Investor Conversation: Mike Montana episode artwork

EPISODE · May 22, 2026 · 42 MIN

Investor Conversation: Mike Montana

from The Gray Report Podcast · host Spencer Gray

What does it look like to build steadily in real estate for 25 years — starting with a duplex, doing the work yourself, and growing one deal at a time — before most people in the industry even know your name? In this episode of The Gray Report, Spencer Gray sits down with longtime friend and LP Mike Montana of Kipper Construction for a candid conversation about an unconventional path from aspiring preacher to pharmaceutical sales rep to full-time real estate investor and builder.Mike's approach has always been straightforward: buy things that cashflow, do right by your partners, and keep showing up. This conversation is a reflection of that.In this episode:• From preaching to properties: the winding road that brought Mike to real estate• The Rich Dad, Poor Dad moment that changed how he thought about money• Flipping houses before 2008 — and getting out just in time• How Kipper Construction grew from managing their own properties to running 90% third-party projects• The leap from value-add to ground-up development, and what that process really looks like• Why Mike is still bullish on multifamily — and how he thinks about housing demand and the Midwest market🔗 Learn more about Kipper Construction: kipperconstruction.com🔗 Learn more about Gray Capital: graycapitalllc.comSubscribe to The Gray Report for more investor conversations, market insights, and multifamily deep dives.

What does it look like to build steadily in real estate for 25 years — starting with a duplex, doing the work yourself, and growing one deal at a time — before most people in the industry even know your name? In this episode of The Gray Report, Spencer Gray sits down with longtime friend and LP Mike Montana of Kipper Construction for a candid conversation about an unconventional path from aspiring preacher to pharmaceutical sales rep to full-time real estate investor and builder.Mike's approach has always been straightforward: buy things that cashflow, do right by your partners, and keep showing up. This conversation is a reflection of that.In this episode:• From preaching to properties: the winding road that brought Mike to real estate• The Rich Dad, Poor Dad moment that changed how he thought about money• Flipping houses before 2008 — and getting out just in time• How Kipper Construction grew from managing their own properties to running 90% third-party projects• The leap from value-add to ground-up development, and what that process really looks like• Why Mike is still bullish on multifamily — and how he thinks about housing demand and the Midwest market🔗 Learn more about Kipper Construction: kipperconstruction.com🔗 Learn more about Gray Capital: graycapitalllc.comSubscribe to The Gray Report for more investor conversations, market insights, and multifamily deep dives.

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Investor Conversation: Mike Montana

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This episode is 42 minutes long.

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This episode was published on May 22, 2026.

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What does it look like to build steadily in real estate for 25 years — starting with a duplex, doing the work yourself, and growing one deal at a time — before most people in the industry even know your name? In this episode of The Gray Report,...

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