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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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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.

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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In this episode of Weiss Advice, Yonah Weiss sits down with Linda Holtz, multifamily investor, property management expert, and co-founder of M2RE (Married to Real Estate).

Originally from France, Linda moved to the United States in 2012 with two suitcases and a dream. What started with door-to-door sales in New York City turned into a decade-long career in property management, eventually leading her and her husband into multifamily investing.

This conversation dives into the real journey behind scaling in real estate: the grit, the networking, the mistakes, and the long-term vision required to build generational wealth.

🔎 What You’ll Learn:

• Why Linda credits door-to-door sales for building her entrepreneurial resilience
• How starting in property management gave her the confidence to invest
• The truth about scaling from small multifamily to larger syndications
• Why networking consistently beats underwriting hundreds of deals
• The philosophy behind holding real estate long-term vs. value-add flips
• How social media and authentic content transformed her business
• Why “Save the Chat” might be the most underrated networking advice

⏱️ Key Timestamps

00:49 – From France to NYC: How door-to-door sales built grit and discipline
02:11 – Falling into property management and discovering real estate
05:00 – House hacking a Chicago triplex and becoming landlords during COVID
09:07 – Why networking and masterminds accelerated their multifamily journey
11:09 – Finding partners vs. chasing 100 deals a month
16:34 – How LinkedIn and consistent content changed Linda’s business
21:41 – “If you own real estate, never let it go” — lessons learned from selling
22:00 – Reconciling short-term syndication models with long-term wealth building
27:19 – The vision behind “Save the Chat” and building real relationships
32:02 – The Millionaire Next Door and redefining what wealth actually looks like
33:18 – What success truly means: choosing how you spend your time

Linda’s story is a powerful reminder that you don’t need to quit your W2 overnight to build wealth. Confidence compounds. Relationships compound. Real estate compounds.

And if there’s one takeaway from this episode, it’s this:

The magic isn’t just in the deal.
It’s in the consistency.

Connect with Linda:

@M2RETX on Instagram
Married To Real Estate on Facebook
LinkedIn https://www.linkedin.com/in/linda-holtz-1493495a/

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