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Wealthyist

Wealthyist

Written by: Annex Wealth Management
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Wealthyist, the podcast that discusses the lifestyles, choices, and strategies of the wealthy. Each week, the Annex Private Client team talks to experts in a variety of areas to discuss trends and paths visited by people who have built or are in the process of building significant wealth.© 2025 Annex Wealth Management Social Sciences
Episodes
  • Wealthyist E47: Less Crying, More Thriving: Jake Biernbaum on Horses, Humans, and Smart Business
    Jan 9 2026

    Guest: Jake Biernbaum, renowned horse trainer and founder of Pear Tree Ranch in Ocala, Florida. Known for his large YouTube following and expertise in natural horsemanship.

    Key Points from the Episode:

    1. Origin and Growth of Pear Tree Ranch
      • Founded in 2011 when Jake went independent after working with Parelli Natural Horsemanship.
      • Started with almost nothing — living on ramen and PB&J, no truck or trailer.
      • Grown into an international operation: clients fly in from Europe, South Africa, and across the US; offers in-person training, lessons, clinics, camps, and online video content (YouTube & Patreon).
      • Now a family business run primarily by Jake and his wife Stephanie (also a skilled trainer); their 8-year-old son Johnny helps occasionally but isn’t pushed into the horse world.
    2. Training Philosophy
      • Focuses on developing both horses and humans, emphasizing that horses are “honest” while humans often complicate things.
      • Starts with the horse first to establish clear, reliable behavior, then teaches the owner to match that level.
      • Goal: Make clients independent (“I want you to not need me anymore”) while offering ongoing education for those who want it.
      • Motto: “Less crying and less dying” — safer, happier horses and riders.
    3. Jake’s Background
      • Not a lifelong horse person — got into horses in his 20s after wilderness survival training (Tom Brown Jr.’s school), various odd jobs (bouncer, carpenter, daycare, etc.), and discovering Parelli Natural Horsemanship.
      • Spent years working for Parelli (from ranch hand to touring arena manager and instructor) before going fully independent in 2017.
    4. Business Strategy & Growth
      • Located in Ocala, “Horse Capital of the World,” for the density of horses, warm climate, and lifestyle (palm trees, beaches).
      • Deliberately keeps the business small and family-run to avoid over-expansion risks; learned from past experiences with employees/interns leaving suddenly.
      • Diversifies income through scalable online content (YouTube, Patreon) — “making money while sleeping” — rather than just trading hours for dollars.
      • Offers various formats: private lessons, workshops, multi-day clinics/camps, and horse training programs.
    5. Clients & Wealth Observations
      • Wide range: backyard hobbyists to Olympic-level competitors; some barely afford lessons, others spend hundreds of thousands on imported horses.
      • Notes that true success with horses requires consistent work and discipline — money helps (better horses, more lessons), but doesn’t replace effort.
      • Many wealthy clients are driven and hands-on because they built their own success the same way.
    6. Work-Life Balance & Future Plans
      • Horses were once 24/7; now prioritizes family time, beach trips, and off-roading/camping in his customized Jeep to avoid burnout.
      • Future: Expand reach through online education and brand exposure (e.g., coaching competitors for “Road to the Horse” colt-starting championship).
      • Long-term legacy: Build the physical ranch into an asset that can be leased or handed to a dedicated successor; no pressure on son to take over.
    7. Closing Wisdom: Five Stages Toward Mastery
      • Awareness → Understanding → Doing → Reproducing (consistent results) → Teaching

    Follow Jake & Pear Tree at https://www.patreon.com/peartreeranch & https://www.youtube.com/@peartreeranch

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    39 mins
  • Wealthyist E46 | Philanthropy and Legacy: Guiding Athletes to Meaningful Impact with Chellee Siewert
    Dec 19 2025

    In this episode of the Wealthiest podcast (hosted by Anthony Mlachnik, Senior Wealth Advisor at Annex Private Client), guest Chellee Siewert (President and Founder of Capture Sports & Entertainment) discusses how her firm helps professional athletes, entertainers, and organizations develop authentic philanthropic strategies.

    Key highlights include:

    • End-of-Year Giving Trends — About 30% of annual charitable donations occur in December, with examples like athletes hosting shopping events for kids, fulfilling both wants and needs (e.g., debate team ties for a high schooler).
    • Building an Authentic "Why" — Capture guides clients to identify personal stories and passions, define 2-3 impact pillars, align philanthropy with their brand, and create realistic plans that fit busy lifestyles (from weekly involvement to a few annual events).
    • Legacy Beyond the Game — Emphasis on defining identity outside of sports, building post-career legacies, and ensuring giving feels genuine and enjoyable.
    • Heartwarming Stories — Touching anecdotes, such as Aaron Jones' "Yards for Shoes" campaign (donating shoes based on rushing yards, revealing a child's need for properly fitted new shoes), J.J. Watt events honoring veterans, and meaningful make-a-wish connections.
    • Human Side of Athletes — Discussion of Vin Baker's recovery from addiction, losing over $100 million, and rebuilding his life, underscoring that athletes face public highs and lows like anyone else.
    • Practical Structures and Benefits — Overview of giving vehicles: Donor-Advised Funds (DAFs) for tax-deductible donations, fiscal sponsorships (preferred for most clients due to compliance support), and private 501(c)(3)s. Insights on offsetting "jock taxes" (state taxes on games played away), donating appreciated stock to avoid capital gains, and leveraging league/team matching programs or awards.
    • Team Support — Importance of a trusted core team (advisors, agents, accountants) to maximize impact, endorsements, and opportunities.

    Chellee shares her own journey founding Capture 14 years ago to balance motherhood and entrepreneurship, starting with clients like J.J. Watt, and finding her "why" in amplifying athletes' ability to change lives. The conversation draws parallels between athletes/entertainers and busy executives in purposeful, tax-smart giving.


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    25 mins
  • Wealthyist E45: Anna Franklin on the Real Psychology of Wealthy Home Design
    Dec 12 2025

    Host: Anthony Mlachnik (Senior Wealth Advisor, Annex Private Client)
    Guest: Anna Franklin – Founder & Creative Director of Stonehouse Collective (Milwaukee/Wisconsin-based luxury interior design firm)


    Anna’s Journey

    • Grew up in small-town Wisconsin → studied Public Relations → moved to Chicago for event planning & major-gift fundraising (10 years).
    • Met husband in Chicago, moved back to Wisconsin (Whitefish Bay, Milwaukee area) ~10 years ago to raise family (now 3 kids).
    • After first child, rediscovered creative passion → accidentally fell into home staging → became “the stager of Milwaukee” → pivoted to full interior design during 2020/COVID.
    • Not a formally trained designer; acts as creative director/entrepreneur.
    • Grew Stonehouse Collective to 15 employees (5 full-time designers), opened first retail store in Shorewood in March 2023, and hit record revenue in 2025.


    Key Themes & Insights on Wealthy Clients

    1. Two Types of Clients Today
      • High-customization, unique, heirloom-quality (willing to pay $30k for a sofa).
      • Want the “look” but at the lowest possible price (tariffs & cost pressures pushing this segment).
    2. Psychology of Spending
      • Wealth does not equal willingness to spend on furniture/design.
      • Some ultra-wealthy clients buy the $3k sofa because “they don’t care about furniture.”
      • Some middle/upper-middle clients will stretch or max out credit for fully U.S.-made, 40-hands-touched heirloom pieces because that is what they value.
      • It’s never about the dollar amount; it’s about personal values, legacy, memories, and emotional connection.
    3. Trends by DemographicYounger / Millennial / Liquidity-Event Wealth
      • Full smart-home integration (Lutron, Sonos, automated showers, security, lighting scenes controlled by phone).
        Wellness spas at home: cold plunges, saunas, steam, red-light therapy — all ideally in one integrated wellness room.
        Hitting all five senses the moment they walk in (scent, sound, light temperature, etc.).
    4. Boomers / 60s–70s
      • Surprisingly also adding wellness/spa elements (many now want saunas & cold plunges too).
      • Grandkid-focused spaces (arcade rooms, integrated TV/gaming areas with sleek motion furniture instead of old dedicated theaters).
      • Aging-in-place planning: wider doors, future elevator shafts, curbless showers.
      • Strong aversion to bold 90s-style patterns/color that millennials are embracing (“grand-millennial” trend).
    5. Tech & Smart Homes
      • Almost everything is now phone-controlled; wall panels and whole-house distributed audio are largely out.
      • TVs hidden or pop-up, projectors still used, but giant TVs are cheap and ubiquitous.
      • Some boomers initially resist phone control but warm up once they see it in action.
    6. Outdoor & Extended Living
      • Big focus on indoor-outdoor flow, pool houses with saunas, outbuildings (elevated “she-sheds,” homeschool barns, wellness barns).
      • Layered exterior lighting (down-lights, up-lights, feature lighting on stone/wood) is huge.
    7. Emerging & Fun Requests
      • Flower rooms / cutting rooms (glass conservatory-style for arranging bouquets).
      • Dog washes still popular but no longer novel.
      • Lighting as “jewelry” of the house — heavy layering (picture lights, sconces, pin spots, etc.).
    8. Social Media & Pinterest Effect
      • 97% of clients arrive with a Pinterest board or saved Instagram images.
      • Pros: helps clients communicate when they lack design vocabulary.
      • Cons: creates unrealistic expectations about cost, lead times, and customization (Amazon-effect).
      • Anna actively discourages excessive scrolling and digs deep (“You say you love this photo — is it the lamp or the feeling?”).


    Closing Message from Anna

    • Emphasizes timeless, classic design with layers of trend so homes don’t need gutting every 5–10 years.
    • Stonehouse Collective retail store in Shorewood, Milwaukee is open to the public.
    • Instagram: @stonehousecollectiveco

    Overall, the episode highlights how deeply personal luxury design is — wealth buys options, but values and life stage dictate what people actually spend money on and how they want their home to feel.

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    30 mins
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