Building Influence: Kevin Sidebottom's Lessons from Sales and the Stage cover art

Building Influence: Kevin Sidebottom's Lessons from Sales and the Stage

Building Influence: Kevin Sidebottom's Lessons from Sales and the Stage

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Summary

 Welcome to another episode of My First Stage, where I sit down with public speakers to dig into the messy, funny, and inspiring stories behind their first moments on stage—and the lessons that changed both their businesses and their lives.Back at the NSA Influence Conference, I had the absolute pleasure of connecting with Kevin Sidebottom—whose journey from introverted engineer to high-powered sales leader and sought-after speaker is packed with jaw-dropping twists, honest advice, and a heavy dose of humor. If you’re an introvert, afraid of the spotlight, or convinced that “speaking isn’t for you,” Kevin’s story will definitely get you thinking twice.With roots in engineering and a self-confessed introvert, Kevin Sidebottom did the unthinkable: he dove headfirst into sales, landed massive corporate deals, and built a thriving career influencing teams and audiences across the country. Today, he blends transparency, self-deprecation, and no-nonsense strategy to demystify what it really takes to succeed on stage—and in business.Here’s a peek into what you’ll hear in this episode:From Sailboats to Sales: The wild story of how a “job interview” for a date with his boss’s daughter unexpectedly launched Kevin into a high-stakes sales career.Becoming an Influencer (the Real Kind): Why Kevin believes that influence—not personality type—is the key to both sales and leadership success.Overcoming Stage Fright as an Introvert: A frank discussion on fear, energy, and how to recharge when speaking drains you.Running Reps and Reviewing Game Tape: The role of “practice, practice, practice” (and cringey self-review) in leveling up as a speaker.Serving Unexpected Audiences: Taking the stage for groups outside your niche, tailoring content, and the simple but overlooked power of “just asking” your audience what matters to them.Trust, Referrals, and Building Reputation: Why Kevin refers business to others and how honesty creates loyal, long-term relationships in sales—and speaking.If Kevin's journey resonated with you, here’s how to take the next step:Share Your First Stage Story – Have your own tale to tell? Visit myfirststagepodcast.com—I’d love to hear it and maybe feature it on a future episode.Connect with Kevin Sidebottom – Head to kevinsidebottom.com or catch his quick-hit tips on his YouTube channel (but start with the recent videos—he’ll thank you).Practice, Review, and Release Your Own Bloopers – Take every opportunity to get on stage (big or small), watch your own “game film,” and remember: we all start somewhere. Don’t be afraid to laugh at yourself!Thanks for tuning in! See you next week for more behind-the-scenes stories, honest advice, and first stage inspiration on My First Stage.Timestamped Summaries[00:00-01:02] – I kick off the episode and introduce Kevin Sidebottom, the introverted engineer turned sales heavyweight, and we get a taste of his quick wit and dry humor.[01:02-02:29] – Kevin Sidebottom shares the hilarious (and slightly terrifying) story of his first “interview”—on a sailboat with an ex-Navy SEAL who happened to be the father of his date. This moment sets off his pivot from engineering into sales.[02:29-03:57] – We explore why he started speaking on stages, the connection between influence in sales and leadership, and why everyone is terrified of public speaking (even more than death!).[03:57-05:04] – Kevin Sidebottom breaks down his approach to overcoming stage fright, managing his energy as an introvert, and why adding value trumps comfort zones.[05:04-06:58] – The details behind his very first paid stage talk, learning through smaller “rep” gigs with rotaries and organizations, and why your first time is never perfect (but you need to do it anyway).[06:58-07:38] – We talk about recording and reviewing your own talks, the value of “game tape,” and why feedback—even if it makes you cringe—is key for improvement.[08:06-09:14] – Kevin Sidebottom introduces his signature keynote, “Sales Titans Built, Not Born,” and shares how his message resonated with unexpected audiences (hello, Women Infants and Children!).[09:32-10:44] – The art of accepting speaking gigs for non-typical audiences, preparing for new crowds, and referring others when they’re a better fit—without losing trust or reputation.[10:44-12:35] – Why honesty and long-term relationships matter, building trust through referrals, and the power of word-of-mouth marketing in the speaking business.[13:39-14:31] – Kevin Sidebottom shares his playbook for connecting with unfamiliar audiences: mandatory pre-event calls, deep dives into attendee pain points, and turning assumptions into actionable questions.[14:32-16:08] – We wrap up with a lighter note on blooper reels, “Fat Kevin,” and why sharing your failures—or your funniest outtakes—can make you more relatable (and maybe go viral on YouTube).
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