One Business Sale, Millions in Taxes: Are You Prepared?

What would you do if a $50 million business sale triggered a $15 million tax bill? In this episode, Mike Canet and Ryan Herbert discuss a real-world case involving a business owner approached by data center developers during the AI boom. They explore how major asset sales can create significant tax and estate planning challenges, and walk through concepts such as 1031 exchanges, Opportunity Zones, and deferred sales trusts. The conversation highlights why taxes, liquidity, estate considerations, and long-term planning are often connected when evaluating the sale of a business or highly appreciated property Want to begin building your retirement and tax plan? Click Here to Schedule a 15-minute Discovery Call Follow us for more helpful insights: 🖱️ Facebook- https://bit.ly/3PmJcSt 🖱️ LinkedIn- https://bit.ly/44T88a9 🖱️ X - https://bit.ly/3PHxqDJSee omnystudio.com/listener for privacy information.

Think you're years away from retirement? You may be closer than you realize, but replacing your paycheck takes more planning than most people expect. Ryan Herbert and Katherine Groce discuss what it really takes to retire before traditional retirement age, including creating multiple income sources, planning for healthcare costs before Medicare, and building a strategy for turning savings into reliable retirement income. They also explain why knowing exactly where your income will come from can be just as important as how much you've saved, and how retirement planning shifts from growing assets to creating a sustainable distribution strategy. Want to begin building your retirement and tax plan? Click Here to Schedule a 15-minute Discovery Call Follow us for more helpful insights: 🖱️ Facebook- https://bit.ly/3PmJcSt 🖱️ LinkedIn- https://bit.ly/44T88a9 🖱️ X - https://bit.ly/3PHxqDJSee omnystudio.com/listener for privacy information.

Would you take a guaranteed $60,000 a year for life over a tax-free $1 million lump sum? That simple question sparked thousands of comments and a heated debate online. Ryan Herbert and Katherine Groce break down the reasoning behind choosing lifetime income, while addressing arguments involving high-yield savings accounts, stock market investing, real estate, inflation, and retirement planning. Along the way, they explore risk, certainty, sequence of returns, and why financial decisions often depend on individual goals and circumstances. Plus, they discuss why short social media clips rarely provide enough context for important retirement and investment decisions. Want to begin building your retirement and tax plan? Click Here to Schedule a 15-minute Discovery Call Follow us for more helpful insights: 🖱️ Facebook- https://bit.ly/3PmJcSt 🖱️ LinkedIn- https://bit.ly/44T88a9 🖱️ X - https://bit.ly/3PHxqDJSee omnystudio.com/listener for privacy information.

What if the years after your kids leave home are the most important years for your retirement plan? As families transition into the empty nest stage, Mike Canet and Ryan Herbert discuss why ages 50 to 60 can be a pivotal time for retirement preparation. They cover catch-up contributions, evaluating whether you're on track for retirement, understanding income needs, tax planning strategies, and the value of having a written plan instead of relying on guesswork. The conversation also explores common retirement planning mistakes and why waiting until the last minute can limit your options. Want to begin building your retirement and tax plan? Click Here to Schedule a 15-minute Discovery Call Follow us for more helpful insights: 🖱️ Facebook- https://bit.ly/3PmJcSt 🖱️ LinkedIn- https://bit.ly/44T88a9 🖱️ X - https://bit.ly/3PHxqDJSee omnystudio.com/listener for privacy information.

Randy announces his retirement and highlights the many emotions that come with the transition away from his career. Jennifer, The Savvy Investor's newest co-host, joins Randy and Mike Canet to discuss how you can spend years preparing for retirement and still feel uneasy when the paycheck stops. In this episode, the team discusses the emotional and financial realities of transitioning into retirement, including identity shifts, spending habits, income planning, and the fear of running out of money. They also explore why many retirees struggle to spend what they've saved, how couples often have different retirement expectations, and why tax planning deserves a place alongside investment decisions. Want to begin building your retirement and tax plan? Click Here to Schedule a 15-minute Discovery Call Follow us for more helpful insights: 🖱️ Facebook- https://bit.ly/3PmJcSt 🖱️ LinkedIn- https://bit.ly/44T88a9 🖱️ X - https://bit.ly/3PHxqDJSee omnystudio.com/listener for privacy information.

One retiree's first required minimum distribution added $42,000 to his tax bill, raising a question many savers never see coming. In this episode, Lawrence Kiely & Katherine Groce discuss how RMDs can affect taxes, Social Security taxation, and Medicare premiums. They explore Roth conversions, charitable giving strategies, legacy planning considerations, and ways retirees may evaluate different tax buckets as part of a broader retirement income plan. Learn why retirement tax planning often requires looking beyond account balances and focusing on how and when money is withdrawn. Want to begin building your retirement and tax plan? Click Here to Schedule a 15-minute Discovery Call Follow us for more helpful insights: 🖱️ Facebook- https://bit.ly/3PmJcSt 🖱️ LinkedIn- https://bit.ly/44T88a9 🖱️ X - https://bit.ly/3PHxqDJSee omnystudio.com/listener for privacy information.

That old stock certificate, forgotten 401(k), or inherited investment could be worth more attention than you think. Mike Canet and Ryan Herbert discuss the overlooked assets many people bring into retirement, from decades-old stock holdings and abandoned accounts to outdated annuities and inherited investments. They share real-world stories of lost assets, paperwork challenges, and financial products that may no longer fit a retiree’s goals. Learn why organizing your financial life, understanding what you own, and reviewing older accounts can play an important role in retirement planning. Want to begin building your retirement and tax plan? Click Here to Schedule a 15-minute Discovery Call Follow us for more helpful insights: 🖱️ Facebook- https://bit.ly/3PmJcSt 🖱️ LinkedIn- https://bit.ly/44T88a9 🖱️ X - https://bit.ly/3PHxqDJSee omnystudio.com/listener for privacy information.

Think taking Social Security early is always the smartest move? Think again. In this episode, Mike Canet breaks down why Social Security claiming strategies are far more personal than most people realize. From life expectancy and income needs to legacy goals, taxes, Roth conversions, and pension decisions, Mike explains why there is no one-size-fits-all answer. Using real-world examples, he shows how the right claiming strategy depends on how every piece of a retirement plan fits together. If you're weighing when to claim Social Security, this conversation highlights the factors that deserve a closer look. Want to begin building your retirement and tax plan? Click Here to Schedule a 15-minute Discovery Call Follow us for more helpful insights: 🖱️ Facebook- https://bit.ly/3PmJcSt 🖱️ LinkedIn- https://bit.ly/44T88a9 🖱️ X - https://bit.ly/3PHxqDJSee omnystudio.com/listener for privacy information.

Your retirement calculator says you're on track, but what if it's missing the factors that matter most? This episode explores the limitations of online retirement calculators, AI tools, and probability-based projections that can make retirement readiness seem simpler than it is. Ryan Herbert and Lawrence Kiely discuss how market timing, taxes, income planning, inflation, lifestyle changes, and unexpected life events can impact retirement outcomes. Learn why a personalized retirement strategy goes beyond projections and how building a plan around your unique goals, spending needs, and income sources can provide greater clarity as you prepare for retirement. Want to begin building your retirement and tax plan? Click Here to Schedule a 15-minute Discovery Call Follow us for more helpful insights: 🖱️ Facebook- https://bit.ly/3PmJcSt 🖱️ LinkedIn- https://bit.ly/44T88a9 🖱️ X - https://bit.ly/3PHxqDJSee omnystudio.com/listener for privacy information.

A larger Social Security benefit sounds appealing, but what if waiting means sacrificing some of your best retirement years? Ryan Herbert and Katherine Groce explore the factors that go into deciding when to claim Social Security, including longevity, cash flow needs, portfolio withdrawals, taxes, and lifestyle goals. They discuss why the “best” claiming age is different for everyone, how delaying benefits can affect your retirement savings, and why quality of life often plays a major role in the decision. Want to begin building your retirement and tax plan? Click Here to Schedule a 15-minute Discovery Call Follow us for more helpful insights: 🖱️ Facebook- https://bit.ly/3PmJcSt 🖱️ LinkedIn- https://bit.ly/44T88a9 🖱️ X - https://bit.ly/3PHxqDJSee omnystudio.com/listener for privacy information.