Too Legitimate to Quit

Too Legitimate to Quit

Instantly Actionable Small Business Strategies with a Pop Culture Spin

Join Annie P. Ruggles and whipsmart guests as they decode the marketing, mindset, sales, and success hacks hidden within beloved movies, tv, music, books, and more. 

Often goofy but never fluffy, each episode ends with easy-to-implement homework that will leave you feeling delightfully legit.

New episodes drop every week.

Recent Episodes

50: On Collaboration, Expectations & John Legend (feat. Pamela Slim)

Dec. 6, 2021

TLTQ celebrates our 1st birthday in this powerhouse interview with Pamela Slim, author of Escape from Cubicle Nation , Body of Work , and The Widest Net ! As a small business owner, it's easy to think of yourself as a rock o…

49: On Habits, Learning Curves & Peloton (feat. Dallas Travers)

Nov. 29, 2021

Habits - they surely don't feel very sexy. We got into self-employment for the freedom, right? But un-shiny necessities like routines, rituals, and consistent behaviors are the keys to your success, confidence, legacy, and m…

48: On Clients, Connection & Mean Girls (feat. Breanna Gunn)

Nov. 22, 2021

By trying to speak to everyone, we actually speak to no one. Kinda like high school, huh? When we tried to fit in with everybody, we wound up sitting alone. This week Annie P. is joined by copywriting and funnel genius, Brea…

47: On Podcasting, Small Wins & Back to the Future (feat. Michelle Abraham)

Nov. 8, 2021

Let's face it - leaning into your uniqueness can be hard, especially when you aren't sure what exactly is so unique about you, or who out there is looking for your particular brand of special sauce. How can we best explore o…

46: On Simplicity, Unsubscribes & *NSYNC (feat. Liz Wilcox)

Nov. 1, 2021

Do you lie awake and drive yourself crazy wondering what to do about your email list? Whether you pelt your audience with too much information, forget to message them at all, or are completely baffled by your open rates - th…

45: On Shame, Magnetism & The Rocky Horror Picture Show (feat. Michelle Clarke)

Oct. 25, 2021

What role does intuition play in your business? Whether you believe that your inner voice comes from God or from your lived experience, there are certain problems you just have to feel your way through. You may not identify …

About the Host

Annie P. Ruggles


For almost a decade, Annie P. has harnessed her Hulk-like disdain for hard-sales, tacky self-promotion, and overly competitive sleazeballs as inspiration to help people find better ways to grow their small bizzes. She's guided hundreds of people toward making deeper connections, lasting impressions, and friendlier, more lucrative transactions and conversations.

Annie is the daughter of an award-winning motivational speaker and an always-ahead-of-his-time business strategist, and the granddaughter of a legendary used-car salesman, a perspicacious wordsmith, a singing waiter, and a cafeteria caterer with a raving fan base. (So clearly, she was literally born for this.)

She lives in Chicago with her hobbit husband (who is also in sales), her furkids, and her disdain for deep dish pizza.