The Lifestyle Investor - Investing, Passive Income, Wealth

It’s crazy when you think about it, but less than 1% of entrepreneurs ever sell their companies. Even fewer do it intentionally, strategically, and on their terms. If you’re building a business without preparing for a future exit, you may be leaving millions on the table or worse, creating a company that can’t function without you.Stephen Scoggins knows this firsthand. He is a speaker, author, and host of the Build podcast who created multiple companies — including one that grew to nine figures in annual revenue and successfully exited in 2023. But his story isn’t just about a financial win. It’s about faith, leadership, identity, and learning how to structure a business so it can scale beyond you and create meaning and purpose in your life.You’ll hear what Stephen believes most entrepreneurs get wrong about selling their business, and the tax strategies he’s now implementing after a massive liquidity event. We also dive deep into his journey from sleeping in his car to building companies that employ hundreds — and how faith shaped every turning point along the way.In this episode, you’ll learn: ✅ Why most entrepreneurs wait too long to prepare their business for sale and what Stephen recommends for runway time prior to an exit.✅ How quality of earnings can dramatically impact your final valuation and why buyers use it to justify lowering your multiple.✅ The difference between asset sales versus stock sales and why an F reorganization can have a dramatic impact on value.Show Notes: LifestyleInvestor.com/281Tax 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.

One of the biggest reasons many entrepreneurs struggle to scale their businesses is that they focus on attracting more clients by casting a wide net and pouring money into marketing that doesn’t generate and convert enough leads.But everything changed when today’s guest did the opposite by narrowing his focus, niching down, which ultimately skyrocketed business growth and positioned his company for a huge exit.Andrew Lassise is the founder of Tech for Accountants, a cybersecurity and IT company built exclusively for accounting firms. After initially struggling to sell his company, Andrew rebuilt it with tighter systems, sharper positioning, and a deliberate niche strategy. The result? A sale at a 10x multiple of projected EBITDA, more than double the industry norm.In this conversation, Andrew shares how sobriety became a competitive advantage and why systematizing your business is the key to turning it into a sellable asset. We also discussed how to leverage AI and automation to scale your business without burning out.In this episode, you’ll learn: ✅ How niching down skyrockets Andrew’s business growth and created market dominance in a crowded industry.✅ Why AI isn’t a silver bullet and how to use it to create real leverage and buy your time back.✅ The mindset shifts from being the operator to building a business that scales sustainably towards a successful exit.Show Notes: LifestyleInvestor.com/280Tax 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.

The strongest and most successful businesses are built on strong and meaningful relationships. And when life delivers unexpected loss, the strength of those relationships becomes an asset that is more valuable than you could ever imagine. Rod Neuenschwander is the longtime business partner of the late John Ruhlin and the operational force behind Giftology. After losing his best friend and co-founder, Rod faced an impossible challenge: preserving John’s legacy while leading the company into its next chapter. What has happened since then has been a remarkable transformation that is still grounded in relationships, faith, and leadership.You’ll hear how Rod helped turn grief and crisis into clarity, why relationships—not tactics—are the most durable growth strategy, and how leaders can build organizations that thrive beyond any one person.For anyone who has never worked with Giftology or isn’t familiar with John Ruhlin’s work, I highly recommend checking out the podcast I did with him on the Art of Gift Giving to learn more about this great company and hear from John himself. In this episode, you’ll learn: ✅ Why gifting and generosity often falls flat and what made John Ruhlin so great at it.✅ How Rob’s book became a case-study in real-time and created a One-Page Recovery Plan to help companies move forward after tragic loss.✅ How Giftology’s new membership program, Rich Relationship Society, helps make relationships your #1 business growth strategy.Show Notes: LifestyleInvestor.com/279Tax 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.

Businesses are implementing AI faster than most entrepreneurs realize. But the best opportunities aren’t always in cutting-edge startups. In many cases, the best returns are in legacy businesses that haven’t kept pace with the innovation curve. Understanding that gap—and how to close it—has defined the career of today’s guest.Bill Tyndall is the founder of Tynrose, a holding company focused on modernizing legacy businesses through digital transformation, data, cybersecurity, and AI. After launching Electric in 2016, which revolutionized IT support for SMBs, he had a huge exit with a billion-dollar valuation just four years later.  You’ll hear how Bill’s newest venture, Tynrose, builds platforms that don’t just implement technology; they reimagine it and help companies move beyond patchwork solutions and into scalable solutions that are built to last in the digital world. His approach challenges outdated models and reframes what’s possible when businesses stabilize their technology, leverage clean data, and deploy AI with intention.In this episode, you’ll learn: ✅ How SMBs and legacy businesses may offer better AI-driven returns than tech startups.✅ Why Bill decided to start a new business after his billion-dollar exit, and what creating a legacy with his businesses means to him. ✅ Why AI is really just a capacity expander for humans and what the future holds for IT and cybersecurity in an AI-driven world.Show Notes: LifestyleInvestor.com/278Tax 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.

Most entrepreneurs believe once they achieve financial success or have the big exit, freedom, fulfillment, and happiness will follow.It’s a trap.And today’s guest learned that the hard way.On today's pod, I'm talking with Pablo Della, an 8-figure founder who went from growing up poor in Argentina to scaling his business into a major consumer brand.From the outside, it looked like he had won.But after the financial success came a deeper question: Now what?In this conversation, Pablo shares what changed after the money stopped being the goal, and how he rebuilt his life around real freedom.He’s also just launched a new show, Freedom Flip, where he and his co-host publicly challenge conventional thinking around money, identity, and achievement. Go give it a follow RIGHT HERE!In this episode, you’ll learn: ✅ Why Pablo believes that spending money on experiences generate a real return on happiness, time, and quality of life that goes beyond ROI.✅ How Pablo evaluates the true cost-benefit of flying private—and why the math looks different once you factor in time, energy, and opportunity cost.✅ Why Pablo believes inflation isn’t accidental, and how that belief shapes his long-term view on money, Bitcoin and wealth.Show Notes: LifestyleInvestor.com/277Tax 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.

Believe it or not, income taxes can become the biggest expense for entrepreneurs. Yet most people approach tax planning reactively, missing powerful opportunities hiding in plain sight.Today’s guest helps investors get ahead of the game by treating tax strategy not as compliance, but as one of the most important wealth-building tools available.Karlton Dennis is one of the leading tax strategists in the country and the founder of Tax Alchemy. Through his work with high-earning entrepreneurs, he helps clients legally reduce taxes, increase cash flow, and reinvest capital intentionally rather than giving it away unnecessarily.In our conversation, Karlton breaks down why proactive tax planning often delivers higher returns than any investment deal—and how understanding the tax code allows you to keep more money working for you, with more investment opportunities, year after year.In this episode, you’ll learn: ✅ Why investing in world-class tax strategy can outperform real estate, private equity, and traditional investments.✅ The most common tax preparation mistakes that cost business owners tens of thousands per year.✅ Which tax strategies attract IRS scrutiny and how to use the tax code to your advantage without crossing red lines.Show Notes: LifestyleInvestor.com/276Tax 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.

For many professionals, the traditional path of investing in 401(k)s and IRAs and waiting until their retirement date, while trading time for money, eventually raises a difficult question: Is there a better way?Today’s guests discovered that by leveraging real estate and strategic relationships, they could build passive income while enjoying the perks of their 9-5 jobs and now teach others to do the same. Rather than chasing shortcuts, they focused on building a foundation that created options using hidden wealth hacks and money habits self-made millionaires use.Cory Jacobson and Ryan Bevilacqua are real estate investors, entrepreneurs, and hosts of the Wealth Juice Podcast. Through strategic partnerships and documenting their journey publicly, they’ve built a growing real estate portfolio while helping others take their first steps toward passive income and financial independence.Cory and Ryan unpacked the mindset shifts, relationship strategies, and long-term thinking that helped them move from early investments to scalable opportunities—while staying aligned with their purpose, lifestyle, and financial freedom goals.In this episode, you’ll learn: ✅ Why financial freedom is less about early retirement and more about creating optionality.✅ How strategic partnerships, masterminds, and relationships accelerate growth faster than trying to do it on your own.✅ Why building in public creates leverage, credibility, and unexpected opportunities.Show Notes: LifestyleInvestor.com/275Tax 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.

For many entrepreneurs and investors, financial success often feels harder than it should. Despite tireless work and long hours spent chasing income, they still end up owing a business that runs them rather than the other way around.Today’s guest has spent decades helping people break that cycle by shifting how they think about money, assets, and financial freedom itself.Sharon Lechter is a globally recognized financial literacy expert, former CPA, keynote speaker, and five-time New York Times bestselling author. She is best known as the co-author of Rich Dad Poor Dad and 14 additional books in the Rich Dad series, including the transformational Cashflow Quadrant. She’s also co-authored many other influential books, including Exit Rich, Three Feet from Gold, and Think and Grow Rich for Women.Sharon has dedicated her career to educating and empowering investors at any level, helping them move from earned income to asset-driven wealth while reclaiming their time. In her newest book, Old Wealth, New Wealth, True Wealth, Sharon offers readers both an inspiring fable and a practical blueprint for crafting a legacy that lasts.In this episode, you’ll learn: ✅ Why the purest definition of financial freedom is when asset income exceeds your monthly expenses.✅ How the Cashflow Quadrant was a game changer for Justin and helps entrepreneurs reclaim time and scale faster by making better decisions.✅ Why Sharon’s newest mission with IQ Hall helps creators and entrepreneurs maintain ownership and protect their intellectual property while using AI.Show Notes: LifestyleInvestor.com/274Tax 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.

Building lasting wealth isn’t just about making money—it’s about designing a system that creates freedom, flexibility, and long-term security. And today’s guest is a real estate entrepreneur who has mastered the art of turning land deals into a powerful cash-generating engine that fuels both lifestyle and legacy.Jack Bosch is a seasoned real estate investor who has flipped over 4,000 land deals and helped hundreds of entrepreneurs build scalable, location-independent businesses. Alongside his wife Michelle, Jack has built land flipping into a high-leverage “cash machine” that funds long-term investments, passive income, and true lifestyle freedom.If you’re looking for a practical framework to move beyond the earn-and-spend cycle and build income that supports life on your terms, this conversation delivers.In this episode, you’ll learn: ✅ Why land flipping can be a simpler and more flexible entry point into real estate than traditional investments✅ Jack’s method for finding deeply discounted land deals that can often be flipped in a very short period of time. ✅ How Jack’s Forever Cash framework turns active income into lasting passive income and wealth.Show Notes: LifestyleInvestor.com/273Tax 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.

Building wealth and time freedom isn’t just about working harder or finding the next opportunity; it’s about surrounding yourself with the right people and designing systems that create leverage over time. And today’s guest has mastered both sides of that equation.Thanh Pham is the founder of Asian Efficiency and host of The Productivity Show, where he has spent more than a decade helping entrepreneurs and executives work smarter, not longer. From hosting 50 magnificently curated Jeffersonian-style dinners to building thriving communities and events in Austin, Thanh has mastered the art of creating relationship capital. Thanh shares how curating meaningful relationships not only accelerated his personal growth but also his business opportunities and his lifestyle freedom. He explains why hosting experiences is one of the fastest ways to build trust and credibility and how positioning yourself as a connector opens doors that money can’t.You definitely won’t want to miss the end of our conversation, where Thanh explains how he’s now leveraging AI and automation, using AI agents to handle entire workflows and reclaim dozens of hours of his time each week. Rather than replacing human connection, Thanh shows how technology can amplify it and free up your time for what matters most.In this episode, you’ll learn: ✅ How hosting intentionally curated events positions you as a connector and builds trust, develops opportunities and accelerates long-term wealth.✅ How Thanh curates relationship capital to grow his business without sacrificing freedom or burning out.✅ The AI agents Thanh uses to automate various aspects of his business and the system that saved him 83 hours in a single week.Show Notes: LifestyleInvestor.com/272Tax 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.

Every entrepreneur wants a business that generates consistent, predictable cash flow. But most end up pouring time and money into typical marketing strategies, only to be left with frustration and inconsistent results instead of passive income and revenue.But today’s guest has unlocked a cheat code that has generated millions in revenue without using paid ads and typical marketing strategies.Pedro Adao is an 8-figure Kingdom Entrepreneur, best-selling author, and founder of multiple ventures who has pioneered a highly effective business model centered on free & paid challenges that has generated over $100 million in revenue for himself and his clients.His expertise has impacted tens of thousands of entrepreneurs worldwide and helped countless individuals achieve levels of success they could only have dreamed of. Pedro has worked with many industry icons, including Russell Brunson, Dean Graziosi, and Daymond John (to name a few), who recognized this approach as a game-changer for entrepreneurs.In our conversation, Pedro shares how he built his challenge framework, why his “taste and see” marketing approach outperforms traditional marketing funnels, and how challenges create low-risk, high-leverage cash flow for entrepreneurs and businesses of all sizes. P.S. Pedro is kicking off the new year with a 31 Day Wisdom Challenge starting on January 1st, 2026. It’s completely free to join, you’ll hear from some amazing guests on a daily journey that over 350,000 people from over 100 countries have experienced. You can sign up by clicking here.In this episode, you’ll learn: ✅ Why live challenges are so effective at creating predictable cash flow with minimal overhead.✅ How Pedro lost everything after the 2008 crisis and how his faith helped him rebuild from rock bottom to the leading expert he is today.✅ How traditional wealth management and investing in the stock market could mean taking on more risk than ever in the year ahead.Show Notes: LifestyleInvestor.com/271Tax 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.

For any entrepreneur, the most valuable currency to buy back is time. Yet many remain trapped, losing time with family and struggling to break free from the business.But today's guest has become the embodiment of building freedom through creativity, community, and leveraging advisory opportunities.Pat Flynn is the creator of Smart Passive Income, bestselling author of Will It Fly? and Superfans, advisor to top tech companies such as Teachable, Circle, SquadCast, and Riverside, and one of the most respected voices in online business. Since being laid off as an architect in 2008, he’s built multiple 7-figure businesses, generating millions of podcast downloads, and launching a wildly successful Pokémon YouTube channel with almost 2 million subscribers. In this episode, Pat shares how he identifies winning opportunities, his Airport Test framework for evaluating business ideas, how advisory shares became one of his highest-ROI wealth builders, and how he’s intentionally designed his life so that work supports family—not the other way around. In this episode, you’ll learn: 1.) How Pat turned a layoff into a launchpad for building multiple passive income businesses.2.) A simple framework to evaluate business ideas before investing time or money.3.) Why advisory shares became one of his highest-leverage income streams—and the criteria he uses to decide which companies to work with.Show Notes: LifestyleInvestor.com/270Tax 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.

Scaling a business is slow and unpredictable. Many entrepreneurs don’t make it to year five, and even fewer figure out how to scale.But what if the key to unlocking exponential growth was to multiply your efforts through strategic acquisitions?Tom Shipley is the co-founder of Atlantic Coast Brands, founder of Queen City Media, and co-founder of DealCon, one of the fastest-growing M&A ecosystems for entrepreneurs. Tom has built, scaled, and acquired companies across beauty and skin care brands like Hydroxatone, Amazon FBA, media, and ecommerce, generating well over $1B in revenue over his career.In our conversation, Tom shares how acquisitions saved his company during a crisis, the mindset that helped him rebuild after losing millions in revenue overnight, and the frameworks you can use to turn stagnation into exponential growth—all while designing a life and business with intention and time freedom.In this episode, you’ll learn: 1.) How programmatic acquisitions can solve cash flow issues, save struggling companies, and 10x enterprise value faster than organic growth alone.2.) Tom’s “Add a Zero” philosophy to think bigger which helps to recruit better talent, attract better capital, and unlock strategic breakthroughs.3.) Why masterminds and peer groups are the ultimate force multiplier for entrepreneurs—and how vulnerability can produce life-changing business insights.Show Notes: LifestyleInvestor.com/269Tax 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.

Experts say that word of mouth is one of the most powerful marketing channels—but in today’s world, publishing a book uniquely establishes credibility and authority by showcasing your expertise.A book can work for you 24/7, build trust before you ever meet someone, and open doors that would otherwise remain closed. Yet most entrepreneurs delay writing one because they think they don’t have the time, clarity, or expertise. Today’s guest is an expert in eliminating those excuses and will show you why writing a book may be the highest-ROI move you can make for your business.Chandler Bolt is the founder & CEO of Self-Publishing School and SelfPublishing.com, one of the fastest-growing companies in the Inc. 5000. He’s helped publish over 7,000 books, has become a multi-seven-figure entrepreneur, and built his entire business by helping people turn their ideas into authority-building books that generate leads, sales, and long-term assets.In our conversation, Chandler explains why a book can be the #1 leverage tool for entrepreneurs and investors, how self-publishing gives you all the upside and the freedom to release updated versions, and the biggest mistakes people make when marketing their book. In this episode, you’ll learn: 1.) Why writing a book is the #1 authority-builder for entrepreneurs and investors—and how it can generate leads, sales, referrals, and high-quality deal flow on autopilot.2.) How Chandler scaled SelfPublishing.com into an eight-figure company and his framework for helping busy founders publish a high-impact book faster than they thought possible.3.) The hard money investing lessons Chandler learned, both wins and losses, that every entrepreneur should hear before partnering on deals and deploying capital.Show Notes: LifestyleInvestor.com/268Tax 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.

Many aspiring investors believe that only significant capital and experience build wealth in real estate. Today’s guests show that with work ethic, resourcefulness, mentorship, and determination, anyone can create extraordinary results.I’m thrilled to be joined by Dedric and Krystal Polite, a husband and wife team and co-founders of Be Polite Properties. Dedric and Krystal are real estate investors, serial entrepreneurs, and stars of the TV series 50/50 Flip on Hulu and A&E.Their journey began in 2012 with listing Krystal’s apartment on Airbnb, which then led to wholesaling and renovating properties, building a real estate education company, and expanding into Sky Zone trampoline park franchises.You’ll hear how creative financing became the springboard for building generational wealth in real estate, the benefits of joining mastermind communities, and how sharing their journey on social media attracted more deals and helped them get discovered by a hit TV show.Together, they’re helping aspiring real investors fulfill their dreams through their coaching and education programs. Whether you’re early in your investing journey or looking for help to grow your real estate portfolio, their story will inspire you to take the next step in your entrepreneurial journey.In this episode, you’ll learn: 1.) How Dedric & Krystal left their corporate jobs and how a single Airbnb led to them flipping over 100 properties and eventually starring in a hit TV series on A&E.2.) Why creative financing and seller financing became their breakthrough strategy—and how these methods can help anyone scale without large amounts of cash.3.) The importance of mentorship, mastermind communities, and surrounding yourself with people who’ve had success at a higher level.Show Notes: LifestyleInvestor.com/267Tax 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.

Experts tell us that every 60 seconds, over one million plastic bottles are sold worldwide. Sadly, most of them will end up in landfills or the ocean, polluting the very thing that all living beings need to sustain life. It’s no secret that the continued use of single-use plastic bottles is unsustainable for our planet and health. Few have made it their mission to solve this issue. But that’s exactly what today’s guest has been doing for almost a decade, and they’ve already eliminated over 500 million plastic bottles so far.Shadi Bakour is the co-founder and CEO of PATH, the world’s first 100% refillable, recyclable bottled water brand. What started as an idea in a CVS parking lot has grown into a purpose-driven company. The mission: eliminate single-use plastics while offering consumers a premium, health-conscious option and eliminate 10 billion plastic bottles in the next few years.In this episode, we explore what it takes to scale a purpose-led company, how sustainability is not just a trend but a permanent shift in consumer behavior, and why aligning profit with purpose might unlock the biggest investment opportunities in the years ahead.In this episode, you’ll learn: 1.) How Shadi turned an idea into a movement that’s eliminated over 500 million plastic bottles from oceans and landfills.2.) Why purpose-led businesses outperform competitors and attract top talent, partners, and investors.3.) The powerful shift toward a refillable economy—and what it reveals about the future of consumer behavior.Show Notes: LifestyleInvestor.com/266Tax 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.

One of the biggest reasons why affluent families and high-net-worth investors have lost trust in financial services and wealth management firms is that most of the advice they receive is biased and driven by incentives that serve institutions instead of clients.Imagine financial advice and strategies that truly align your wealth with value-aligned guidance. Most investors expect traditional wealth managers and RIAs to act in their best interests. Today’s guest will reveal how the financial industry actually operates—and how they are disrupting the status quo.That’s why I’m thrilled to welcome Mo Lidsky to the podcast. Mo is CEO and Partner at Prime Quadrant, one of North America’s leading multi-family offices. With $26B+ in AUC (Assets Under Consultation™) and over 400 years of combined experience, they’ve cracked the code on providing financial services that aren’t focused on selling products, and empower families to make better financial decisions.They believe that typical family offices with 7-figure net worth should have the same access to institutional-quality options that are enjoyed by billion-dollar corporations, offering aligned interests, a diversity of opportunities, exceptional planning, and predictable outcomes. In our conversation, Mo shares how Prime Quadrant designed a cost-effective family office model that bridges the gap between retail investors and institutions, giving clients access to institutional opportunities and advice tailored solely to their needs. We’ll also discuss how their fee-only structure creates transparency and how focusing on your real goals leads to genuinely personalized financial advice.In this episode, you’ll learn: 1.) How to identify misaligned incentives in traditional wealth management and avoid paying for biased advice.2.) How Prime Quadrant’s family office model delivers institutional-quality access and advice for affluent families.3.) How to clarify what you truly want—and build your financial life around purpose, freedom, and alignment.Show Notes: LifestyleInvestor.com/265Tax 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.

Far too many entrepreneurs equate growth with complexity and remain hyper-focused on offering more products on more platforms, spending countless hours for minimal profit. This mindset often results in burnout, wasted spending, and a business that owns them instead of a business that runs without you.But it doesn’t have to be that way. And today’s guest is here to show you how.Allan Dib has built and scaled multiple companies by simplifying the complex. As the bestselling author of The 1-Page Marketing Plan and Lean Marketing, he’s helped millions of business owners cut through the noise, strip away what isn’t working, and create marketing systems that scale and generate profit. His mission is simple: turn chaos into clarity and help leaders reclaim their time freedom while still making a profit.In our conversation, Allan and I explore what it really means to build a “lifestyle empire”—a business that not only runs efficiently, but one that generates wealth and fuels your life without sacrificing everything you love. In this episode, you’ll learn: 1.) How subtraction leads to exponential growth and why simplicity—not more tactics—is the ultimate growth strategy in marketing and business.2.) How to focus on your “Genius Zone” by building a business that allows you to focus your time on where it matters most.3.) The biggest expense for most entrepreneurs and why hiring a tax strategist is a gamechanger to preserve your wealth.Show Notes: LifestyleInvestor.com/264Tax 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.

Far too many investors seek out advice and chase ROI without realizing how much bias and hidden costs are influencing their decisions. Pay-to-play is very common in the mastermind space, but there is one community that has a different set of rules.I’ve been a member of many mastermind groups over the years, and that’s why I want to highlight what sets the Lifestyle Investor communities apart from the rest. What started as a handful of friends talking shop and sharing deals over a glass of wine has become one of the fastest-growing investment communities in the world.Today, I’m joined by Ryan Casey, Chief Operating Officer of The Lifestyle Investor, to pull back the curtain on how our communities have evolved into a global ecosystem with world-class due diligence, exclusive deal flow, and unforgettable live event experiences around the world.You’ll hear how we’ve redefined the way people build wealth. From eliminating bias in investing and spending upwards of $300k/year on vetting and due diligence, to creating programs like our Foundations group for young adults, the Open Community for new investors, and even a financial literacy book for kids.Whether you’re just starting your wealth journey or scaling into financial freedom, this episode shows how to build a life designed around freedom, purpose, and the people you love.In this episode, you’ll learn: 1.) How we’ve built an investment ecosystem that is the opposite of a “pay-to-play” group and helps our members avoid costly mistakes with industry leading experts and strategies.2.) The difference between our four communities—Lifestyle Investor, Tribe of Investors, Foundations, and the Open Community—and how to know which one’s right for you.3.) How we’re empowering families to build wealth across generations through mentorship, education, and actionable investment frameworks.Show Notes: LifestyleInvestor.com/263Tax 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.

What if you could spend just one day sharing your product or service with an irresistible offer—and turn that one event into a multimillion-dollar business by harnessing the power of a single presentation?Most entrepreneurs spend years trying to grow their business through endless marketing tactics, but few realize they could be just one presentation away from the breakthrough they’ve been chasing. Whether it’s on a stage or in a boardroom, one powerful presentation can change everything. Which is exactly what happened to today’s guest.Today, I’m thrilled to welcome Colin Boyd back on the podcast. Colin is a Certified Speaking Professional, founder of the Sell From Stage Academy®, and author of One Presentation Away. Colin has helped some of the biggest names in the expert space design presentations that convert clients without sales-y or slimy tactics. In addition to experts such as Amy Porterfield, James Wedmore, and Jenna Kutcher, he has also collaborated with major corporations, including Coca-Cola, Suncorp, and Hewlett-Packard, to name a few.In our conversation, Colin explains how anyone can craft their origin story into a conversion story, one that connects and converts authentically to drive exponential growth in their business.In this episode, you’ll learn: 1.) How to reframe selling as an act of service and remove feelings of guilt from your mindset. 2.) How to structure presentations that organically leads to a yes and convert more prospects into clients.3.) How to sell from stage without feeling “salesy,” by using Colin’s framework for turning selling into serving and making irresistible offers that people are excited to say yes to.Show Notes: LifestyleInvestor.com/262Tax 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.