In this episode of The Tyler Dickerhoof Show, host Tyler Dickerhoof sits down with serial entrepreneur, marketing agency founder, and former Division 1 soccer recruit Lindsey Huettner for an unfiltered, energizing conversation about leadership, business, identity—and the high-stakes human side of running a company.

Lindsey opens up about her journey from turning down a D1 soccer scholarship for love, to rebuilding her life and launching a successful creative agency from a Starbucks table. She shares the gritty truth about entrepreneurship: the financial shell games, the emotional toll of managing people, and the turning point that came when she stopped leading like a boss and started leading like a human. From learning to pay herself first to firing with empathy (and not firing during COVID), Lindsey pulls back the curtain on what it really takes to grow a values-driven business—and how embracing vulnerability changed everything.

Together, they explore the cost of ignoring your instincts, the messy middle of leadership evolution, and why building a business that fits your life—not the other way around—might be the boldest thing you can do. If you’ve ever questioned your management style, struggled with delegation, or wondered whether it’s possible to lead with both strength and softness—this episode will show you that it absolutely is.

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

https://www.instagram.com/lindseyloufromkalamazoo/

The Tyler Dickerhoof Show

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What We Discussed:

00:00 Introduction

01:55 How 'Letters from Lindsay' started in the pandemic

03:11 Mastering the financial shell game as a founder

06:54 What no one tells you about starting a business

10:06 “I never laid anyone off—even during COVID”

13:10 From soccer star to soccer mom

17:05 How to lead with compassion without losing clarity

22:08 You don’t get to have a bad day as a founder

27:06 The double standard in leadership styles

30:30 From divorce to entrepreneurship

35:18 “How Starbucks helped me build my network”

40:53 Priorities shift when life gets busy

43:27 What COVID taught us about work and life

47:17 The power of delegation in leadership

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