Every successful founder has a story worth learning from. In this episode, Jake & Gino sit down with Brian Smith to unpack his incredible entrepreneur journey—from surviving political challenges in Denver real estate to building and scaling businesses across the U.S. and Mexico.

Brian shares candid lessons on entrepreneurship, resilience, and growth. Discover how his early days in commercial real estate shaped his mindset, why burnout forced him to pivot, and how he eventually launched Strategy Ladders to help founder-led B2B service businesses scale beyond the owner. You’ll also hear his perspective on Mexico City as an entrepreneurial hub, the shift from consulting to implementation, and how he helps businesses achieve 2–8X growth. If you’re an entrepreneur or investor, you won’t want to miss Brian’s insights.

Connect with Brian Smith: StrategyLadders.com | LinkedIn: S. Brian Smith

Chapters:

00:00 – Introduction

03:12 – Breaking into Denver real estate with master leases

07:39 – Politics, burnout, and lessons from failure

14:43 – Redefining success: survivalist roots to investment banking

20:24 – Founders Organization & why many groups miss real entrepreneurs

32:52 – Myths vs. reality of living in Mexico as an entrepreneur

42:45 – Why implementation beats coaching in today’s consulting market

We're here to help create real estate entrepreneurs...

About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com.

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