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

100: On Big Leaps, Busywork & Elton John (feat. Bri Seeley)

Dec. 5, 2022

Are you stuck on the "rollercoaster of inconsistent income?" We all know entrepreneurship is a marathon, not a sprint, but it can feel extra cumbersome when we're stuck in a marketing rut, drowning in admin tasks, or struggl…

99: ICYMI: The Business of Fandom: Live from FAN EXPO Chicago 2022

Nov. 28, 2022

Holy heck! Annie P. Ruggles' strategy novella and companion guide, "The Coach Who Would Not Sell" comes out today! To mark the occasion (and give Annie a bit of a break), we're bringing back our 1st ever LIVE episode - recor…

98: On Enthusiasm, SEO, and The A-Team (feat. Seth Goldstein)

Nov. 22, 2022

We all know mindset is a critical tool for entrepreneurs - but is your mindset working harmoniously with your marketing, and vice versa? In the struggle to break through the noise and reach potential buyers, how do we ensure…

97: On Leaders, Role Models & Scandal (feat. Kristen Edwards)

Nov. 15, 2022

What the heck does it actually mean to be a "natural leader?" And, if you're an un-natural leader, are you just out of luck? For being an isolated endeavor, solopreneurship sure demands a lot of people-wrangling. What skills…

96: First Impressions, Bad Clients & Avatar: The Last Airbender (Feat. Damion Taylor)

Oct. 31, 2022

So - what do we do about the "just not your people" people? The bad fits? The awkward encounters? And - on the flipside - how can we ask for and receive support without feeling clingy, desperate, or amateur? It's time for a …

95: On Joyfulness, Overworking & A League of Their Own (feat. Dr. Erin M. Baker)

Oct. 25, 2022

Is joy fluffy or essential? A soft skill or a beacon? And on the flipside, is burnout a badge of honor? How can we keep the love alive in our small businesses, in spite of recessions, upheaval, bad news, and bitchy people? U…

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.