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).
Transcript
Welcome back to my first stage podcast. We are here live at the NSA Influence conference meeting. So many amazing speakers, amazing people, including my new friend, Kevin Sidebottom.
Kevin Sidebottom [:Thank you.
Sara Lohse [:Thank you for being here. Kevin is the introverted engineer who has spent his career in sales and sales. Sounds like the worst possible nightmare career for an introvert.
Kevin Sidebottom [:Yes.
Sara Lohse [:Why did you do this to yourself?
Kevin Sidebottom [:Well, it started with me on an interview on a sailboat with a gentleman that was trying to vet me for a really specific position to date his daughter. And so did it. Yeah, it worked. It worked out. It worked out. So we're having this discussion. Great days. Teaching me all about sailboats, because I know nothing about sailboats.
Kevin Sidebottom [:And so we're out there. He's also an ex Navy seal.
Sara Lohse [:Oh.
Kevin Sidebottom [:So part of the reason I Not terrifying. Yeah, I think part of the reason he was taking me out there on
Sara Lohse [:the boat was maybe bring the concrete shoes with him.
Kevin Sidebottom [:I don't think he needed them. Just. Just throwing it out there. So we're out there and he says, well, where do you see yourself in five years? And I said, well, manager, some leadership position, something. And he says, great. Can I give you some advice? I'm trying to date his daughter, so I'm probably not gonna sit there and say no, especially since he could just literally kill me. We can say that on here, right?
Sara Lohse [:Yeah.
Kevin Sidebottom [:Okay, perfect.
Sara Lohse [:With one hand.
Kevin Sidebottom [:So, yeah. Yeah. So I said, well, tell me a little bit more about it. And so he's like, well, you know, I've been doing it for so many years. I'm ex navc, all the yada, yada, yada. And I said, is there much money in there? And he said, well, I've got three jets. And I said, tell me more. And that's literally where we just started going with it.
Kevin Sidebottom [:And I leapt out of being an engineer and I went to learn from this guy. And, you know, I've won awards, I've done $100 million deals. I've managed about a billion dollars spend from an organization. You know, his initials are fca, and I've just done well. And that means anybody can do it. Because if I can do it as an introverted engineer, anybody can do sales.
Sara Lohse [:Now, the most important question here is that now your father in law.
Kevin Sidebottom [:No, everybody asked that. And no, that is not my father in law, But I stopped dating her. He was a businessman. He kept me employed because he said I make him money. So there you go.
Sara Lohse [:Fair enough. Yeah, fair enough.
Kevin Sidebottom [:Yeah. It's respectable.
Sara Lohse [:So now you. You're an introvert who works in sales who also, based on your presence at this conference, speaks on stages.
Kevin Sidebottom [:I do, yes.
Sara Lohse [:Why?
Kevin Sidebottom [:So I spent two decades in sales, and there's one ingredient in sales that actually works in leadership, and it's called influence, which is kind of funny because that's what it's titled here, right? Influence. And the more influence you have, the more you sell and the more influence you have, the more people follow you. And I've been in different kind of positions where I've had all this influence and people would help me and go do everything. And you know what? It just something I said. I think anybody can do this, but everybody's scared to do it. And so here I am just speaking on stages to help people understand it's not that difficult because again, if I can do it, anybody can do it. And let me show you the path and the process, because that's all it really is, is following the same process over and over again. And that's what you learn at this conference.
Kevin Sidebottom [:And just about anywhere you go is those that succeed follow the process.
Sara Lohse [:Now, what was your process for getting past. I don't like being an introvert. It can't be natural for you to get up on stage and talk in front of people.
Kevin Sidebottom [:No.
Sara Lohse [:What was your process for getting past that and working past the stage fright, the fear, all of it. So that you could become that speaker that you are now.
Kevin Sidebottom [:So obviously there's going to be a little bit of fear being in front of anybody. It's the worst fear. It's. People feared public speaking over death, which is ironic. But for me, I took it and channeled my sales stuff. And I mean, I can do all this stuff and I'll go and speak on stage and I'll, you know, do sales calls, I'll, you know, do negotiate deals, look over the lawyer papers, all that stuff, legal documents. And at the end of the day, being an introvert is just where you get your energy or extrovert. Some people get their energy from groups of people, like my best friend, Mimi Brown.
Kevin Sidebottom [:She is fantastic. Me, I go get my energy when I get out of here and I go to the gym, work out and just kind of think things through. And so you can do anything you want. You just got to be able to go and recover afterwards. So I just do it. And it's not just. I mean, the pay is pretty nice, but to be able to go out there and just do it to add value to people, that's what it's about. So if I got to do something that takes me out of my comfort zone.
Kevin Sidebottom [:Let's do it.
Sara Lohse [:I love that. Now, what was the experience like? The show is called my first stage. What was the experience like for you the first time you did step on stage? Because I'm sure it's taken a while for you to get comfortable.
Kevin Sidebottom [:Yes, the first time. You know, you never see a comedian do his first bit on the main stage. They do it in the nightclubs.
Sara Lohse [:Yeah.
Kevin Sidebottom [:So I went out and did it with rotaries and I talked to different organizations and the organization I worked for, I was helping engineers do this. And so I did all my reps and I would watch the video so I was prepared. And when I first got out onto the stage for somebody who paid me money, which was kind of nice, I hit it as best I could, but I had the video to review to do it again. But, you know, it's just taking that step. You're going to suck at the first time you do anything.
Sara Lohse [:Yes.
Kevin Sidebottom [:I mean, I fell off my bike multiple times. I got the scars all over missions, but I got back up and did it. And so if you can think through that of, hey, you're not going to be as good as you do it. The first time is your thousand time. So if you can just keep doing it, you're going to get better. And so I just take it in that I'm not going to be perfect. I'm going to cringe when I watch the video and I'm just going to go do it.
Sara Lohse [:I give you credit, though, for watching the video.
Kevin Sidebottom [:Yeah.
Sara Lohse [:I. I don't think I can do that.
Kevin Sidebottom [:Well, think about this. The football teams, the professional football players, they watch game film.
Sara Lohse [:Yeah.
Kevin Sidebottom [:They watch what they made mistakes. So they can get better.
Sara Lohse [:Yeah.
Kevin Sidebottom [:How are you gonna get better if you don't watch yourself?
Sara Lohse [:I think I've just decided that I'm just won't because the thought of watching myself speak from stage feels like punishment or bullying.
Kevin Sidebottom [:No, it's. It's like, okay, and you can frame it two different ways. You can frame it as that or you can frame it as what's one or two things I can tweak to get better.
Sara Lohse [:Yeah.
Kevin Sidebottom [:And if you look at like Tom Brady or Peyton Manning, they're always going, how can I advance? Was that one thing. I can do a little bit better next time to land that joke. And hey, those guys can do it. I can do it.
Sara Lohse [:I still can't, but I am very proud of you. Very proud of you.
Kevin Sidebottom [:Thank you.
Sara Lohse [:What is it now? That you are speaking on the most. And like, do you have your signature talk, your keynote?
Kevin Sidebottom [:Yeah. Sales titans built, not born is. Is my signature one I am being asked to do Mastering Influence, which is the leader's edge. And I'm being asked by. I actually got called by an organization called wic, Women Infants and Children. And I said, okay, Women Infants and Children. I'm not female. Okay.
Kevin Sidebottom [:I don't have an infant. I have an 18 year old and a 13 year old. But why did it resonate with you guys that I should come talk? Because I don't think I was like feeling that I was there for that. Right. I would think you would want a woman that's empowered and done all that stuff.
Sara Lohse [:WIC is the one that they provide like financial support for for Women, Infants and children.
Kevin Sidebottom [:Right. And so they said your message and your videos have actually resonated with us. And so I was like, you know what, it's not who I usually target, but I'll go and help and add value and we'll see if that helps them and. And grows them.
Sara Lohse [:That's really interesting.
Kevin Sidebottom [:Yeah.
Sara Lohse [:Is have you done that before where you've gone and spoken to an audience that you weren't really, I don't want to say, not prepared for because I'm sure you're going to prepare for this as best as you're able. But have you gone to speak in front of an audience that isn't your norm?
Kevin Sidebottom [:Yeah, I've had financial planners come talk to me and I'm like, if you've seen my bank records, you would not hire me. But the topic is there and that specific thing is what they need and so that resonates with them. And hey, I've been able to help them. It's not who I target. But. But I will see and I will have interview calls with people and you know, just make sure that I'm a decent fit.
Sara Lohse [:Yeah.
Kevin Sidebottom [:But if I think somebody else would be better, I've actually referred a few of my friends and said, no, no, no, you should actually go talk to this person. And they've actually gotten the gig.
Sara Lohse [:Yeah.
Kevin Sidebottom [:So, you know, to me, and that's the other thing about sales is you can try to say you are the best at everything, but you're not. And if you guide a customer and say, you know what, I can do this. Okay, but you're actually going to be. And that's one of the big things I talk about is how do you make them a hero of their story in sales? And I go I think this person's going to be better or my competitor actually has a better offering for you in this segment for that thing. And I've had people go and buy that, but they'll still buy from me long term and come back to me because of the fact I've done that.
Sara Lohse [:I feel like that's a really great strategy for building trust.
Kevin Sidebottom [:Yeah, well, you need that. I mean, why, why lie to people and say you're going to be good and then you epically fail? You think they're going to hire you back or listen to you or tell any of the people that they know? No. Word of mouth marketing is the best marketing still.
Sara Lohse [:It is. Now, have you ever had the experience of you recommended someone, they hired them and they didn't do well?
Kevin Sidebottom [:I have not because I'll vet my friends that speak and I have trust in those people. So if I'm going to, if I'm going to give a reference, it's not because they paid me $50 or gave me a gift card. It's because I know they're really good.
Sara Lohse [:Good. I feel like that's, that's another fear is if I'm going to put my, my name behind this person, they now represent me.
Kevin Sidebottom [:Correct.
Sara Lohse [:And that can be really difficult to navigate. Especially we want to elevate our friends. We want to like bring them with us and everything. But they have to be able to take on that role.
Kevin Sidebottom [:Yes.
Sara Lohse [:And yeah, it's definitely good that you haven't had to deal with that.
Kevin Sidebottom [:Yes. I mean, it's just, it's people dealing with people. How would you want to be, you know, worked with and how would you want someone to help you? I am not having my sister come out and do a motivational speech ever. But if somebody needed hard truth, she's the person to go to. And you know, and everybody knows different people that they would recommend for certain things and they're just not going to willy nilly. But, you know, if we help enough people get what they want, will come back to us. Right. And that's, you know, I forget who was it Les Brown or one of those great speakers.
Kevin Sidebottom [:That's what they said. And I said, you know what? That's what I want to live by.
Sara Lohse [:I think it was my great grandfather, he had a saying that was when you lay your breads upon the waters, they come back to you in sandwiches.
Kevin Sidebottom [:Yeah.
Sara Lohse [:Which is a bizarre saying. And I do not think it's real, but I always think of it and I, it's that just that idea that if you give, if you give, more will come back to you. And, and I'm glad that you're able to be an, a embodiment of that.
Kevin Sidebottom [:Thank you.
Sara Lohse [:And what you've been doing.
Kevin Sidebottom [:And let's just put it out there. I love sandwiches.
Sara Lohse [:Who doesn't?
Kevin Sidebottom [:You don't have a body like this without having sandwich love.
Sara Lohse [:So I, I was built by tacos.
Kevin Sidebottom [:Yeah. You know, let's not get into the food topic because I will go on for hours.
Sara Lohse [:We don't need, we don't need drool on the microphone.
Kevin Sidebottom [:No, Fat Kevin will come out. It'll be a party. We'll.
Sara Lohse [:Yeah, I love it. And now jumping a little bit back to that, speaking in front of your non typical audience, do you have any tips and tricks for tailoring your content to really connect with that audience?
Kevin Sidebottom [:Yep. Yeah. So when I do the call with the people who want to hire me, I make it mandatory that we have a follow up call at least three, maybe six months out. And I want to talk to people who are going to be there. What are your pain points? And we go through it. I had six people on for WIC because I wanted to really make sure I understood them right. And I said, what are your pain points? And everybody said, well, mine's different. Mine's different.
Kevin Sidebottom [:Okay, well let's, let's lay them out there. And a lot of them are actually similar because they're all in the same category and they're all about people. But I want to make sure that I understand them. You're going to do your research, but having those calls where you have all those other people that are going to be there in attendance and ask them questions so you can put your best foot forward, it's going to set you up for success.
Sara Lohse [:It's amazing how many times the answer is just ask. I, I get asked all the time. How do I know what my audience wants? And I'm like, it's the most simple answers. Ask them.
Kevin Sidebottom [:Yes.
Sara Lohse [:And yet it's overlooked.
Kevin Sidebottom [:Yeah. Assumption. You know how the, the whole thing about assumption. Right?
Sara Lohse [:Yeah.
Kevin Sidebottom [:We won't go there.
Sara Lohse [:It's a clean show, guys.
Kevin Sidebottom [:Yes.
Sara Lohse [:But keep it clean. Y' all can fill out the blanks now. This has been really great advice and I love everything you have to say. How can people find out more about you? You're speaking your brand, everything that you're doing.
Kevin Sidebottom [:Yep. You can find [email protected] and I have a YouTube channel where I put out videos. So there's tons of videos in there that have just one takeaway, just so you can go in there and go, okay, this I can use. I can use this. And they're not very long. I don't want to be that boring guy. But don't look at what's two years ago. Let's go with the fresh ones.
Sara Lohse [:Look at the old ones.
Kevin Sidebottom [:Yeah. No, no. In fact, I used to have blooper reels in there just to show people how bad it was. It looked like Jim Carrey in some of his movies. It was great.
Sara Lohse [:Oh, we. We still put out blooper reels.
Kevin Sidebottom [:Oh, do you?
Sara Lohse [:If we have an episode that just, like, goes sideways, and we'll take it out of the episode, but we will release it almost like a trailer to the episode.
Kevin Sidebottom [:Really?
Sara Lohse [:Oh, my God, yes.
Kevin Sidebottom [:Do you get a lot more hits on that?
Sara Lohse [:Oh, of course. It's the best.
Kevin Sidebottom [:Oh, my God. Okay, I'm doing this part. I'm doing it. Thank you. Thank you for that.
Sara Lohse [:Yes. Go release your bloopers.
Kevin Sidebottom [:Oh, I am now.
Sara Lohse [:We're all human. We all make mistakes.
Kevin Sidebottom [:Oh, yeah.
Sara Lohse [:And if you're lucky enough to catch it on camera, the world deserves to see it.
Kevin Sidebottom [:Oh, they will. They will now.
Sara Lohse [:I love it. And I cannot wait to see those bloopers, and I cannot wait for y' all to hear this next episode. So hit that subscribe button and come back every week for more conversations with speakers about their first stage talk next time.