For over a decade, Annie Ruggles 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 businesses. As founder and dean of The Non-Sleazy Sales Academy, she’s guided hundreds of people toward making deeper connections, lasting impressions, and friendlier, more lucrative transactions and conversations. Her pride and joy is her podcast, Too Legitimate to Quit, serving up instantly actionable small business strategies with a pop culture spin every Monday.
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Table of Contents
Thank you for joining us today. Please introduce yourself to our readers. They want to know you, some of the background story to bring some context to your interview.
Annie Ruggles: Hey there! I’m Annie P. Ruggles and I’m a recovering over-deliverer. I’ve been a small business strategist for over a decade now but I’m lucky my business survived at all because I was wholly unwilling to sell. I focused all my energy and attention on marketing, branding, and client wooing that I didn’t consider myself in my own success. Thus, I was tired, broke, and growing resentful of the folks who hung on my every word but never hired me. I realized that the issue was the massive gap in my sales knowledge and that no one had given me the permission slip to sell without gimmicks or tricks that I seemed to be waiting for. Moreover, my clients were modeling my sales avoidant ways and were struggling beside me.
I knew something had to change, so in 2017 I became wholly obsessed with the idea of ethical, empathy-driven selling. By October of 2019, I had sunset all of my marketing, branding, and copywriting services in order to focus exclusively on teaching wonderful people how to ask and receive with their dignity intact.
You are a successful entrepreneur, so we’d like your view point, do you believe entrepreneurs are born or made? Explain.
Annie Ruggles: I was quite literally born into it – as everyone under my roof growing up was an entrepreneur. But, even so, my answer is made. So many things came naturally to me on my road to entrepreneurship, but the vast majority of the experience has been learning curve after learning curve. Natural talent only gets you so far – if you’re going to compete you have to be flexible, tenacious, brave, and humble. That takes practice, practice, practice.
If you were asked to describe yourself as an entrepreneur in a few words, what would you say?
Annie Ruggles: Sales strategist with the soul of a muppet.
Tell us about what your company does and how did it change over the years?
Annie Ruggles: As I mentioned in my backstory, the first main iteration of my business was a marketing and branding firm for very small businesses. I still serve solopreneurs (especially in helping professions) but now I focus exclusively on growth phase selling skills and product/service revamps.
Thank you for all that. Now for the main focus of this interview. With close to 11.000 new businesses registered daily in the US, what must an entrepreneur assume when starting a business?
Annie Ruggles: You will wear every single hat imaginable within your business for at least one hour if not forever – so get used to a ton of learning curves. To be an entrepreneur means to seek out education and innovation constantly. If you’re unwilling to experiment, you will not go far. If you’re unwilling to get your hands dirty and learn every corner of your business from customer service to logistics to HR to finances to sales, you will discover holes in your business’ foundation only when there is a problem. And if you don’t get to know your customer on a level just as deep and true (especially if you rush to farm out your sales processes to an outside team), you’re robbing yourself of critical R&D, demographics, psychographics, and opportunities to build trust in realtime.
Did you make any wrong assumptions before starting a business that you ended up paying dearly for?
Annie Ruggles: OH ABSOLUTELY. I thought all my fun and flashy marketing – if perfectly executed – would keep me from ever having to actually sell. And it did – sort of. Some folks did hunt me down and beg to pay me – but I’m sure I left more than one fortune on the table by not taking selling more seriously. And it’s not just money – it fueled years of inefficiency, frustration, and doubt that were entirely avoidable if I had simply learned to honor my own value and ask to be compensated accordingly.
If you could go back in time to when you first started your business, what advice would you give yourself and why? Explain.
Annie Ruggles: Don’t listen to what anyone says about sales or salespeople. None of the nasty, gimmicky, hard-sell tactics are required. You do not ever have to stray outside of your ethics or values in order to be successful, but you do have to self-advocate!
What is the worst advice you received regarding running a business and what lesson would you like others to learn from your experience?
Annie Ruggles: “Never stop expanding.” Please, for the love of everything, stop expanding. Go deep into the problems that you solve instead of bending over backward to solve problems outside your zone of genius. New markets are great – but the thought leadership you already have, the connections you’ve already made, the reputation you’ve already earned are better. Be known for doing a handful of things powerfully – not a one-stop-shop.
In your opinion, how has COVID-19 changed what entrepreneurs should assume before starting a business? What hasn’t changed?
Annie Ruggles: Don’t assume that older people are still completely clueless when it comes to technology. Sure, my own parents still don’t know how to turn on Hulu sometimes, but most adults have spent far more time online in the post covid world than before out of sheer necessity. Utilizing a tool like Zoom or Slack may have seemed like a misstep in the past when online was optional – but now have become a part of day-to-day life. Revisit offering both online and offline options, regardless of age. What hasn’t changed is that entrepreneurship is freaking hard and utterly unpredictable.
What is a common myth about entrepreneurship that aspiring entrepreneurs and would-be business owners believe in? What advice would you give them?
Annie Ruggles: That you’ll make a billion dollars by next Tuesday, especially if you take your laptop to a beach and follow this one very specific 4 step process that the gurus sell you. Nope. Entrepreneurship is not a one-size-fits-all endeavor and it certainly isn’t a get-rich-quick scheme. It’s a slog, and a bore, and a mess, and an energy vampire – and when done right can be one of the most beautiful, powerful, life-affirming, joyful experiences on Earth. But that is earned – not granted by magical Facebook ads.
What traits, qualities, and assumptions do you believe are most important to have before starting a business?
Annie Ruggles: Tenacity, courage, vulnerability, honesty (to self and to others), integrity, humility, hope, determination, and a healthy dose of fear to keep it all in check.
How can aspiring leaders prepare themselves for the future challenges of entrepreneurship? Are there any books, websites, or even movies to learn from?
Annie Ruggles: In my small business strategy meets pop-culture podcast (Too Legitimate to Quit), we pull business gems out of movies, tv, and more all the time. Inspiration truly is everywhere. But across the board, I think you’ll find the best tips hidden in the story of underdogs that made it through their sheer will and kindness, motley crews that come together to combine their talents, and the unsung hero who finally gets their moment and seizes the heck out of it.
You have shared quite a bit of your wisdom and our readers thank you for your generosity but would also love to know: If you could choose any job other than being an entrepreneur, what would it be?
Annie Ruggles: A librarian! The idea of living surrounded by all those books is dreamy.
Thank you so much for your time, I believe I speak for all of our readers when I say that this has been incredibly insightful. We do have one more question: If you could add anyone to Mount Rushmore, but not a politician, who would it be; why?
Annie Ruggles: I would poll the Indigenous and First Nations tribes that view that land as sacred ground and ask them who’d they like to see up there to represent their rich history. Now, if you want to erect a statue in my home city of Chicago, my vote will always be Dame Angela Lansbury.
Jed Morley, VIP Contributor to ValiantCEO and the host of this interview would like to thank Annie Ruggles for taking the time to do this interview and share her knowledge and experience with our readers.
If you would like to get in touch with Annie Ruggles or her company, you can do it through her – Linkedin Page
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