108 Reinventing on the Entrepreneurial Roller Coaster

Serial entrepreneur and Internet marketing phenom Heather Ann Havenwood has built companies from zero to millions in less than a year. She’s also lost everything in bankruptcy and foreclosure, only to rebuild again. Author of the bestselling SexyBoss™ books and host of the national radio show “The Win”, Heather puts on the Advice Wings to talk reinvention, her new chatbot gig and her passion to boost the fortunes of female entrepreneurs.

Melinda Wittstock:         Heather, welcome to Wings.

Heather Havenwood:    Thank you. Thanks for having me. This is fun.

Melinda Wittstock:         I am looking forward to talking to you and I always love to start with what is inspiring you right now?

Heather Havenwood:    God, so many things right now. I’m doing a bunch of different things with these things called Chatbots, which is super-fun and exciting. Not always inspiring. I think what’s inspiring right now is I’ve been focusing on my mission.

My mission has been to help all women in the world be financially self sufficient and I’ve been looking at how do I create that to happen. So, that’s kind of fun.

Melinda Wittstock:         Oh, that’s wonderful.

Heather Havenwood:    Thank you.

Melinda Wittstock:         And so what are some of the challenges, because in every entrepreneur’s life there’s always some sort of challenge. So, what’s the challenge right now?

Heather Havenwood:    Well, I’m rebuilding right now and so I am … I just went after a … I’m in a divorce but I’m in the middle of a business divorce and a break up about nine months ago where my business partner, and I, and finance, and whatnot, built a business from zero to $1.5 million in sales.

And so I’m now recreating who I am after the relationship, right, and figuring out who am I? What am I creating, what am I doing? And it’s been a lot of fun to kind of resurface that. Especially … I thought I knew who I was inside the context of a relationship, and a business partner, and now I’m really looking at what that looks like.

That’s always a big challenge. This is like the third, or fourth, time I feel like I’m reinventing myself again. And it’s challenging but it’s fun, it’s different, it’s unique and I have some great people around me that are helping me through that process differently. So, it’s a challenge but it’s fun.

Melinda Wittstock:         Yes, I mean, we’re in constant reinvention as entrepreneurs and I think once you accept that, that change is the only thing you can take for granted, it does become fun.

Heather Havenwood:    It does and grew up in the ’80s, right? So I grew up watching Madonna. She’s one of my … I just love her. But I watched her, someone who has  reinvented and reinvented, and reinvented and so when I think of myself I’m like, “You know, it’s okay to reinvent again, and again, and again. It’s okay to just step it up.”

So it is challenging for me right now just because I feel like there’s so many things coming at me. But that’s part of entrepreneurship and as one of my friends said, “If you don’t like the heat then get off the game.” Right?

So, if you’re not going to be willing to get hit … What I call hit just like things coming at you and things happening then get off the field, right. And that’s part of the entrepreneurship. I chose this game. I chose this world and I probably wouldn’t have it any other way ’cause I don’t want a boring life. That would be boring.

Melinda Wittstock:         Oh, that’s so funny. My whole life has been about avoiding boredom.

Heather Havenwood:    Yes.

Melinda Wittstock:         So that so resonates with me, right. And if you ask for that you certainly get a much more exciting life. But also just the interesting thing about uncoupling, like not only in a personal situation, but also a business situation. Both of those things at the same time, you know, that is a lot.

Heather Havenwood:    It is a lot. It’s my second time that I’ve done this. The first one was a zero to a million dollars in 12 months in ’05, ’06. We weren’t in the relationship with my business partner but it was a business partner and he still has that business today.

And then here I did it again in 2015 through 2017 in zero to $1.5 million in sales and he still has that business and we’re going through the … I call it the business divorce process, you know. It was our child together so I’m going through that process.

I’ve let it go so he’s going to end up with that business. So I’m looking at what is that? What’s that pattern inside of me that continues to drive sales, drive businesses, and then end up not with them. Like what is that? So I’m having to really look at that.

And it is a whole other layer when we were in a relationship and we were engaged and creating this whole other world. So, I think as a woman I’ve learned quickly that I’m really great … A lot of people are … A lot of women are. We’re great as supporting other people.

Melinda Wittstock:         Ah.

Heather Havenwood:    It’s what we do, right? It’s just what we do. It’s just like we’re cheerleaders, right?

Melinda Wittstock:         Okay, but now you’re going to go out and kick ass on your own, right?

Heather Havenwood:    Exactly. Yeah, now I’m kicking ass on my own and it took me, what I call the universe giving me these situations, quite costly. It could have just hit me over the head, not as hard, but here we are. And then now I feel like it’s all me. You know, it’s all me, for me, and that’s a different viewpoint.

I’ve always kind of come from that view of supporting, helping others. And so with that change and shift in mindset where it’s only me for no other reason other than just me it’s definitely different kind of mindset that I’m moving through. And I’m sharing that because I think women who are listening could resonate with that.

Melinda Wittstock:         Absolutely. So I know that you are going to be a font of advice and so what are your top three go to pieces of advice for female entrepreneurs?

Heather Havenwood:    So there are three that were given to me. I’m going to pass them on. They were given to me at a very low time in my life. The first time I went through bankruptcy and financial foreclosure. I was literally wiped out.

And I was completely broke. And one of my dear friends who, thank God, bought me dinner that night and gave me some gas money to go back home. He said to me, “I want you to ask three things in your life. There’s these three life lessons. They’re kind of time tested things I live from and they’re sitting right here on my desk. And the first one is, does this feed my confusion or strengthen my clarity?”

It’s really powerful. There’s so much there, right, because when we are confused we can never have power. Think of a train. A train can never get to power which is … Until it gets momentum. It could never get to momentum until it’s clear of the track it’s on.

And so we have to get really super clear sometimes on the track we’re on. And that’s hard to do it when we’re, let’s say, down in the dirt. You know, and so you can start asking yourself this really simple question. “Does this feed my confusion or strengthen my clarity?”

Down to let the tiniest little thing like, “Am I going to eat that piece of chocolate? Does it feed my confusion or strengthen my clarity?” You know what I mean? It can really start as the simplest things and then the next one is, “Never, never keep anyone in your life that’s not part of your fan club.”

Melinda Wittstock:         Right. Oh, that’s so important too.

Heather Havenwood:    So, I mean, when he told me that he’s like, “Heather, you have people in your life … They’re in your life and they look like they’re friends but they’re not. You know, are they really part of your fan club or are they trying to take from you?”

Melinda Wittstock:         Right.

Heather Havenwood:    And I had to kind of clear the closet. It’s like going through your closet going, “Does this really fit, come on, my 1985 stuff wants their stuff back.”

But you want to hold on to it. “But it looks really good on me.” Or something. The people in your life, you don’t want to let go of them, you know. It’s like actually, you have to let go of them to be able to move.

Melinda Wittstock:         This is really, really true. I mean, you are only … There are a lot of studies that suggest you are the kind of median of the five people closest to you at any given time.

So if you’re around toxic people, or people that take your energy from you, or people who are kind of give you back handed compliments … It can be subtle sometimes but it can be just as debilitating even when it’s subtle.

So to take that full inventory and, yeah, create your cheerleader fan club. So what is the third piece of advice?

[tweet_box design=”default” float=”none”]Never stay where your presence is not valued. #WingsPodcast #WomeninBusiness @hhavenwood[/tweet_box]

Heather Havenwood:    The third one is, “Never stay where your presence is not valued.” There’s a lot there. I found myself going to sometimes, events, sometimes I would be trying to be part of a group or whatever I was trying to be a part of. And I realized, “You know, they don’t value me. Why am I even trying?”

‘Cause I … This is my tendency. I’m not saying it’s yours, or anyone else that’s listening, but I have this tendency to try to get people to like me.

Melinda Wittstock:         Ah, yeah. Women are like that. I think we’re like that. We’re people pleasers, you know, a lot of us.

Heather Havenwood:    I’m a people pleaser and I want you to like me so I’m going to try really freaking hard. You know, and then you’ve got to sit back and go, “Okay, is my presence valued?” It’s very different versus I’m valued. Like, “Is my presence here valued?” And you know when you’re in an organization, or a group, or a group of friends, whatever where your presence is just valued being there.

You know, you can feel it when your presence is valued. You can also feel when they’re like, “No matter how many tricks I do, and circle saults, and whatever, flip flops they’re never going to like me. Or they’re never going to value me no matter how much I try to prove.”

You can feel it in your body so I started to take inventory of that as well. I was like, “Where am I really valued? You know, and the moment I feel myself like, “I’m just not valued here anymore or maybe I don’t value them anymore. I can remove myself and it’s okay. It’s okay they don’t value me. It’s okay that I don’t value them. It’s okay. I can remove myself and it’s all good.”

You know, and I think that gave me a huge permission to just not feel like I had to be part of certain groups, or organizations, or masterminds, or whatever. I didn’t feel like I had to constantly prove myself. But those are three.

Melinda Wittstock:         Lovely. Well, thank you for that. Those are all really valuable pieces of advice. So, how can people find you and work with you Heather?

Heather Havenwood:    So they go to heatherhavenwood.com. If they’re interested in working with me they can go to callwithheather.com and they can get on the phone call with me and we can have a conversation.

Melinda Wittstock:         Oh, that sounds wonderful. Thank you so much for putting on your wings and flying with us today.

Heather Havenwood:    Thank you.