Gino Barbaro was shoveling snow outside his restaurant at midnight — no gloves, no customers, no paycheck, when he looked up and saw a light on in the apartment above. His mother was home, asleep, getting paid. He wasn't. That was the moment. From that parking lot, Gino went on to co-found the Jake and Gino platform, scale over 1,500 multifamily units in under five years, and transact north of $350 million in assets all anchored to a framework that fits in three words: buy right, manage right, finance right.

In this episode, Kyle and Gino get into:

• Why the restaurant business is the best and worst training ground for real estate
• The buy right, manage right, finance right framework — and exactly where operators violated every tenet of it in 2021 and 2022
• Why no deal is better than a bad deal, and how hope became the most expensive underwriting assumption in the last cycle
• The "I'm-a mentality" — why the instinct that gets you started is the ceiling that caps you
• Values-based investing: the deal Gino walked away from that would have made him over half a million dollars
• What Gino learned as a Certified Money Coach about why some investors close and others — with better balance sheets — never do
• Legacy as something you activate today, not something you leave behind

If you've ever wondered whether the grind is worth it, whether the timing is right, or whether you're building something that actually lasts — this one's for you.

🔗 Jake & Gino: jakeandgino.com🔗 Barbaro 360: barbaro360.com🔗 Follow Gino: @ginobarbaro on social

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Ken Ashley has spent 30 years as a top producer at Cushman & Wakefield, but his real legacy is the people he's built. As founder of CREi Summit and now bestselling author of The Prescription, Ken has spent decades writing custom 6–8 step action plans for aspiring brokers, signing them, and saying "call me in 90 days." Less than 5% ever did. Now he's written the book so no one has an excuse.

In this episode, Kyle and Ken get into:

• Why AI won't take the commercial real estate career — and where it will make a dent
• The signed prescription ritual that became a book two years in the making
• The follow-up framework that makes you impossible to ignore (hint: send the sailing article)
• Cold calling reframed , why Ken calls it "direct contact calling" and how to lead with value instead of an ask
• The 24-hour mourning cycle for handling lost deals
• The point system: a gutter guard for your week that gamifies business development
• Why right now, at the bottom of the cycle — is the best time in a generation to get into this business
• CREi Summit 2025 in Savannah: digital tools, AI search optimization

If you're in the first third of your career, considering the leap, or just need a reminder of why this industry is worth the grind — this one's for you.

📖 Get The Prescription: theprescription.pro🎟️ CREi Summit: creisummit.com🔗 Follow Ken: @kenashley on X | LinkedIn: kenashleyatlanta

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In this series, Kyle sits down with Carson Baird, an industrial broker from Southwest Florida, to uncover the hidden pitfalls in industrial deals. They discuss how overlooked zoning details and unexpected easements can derail transactions, and share strategies to navigate these challenges. Carson offers insights on managing client expectations, leveraging local relationships, and using technology to streamline deal processes. Whether you're a broker, investor, or developer, this series provides practical advice to close deals efficiently and avoid costly mistakes in the competitive industrial market.

Connect with Carson

LinkedIn

https://www.linkedin.com/in/carsoncre/

X

https://x.com/Carson_CRE

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https://www.linkedin.com/company/commercial-real-estate-school/?viewAsMember=true

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https://www.instagram.com/creschoolshow/

In this series, Kyle sits down with Carson Baird, an industrial broker from Southwest Florida, to uncover the hidden pitfalls in industrial deals. They discuss how overlooked zoning details and unexpected easements can derail transactions, and share strategies to navigate these challenges. Carson offers insights on managing client expectations, leveraging local relationships, and using technology to streamline deal processes. Whether you're a broker, investor, or developer, this series provides practical advice to close deals efficiently and avoid costly mistakes in the competitive industrial market.

Connect with Carson

LinkedIn

https://www.linkedin.com/in/carsoncre/

X

https://x.com/Carson_CRE

Follow CRE School on Social

LinkedIn

https://www.linkedin.com/company/commercial-real-estate-school/?viewAsMember=true

Instagram

https://www.instagram.com/creschoolshow/

In this series, Kyle sits down with Carson Baird, an industrial broker from Southwest Florida, to uncover the hidden pitfalls in industrial deals. They discuss how overlooked zoning details and unexpected easements can derail transactions, and share strategies to navigate these challenges. Carson offers insights on managing client expectations, leveraging local relationships, and using technology to streamline deal processes. Whether you're a broker, investor, or developer, this series provides practical advice to close deals efficiently and avoid costly mistakes in the competitive industrial market.

Connect with Carson

LinkedIn

https://www.linkedin.com/in/carsoncre/

X

https://x.com/Carson_CRE

Follow CRE School on Social

LinkedIn

https://www.linkedin.com/company/commercial-real-estate-school/?viewAsMember=true

Instagram

https://www.instagram.com/creschoolshow/

In this series, Kyle sits down with Carson Baird, an industrial broker from Southwest Florida, to uncover the hidden pitfalls in industrial deals. They discuss how overlooked zoning details and unexpected easements can derail transactions, and share strategies to navigate these challenges. Carson offers insights on managing client expectations, leveraging local relationships, and using technology to streamline deal processes. Whether you're a broker, investor, or developer, this series provides practical advice to close deals efficiently and avoid costly mistakes in the competitive industrial market.

Connect with Carson

LinkedIn

https://www.linkedin.com/in/carsoncre/

X

https://x.com/Carson_CRE

Follow CRE School on Social

LinkedIn

https://www.linkedin.com/company/commercial-real-estate-school/?viewAsMember=true

Instagram

https://www.instagram.com/creschoolshow/

In this series, Kyle sits down with Carson Baird, anindustrial broker from Southwest Florida, to uncover the hidden pitfalls in industrial deals. They discuss how overlooked zoning details and unexpected easements can derail transactions, and share strategies to navigate these challenges. Carson offers insights on managing client expectations, leveraging local relationships, and using technology to streamline deal processes. Whether you're a broker, investor, or developer, this series provides practical advice to close deals efficiently and avoid costly mistakes in the competitive industrial market.

Connect with Carson

LinkedIn

https://www.linkedin.com/in/carsoncre/

X

https://x.com/Carson_CRE

Follow CRE School on Social

LinkedIn

https://www.linkedin.com/company/commercial-real-estate-school/?viewAsMember=true

Instagram

https://www.instagram.com/creschoolshow/

In our first series of 2026, Kyle sits down with Kevin Moss, a retail broker at CBRE in Cleveland, shares his insights on navigating the commercial real estate industry, particularly for young brokers. He emphasizes the importance of saying yes to opportunities, the benefits of teamwork, and the evolving landscape of retail brokerage. Kevin discusses the significance of social media in building a personal brand and the impact of AI on the industry. He also highlights the importance of morning routines for productivity and maintaining a balance in the fast-paced world of real estate.

Connect with Kevin

LinkedIn

https://www.linkedin.com/in/kevinmoss24/

Instagram

https://www.instagram.com/kevinmosscre/

X

https://x.com/KevinMoss216

Follow CRE School on Social

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https://www.linkedin.com/company/commercial-real-estate-school/?viewAsMember=true

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https://www.instagram.com/creschoolshow/