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  • Bryan Clayton: From $20 Lawns to GreenPal — Grit, Growth, and the Real Education of an Entrepreneur

    Bryan Clayton: From $20 Lawns to GreenPal — Grit, Growth, and the Real Education of an Entrepreneur
    2026/07/14
    From $20 lawns as a teenager to a national tech platform, this episode dives into the unfiltered realities of building, scaling, and selling businesses in the real world, not the classroom.In this episode, Leonard and Bryan Clayton discuss:Early days mowing lawns and organic business growthOperator vs. owner mindset and the E-Myth frameworkPreparing a lifestyle business for eventual saleOrigin story and validation journey of GreenPalUsing technology, data, and AI to empower small service businessesKey Takeaways: A simple service business can teach most of the fundamentals of entrepreneurship, often faster and more effectively than formal business school.Moving from self-employed to true business owner requires intentional time working on the business: building processes, systems, and people that can operate without you.If there’s even a chance you might sell your company one day, you must build it to be sellable from the start, with clean systems, numbers, and an org chart that a buyer can understand.The real value of a marketplace platform lies not just in consumer convenience but in helping small operators win: getting customers, managing reviews, handling payments, and growing their income.Successful founders practice “constructive dissatisfaction”; they’re constantly, productively unhappy with the current state of the business and use that tension to drive continuous improvement. “I think you can learn more in a weekend starting and launching a business and getting three customers than you can in a year of business school.” - Bryan ClaytonAbout Bryan Clayton: Bryan Clayton started mowing lawns as a teenager with a push mower. Twenty years later, he’s the CEO of GreenPal — the app Entrepreneur Magazine calls *the Uber for lawn care. Before GreenPal, Bryan built one of Tennessee’s largest landscaping companies, growing it to over $10 million a year before selling it. Now he’s doing it again — this time with technology. GreenPal connects 300,000 homeowners with reliable lawn pros, handling thousands of jobs every day all over the US. Bryan’s on a mission to bring AI into one of the oldest industries out there — helping small lawn care businesses use data and automation to compete like big companies. From pushing a mower to building a $30 million tech platform, Bryan’s story is all about grit, adaptation, and how old-school hard work can thrive in a high-tech world.Connect with Bryan Clayton:Website: https://www.yourgreenpal.com LinkedIn: https://www.linkedin.com/in/bryan-clayton-a96b33214 Instagram: https://instagram.com/bryanmclayton X: https://x.com/bryanMclayton YouTube: https://www.youtube.com/@BryanClayton1 Other Resource: https://en.m.wikipedia.org/wiki/Bryan_M._Clayton Connect with Leonard Raskin:Website: https://www.raskinglobal.com/ LinkedIn: https://www.linkedin.com/in/leonardraskin/ Facebook: https://www.facebook.com/RaskinGlobal Email: lraskin@raskinglobal.comShow notes by Podcastologist: Francine PobleteAudio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.
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    39 分
  • Classic Rewind - Eric Dyson: The 401(k) Wake-Up Call

    Classic Rewind - Eric Dyson: The 401(k) Wake-Up Call
    2026/07/10

    A 401(k) plan isn’t just an employee benefit; it’s a fiduciary responsibility. Eric Dyson explains how hidden fees, vague oversight, and too many investment choices can quietly put plan sponsors at risk.


    In this episode, Leonard and Eric discuss:

    • The four core fiduciary duties under ERISA and why they matter
    • The risks of overlooking retirement plan fees and transparency
    • How small businesses can start retirement plans the right way
    • Why more investment options aren't always better for 401(k) participants
    • Real-world lessons from ERISA class action lawsuits


    Key Takeaways:

    • Crafting a strong retirement plan begins not with paperwork, but with intentional goals and a trusted advisor who can align the structure with the business's unique vision.
    • Beneath the surface of fiduciary compliance lies a common oversight—many plan sponsors are unaware that failure to ensure fee transparency and act solely in employees’ best interests may place them on shaky legal ground.
    • Rather than offering a buffet of investment choices, the conversation challenges the “more is better” mindset, advocating instead for simplicity and structure that empower—not overwhelm—plan participants.
    • In a world where assumptions can be costly, the message is clear: fiduciaries must demand precise, itemized cost breakdowns to uphold their duty—vague approximations no longer suffice.
    • Wrapped in a legal framework but rooted in ethics, transparency isn't just a smart move—it’s a non-negotiable pillar of responsible plan management under ERISA.


    "Picture it as the foundation to your house, ladies and gentlemen; we don't need to be talking about what color the sconce is and whether it's silver or brass, or what the color of the throw pillows are on the bed before we have a foundation, and those investments in your ERISA plan should be foundational and nothing more.” - Eric Dyson


    About Eric Dyson: He is a U.S. Naval Academy graduate and former nuclear-trained submarine officer with over 30 years of experience in the financial services industry. A seasoned ERISA advisor, he has worked as both a 3(21) and 3(38) fiduciary on defined contribution and benefit plans. Eric is the Executive Director of 90 North Consulting, where he specializes in conducting ERISA advisor RFPs, fiduciary training, best practices audits, and serving as an expert witness. His expertise has been trusted by both plaintiffs and defendants, the U.S. Department of Labor, and the CFP Board.


    Connect with Eric Dyson:

    Website: https://90northllc.com/

    LinkedIn: https://www.linkedin.com/in/401kguy/


    Connect with Leonard Raskin:

    Website: https://www.raskinglobal.com/

    LinkedIn: https://www.linkedin.com/in/leonardraskin/

    Facebook: https://www.facebook.com/RaskinGlobal

    Email: lraskin@raskinglobal.com


    Show notes by Podcastologist: Angelo Paul Tagama


    Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.

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    38 分
  • Jonathan Blau: Beating Investor Bias and Winning the Long Game with Equities

    Jonathan Blau: Beating Investor Bias and Winning the Long Game with Equities
    2026/07/07
    Behavioral biases quietly destroy more wealth than market volatility ever will. In this episode, you’ll hear how a fiduciary advisor helps successful investors avoid their own worst instincts and stay wealthy for the long run.In this episode, Leonard and Jonathan Blau discuss:Common behavioral biases of wealthy investorsOverconfidence, loss aversion, regret, and status quo biasHow Wall Street sales culture differs from true fiduciary adviceIndex funds, “sevens vs. threes,” and inflation as the real riskMedia noise, market timing, and the value of a qualified advisorKey Takeaways: The wealthiest investors are often the most vulnerable to behavioral mistakes because their confidence from business success doesn’t translate into skill with markets.Powerful biases such as loss aversion, regret aversion, and status quo bias can lead investors to avoid stocks altogether, inadvertently exposing them to long-term inflation risk.Many parts of the advisory industry still revolve around sales, timing, and selection stories, even though persistent outperformance is rare and often tax-inefficient.Volatility is temporary and often overemphasized compared to inflation, which permanently erodes purchasing power; owning more equities (“sevens”) than bonds (“threes”) is critical for long retirements.One of the best investments most people can make is in a truly qualified financial advisor who focuses on behavior, planning, costs, and taxes rather than chasing “hot” ideas or timing calls. “If you're going to survive a 30-year retirement marked by 3 to 5% inflation, you better have a lot more sevens than threes.” - Jonathan BlauAbout Jonathan Blau: Jonathan Blau is the founder and CEO of Fusion Family Wealth, a fee-only registered investment advisory firm in Long Island that focuses on helping investors recognize and overcome behavioral biases that can lead to poor financial decisions. His career began with a summer internship at Lehman Brothers, where he noticed the need for objective, planning-based advisory services for wealthy investors. He later earned advanced degrees in taxation and accounting, worked in tax and family wealth planning, and gained extensive experience at firms such as Sanford C. Bernstein, Morgan Stanley, Smith Barney, and UBS. These experiences shaped his belief that investor behavior is often more important than investment products.As a behavioral finance thought leader, Jonathan helps clients make rational financial decisions, especially during periods of uncertainty. He emphasizes that true wealth risk comes not from temporary market fluctuations, but from the permanent loss of purchasing power caused by inflation. Through his advisory work and the “Crazy Wealthy Podcast,” he shares practical insights on improving money behavior and avoiding common investment mistakes. Fusion Family Wealth’s recognition among Forbes’ Top 250 Registered Investment Advisory Firms reflects its commitment to integrity, client focus, and meaningful financial guidance.Connect with Jonathan Blau:Website: https://www.fusionfamilywealth.com/ LinkedIn: http://www.linkedin.com/in/jonathanblau1 Instagram: https://www.instagram.com/moneeeementor/ Podcast - Crazy Wealthy Podcast: https://crazywealthypodcast.fusionfamilywealth.com/ Connect with Leonard Raskin:Website: https://www.raskinglobal.com/ LinkedIn: https://www.linkedin.com/in/leonardraskin/ Facebook: https://www.facebook.com/RaskinGlobal Email: lraskin@raskinglobal.comShow notes by Podcastologist: Francine PobleteAudio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.
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    45 分
  • Classic Rewind - Fritz Gilbert: Living The Retirement Manifesto

    Classic Rewind - Fritz Gilbert: Living The Retirement Manifesto
    2026/07/03
    Retirement isn’t just a money milestone. Fritz Gilbert shares why identity, purpose, and “refirement” may matter just as much as your portfolio.In this episode, Leonard and Fritz discuss:How Fritz launched The Retirement Manifesto blog and wrote 440+ articles on retirement strategyThe most overlooked yet critical element of retirement successWhy many retirees struggle with identity and purpose post-careerThe story behind Fritz and his wife founding the nonprofit “Freedom for Fido”The essential difference between “retirement” and “refirement”Key Takeaways:A fulfilling retirement doesn’t come from savings alone—it requires thoughtful planning around identity, structure, and a renewed sense of purpose. Without this preparation, many retirees find themselves unfulfilled despite being financially secure.Starting the mental and emotional preparation for retirement at least two to three years before leaving the workforce significantly increases the chances of a smooth and meaningful transition. It’s not just about the money—it’s about mindset.Think of retirement not as a finish line, but as the beginning of a new chapter filled with passion projects, adventure, and personal reinvention. It's the opportunity to finally do what lights you up—on your own terms.When you contribute your time and energy to causes that matter, like volunteering, you often discover deeper relationships and a renewed sense of connection. Giving back adds purpose that money simply can’t buy.Following your curiosity can unlock unexpected joys in retirement. For Fritz, that curiosity led to founding a nonprofit that builds fences for dogs—proof that passion often starts with a single step.“The number one key to a successful retirement is to start planning early—ideally two years out, one year at minimum. And don’t just focus on the financials. That’s a common mistake. You’ve got to expand your thinking into the non-financial areas as well.” - Fritz GilbertAbout Fritz Gilbert: He is the founder of The Retirement Manifesto, an award-winning blog dedicated to “Helping People Achieve a Great Retirement.” He’s also the author of Keys to a Successful Retirement: Staying Happy, Active, and Productive in Your Retired Years. After a 33-year career in Corporate America, Fritz retired in 2018 at age 55 and now shares practical lessons to help others navigate their own retirement journey. He and his wife live in the Appalachian Mountains of Blue Ridge, Georgia, with their three dogs, where they also run Freedom for Fido, a 501(c)(3) nonprofit that builds free dog fences for low-income families with chained pets.Connect with Fritz Gilbert:Websites: https://www.theretirementmanifesto.com/ , https://freedomforfido.com/ LinkedIn: https://www.linkedin.com/in/fritzgilbert/ Facebook: https://www.facebook.com/TheRetirementManifesto Fritz’s Book: https://www.amazon.com/Keys-Successful-Retirement-Staying-Productive/dp/164611339X Connect with Leonard Raskin:Website: https://www.raskinglobal.com/ LinkedIn: https://www.linkedin.com/in/leonardraskin/ Facebook: https://www.facebook.com/RaskinGlobal Email: lraskin@raskinglobal.com Show notes by Podcastologist: Angelo Paul TagamaAudio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.
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    40 分
  • Ari Rastegar: Risk, Resilience, and Playing the Long Game in Real Estate

    Ari Rastegar: Risk, Resilience, and Playing the Long Game in Real Estate
    2026/06/30
    Real estate “passive income” is anything but passive, especially when markets are volatile and fear is high. In this episode, you’ll hear how disciplined risk management, zoning arbitrage, and psychology-driven investing can create long-term wealth.In this episode, Leonard and Ari Rastegar discuss:Risk management and “risk-adjusted returns” in real estateZoning, entitlements, and asset-class agnostic developmentNavigating fear, market cycles, and investor psychologyMisconceptions about “passive income” and DIY real estate investingInvestor alignment, accessibility, and co-investment with institutionsKey Takeaways: Effective real estate investing starts with obsessing over how you could lose money and building structures to manage, not eliminate, that risk.Being asset-class agnostic and focusing on zoning and entitlements can unlock hidden value long before a shovel ever hits the ground.The most attractive deals often emerge during periods of fear, volatility, and negative headlines, precisely when most investors are the most reactive and hesitant.So‑called “passive income” in real estate usually demands intense, around-the-clock active management, making professional oversight far more valuable than many high performers assume.Long-term success in investing and business requires psychological endurance: the willingness to endure cycles, confront hard conversations, and continuously learn from failure. “Private equity in real estate, in particular, real estate is about counter-punching, and it's about knowing when to, when others are scared, when others are selling, when things are going whatever, knowing when to be aggressive and buy things at a discount, and that's exactly what this time is right now.” - Ari RastegarAbout Ari Rastegar: Ari Rastegar is the Founder and CEO of Rastegar Capital, a vertically integrated real estate investment firm based in Austin, Texas. Known as one of America’s most forward-thinking real estate investors, Ari has built a diverse national portfolio spanning multifamily, industrial, self-storage, and mixed-use assets. A first-generation Iranian-American and author of the acclaimed book The Gift of Failure, Ari’s journey from modest beginnings to building a billion-dollar enterprise embodies his core belief: failure isn’t final — it’s fuel. His philosophy of turning adversity into opportunity has made him a sought-after voice on leadership, resilience, and the future of American growth markets. Ari has been featured on Fox News, CNBC, Forbes, Bloomberg, and Business Insider, where he speaks on the intersection of real estate, economics, and mindset — offering sharp insights into why people and capital flow where they’re treated best.Connect with Ari Rastegar:Website: http://www.rastegarcapital.com LinkedIn: https://www.linkedin.com/in/arirastegar X: https://twitter.com/AriRastegar Instagram: https://www.instagram.com/arirastegar YouTube: https://www.youtube.com/@Ari_Rastegar Book: The Gift of Failure – https://www.amazon.com/Gift-Failure-Turn-Missteps-Success/dp/1544523211/ref=asc_df_1544523211/?tag=hyprod-20&linkCode=df0&hvadid=598354936952&hvpos=&hvnetw=g&hvrand=12557661389217729104&hvpone=&hvptwo=&hvqmt=&hvdev=c&hvdvcmdl=&hvlocint=&hvlocphy=9028310&hvtargid=pla-1678938210209&psc=1 Connect with Leonard Raskin:Website: https://www.raskinglobal.com/ LinkedIn: https://www.linkedin.com/in/leonardraskin/ Facebook: https://www.facebook.com/RaskinGlobal Email: lraskin@raskinglobal.comShow notes by Podcastologist: Francine PobleteAudio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.
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    35 分
  • Classic Rewind - Jesse Cramer: Smart Planning Beats Smart Investing

    Classic Rewind - Jesse Cramer: Smart Planning Beats Smart Investing
    2026/06/26

    What if the smartest retirement move isn’t picking better investments, but understanding how your whole financial life actually works? Jesse Cramer joins Leonard to explain why smart planning beats smart investing.


    In this episode, Leonard and Jesse discuss:

    • Journey from aerospace engineer to personal finance educator
    • Why understanding your real spending habits is critical to retirement planning
    • How the engineering mindset helps break down complex financial systems
    • The most common financial mistakes people make—and how to prevent them
    • How podcasting and financial education can empower individuals at all life stages


    Key Takeaways:

    • Many individuals drastically underestimate their actual monthly spending, leading to flawed financial plans that feel solid—until the numbers don't add up.
    • Financial planning mirrors a spider web: every financial decision pulls on another thread, revealing an intricate system where nothing exists in isolation.
    • While investments often take center stage, the true value lies in holistic planning—blending tax strategies, risk protection, and long-term income coordination.
    • Clarity begins with humility: assuming no prior knowledge, effective educators break down complex topics to their first principles, avoiding industry jargon.
    • When people truly understand both their risk exposure and spending habits, they gain the confidence to make intentional, informed financial choices.


    "It's the idea that I don't want to say investing is table stakes in our industry, because it's probably not, but I think investing can be the easier part of our job... I just like learning all the cool stuff in the planning world that I didn't know before.” - Jesse Cramer


    About Jesse Cramer: He is the founder and voice behind The Best Interest Blog and the Personal Finance for Long-Term Investors Podcast, where he educates over 25,000 DIY investors and financial advisors every month. With a background in mechanical and aerospace engineering, Jesse has a gift for making complex financial topics surprisingly simple. Today, he brings that same clarity and precision to his work as a fiduciary, fee-only advisor at a wealth management firm in Rochester, New York.


    Connect with Jesse Cramer:

    Website: https://bestinterest.blog/

    LinkedIn: https://www.linkedin.com/in/jesse-cramer-11b58155/

    Podcast: https://podcasts.apple.com/us/podcast/personal-finance-for-long-term-investors-the-best-interest/id1553180943


    Connect with Leonard Raskin:

    Website: https://www.raskinglobal.com/

    LinkedIn: https://www.linkedin.com/in/leonardraskin/

    Facebook: https://www.facebook.com/RaskinGlobal

    Email: lraskin@raskinglobal.com


    Show notes by Podcastologist: Angelo Paul Tagama


    Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.

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    44 分
  • Tom Ruwitch: From Boring to Brilliant with the PLAN Storytelling Framework

    Tom Ruwitch: From Boring to Brilliant with the PLAN Storytelling Framework
    2026/06/23
    Discover why most expert content falls flat and how a simple PLAN framework can turn everyday stories into client-magnet messages.In this episode, Leonard and Tom Ruwitch discuss:Early days of email marketing and media industry lessonsWhy information-only content fails to attract clientsThe PLAN framework: Promise, Lesson, Anecdote, Next StepStories as a repeatable system for content creationImplementum: combining strategy, technology, and team support to help business owners execute consistentlyKey Takeaways: Information alone rarely moves prospects; pairing a meaningful promise with a clear lesson is what makes content matter.Story-driven content keeps people engaged for years, so that when the timing is right, they’re already primed to buy.A simple framework, Promise, Lesson, Anecdote, Next Step, turns content creation from a creative struggle into a repeatable assembly process.Great marketing isn’t just about better tools; without strong content and consistent implementation, even the fanciest tech underperforms.Business owners often become their own bottleneck, and freeing them from tech and execution work lets them focus on serving clients and closing sales. “The difference between content that is blah and boring and prospect repelling and content that is captivating and entertaining and client attracting is that framework promise lesson anecdote next step.” - Tom RuwitchAbout Tom Ruwitch: Tom Ruwitch is a business advisor, storytelling standout, and content marketing pioneer who helps business leaders create, deliver, and track client-attracting content and cure tech headaches.In 2001, Tom founded the email marketing software and services company MarketVolt. This was before most business people had even heard of email marketing, much less tried it. MarketVolt licensed its groundbreaking software to businesses around the globe, and it operated as a full-service agency – helping businesses of all sizes attract prospects and land clients with online and offline marketing strategies and tactics.After selling MarketVolt in 2019, Tom founded Story Power Marketing. Authors, coaches, and other experts hire Tom to transform their content from boring to brilliant – without writer’s block – so prospects tune in, turn on, and buy.In 2021, Tom launched Implementum -- an all-in-one marketing, operations, and analytics platform that includes customized, done-for-you campaigns, strategy, and hands-on training. Implementum helps business leaders build automated marketing machines so they can grow and profit without tech headaches.Connect with Tom Ruwitch:Website: https://storypowermarketing.com LinkedIn: https://linkedin.com/in/tomruwitch Facebook: https://facebook.com/tomruwitch YouTube: https://youtube.com/@tom-ruwitch Book: https://storypowerbook.com Connect with Leonard Raskin:Website: https://www.raskinglobal.com/ LinkedIn: https://www.linkedin.com/in/leonardraskin/ Facebook: https://www.facebook.com/RaskinGlobal Email: lraskin@raskinglobal.comShow notes by Podcastologist: Francine PobleteAudio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.
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    42 分
  • Tommy Whitehead: Building Success Through Community, Construction, and Leadership

    Tommy Whitehead: Building Success Through Community, Construction, and Leadership
    2026/06/18

    A layoff in the Great Recession pushed him out of hospitality and into thousands of renovation projects—now he’s building homes, communities, and entrepreneurs across Tampa Bay. In this episode, discover how he uses construction, strategic networking, and large‑scale events to create lasting impact and opportunity.

    In this episode, Leonard and Tommy Whitehead discuss:

    ● Transition from finance and hospitality into construction and development

    ● ADUs, affordable housing, and Florida’s evolving regulations

    ● Disaster renovation, floodplains, and long-term real estate plays

    ● Leadership, hiring, and building an executive team for growth

    ● Community impact, networking strategy, and the Building Success Summit

    Key Takeaways:

    ● Career pivots often start in crisis: unemployment during the Great Recession led to thousands of renovation projects and ultimately a thriving construction firm.

    ● Accessory Dwelling Units are becoming a critical tool for affordability, multi‑generational living, and rental income, but they live and die by local zoning and regulation.

    ● Reputation is built less by ads and more by visible community contribution, from nonprofit partnerships to hosting high‑value networking events without expecting an immediate return.

    ● Trying to save money by skipping professionals—accountants, attorneys, permits, inspections—almost always creates bigger, more expensive problems down the road.

    ● Over‑customizing a property and making emotional renovation decisions can crush resale value; smart owners run the numbers first and design with the next buyer in mind.

    “You're your number one fan, and you're your number one obstacle.” - Tommy Whitehead

    About Tommy Whitehead: Tommy is the Founder and CEO of TomCo Solutions, a rapidly growing design-build construction firm focused on innovative housing solutions, including custom builds, renovations, and accessory dwelling units (ADUs). A recognized leader in the Tampa Bay business community, Tommy is also the founder of the Building Success Summit and author of the Amazon Best-Selling book Building Success: A Toolbox for Coming Out On Top. With a passion for entrepreneurship, economic empowerment, and community impact, Tommy has built multiple ventures spanning construction, real estate development, and business education. His work blends practical industry expertise with thought leadership, helping others scale their businesses and build lasting success.

    Connect with Tommy Whitehead:

    Website: https://tommywhitehead.com/

    LinkedIn: https://www.linkedin.com/in/tommywhitehead/

    Facebook TomCo: https://www.facebook.com/TomCoSolutions

    Connect with Leonard Raskin:

    Website: https://www.raskinglobal.com/

    LinkedIn: https://www.linkedin.com/in/leonardraskin/

    Facebook: https://www.facebook.com/RaskinGlobal

    Email: lraskin@raskinglobal.com

    Show notes by Podcastologist: Francine Poblete


    Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.

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    40 分