The Lifestyle Investor - Investing, Passive Income, Wealth

Retired trader and founder of Unlearn Ventures, Cal Callahan, shares wealth-building challenges and practical investing advice. Topics include cash flow strategies, private equity investments, tax benefits, and long-term financial freedom. Learn to avoid common wealth-management mistakes and leverage opportunities for steady returns.

Today, I’m talking with Charles Gaudet, founder of Predictable Profits and recognized as the go-to business coach for 7 and 8-figure entrepreneurs. Charles’ strategies for creating company growth and building scalability are regularly featured in publications such as Inc., Forbes, Success, Entrepreneur, and International Business Times. His distinctive concepts and processes are often credited for getting his clients recognized among America’s fastest-growing companies. In this episode, we dive into Charles's remarkable entrepreneurial journey. He’s been an entrepreneur since the age of 4, created his first multi-million dollar business at 24, and has helped others generate millions with his strategies.Despite his numerous successes, Charles has also encountered his fair share of challenges along the way. You'll hear firsthand about how a failing business led to hitting rock bottom and the steps he took to overcome his biggest sticking points as an entrepreneur.In this episode, you’ll learn:✅ The $250k advice Charles received from Tony Robbins that allowed him to overcome his toughest business obstacles and become the go-to coach for 7 and 8-figure entrepreneurs.✅ How Charles sparked his son’s entrepreneurial spirit by guiding him through a lemonade stand business, showing him the value of working for yourself and the rewards of hard work. ✅ The difference between owning a business and working in it – and how to shape your business to fit your ideal lifestyle.Free GiftGet a free copy of Charles' book "The Predictable Profits Playbook: The Entrepreneur’s Guide to Dominating Any Market and Staying on Top". Visit LifestyleInvestor.com/181Show Notes: LifestyleInvestor.com/181Tax Strategy MasterclassIf 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/taxStrategy 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 thrilled to be talking with Ann Hiatt – a seasoned Silicon Valley veteran boasting 15 years of invaluable experience serving as the right hand to some of the tech world's most prominent figures – including Google’s Eric Schmidt, Yahoo!’s Marissa Mayer, and Amazon’s Jeff Bezos. Ann now consults with executives and companies around the world, helping them to grow, scale, and innovate to increase revenue, attract the right investors, hire competitive talent, and align internal growth strategies. She also shows them how she reinvented her role at Google three times during 12 years and how any employee can act as an Intrapreneur and create opportunities for professional growth and advancement regardless of their current title or seniority.Ann also authored the bestselling book, “Bet on Yourself: Recognize, Own, and Implement Breakthrough Opportunities” which uncovers the daily habits and long-game strategies she learned working side-by-side for decades with the giants of technology at Amazon and Google.In this episode, you’ll learn:✅ How Ann pivoted from pursuing a career as a professor to becoming Jeff Bezos’ Executive Business Partner – and the story of how she nearly killed him!✅ The character traits that set unicorn founders apart and the strategies that enable them to build iconic companies.✅ The leadership and mindset lessons Ann picked up from working alongside Marissa Mayer, Jeff Bezos, and Eric Schmidt.Free GiftGet access to Ann's resource library for entrepreneurs! Visit LifestyleInvestor.com/180Show Notes: LifestyleInvestor.com/180Tax Strategy MasterclassIf 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/taxStrategy 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, Brock Fortner, is an investor, cash-flow specialist, and the founder of StoneCentury Financial who’s carved a niche for himself by specializing in wealth protection and helping clients understand how they can achieve their financial ambitions. What’s incredible about Brock is that he’s the youngest-ever member of The Lifestyle Investor Mastermind. In our conversation, I wanted him to share the drive and motivation that propelled him into financial prominence at such a young age, alongside the invaluable insights he picked up by rubbing shoulders with some of the best financial minds in the game. Brock also takes us through his top investing strategies, shedding light on how he maximizes the potential of whole life insurance for accumulating wealth, offering liquidity and flexibility in tax-free investment choices, all the while securing a financial foundation that strengthens over time. In this episode, you’ll learn:✅ The benefits of choosing whole life insurance over term insurance.✅ How to leverage whole life insurance as collateral for investment or property acquisition.  ✅ The potential of whole life insurance to generate substantial wealth under any market condition, with the added benefit of tax-free growth.Show Notes: LifestyleInvestor.com/179Tax Strategy MasterclassIf 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/taxStrategy 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 the one and only, Jay Abraham – who is known as The “$21.7 Billion Dollar Man” and the highest paid marketing consultant in the world! As Founder and CEO of The Abraham Group, Jay has spent his entire career solving complex problems and fixing underperforming businesses. He has significantly increased the bottom lines of over 10,000 clients in more than 1,000 industries, and over 7,200 sub industries, worldwideIn this episode, Jay draws from his rich, 40+ years of experience, sharing proven strategies and thinking that have generated billions of revenue for his clients. You’ll also learn:✅ How to crush self-doubt and unlock your full potential in both business and life. ✅ Jay’s techniques for seeing overlooked opportunities, hidden assets, and underperforming areas of a business that no one else recognizes.✅ Jay’s playbook for exponentially growing your business, increasing profits, and minimizing risks – including the fascinating stories of brands transformed by his expertise, such as Icy Hot, Entrepreneur Magazine, a Chinese candy company that Hershey’s bought for half a billion, and Wesley Financial, the world’s leading timeshare cancellation company. Free GiftGet 4 of Jay's Best Book! Visit LifestyleInvestor.com/178Show Notes: LifestyleInvestor.com/178Tax Strategy MasterclassIf 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/taxStrategy 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 Jedidiah Collins. Jed is a former NFL player turned Certified Financial Planner. The moment he got his first NFL paycheck was the moment he had already spent it! This interaction with money and his perspective of how he saw money woke him up to the reality that he was financially illiterate. Never in school nor in his family had someone explained to him how money works, let alone how to make it work for him.This experience led him to founding Money Vehicle – an education technology company that’s transforming how people think about money and whose financial literacy curriculum has been used in 23 schools across the US.In this episode, you’ll learn: ✅ Jed’s journey from being an NFL player to building an innovative education company that’s disrupting the way kids learn about money. ✅ How Jed transformed financial theories into practical money-making strategies, addressing the widespread lack of financial education.✅ Principles for wisely managing your finances and effectively growing your wealth. Whether you’re trying to figure out what to do with your first BIG paycheck, or hunting down strategies on how to take your hard-earned wealth to the next level, these principles are foundational to success.Free GiftGet a free 1-hour digital course: "Money Vehicle". Visit LifestyleInvestor.com/177Show Notes: LifestyleInvestor.com/177Tax Strategy MasterclassIf 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/taxStrategy 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 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 GiftGet a digital copy of "UPSIDERS" + join the Upsiders Community Visit LifestyleInvestor.com/176Show Notes: LifestyleInvestor.com/176Tax Strategy MasterclassIf 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/taxStrategy 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.

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/175Tax Strategy MasterclassIf 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/taxStrategy 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 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 GiftGet Noah's The Ultimate Million Dollar Weekend Resource Guide! Visit LifestyleInvestor.com/174Show Notes: LifestyleInvestor.com/174Tax Strategy MasterclassIf 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/taxStrategy 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.

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 GiftGet Levi's free guide on Investing in Industrial Real Estate! Visit LifestyleInvestor.com/173Show Notes: LifestyleInvestor.com/173Tax Strategy MasterclassIf 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/taxStrategy 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.