EP205 - The Divorce That Launched a 7-Figure Business with Lindsey Huettner
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.
Lindsey Huettner
Serial Entrepreneur, Lindsey Harrison is a seasoned veteran to starting and selling businesses. She seized her first opportunity to make it “in the real world” with a job in commercial real estate for a UK firm. Juggling key territories (Manhattan, Chicago, D.C.), Lindsey’s initiation was a trial-by-fire sort… she loved every moment of the fast-paced, jet-setting lifestyle! When she was presented an opportunity to stay closer to the Big D, she jumped at the chance as an advertising exec job with an impressive book of clientele.
Lindsey learned a tremendous amount working in the corporate world but banker's hours weren't her thing. While climbing the corporate ladder, she was also finding her wings as an entrepreneur. Her pet sitting hobby turned into a 1,200-client empire, she bought a snow-cone stand and DVD-rental machines, and while those were fun and profitable, she felt the undeniable pull of the tech world. She sold the 25,000-subscriber online “deal-a-day” website she created to a national brand after just 2 years. That payday allowed her to purchase Krimson & Klover, which she transitioned from one small clothing store to two buzzworthy brick-and-mortar stores and a thriving e-commerce store.
In 2014 it was time for the next chapter, Lindsey is putting her business acumen to work helping other businesses to achieve success with a fractional marketing agency, The it Crowd. The agency started small but has exploded as the word has “gotten out” on how different their approach is on marketing. Lindsey has been positioned as a national marketing expert and regularly gives speeches as well as radio and tv interviews based on marketing. She also gives seminars in coordination with micro loan programs around the world to teach and promote business ownership to climb out of poverty.
If you’ve always wanted to be part of the "it crowd", consider yourself IN. Lindsey and her team are ready to jump right in and help you achieve your goals … just say the word!
IN THIS EPISODE WE DISCUSS:
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
Resources, books, and links mentioned in this episode:
Follow Lindsey:
https://www.linkedin.com/in/lindseyhuettner
https://www.instagram.com/lindseyloufromkalamazoo/
The Tyler Dickerhoof Show
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About the Tyler Dickerhoof Show Podcast
The Impact Driven Leader Podcast, hosted by Tyler Dickerhoof, is for Xillennial leaders who have felt alone and ill-equipped to lead in today's world. Through inspiring interviews with authors from around the world, Tyler uncovers how unique leadership strengths can empower others to achieve so much more, with real impact.
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