Part 3 - Why This Entrepreneur Gave Up A 20-Year TV Career For A Tech Startup

Welcome to this edition of the million Dollar Mastermind podcast. This is where we pick the brains of high achievers from all walks of life and get their hard earned real world insights on winning. I'm your host, Larry Wydell.

What criteria did you use at age 37, without a lot of business experience, except from reporting and things like that, what criteria did you use to guide you to find? Because obviously you found a real good spot to, you know, to go in and to learn. You hate to go put yourself through and learn this get, and then it's fine. This is a dud industry or a dud company, you know, so obviously you made some good choices there. What, what instincts were you following? What, how did you find the place you landed up at?

Okay, this is good advice for anybody. So I found, I looked in lots of areas, I looked at what I was good at and stuff. But I reached out to three people who I looked at as mentors and said, what am I good at? Because I didn't know. One was in a marketing space. And I met with him and he had a big international marketing firm and I asked him to have coffee with me and he sat there across from me. He goes, you don't know marketing. I wouldn't hire you. You could go like, be the front person for a carpet salesman or something, or like dog and pony show for somebody. I was like, okay, what? I don't want to do that. And then I met with another woman who was big and the women in business and she ran the women in business. And I sat down with her and said, what am I good at? And she saw me very differently and told me what she thought I was good at. And then I also met with a friend who had this startup and he, Google had just bought YouTube. Little bit of luck there. And he was looking for someone who understood video. And so I met with him, I said, where would you use me? What do you, what skills do you need? So I sat down and looked at those three and then I did the thing that I always tell people to do. I followed the money. Where was the money going to be in the future? And it was healthcare and technology. And the money was given to be in healthcare and technology. And if I was going to make a big move and step away from my very, I could have stayed on TV forever. They were happy with me here. If I was going to step away from a lucrative career that I'd spent 20 years building, I, I wanted to step into something that was bigger and more successful. So I, for me that was what success looked like. I wanted more money, more opportunity for my family. So I said, where was the money? And I definitely healthcare and technology was where the money was. One of the jobs I looked at was also coaching attorneys to do, you know, media coaching for attorneys at some of the big law firms. That wasn't as long of a path that I could see. And then I had the best thing happen to me. So I was going through that conversation. I really liked the guy that was starting the startup. I believed in his values. I believed in him as a person. I believed in the software he was building. Even though I didn't really understand what software did or what software as a service was, I didn't really understand it all, but I believed in him as a person. And I went to a gala. This is a fun story. So I went to this gala, and I was all decked out as the news anchor, and I'm up in the front auctioning off some gicles. I was amc, so I'm auctioning off some G. And doing the things that you do when you're a news anchor in a small town. You. You do the big heart gay, the heart balls and the big galas. And this is for the American Cancer Society. And a buddy of mine came up to me who hadn't seen in a while, and he said, hey, I hear you're talking. This guy's name was Sean. I hear you're talking to Sean about working for him. And I said, yeah, how did you know that? And he goes, well, I just wanted to tell you, I. And this guy's super successful. He said I would work for him for free for the options. And I was like, oh, thanks. You know, I nod my head. I didn't know what the hell an option was, Larry. I didn't know I was a news anchor. And he said I would work with him for the options. I was like, yeah, oh, yes, absolutely. And then I had to go home and look up what an option was. And so then that gave me the opportunity to look and really look at what wealth could look like from that perspective. And so that's how I made that choice. I was like, wow, like some really thoughtful processes and a few bits of luck and people that came into my life to be able to figure out, to go down that path, but truly look at what you're good at. Talk to the people around you, ask them what you're good at, and then keep your eyes open for opportunity.

That's funny what you said about options. I just listened to something From Charles Barkley yesterday. And he was telling a story. He said when he was signing with Nike, Michael Jordan called him and he said, don't take the money. He said, you got a contract from basketball. You don't need money. He said, take a little bit of money and as many options as they'll give you. Barclay was like, options? I never heard of options.

Right. Well. And someone said to me, like, don't go for the paycheck. Go for the long term wealth. And I had to really wrap my head around it. I hadn't thought about it. But then I will tell you. So when it came time for this company to go public, I became vice president of not just media, but marketing, communications, all of it. And ran that roadshow with the leadership team. Because I had skin in the game. They knew I would wake up in the middle of the night as worried as they were because I had a lot of options.

Skin in the game. Skin.

Lots of skin in the game. So when those long, ridiculous hours and splitting sleep to even stay up enough hours to make this happen, and the IPO roadshow and the whole thing, I.

Mean, it was a lot and turns out for, you know, just kind of a side thing. It's amazing how educational those IPO road shows are. Are they. Was that an eye opener for you? The questions you get asked and things like that?

What was really interesting is it's such a quiet process. You have to have a quiet period. So for those of us who'd never been through it to find someone to ask questions about, what is this gonna look like? What do we do? Like, no one knew. Now there's more out online and stuff, I think, than there was. But you're in, literally, what's called a quiet period. You're not allowed to talk about it. So it's hard to find someone to help guide you through that. And now I've done that with other companies now that I've been out of this space for a little bit. I've worked as a consultant and helped some other people put their ip, their roadshow decks together. But they do. They ask you and they're really quick and you're in and out. And the CEO does that talking. I did not. I just was help. I was a support staff, but I would travel and go. But prepping him and getting him ready and treating it like it was journalism, like, it doesn't matter what they ask you. Here are your 5 answers. Whatever they ask you pivot, just like journalism prep you. Whatever they ask you, this is what you're going to talk about. You're going to talk about the green pasture. We only have this much percentage, but look at what we could like. Creating the story and the narrative was so important. But, yeah, they ask you very difficult things. The first time we walked into a Goldman meeting, these young people in these ridiculously gorgeous suits, they were all beautiful people, too. They were all in, like, their 20s and early 30s. This whole room full of people asking questions, and they were so smart, and they asked the most difficult questions. We walked out of that first one, looked at each other and went, oh, my gosh, how many of these do we have? Is difficult. Yeah.

Now, as you got in, what did you do right when you hit the company? Now you're in. And now your ignorance is front and center. And I got to get competent in something to make myself useful and you get some respect and, you know, to give some confidence and get your toe hole on the mountain. What did you do right to make progress in a short period of time there?

I've always been comfortable. Maybe it comes from being a journalist and being an athlete who is coachable. I'm very comfortable not being the smartest one in the room. I don't expect to be. I don't want to be. I want to learn from everybody around me. So I asked a lot of questions and I went in using my journalism skills because that's what I had to work with. So when the tech guys, you know, the chief technology officer is talking, I would go, wait, explain that to me like, in layman's terms, just like I would in an interview. Like, I don't understand how that fits together or why we care about it. I would use words that I knew and I would ask what we would say were dumb questions, and he would explain it over and over. But then when it came time to explain it to the sales team or solutions engineers or somebody else, I had that language and I just became sort of the. The communications person. Like, I could be the tech whisperer because I was not afraid to ask the questions. I think that was the. Not being the smartest one in the room and not afraid to ask questions was really, really good. The things that I did right, what I did wrong is I stayed in that role too long. I never really stepped into my power and spoke up in some meetings where I actually saw where things could improve, like two or three years down the road. If I could do it over, I would have stepped into my power a little more and spoken up when I saw things going south because I thought People were smarter than me. And I was like, oh wait, I actually did understand that. And I should have said that I did understand it. Well, so it was a mix or that was it.

Or you could have asked a question that would point it out, you know.

Right. And I would.

And so the thing is, sometimes we get intimidated to ask questions that need to be asked and there's just nobody else in the room to ask the question but us. And if we ask it, a lot of good things unfold.

Well, I had the advantage of being an Emmy award winning news anchor, so I wasn't intimidated by a whole lot. I'd already had big, big success, so I didn't need to prove myself. I felt like, now, don't get me wrong, I was very intimidated and had a lot of imposter syndrome and studied really hard. I read Crossing the Chasm and Inside the tornado, like those two books probably 10 times over.

And I just talk about those, talk about those.

Oh, there's some old school book on technology and how technology is accepted early adopters and the bell curve and how you get your products for people to see them in a new light and how you take advantage of early adopters and find those people who will believe in you and let you make mistakes. And then how once you hit a certain point, so many people pile in, competition comes in and then there's this gorilla you want to become the gorilla on the other side of the bell curve and one person becomes a gorilla and everybody else's company dies. That's kind of how it works. But those books I found, books that became my bible and that was part of my journey too. I had to learn. So I did have a lot of imposter syndrome. I don't want you to think that I was very confident.

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Not give us a few journalism skills that would be useful to us.

Oh, goodness, there's a lot. There's a lot.

Or give us a book to read to get some.

Well, here's what I think. If there's one phrase that I always say, and I always said this to my children, I have to remind myself of this, too. Be more interested than interesting. Always step in and be more interested than interesting. And I have a hard time with that because I have stories and I get really excited like you and I can talk and I just interrupted you. And then I felt bad because I did it because I'm like, I should shut up. But yeah.

Wait a minute, wait a minute. When did you interrupt me? I've been spending the whole time interrupting you. If you interrupted me, good for you.

I did just a minute ago because I wanted to get that part in, so I felt bad.

Good for you.

Yeah. I think the big thing about journalism is it is ask good questions and always be interested, be curious. I think the thing that I was old school journalism, too, when I got out of school, it was fair, balanced and accurate, you know, so if one side was talking a lot, I wanted to know what the other side said. It was very different.

That's gone now.

Yeah, it's gone. That's one of the. I'm so glad I'm not in that business anymore. Let me tell you. I am very good. I watch all the time. Wait, and get this. You'll love this, Larry. I married the weatherman. Yeah.

Oh, you did.

Very scandalous. Second marriage. Anyway, we will watch the news together and both be so glad we're not in that business anymore. He's an attorney now.

Yeah. Oh, is he?

Yeah.

Well, good for him. And so you reach the point in this thing. So I'm going to write a book. You know, the one you did was that, you know, basically, you don't have to give up. You know, it doesn't have to be the end of the line. And what particularly was on your mind at that point to where you said, I just need to say this, you know, I'd gotten. You had bounced back. You had bounced back at this point, you know.

Oh, yeah, I had bounced back and done TV and I'd taken on a new career in technology and had huge success and was a leader in that community and in that. In the, in the stock.

Second family. Three kids.

Yeah.

Yeah.

On top of my game. And financially, I went from debt to wealth really quick after the ipo. Everything. House paid for, car paid for, things like just a different world. And my father got Alzheimer's and so I spent a lot of time with him and I Had so many questions and I hadn't asked them for most of my life. We didn't have. We weren't particularly close. We became closer as adults. He's using the Navy when I grew up, and then I moved away from home. So we became closer as adults. And then. And when he was having Alzheimer's and not there to tell me things, I thought, shoot, this could hit me next. What do I need to put out into the world? What do I need to tell my kids if I'm not around? And so that starts. That started the wheels turning. And then I looked at my life and I realized where I was having the most, where I felt like I was adding the most value, was certain moments in my job. And I think I read it in a book somewhere. They said, go back and take your last 30 to 60 day calendars, because we all have digital calendars now. And they said, print them out and then get some colors and circle the things that you liked with one color. Circle of things you didn't enjoy another color. Circle things with you felt like you were making a difference in one color. And I went back and did that exercise and I looked at my calendars and the pieces where I had the. Where I thought I was adding value and I enjoyed were mostly when people had scheduled a sync on my calendar. Like maybe they didn't even work for me or one of my departments. And they were like, hey, I hear you're great at getting people through tough times. And I'm having panic attacks because my wife's pregnant. I've had panic attacks on the bridge or I lost a spouse and I. And I'm struggling and. Or times when a neighbor knocked on my door once and said they stood there and he had two beers in his hands and tears running down his face. He's like, nina, I just got fired and I'm afraid to go home and tell my wife. I don't know what to do. And I was like, come on in. We walked through the house and sat on the end of the dock and we worked it out. I'm like, that's what I actually like that. And I'm saying and doing things that are helping, but I don't know exactly what it is that I'm saying and doing that's right. So what if I. So what if I stepped away and did the homework, did the research like a journalist and found out what are the commonalities? What did I do right, looking back at my life and what do other people who get through tough times do to not just survive. And you'll get this, Larry. Like, not just survive it, but thrive on the other side. Like, have big, even bigger success. How do they make sure they're stronger? So that's what I did. I did research, and I stepped away and quit my corporate job. Very scary to step away from that paycheck, let me tell you. But once again did that and wrote the book and started this journey.

So you walked away, away from business to write the book?

Yeah, I wrote it while I was still there. I wrote it very early in the morning. Like 4 and 5 in the morning. I would set my alarm and get up and write. But I wrote that first book while I was still working, but then really felt passionate about the work I was doing. And then stepped away.

Yeah, yeah. And so how did your work with nonprofits just naturally evolve? Because it seems like once you open the door that you're willing to do that, the invitations will keep coming, and at some point, you just got to say no.

Sounds like you're speaking from experience there. Yeah. Once you start down that path, it was always part of my journey as a journalist, as a news anchor, with being a very public figure. I was approached very early to be a part, donate my time to help out with a cause, as the face of the cause. And then as I became older and really had an understanding of how boards worked and the difference I could make, then I chose things that were near and dear to my heart. I was on the board at this South Carolina aquarium for a while. It was something that I was passionate about, being living near the ocean, and they do a lot on the environmental causes. It's not just a bunch of fish, some people say. But then I was also doing work with areas in which I felt like there was a need. So I did the Palmetto project, which is filling the gaps and wherever other nonprofits are missing, like, the overlap. And so I found places where I felt passionate about them and said yes, but you're correct. For a while, I said yes to too many, and I too many things on my calendar. And I felt like I wasn't making a difference in any way because I just was barely there.

And it's hard to back out of that. It's like getting rid of us. It's like getting rid of a splinter. It's easy to go in and hard to get out.

Right. And so what I had done is when. Same thing when my father had Alzheimer's. And then after he passed, I started with doing the Alzheimer's walks and the cycling across the state for Alzheimer's and different things. But then when he passed and I looked at this disease and I become more knowledgeable about it and the understanding that me in my late 50s, I'm likely next, I very openly got in touch with all of my boards and said I will be backing off of these. I'm putting all my eggs in this basket and I'm going to be. This is where I'm going to put my. My energy so I can actually make a difference.

Yeah. Let's face it. There's just no end to the causes. And they're all. Are most of them. Incredibly, you can make a great case for it. Like down in Palm beach county, it's a big thing, the turtles.

Yeah.

And they. This incredible thing to get up at 5 in the morning and go down and protect the places where the turtles bury the eggs, you know, and it's the only place where they do it and whatever. And the loggerheads and. But I mean, it's just such a big but if you get into it, all of a sudden you're up at five in the morning going down to the beach, walking up and down, or you're working with the people that are doing that. But it's just no into it, you know.

Right.

And you do have to pick the ones you did make a great point about, you know. Well, they're all great points.

I hope I made one in there somewhere. I don't know. We've been on for a long time. I'm. Something's got to be decent.

Either me or you. One of us. Let's just.

One of us said something brilliant, I'm sure.

Let's just hope there's one in there. But the thing about not just survive, but thrive, you know, what that is really needs to be behind the thinking because survive is to be average. That's making a living. And really, if you get yourself to just survive, you're really sell. The problem with that is you're selling yourself short because in almost every person out there, there's some place they can, like you say, go pro or thrive. We're all created with certain skills, but we need to be proactive really in all areas of our life. Like if you got a doctor, like you mentioned it, with a therapist, you know, if you got a therapist, it's not clicking. It's not up to the therapist to tell you go find another therapist. Up to you to say, this is not working for me. I got to move on. If you go through a doctor and you know, it's just not clicking. You know, it's just like somehow they're not listening or you're in a hospital. If you're in a hospital or you have a relative in a hospital and they come in and they don't pay any attention, get that family member out of there into another hospital. You know, be proactive in life to go for the best. Don't hold back and be timid about going when you got something inside your gut that tells you there's something better, this can be better. This needs to be better. Speak up. Go. Be proactive in life. And really, the people that are high achievers are people that respond to that inner instinct or drive. And that's what I see inside of you. You know, you're not going to just sit there and let yourself be pushed around and get secondhand and do Shaquille's laundry for rest of his life. Yeah.

I think you have to advocate for yourself. And then you mentioned hospitals. It made me think of patient advocate. So my mom was in the hospital, she had a fall. She's 90, and I had to fight for her. Like, they, like, if you said your goodbyes, I was like, no, we have not said our goodbyes.

Right.

This is a picture of us having wine at the Biltmore six months ago. She's not ready for goodbye yet. So let's. But you have to advocate for your people in a hospital. You have to advocate for yourself. You have to go, hey, this isn't right. This isn't enough. I want more. And part of that, you know, advocating for yourself goes back to knowing what you want or being willing to accept that wherever you are right now isn't enough. Now, I do think for some people, they do get to a point where, like, this is it. I'm doing what I want to be doing. I'm living this life. This is enough for me. So you have to decide what your enough is. You know, some people want a very simple life. They need the stability and the simplicity of. That's their definition of success. Fantastic. Mine, I'm wired a little weird. Like, I always got to level up and find some new adventure. And every X number of years, I want to jump into something new. That's just who I am. I think life is an adventure that way.

And now you appear to be really excited about your workshop.

I am. I am. So I'm a keynote speaker. Right. So I've gotten that piece of my business going, and I really enjoy corporate speaking. I like doing like, executive off sites where you get your back like 50 or so people. That's my favorite. But big audience, a big stage, also a lot of fun. I got that piece down and then people would come up to me afterwards and go, can I work with you one on one? And I don't have it in me to do that. Plus the space that I'm in, I'm not sure. I feel like they need probably a therapist or other things. I don't feel like I'm qualified. But I started this now what Workshop, because it's just me being me and I can just get you through to the other side of whatever you're dealing with. And I know I can do that. And it's been really a fun thing to put together together. And I again, I found people smarter than me who have done workshops before to talk to me about what technology to use, how long these things should be, where to put worksheets, how often to put it out there. And people who are really good at that have helped me put this thing together. So I am, I'm very excited about putting it out into the world. And it's going to be at a low price point. Everybody can jump in. I just want to be able to help people in it. And how do they find more meaningful way?

How do they find it?

It's now what workshop.com and it's use. People always go, now what? Like, I just got divorced. Now I just got fired. Now what? You know, whatever your now what is.

So it's nowwhatworkshop.com nowwhatworkshop.com now what is. We're going to wrap this up, but I am curious, when you speak to keynotes, what do you focus on versus say the individual, smaller group, the workshop, 50 or 60 people off site. What do you find yourself as your main point, the difference in how you approach those things?

Well, I speak on resilience. That's what my research is all around. Resilience, the ability to adapt in a positive way to whatever happens in your life. So the adapt piece, when I'm speaking at a big, on a big stage, to a big group, I really focus on the change piece. Like why our brains don't like change, how hard change is. Yet the world is changing around us. Your industry is changing. Like we all got to deal with change. So it's that piece of it is what I focus on for a big group in a smaller group. And I'll make the whole room really uncomfortable with change and then get them excited about thinking about it for a big group. For a smaller group, I can really get to know their specific challenges. So I like that smaller space where I can say, okay, I know this group, this company. I'll do a lot of stuff in the tech space and some financial tech space. So I can really understand what their specific challenges are and speak to those challenges and let them see them, the challenges and the changes in their industry in a new way. And I like working with that size because I can ask questions and get feedback. I can pose a question and actually give it a minute for them to think. When you're on a big stage and doing a big keynote with a big audience, it's a little more performative. It's edutainment. You know, I've got videos that play and stuff that happens. And it's a little more edutainment when I'm in a smaller keynote for an offsite or a workshop or a company hires me to bring in something to do with change management. That's really an opportunity for me to get to know that company a little better. I spend a little more time in that space, you know, to really understand them. And a few individuals in there who I can tap into. It's just a different vibe. And I can see their responses and I can see their faces and I can see that it's working. When you have a big stage, sometimes the lights are bright and you can't really tell if people are laughing at your jokes. I think I'm hilarious, but, you know, not always do they. I can't tell if they're laughing at my jokes. So it's just a different vibe. I enjoy both of them.

You know, the thing about the value of what you're doing, especially in the big group, is that, you know, I've heard it's like this thing we're on. We're on a spinning planet. You know, we're in a. You know, you go through all the things, you know, we're the little dot. We're only going to live. So period. A period of time. Like, what are you so rigid about? You know.

Yeah, I actually use. Speaking of spinning, I use. The analogy I use in my big keynotes is do you remember the old. You'll remember this because you and I were this era. Do you remember the old merry go rounds, the metal ones and the playground when you're a kid and you would. It gets spin and you jump on it, kind of like burn the back of your legs because it would be so hot. Yeah. And you'd hold on like for dear life. And some kid would like Stomp on your fingers. Everybody would sling off. The one bully would be left. Everybody would sling off. And then you land in actual dirt back then, too. So you sling off this metal thing into dirt, and then it would slow down. Right. And then what did you do?

Yeah.

And then when it's. What happened when. Then it would slow down, what would you do?

Slow down.

The whole. The whole thing slows down. All the kids wait. And then what do we do?

Get back going again.

We jump back on and win again.

Yeah, get back going again.

That's what success is like. That's what being a high achiever is like. You just get thrown off. You keep jumping on. We're just gluttons for punishment. But if you get a room full.

Of electricity, you never stop. Yeah, you never stop.

Or the technology changes, or we have this global connectivity and we never get to stop. Really? So that idea, we just keep jumping back on no matter how many times we get thrown off this thing.

Well, I'm going to assume you still have one last word to pass on to our listeners. And I always give my guests the last word. And thank you so much. It's been really enjoyable. You've been very generous with your time, and I've enjoyed stomping on you and interrupting your conversations.

Not at all. Not at all. Larry Fairly, it's a pleasure, a pleasure to get to know you and to be here. Thank you for having me. My final thought is in that the concept around it's okay to not be okay, but it's not okay to stay this way. If you are listening and you are in a tough chapter, if you're in a tough space right now or something horrible's happened and you're trying to get through it, if you're just in a tough chapter of your life, it is just a chapter of your life. It is not your whole story. Don't let it be.

What a great final thought. Thanks so much. I look forward to getting you on again down the road and hearing about the workshops.

Excellent. Thanks.

And the new things that come after that. So thanks so much.

Thank you. I interrupted you there. Again, thank you so much, Larry, for having me. It has absolutely been a pleasure.

All right, goodbye.

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