (and winning 1st place), he and his two co-founders decided to go all-in. In a remarkable span of three years, Modus experienced rapid growth, scaled to ~$20 million in annual revenue, and expanded its operations to Washington, Florida, and Texas, employing a dedicated team of more than 150 full-time employees at its peak.

In October 2020, a significant milestone in Alex's career was the acquisition of Modus by Compass, in a notable high 8-figure deal.

In this episode, you’ll learn:

✅ Alex's motivational journey from startup to $20 million in revenue in three years, scaling up to 150 employees, and achieving a high 8-figure exit within the same timeframe, all amidst the challenges of COVID.

✅ Strategies for managing and leveraging wealth after an exit to fuel further successes, embark on new ventures, and make a positive impact on the community.

✅ An in-depth account of all the rewarding as well as excruciating details founders face during the exit process.

Show Notes: LifestyleInvestor.com/175

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

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Today, I’m talking with Noah Kagan. Noah’s an entrepreneur, author, and the founder and CEO of AppSumo. His journey in the tech industry began with roles at Intel, Facebook (where he was the 30th employee), and Mint.com, but it was his entrepreneurial ventures that truly defined his career. Despite some initial setbacks and ventures that didn't pan out, Noah's persistence led to the creation of AppSumo in 2010, aiming to democratize access to software for entrepreneurs. Today, he's not just the guy behind AppSumo, but also an influential figure in the startup community, sharing his knowledge through his podcast, YouTube channel, and the OKdork blog. 

In this episode, Noah shares insights from his new book, Million Dollar Weekend: The Surprisingly Simple Way to Launch a 7-Figure Business in 48 Hours – and provides a step-by-step guide for anyone looking to test the waters with their idea.

Noah’s big on that first step - which is almost always the most difficult one, yet the most rewarding. He dives into practical tips on how to find your first customer and why talent is not required to be a successful entrepreneur. Instead, it’s about rolling up your sleeves, learning from bumps along the way, and getting better as you go.

In this episode, you’ll learn:

✅ Why playing it safe and is riskier than you think.

✅ Noah’s inspiring journey from being fired from Facebook and Mint.com to building one of the top software marketplaces in the world. 

✅ Why every BIG business starts with a single customer – and practical tips for identifying and validating your business idea and attracting your first customer in 48 hours. 

Free Gift

Get Noah's The Ultimate Million Dollar Weekend Resource Guide! Visit LifestyleInvestor.com/174

Show Notes: LifestyleInvestor.com/174

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

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Rate & Review

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Levi Benkert is the founder and CEO of Harbor Capital, a real estate private equity shop focused on industrial properties in Texas. 

Levi has bought, managed, and developed over $400M in real estate properties in his 20+ year career – and in this episode, he’s going to share the secrets to his success! 

You’ll learn why he prefers Class B industrial real estate investing to other real estate asset classes, how he acquires properties with minimal risk and big returns, strategies for reducing your taxable income, why it’s still possible to find off-market deals, and so much more!

In this episode, you’ll learn:

✅ The strategic value of accepting leasing risks over construction risks, why Levi prefers Class B industrial assets in the Texas market, and how he secures high return, minimal risk deals for clients.

✅ The critical role of transparency with investors and why honesty in difficult situations fosters trust and supports long-term relationships. 

✅ How to take advantage of accelerated depreciation in order to reduce net taxable income. 

Free Gift

Get Levi's free guide on Investing in Industrial Real Estate! Visit LifestyleInvestor.com/173

Show Notes: LifestyleInvestor.com/173

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

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Rate & Review

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Today’s guests, Jay and Steph Rose, are the powerhouse couple behind Phase SiX, a fitness media brand that’s focused on athletic performance, education, entertainment, and content creation. 

Fueled by a vision and what little savings they had, two immigrants embarked on a six-month journey across the US, to absorb as much knowledge as they possibly could from leading experts in the world of fitness. This adventure became the foundation for a global multimedia company. 

At the core of their success lies the Phase SiX: Content Dojo in Austin, Texas—a state-of-the-art multimedia hub that transcends traditional fitness spaces and gym models, merging cinematic quality content with social media engagement and the home for many fitness creators.

In today’s episode, you’ll learn:

✅ Jay and Steph’s inspiring entrepreneurial story and how they built global fitness media brand with over 2 million followers.

✅ The common pitfalls that lead most businesses to failure.

✅ The secret to building a strong relationship that stands the test of time – including how Jay & Steph both empowered each other to create a business and life that they love.

Free Gift

Get Jay and Steph's 5 free Health & Fitness eBooks! Visit LifestyleInvestor.com/172

Show Notes: LifestyleInvestor.com/172

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

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Rate & Review

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Dave Durand is the co-founder and Executive Chairman of Best Version Media, a top 20 fastest-growing media company in North America. A best-selling author and professional speaker, Dave has mentored over 150,000 individuals, including entrepreneurs, sales teams, Fortune 500 executives, and CEOs, to grow successful, thriving businesses.

Over the years, Dave’s built and sold companies valued in the hundreds of millions and done over a billion dollars worth of sales. Today, I wanted to speak to him about the principles and tactics for creating outstanding leadership teams and exploring how those strategies have been instrumental in building and scaling multiple successful companies.

He also shares his decision-making formula that’s helped him to build thriving businesses without ever losing track of what really matters to him: making memories with friends and loved ones. 

In this episode, you’ll learn:

✅ Dave’s top tips for building and cultivating an amazing leadership team that will take your business to new heights.

✅ The three-step decision-making formula that’s helped Dave build and exit multiple companies without sacrificing personal fulfillment and time spent with loved ones.

✅ The keys to building a great culture in your organization that brings everyone together under a singular mission.

Free Gift

Get 4 free modules for Dave's Leading Giants Masterclass! Visit LifestyleInvestor.com/171

Show Notes: LifestyleInvestor.com/171

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

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Rate & Review

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Daven Michaels is a serial entrepreneur, bestselling author, and founder of 123Employee, known for pioneering remote business solutions and his influential role in the music and digital finance industries.

Today, we dive deep into Daven’s incredible journey, starting from his early days working with rock music icons at only 15. His story only escalates from there. He has not only launched and exited multiple businesses, but he also established 123Employee as a leading name in outsourcing.

In this episode, Daven pulls back the curtain and shares what it’s like to live in Puerto Rico, including the opportunities he’s creating and the incredible tax saving and wealth building advantages to living there. 

In today’s episode, you’ll learn:

✅ Daven's extraordinary journey, from his early days in the music industry to founding and exiting several lucrative businesses and shaping 123Employee into a top outsourcing powerhouse.

✅ Insights into the extensive tax advantages available in Puerto Rico for U.S. citizens and how to effectively leverage them.

✅ How to leverage “opportunity zones” to maximize tax savings when investing in Puerto Rican real estate as a non-resident.

Free Gift

Get Daven's 10-hour free Premium Virtual Assistant! Visit LifestyleInvestor.com/170

Show Notes: LifestyleInvestor.com/170

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

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Rate & Review

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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 Gift

Get Ryan's Healthy Brain Cheat Sheet! Visit LifestyleInvestor.com/169

Show Notes: LifestyleInvestor.com/169

Free 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

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Rate & Review

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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/168

Free 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

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Rate & Review

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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 Gift

Get Jeff's free PDF titled 23 Overlooked Tax Strategies for Entrepreneurs. Visit LifestyleInvestor.com/167

Show Notes: LifestyleInvestor.com/167

Free 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

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Rate & Review

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