Office Hours with Kuldeep Madan

Office Hours with Kuldeep Madan

By Kuldeep MadanBusinessInvestingCareersManagement
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Office Hours with Kuldeep Madan episodes

  • Will Guidara on Unreasonable Hospitality for Financial Advisors

    Live from the M+ Masterclass in Miami Beach, Kuldeep Madan sits down with Will Guidara, former co-owner of Eleven Madison Park and author of Unreasonable Hospitality, right after his keynote. Will makes the case that advisors, who walk alongside clients for decades, have a bigger opportunity to deliver personalized care than any restaurant ever could.

    Guidara breaks down the specific tactics he'd use if he were running an advisory practice:

    • Gift outside the gifting cycle, when you won't get lost in the pile
    • Show up for the people your clients love, not just the clients
    • Keep detailed notes so you can follow up on conversations from years ago
    • Prioritize ideas with the impact vs. resource matrix, and start with low-resource, high-impact moves

    They also cover how to lead and build culture:

    • Why inspiration matters as much as training
    • How to give constructive criticism: private, about the behavior not the person, and consistent
    • Why repair after a mistake builds more loyalty than never making one
    • How to handle imposter syndrome and self-limiting beliefs as a leader

    Guidara also tells the story of an advisor who earned ten years of client loyalty with one extraordinary gesture, and explains why clients remember care long after they forget returns. The episode closes with rapid-fire questions on his favorite restaurants, wine, books, and the best money he's ever spent.

    Ideal for financial advisors, wealth managers, RIAs, and business leaders who want to improve client retention, client experience, and team performance.

    BOOKS MENTIONED

    • Unreasonable Hospitality by Will Guidara: https://www.penguinrandomhouse.com/books/674289/unreasonable-hospitality-by-will-guidara/
    • The Art of Fighting by Priya Parker: https://www.penguinrandomhouse.com/books/678581/the-art-of-fighting-by-priya-parker/
    • Theo of Golden by Allen Levi: https://www.simonandschuster.com/books/Theo-of-Golden/Allen-Levi/9781668236567

    REFERENCES

    • Eleven Madison Park: https://www.elevenmadisonpark.com
    • Milk Bar: https://milkbarstore.com
    • Rezdôra (NYC): https://rezdora.nyc
    • Le Bernardin (NYC): https://www.le-bernardin.com
    • Asador Etxebarri (Spain): https://www.asadoretxebarri.com

    28 min
  • Tax Attorney Matt Foreman on Succession Planning, Tax Myths & Bobbleheads

    On this episode of Office Hours, Kuldeep sits down with Matt Foreman, partner at Falcon, Rappaport & Berkman, co-chair of the firm's taxation practice group, and host of the podcast How Tax Works. Matt is one of two tax attorneys Kuldeep works with closely, and he's known for explaining tax law in plain English.

    Matt breaks down why so much tax advice on social media bears no resemblance to the actual rules, and why his job isn't to help clients avoid tax but to help them understand it. They get into succession planning for business owners, including why Matt reaches for Tommy Boy and Billy Madison to explain it, and what happens when a $100 to $300 million business has no plan. Along the way come the tax troubles of celebrities (yes, Nicolas Cage), partnership taxes and crypto staking, and the art of telling a client no without being a jerk.

    Then Kuldeep gets to the collection he's been waiting to ask about: roughly 130 sports bobbleheads, Starting Lineups figures and Funkos on a shelf behind Matt's desk, which includes a Stay Puft Marshmallow Man, and how a tax attorney became a bobblehead guy. Matt shares his favorite movies, shows and halftime performances, his best-read book of the year, and why he thinks a little humanity makes tax attorneys better at the job.

    Listen to Foreman's Podcast "How Tax Works":

    Apple: https://podcasts.apple.com/us/podcast/how-tax-works/id1751296470

    Spotify: https://open.spotify.com/show/59mZSlMokf3AiodWPXN6oU

    Books mentioned:

    Thinking, Fast and Slow by Daniel Kahneman

    https://www.amazon.com/dp/0374533555

    The Wealth of Nations by Adam Smith

    https://www.amazon.com/dp/0553585975

    The Firm by John Grisham

    https://www.amazon.com/dp/0440245923

    Movies and shows referenced:

    Tommy Boy (1995): https://www.imdb.com/title/tt0114814/

    Billy Madison (1995): https://www.imdb.com/title/tt0112508/
    The Firm (1993): https://www.imdb.com/title/tt0106918/
    National Treasure (2004): https://www.imdb.com/title/tt0368891/
    Ghostbusters (1984): https://www.imdb.com/title/tt0087332/
    This Is Spinal Tap (1984): https://www.imdb.com/title/tt0088258/
    Seinfeld: https://www.imdb.com/title/tt0098904/
    Hamilton (2020): https://www.imdb.com/title/tt8503618/

    2 hr 15 min
  • Joe Gaglio on Being a Third-Generation Advisor, His Family Business & Scaling Shepherd Wealth

    Joe Gaglio, founder and CEO of Shepherd Wealth and a third-generation specialist in the qualified plans and ERISA space, sits down with Kuldeep Madan on Office Hours to talk about carrying a 70-year family legacy forward without being trapped by it.

    From a first meeting that turned into a legendary 12-hour lunch, Joe opens up about growing up as the third generation in a business his grandfather started in the 1950s, the decision to break off and build Shepherd his own way, and the "full send" mindset that changed his career. He and Kuldeep get into the real tension of a multi-generational family firm, why he refused to run the "old-format" playbook, and the discipline behind scaling: getting the right people in the right seats, building systems that don't depend on any one person, and his hard-won framework for growth — People, Training, Systems, and Distractions (yes, PTSD). Funny, intense, and refreshingly honest, it's a blueprint for anyone trying to modernize a legacy business or bet on themselves.

    In this episode:

    • The 12-hour lunch that kicked off the friendship
    • Being the third generation in a 70-year family business — and the pressure that comes with it
    • Why he broke off to build Shepherd Wealth his own way
    • The "get uncomfortable / full send" mindset that changed everything
    • Scaling a mega-niche firm: people, training, and systems
    • The "PTSD" framework — People, Training, Systems, Distractions
    • Why most third-generation businesses fail — and how he's beating the odds

    Referenced in this episode:

    • Shepherd Wealth - https://shepherd-wealth.com/
    • Alex Hormozi's "burn the boats / full send" philosophy — https://www.acquisition.com
    • MassMutual — https://www.massmutual.com

    Connect with Joe Gaglio: @mr_gaglio @shepherdwealthgroup

    Subscribe to Office Hours for conversations with the smartest people in financial services.

    1 hr 28 min
  • Rick Hu on Fee-Based Planning, Business-Owner Mindset & Building Midas Wealth
    Rick Hu is known as "The Titan," a top 1% producer and founder/CEO of Midas Wealth. On this episode of Office Hours, he sits down with Kuldeep Madan to talk fee-based planning, the business-owner mindset every advisor needs, and why he walked away from the #1 practice in the country to start over.
    From food stamps and Medicaid in Brooklyn to Northwestern Mutual's youngest-ever managing director at 25 and back-to-back Forbes recognition, Rick's story is equal parts deeply personal and intensely practical. He opens up about the immigrant childhood that shaped him, buying his father's dream car, the moment his wife's ultimatum made him rethink everything, and coughing blood from overwork. Then he turns to the hard-won business lessons behind Midas Wealth: protecting your time, knowing your hourly rate, hiring people smarter than you, and treating yourself as a business owner first and an advisor second. He closes on the future of the profession — fee-for-advice, education over product, and why he believes AI will wipe out transactional advisors but never the ones who lead with people.
    In this episode:

    • Growing up on food stamps and the "love is spelled T-I-M-E" philosophy

    • Buying a Rolls-Royce Cullinan and why

    • The wife's ultimatum that made him retire from a #1 practice

    • Losing 70% of his revenue overnight and replenishing it in two years

    • "You're a business owner first, not an advisor."
    • Fee-based planning vs. product-based selling, and the AI reckoning ahead

    • Building a team from 3 to 27, and firing his own mom
    Referenced in this episode:

    • Midas Wealth (Rick's firm) — https://www.midas-wealth.com/

    • Northwestern Mutual — https://www.northwesternmutual.com

    • Forum 400, the elite advisor community where Rick & Kuldeep met (now part of Finseca) — https://www.finseca.org/forum-400/

    • Forbes Best-in-State / Top Financial Security Professionals — https://www.forbes.com/best-in-state-wealth-advisors/

    • Steve Jobs biography by Walter Isaacson (the ousted-then-returned story Rick references) — https://www.amazon.com/s?k=Steve+Jobs+Walter+Isaacson

    • Rick's session at the M+ Masterclass (September) on fee-based planning — https://events.madanplus.com/registration
    Connect with Rick Hu:
    https://www.linkedin.com/in/iamrickhu/
    https://www.instagram.com/iamrickhu/?hl=en
    @Iamrickhu
    Subscribe to Office Hours for more conversations with the smartest people in financial services.
    #FinancialAdvisor #FeeBasedPlanning #FinancialPlanning #OfficeHours #MidasWealth #BusinessOwner #FinancialServices #Entrepreneurship
    1 hr 32 min
  • Buses, Beginnings, and the Brains of Michael Book
    On this episode of Office Hours, Kuldeep Madan sits down with Michael Book, founding partner of Lenox Advisors, a 35-year industry veteran, a member of the Finseca Hall of Fame for leadership and mentorship, and a new grandfather. The two trace how they met, a chance encounter when their Jeeps got stuck in the Dubai desert, before Michael walks through his whole arc: a sports-obsessed Long Island and New Jersey childhood, a college career he admits was more fun than academic, three and a half years selling for his dad's plastics company, and the cousin's tip that pulled him into the life insurance business.
    From there, he unpacks how Lenox grew into one of the most productive firms in the country, the leadership lessons behind it, getting the right people "on the bus," delegating and empowering, reading people, and never being afraid of the hard conversation. He outlines his personal philosophies, which he's become known for, like "be where your feet are." Warm, funny, and full of hard-earned wisdom, Michael Book walks us through how he built a remarkably successful career, and how he learned to stay focused on what he cares about most along the way.
    1 hr 29 min
  • Bracelets, Backgammon, and the Bets of Gershon Distenfeld
    On this episode of Office Hours, Kuldeep Madan sits down with Gershon Distenfeld — outgoing Co-Head of Fixed Income at AllianceBernstein, a regular on Bloomberg TV and CNBC, and a World Series of Poker bracelet winner who gave the winnings to charity. They open with the origin story: how a "difficult" client relationship with Vince D'Addona turned Gershon into one of Kuldeep's clients, and the running joke that came out of it. From there, Gershon traces the path from a modern Orthodox childhood in Teaneck, New Jersey, through a Y2K-era start at Alliance Bernstein to three decades running fixed income. The real thread of the conversation is probability — how he separates good decisions from good outcomes, the red-ball/blue-ball thought experiment he uses on clients and his own team, and how that same mindset drove him to chase a WSOP bracelet and now a shot at the World Backgammon Championship in Monte Carlo. Along the way: the on-air freeze that became trading-desk legend ("Are you there, Gershon?"), his philosophy on media training, becoming co-head of a 200-person department with the help of an executive "marriage counselor," and a candid rapid-fire round on books, advice, and what's next after retirement.
    References & links
    - No Rules Rules — Reed Hastings & Erin Meyer · his top recommendation for "philosophy" reading · No Rules Rules: Netflix and the Culture of Reinvention: Hastings, Reed, Meyer, Erin: 9781984877864: …
    - Thinking in Bets — Annie Duke · his other recommendation, ties directly to his decisions-vs-outcomes philosophy · https://www.amazon.com/s?k=Thinking+in+Bets+Annie+Duke
    - Frida McFadden (thriller author) — his one non-work reading this year; no specific title named, so link his author page rather than a single book · https://www.amazon.com/stores/Freida-McFadden/author/B08JQBLQXV
    - World Series of Poker — for the bracelet reference · WSOP | The Official Site for Poker News, Schedules & Stats | WSOP.com
    - AllianceBernstein — his firm · Our Firm | AllianceBernstein
    1 hr 9 min
  • Pain, Presence, and Purpose with Joe Mallee
    Live from the MassMutual Disney Leaders Conference, and after winning the 2025 Advisor of the Year award, Kuldeep sits down with Joe Mallee, Head of MassMutual Financial Advisors, for a wide-ranging conversation recorded on-site. They dig into Joe's "expensive book club" friendship with Kuldeep, the loss of his mother and the cause it inspired, what it takes to go from advisor to GA to home office leadership, and his rules for staying present under pressure.
    Books mentioned:
    - Principles: Life and Work — Ray Dalio: Principles: Life and Work: Dalio, Ray: 9781501124020: Amazon.com: Books
    - The Power of Now — Eckhart Tolle: The Power of Now: A Guide to Spiritual Enlightenment: Tolle, Eckhart: 9781577314806: Amazon.com: Books
    - 1929: Inside the Greatest Crash in Wall Street History — Andrew Ross Sorkin: 1929: Inside the Greatest Crash in Wall Street History-and How It Shattered a Nation: Sorkin, Andrew
    - Deep Survival: Who Lives, Who Dies, and Why — Laurence Gonzales: Deep Survival: Who Lives, Who Dies, and Why: Gonzales, Laurence: 9780393353716: Amazon.com: Books
    - War — Sebastian Junger: War: Sebastian Junger: 9781455501588: Amazon.com: Books
    27 min
  • Sneakers, Strategy, and the Success of Sahand Elmtalab
    Office Hours with Kuldeep Madan

    They open with Sahand's passions outside the office — a serious sneaker collection that includes a legendarily rare pair of Freddy Krueger Nike SBs, and a Hublot earned when he was named Advisor of the Year — before going all the way back to his roots as the son of an Azeri-Iranian father and a Kurdish-refugee mother who ended up building a life in Montana. From there, Sahand opens up about the relationship that shaped his career — his partner and general agent, Dave — and the philosophy at the heart of everything he does: that nobody gets good at this alone. He and Kuldeep dig into joint work, relentless role-playing, building a team and a culture where mistakes are safe, understanding each person's "makeup," and approaching the business with an abundance mindset rather than treating it as a competition. Candid, funny, and full of real perspective for any advisor who wants to grow.

    How to Be Like Mike: Life Lessons About Basketball's Best - Pat Williams · https://www.amazon.com/s?k=How+to+Be+Like+Mike+Pat+Williams

    The Last Dance (2020 documentary) Watch The Last Dance | Netflix
    Hook (1991 film) - https://www.amazon.com/s?k=Hook+1991+film
    M&E Catalyst Group - https://mecatalyst.com/

    1 hr 22 min
  • Permission to Spend, Whole Life Wisdom, and Lie-UL’s with Tom Wall
    On this episode of Office Hours, Kuldeep sits down with Tom Wall, founder of Whole Life Masterminds, host of the Fast Start Forum, and author of Permission to Spend.
    Tom traces his path from financial advisor at Northwestern Mutual to home office wholesaler to one of the industry's most trusted educators. They dive into the real mechanics of whole life versus IUL (which Tom calls "Lie-UL"), who should and shouldn't own whole life, the truth behind dividend interest rates, the history of mutual insurance companies (yes, they go surprisingly deep), and the risks hiding inside premium financing.
    Tom also shares the origin story behind Permission to Spend, why he's rewriting it, and a preview of his next book, built around the "2% Solution."
    The two also swap stories about risk-taking, mentorship, and the friendship that brought them together, before Tom closes out with what makes Whole Life Masterminds special and a look ahead to the 2027 Fast Start Forum at The Phoenician in Scottsdale, Arizona.
    Books featured:
    Permission to Spend: Maximize Your Retirement with the Best-Kept Secret in Personal Finance by Tom Wall
    https://www.amazon.com/dp/1959840215
    Events referenced:
    Whole Life Masterminds — A Premier Mastermind for Financial Advisors
    https://whole-life-masterminds.mykajabi.com/
    Fast Start Forum 2027, January 17–20, The Phoenician, Scottsdale, AZ — sign up at https://faststartforum.com/
    Madan+ Masterclass Event, September 27–29, Miami
    https://madanplus.com/masterclass
    36 min
  • Billiards, BDITs, and the Brilliance of Vince D'Addona

    Vince traces his path from a Bronx upbringing and a misspent (but oddly formative) college career shooting straight pool at Cornell, to falling into the insurance business by accident, and becoming a top-ranked advisor + founder of a fintech focused on helping clients build wealth through free cash flow.

    Along the way, they dig into behavioral finance and why people are wired not to save, the art of earning trust with sophisticated clients, persistence and mentorship, and Vince's conviction that advisors are the guides of a client's story.

    Listen to the end, where Vince walks through a generous reading list spanning language, leadership, and behavioral economics.

    Hear it all from the guy who once gave Kuldeep the cold shoulder. Only on Office Hours.

    Book Recommendations

    • On language and leadership:

      • The Last Word on Power — Tracy Goss · https://www.amazon.com/s?k=The+Last+Word+on+Power+Tracy+Goss

      Language and the Pursuit of Happiness — Chalmers Brothers · https://www.amazon.com/s?k=Language+and+the+Pursuit+of+Happiness+Chalmers+Brothers

      Leadership and the Art of Conversation — Kim H. Krisco · https://www.amazon.com/s?k=Leadership+and+the+Art+of+Conversation+Krisco

      Conversations for Action and Collected Essays — Fernando Flores · https://www.amazon.com/s?k=Conversations+for+Action+Fernando+Flores

      • On influence and behavior:

        • Influence: Science and Practice — Robert Cialdini · https://www.amazon.com/s?k=Influence+Science+and+Practice+Cialdini

        Pre-Suasion: A Revolutionary Way to Influence and Persuade — Robert Cialdini · https://www.amazon.com/s?k=Pre-Suasion+Cialdini

        Mistakes Were Made (But Not by Me) — Carol Tavris & Elliot Aronson · https://www.amazon.com/s?k=Mistakes+Were+Made+But+Not+by+Me

        Thinking, Fast and Slow — Daniel Kahneman · https://www.amazon.com/s?k=Thinking+Fast+and+Slow+Kahneman

        Why Smart People Make Big Money Mistakes — Gary Belsky & Thomas Gilovich · https://www.amazon.com/s?k=Why+Smart+People+Make+Big+Money+Mistakes+Belsky

        Predictably Irrational — Dan Ariely · https://www.amazon.com/s?k=Predictably+Irrational+Dan+Ariely

        The Three Laws of Performance — Steve Zaffron & Dave Logan · https://www.amazon.com/s?k=Three+Laws+of+Performance+Zaffron+Logan

        Drive — Daniel Pink · https://www.amazon.com/s?k=Drive+Daniel+Pink

        1 hr 15 min

      About Office Hours with Kuldeep Madan

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