Too Legitimate to Quit

Too Legitimate to Quit

***Instantly Actionable Small Business Strategies with a Pop Culture Spin***

Join non-sleazy sales specialist Annie P. Ruggles and highly successful but utterly relatable 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 Monday.

Recent Episodes

85: On Financial Confidence, Control & Yellowstone (feat. Danielle Hayden)

Aug. 15, 2022

How well do you know your numbers? For many, many small business owners, the answer is "not nearly enough." When you wear 17 different hats on any given day, it's easy enough to ignore the books and bank accounts and wait un…

84: On Hype, Consistency & Seinfeld (feat. Jason Cercone)

Aug. 8, 2022

On your path to connection and service, what metrics really matter? Should you aim to go viral, or allow yourself to move slowly and deliberately? And what's more important in podcasting and content creation - quality or con…

83: The Business of Fandom: Live from FAN EXPO Chicago 2022

Aug. 1, 2022

Holy heck! It's the very first special episode of TLTQ - and it's a glorious nerdfest. Annie P. Ruggles recently brought her brand of entrepreneurial enthusiasm to the show floor at FAN EXPO Chicago and sat down with 14 phen…

82: On Healing, Hustle Culture & Kesha (feat. Jessica Butts)

July 25, 2022

Is your definition of success truly your own or has it been cobbled together from other peoples' mandates and expectations? Are you more likely to succeed if you show up fully and frantically every day or if you slow down an…

81: On Closers, Compassion & Attack on Titan (feat. Jason Marc Campbell)

July 18, 2022

When you define selling, is your answer more synonymous with greed, manipulation, and regret or to love, empathy, and enthusiasm? You've been sold to horribly and unethically countless times - but have you ever had a sales h…

80: On Expertise, Unlearning & The OC (feat. Rachel Kurzyp)

July 11, 2022

Do we expand our skills by learning or by doing? How do you identify what falls inside our expertise and where we have growth options? And - what if we're experts in something that we just don't love anymore? Entrepreneurshi…

About the Host

Annie P. Ruggles Profile Photo

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.