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Mike 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.

Timestamps

00:52 – 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 Star

Mike’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/

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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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In this episode of Weiss Advice, host Yonah Weiss sits down with Faraz Cheema, SIOR, CCIM, a Manhattan office specialist at BKREA, to unpack what it really means to understand commercial real estate from the inside out.

Faraz shares his journey from growing up around a family office to working as a financial analyst and asset manager, and how that foundation shapes the way he approaches brokerage today. With deep experience across hospitality, retail, multifamily, and now office, Faraz explains why investors value advisors who truly understand the numbers, operations, and long-term strategy behind every deal.

The conversation dives into the realities of the Manhattan office market, how capital thinks in today’s environment, and why credibility is built through experience, not just transactions.

 Episode Highlights

• 01:00 – Welcome to Weiss Advice and Faraz’s return to the conversation after a social media hiatus
• 02:15 – Faraz’s background in commercial real estate and growing up in a family office environment
• 04:30 – Limited-service hospitality explained and early exposure to real asset operations
• 07:45 – Transitioning from analyst and asset manager to brokerage
• 12:30 – How investment experience changes the way brokers add value
• 18:10 – Insights into the Manhattan office market and current investor mindset
• 24:00 – Why designations like SIOR and CCIM matter in complex transactions
• 28:40 – Lessons learned from managing, owning, and now advising on real estate

This episode is a must-listen for investors, operators, and brokers who want a clearer picture of how experience across ownership, analysis, and brokerage creates better outcomes in commercial real estate.

Connect with Faraz

https://www.linkedin.com/in/farazcheemacre/
https://x.com/FarazUCheemaCRE
https://www.instagram.com/faraz.cheema.cre/

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In this episode of Weiss Advice, host Yonah Weiss sits down with real estate investor and broker Christina Kovacs to unpack her full journey through residential flips, short-term rentals, multifamily ownership, and asset management at scale.

Christina shares how getting her hands dirty early in her career shaped her as an operator, why she ultimately pivoted away from single-asset investing, and the lessons she learned the hard way about property management, partner selection, and staying focused in one lane.

They also dive into tenant management, underwriting realities in Class C assets, the power of LinkedIn as a business tool, and why Christina is now doubling down on multifamily and commercial brokerage heading into 2026.

This is a must-listen for investors who want real, operator-level insight into what actually drives performance in multifamily deals.

⏱️ Episode Timestamps

00:01:30 – Christina’s early real estate journey and live-in flips
03:30 – Pivoting from single-family and STRs into multifamily
06:45 – Joint ventures vs syndications and building confidence as an operator
07:50 – Why property management can destroy a great deal
09:00 – The 42-question property manager vetting process
11:00 – Auditing ledgers, hidden expense creep, and CapEx tracking
16:15 – Tenant horror stories and inherited problems after acquisition
18:45 – Managing delinquency and underwriting reality in Class C assets
20:00 – How LinkedIn became a powerful networking and deal-making tool
22:20 – The “Final Four” questions: books, skills, failure, and success
26:30 – Transitioning into commercial real estate brokerage
28:15 – What success truly means to Christina today

🔑 Key Topics Covered

• Scaling from hands-on investing to multifamily operations
• Property management due diligence and accountability
• Asset management systems that protect investor returns
• Avoiding shiny object syndrome
• Leveraging LinkedIn for real business growth
• Building a long-term, focused investment strategy

🌐 Connect with Christina

Learn more and connect with Christina at ChristinaKovacs.com

 www.linkedin.com/in/kovacsmultifamily

facebook.com/christinakovacs8

instagram.com/christina_kovacs

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In this episode of Weiss Advice, host Yonah Weiss sits down with Gabe Einhorn, a 23-year-old entrepreneur building at the intersection of real estate, technology, and faith.

Gabe shares his journey from capital markets into founding VryfID, a renter-first real estate tech platform designed to securely store and verify sensitive rental documents—solving one of the biggest pain points in competitive rental markets like New York City. With no prior tech background, Gabe breaks down how he assembled a team, learned the space, and turned a real-world problem into a scalable startup.

The conversation also dives deep into Gabe’s faith-based clothing brand Prays, and the viral street interviews that unexpectedly transformed his confidence, personal growth, and connection to God. Gabe explains why he chose to speak openly about faith in professional spaces where it’s often discouraged—and how doing so has opened doors instead of closing them.

Finally, Gabe reflects on entrepreneurship, cold calling, personal discipline, and what success truly means at an early stage of life and business.

⏱️ Key Timestamps

• 00:00 – 02:10 | Gabe’s background: capital markets, real estate finance & early career
• 02:50 – 06:00 | Launching Prays: faith, clothing, and viral street interviews
• 07:30 – 09:55 | Overcoming fear, confidence growth & approaching high-profile figures
• 10:50 – 14:00 | The problem with NYC rentals & the idea behind VryfID
• 14:00 – 17:30 | Renter fraud, document verification & landlord buy-in
• 18:45 – 20:10 | Balancing a startup with brokerage work & long-term vision
• 24:50 – 30:30 | Final Four questions: books, skills, success & mindset

🔗 Connect with Gabe

• Social: Gabe Einhorn (all major platforms)

linkedin.com/in/gabe-einhorn-55b74822b 

https://www.instagram.com/praysstudios/ 

• Faith Brand: Prays / Pray Studios
• Real Estate Tech: VryfID (VerifyID)

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What if the greatest investment you could make isn't in real estate, stocks, or even private credit—but in yourself? Dave Wolcott, former Marine officer turned alternative investment expert, shares how studying millionaires and billionaires led him to discover a holistic approach to wealth that goes far beyond your bank account. In this episode, Dave breaks down private credit (the hard money lending of the business world), explains why he focuses on just three asset classes, and reveals how investors are achieving 20%+ returns by cutting out the middlemen.

[00:00 - 05:30] From Marines to Triplets: The Wake-Up Call

• Served as an officer in the Marine Corps, traveled the world including Israel
• Had triplets in 2000, quadrupling his family size overnight with an 18-month-old at home

[05:31 - 09:25] The Six Forms of Capital: Beyond Financial Wealth

• The greatest investment is in yourself—not just the next deal
• Defines holistic wealth across six dimensions: financial, intellectual, spiritual, human, emotional, and social capital
  
  
  

[09:26 - 15:05] Private Credit Explained: The Business World's Hard Money Lending

• Banks are tightening regulations, creating gaps in funding for growing small businesses
• Private credit fills the need for fast capital—think roofing companies with 3 years of backlogged work after hurricanes

[15:06 - 20:05] How to Access Institutional-Quality Returns

• Pooling investor capital through a fund model to bring $10M+ to sponsors
• Gets the same terms as major institutions by working directly with sponsors (no middlemen)

[20:06 - 25:10] The Three-Asset Strategy: Real Estate, Energy, and Private Credit

• Ultra-wealthy get really good at 1-3 asset classes for best due diligence and deal flow

[25:11 - 31:00] Time Is the Real Asset

• Questions the accumulation theory: why defer taxes in a 401(k) when taxes will likely increase?

[31:01 - 33:05] Final Four & How to Connect

Connect with Dave:

Website: https://holisticwealthstrategy.com (free book download)

Podcast: Wealth Strategy Secrets of the Ultra Wealthy

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.

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www.yonahweiss.com

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Key Quote:
The real asset is time. Time is the asset. - Dave Wolcott

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What if the key to successful multifamily investing isn't just about the numbers—but about the people living in your properties? Joe Rinderknecht, the cowboy-hat-wearing founder of Cowboy Capital, shares his unconventional path from shoveling manure on a Utah ranch to operating over 1,000 multifamily units. 

[01:40 - 06:15] From Ranch to Real Estate: Building on Grit

• Grew up ranching and breaking horses in northern Utah—learned that your word is your bond
• Father left the ranch for construction and cabinet making, taught Joe everything from concrete to framing

[06:40 - 10:10] Trial by Fire: The 80-Unit Section 42 Property

• Asked for a property management job with zero experience—got thrown into an 80-unit low-income housing property
• Property had no manager for two weeks, with sky-high delinquency, vacancy, crime, drugs, and cockroaches

[10:11 - 15:20] The Path to Becoming a Sponsor

• Never planned to stay in property management long-term—goal was always to learn and move on
• Admits being "unemployable" with a resume showing 6-8 month stints at various companies

[16:35 - 23:35] Impact Investing: Making Every Dollar Matter

• Lost his brother (age 20) and grandmother in a 2013 car accident—nearly died himself
• Provides four types of support: capital, food, construction/home modifications, and mindset coaching

[23:36 - 26:40] Why Treating Tenants Well Is Good Business

• Questions how slumlords succeed when they don't care about people's lives
• When tenants feel like a unit is their home, turnover drops, repairs decrease, delinquency falls

[26:41 - 32:00] Rapid Growth and What's Next

• Bought 4 deals (419 units) since September 2024, currently under contract on 117 more units
• Believes there's a great buying opportunity in the next 10-24 months

[26:45 - 32:55] Final Four & How to Connect

Connect with Joe: 

Website: https://cowboycapital.us
Email: [email protected]
LinkedIn: Joe Rinderknecht
Instagram: @joe_rinder

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.

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None 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.

Key Quote:
"If you can get a tenant to feel like their unit is their home, your turnover goes down, your repairs and maintenance go down." - Joe Rinderknecht

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Sometimes the best business decision is knowing when to let go. Amy Calandrino, founder of a commercial real estate brokerage, shares her journey from hammering in her own signs during the 2010 recession to building a team of nearly 10 advisors—and why she ultimately chose to close her firm to join Cushman & Wakefield. In this episode, Amy reveals the hidden costs of entrepreneurship, the importance of aligning your work with your values, and how she's redirecting her energy toward meaningful impact through her family foundation's financial literacy programs.

[01:05 - 04:10] From Vermont to Orlando: Building a Career on Grit

• Started working full-time at age 13 and put herself through college debt-free
• Worked alongside her husband in a law office where she learned about commercial real estate

[04:25 - 07:20] The Hidden Costs of Running a Brokerage

• Founded her brokerage in 2010 during the economic downturn with a shoestring budget
• Grew from solo founder to nearly 10 advisors by 2022

[07:21 - 11:45] Making the Leap: Consulting the Best in the Business

• Sought advice from industry leaders Sarah Malcolm, Allison Weiss, and Beth Azor
• Realized she could still be an entrepreneur without owning a brokerage

[11:46 - 19:30] The Three-Month Transition and Its Unexpected Lessons

• Spent 90 days transitioning clients and wrapping up her brokerage
• Experienced grief despite making the right decision

[19:31 - 27:15] Redirecting Energy: The Aspiring Entrepreneur Program

• Founded a family foundation with her husband to give back to the community
• Created an entrepreneurship program for elementary school students

[27:20 - 31:50] Final Four & How to Connect

Connect with Amy: 

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

Email: [email protected]

Book: "From Perfect to Real" (available on Amazon)

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.

LinkedIn

Youtube

Exclusive Facebook Group

www.yonahweiss.com

None 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.

Tweetable Quote:

"Success to me is serving my clients in the best way possible and knowing each and every day that I've put forth the most amount of effort that I can. I never want to phone it in." - Amy Calandrino

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