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Weiss Advice

Weiss Advice

By: Yonah Weiss
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Learning from the Best in Real Estate Business and Beyond. I love talking to successful people, and asking them for advice and tips on business and life. I'm very blessed to have an amazing network. They say your Network is your Net Worth, and it's true. If you want to learn more from these successful people, listen in. Learn more at www.yonahweiss.com© 2026 Weiss Advice Economics Leadership Management & Leadership Personal Development Personal Finance Personal Success
Episodes
  • “Be a Cat When Everybody’s a Dog”: How Mike Preshman Built a 220-Unit Portfolio

    “Be a Cat When Everybody’s a Dog”: How Mike Preshman Built a 220-Unit Portfolio
    10 Sep 2026
    Send us Fan MailMike Preshman didn’t start out planning to build a 220-unit multifamily portfolio. With a background in computer science and tech entrepreneurship, his entry into real estate began almost accidentally—with a vacation home on Cape Cod.That first property opened his eyes to the income potential of real estate. He added more vacation rentals before realizing that the model was difficult to scale. Over the next decade, Mike shifted toward multifamily properties throughout Greater Boston and the Northeast, ultimately building his portfolio without bringing in outside equity investors.In this episode of Weiss Advice, Mike explains why his strategy has centered on cash flow, downside protection, and owning assets that can be held for the long term rather than relying on appreciation and a future sale.He also shares the contrarian philosophy behind his investing: “Be a cat when everybody’s a dog.” When investors pile into the hottest markets and strategies, Mike would rather look for opportunities others are overlooking.The conversation goes beyond real estate into decision-making, masterminds, poker, asymmetric risk, and why successful investing requires being comfortable making decisions when the outcome is uncertain. Mike also explains how his definition of success has evolved—and why building wealth today is increasingly tied to a much bigger mission.Timestamps00:52 – Mike’s journey from tech entrepreneur to real estate investor 01:56 – The accidental vacation rental that started everything 07:15 – Why Mike wants “generational assets” instead of playing real estate “hot potato” 12:19 – “Be a cat when everybody’s a dog”: Mike’s contrarian investing philosophy 15:00 – Masterminds, surrounding yourself with growth-minded people, and avoiding shiny objects 19:51 – What poker taught Mike about investing and decision-making under uncertainty 21:55 – Avoiding paralysis by analysis and taking risks that won’t wipe you out 27:17 – Asymmetric risk: protecting the downside while preserving the upside 30:45 – What success means to Mike today 32:49 – The ambitious lifetime giving goal that became Mike’s North StarMike’s story is a reminder that building wealth doesn’t necessarily require following the hottest market, raising large amounts of outside capital, or constantly selling assets. Sometimes the bigger opportunity comes from thinking independently, protecting the downside, and building something you’re comfortable owning for decades.Connect with Mike:https://www.linkedin.com/in/mike-preshman-4347a31/LEAVE A 5-STAR REVIEW by clicking this link.WHERE CAN I LEARN MORE?Be sure to follow me on the below platforms:Subscribe to the podcast on Apple, Spotify, Google, or Stitcher.LinkedInYoutubeExclusive Facebook Groupwww.yonahweiss.comNone of this could be possible without the awesome team at Buzzsprout. They make it easy to get your show listed on every major podcast platform.Support the showSupport the show
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    36 min
  • The Power of Content in CRE: Fly Jamerson on Social Media, Storytelling, and Standing Out

    The Power of Content in CRE: Fly Jamerson on Social Media, Storytelling, and Standing Out
    17 Mar 2026

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    In this episode of Weiss Advice, we sit down with Fly Jamerson, a commercial real estate marketing strategist known for her creative approach to social media and storytelling in CRE. Fly shares how she transitioned from a 15-year career in theater, film, and academia into the world of commercial real estate marketing—and how content creation helped her build relationships across the industry.

    Fly discusses the power of authentic online engagement, the story behind her viral video series “Cold Calling Cold Callers,” and why social media is becoming one of the most powerful networking tools in commercial real estate today.

    Through candid stories and practical insights, this conversation explores how creativity, curiosity, and consistency can open unexpected doors in business.

    Key Topics & Timestamps

    00:03 – Introduction and why Fly Jamerson is a longtime listener of the show
    02:14 – Fly’s unconventional path from theater, film, and academia into commercial real estate marketing
    05:47 – The origin story behind the Cold Calling Cold Callers video series
    15:31 – How social media creates real relationships and opportunities in CRE
    25:56 – Turning everyday brokerage activities into compelling content
    31:16 – Overcoming fear of public speaking and cold calling through content creation
    38:05 – Advice for professionals trying to build a presence on social media in CRE

    About the Guest

    Fly Jamerson is a commercial real estate marketing strategist specializing in social media, storytelling, and digital media. She works with MoVO Media Marketing, where she co-hosts Social Surge, a bi-weekly live show focused on social media in commercial real estate. Fly is active in the CREi and ICSC communities and is widely recognized for her video series Cold Calling Cold Callers, where she features candid conversations with CRE professionals across the industry.

    Connect with Fly:

    LinkedIn: https://www.linkedin.com/in/flyjamerson
    Instagram: https://www.instagram.com/hey_itsfly
    X (Twitter): https://x.com/hey_itsfly

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    40 min
  • From the Military to $150M in Multifamily: Rey’s Playbook for Passive Investing

    From the Military to $150M in Multifamily: Rey’s Playbook for Passive Investing
    11 Mar 2026

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    In this episode of Weiss Advice, Yonah Weiss sits down with Rey, a former U.S. military officer turned multifamily real estate investor and fund manager. Since entering the space in 2016 and retiring from the Armed Forces in 2019, Rey has helped lead acquisitions of over $150 million in multifamily assets.

    Rey is the Co-Founder and Senior Managing Principal of Stressless Capital Fund, a customizable real estate investment fund focused on helping investors participate in multifamily opportunities. He is also the bestselling author of “BLUF: The Bottom Line Up Front,” a guide designed to help passive investors better understand multifamily investing.

    In this conversation, Rey shares how his military training shaped his investment philosophy, why he started as a passive investor before becoming a sponsor, and the critical lessons he learned raising capital and navigating changing market conditions.

    Whether you're an experienced investor or someone curious about passive real estate investing, this episode breaks down the mindset, discipline, and strategy needed to succeed in multifamily real estate.

    Key Topics & Timestamps

    00:00 – Introduction
    Yonah welcomes Rey to the show and introduces his background in multifamily investing and military service.

    01:14 – Military Beginnings
    Rey shares how joining the military at 17 shaped his discipline, leadership skills, and long-term career path.

    04:43 – Learning the Business Through Passive Investing
    Before leading deals himself, Rey invested as a limited partner (LP) to understand multifamily syndications and how deals are structured.

    06:07 – Raising Capital and Stewardship of Investors
    Rey explains the responsibility that comes with managing investor capital and the importance of trust in syndications.

    08:32 – Market Shifts and Interest Rate Changes
    How rising interest rates changed the multifamily landscape and how experienced investors adapt to new market conditions.

    38:15 – What “Passive Income” Really Means
    Rey breaks down common misconceptions about passive income and how investors should think about long-term wealth building.

    40:40 – Where to Connect with Rey
    Rey shares how listeners can learn more about his investing approach, consulting, and his book BLUF: The Bottom Line Up Front.

    Connect with Rey here:

    https://ismaelreyreyes.com/link-in-bio/

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    40 min
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