86 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. Heather talks 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.

Melinda Wittstock:         I am so excited to talk to you. When I think of the successes that you’ve had but also the dips, you know that rollercoaster ride that all of us entrepreneurs are on. You, to me, seem like an expert in reinvention.

Heather Havenwood:     Thank you for that. I don’t see it that way but I’m going to choose to see it that way. That’s a nice reframe. I’m going to own that.

Thank you. I really do admire Madonna. My very first concert in 1982 was, Like a Virgin. I was in like second grade. My mom took me out of school and me, and my sister, and my mom went to, Like a Virgin tour.

And we’ve actually seen about seven of her concerts. And what I always find just so powerful about her is that she does reinvent herself. And there’s just … It’s just like, “What’s next for her?” And this is just what’s next, and this is just what’s next, and I’m like, “Wow. I wonder if I ever need to do that in my life?”

And here I am. I feel like that’s kind of where I’m at. But every time that I’m going to reinvent myself … Again, I’m reframing that. I think that every time there’s a big change there’s a piece of me that is sad of what the process is and what I’m going through. ‘Cause there’s kind of a release of an old life, you know?

Melinda Wittstock:         Yeah, you got to say goodbye.

Heather Havenwood:     There are a lot of goodbyes. Yeah, in the year 2017 I’ve said a lot of goodbyes. And not always in the best way, you know, not in the most loving way. Some were really loving, and my life right now is … I don’t want to say small ’cause I know a lot of people but my inner circle is quite inner. And there’s only like three.

And one of my dearest friends whose a speaker in our world and has been in this business for a lot longer than me, I told him that. And he said, “Heather, my best friends are on one hand.” And this person is well known. Has got like books.

He’s like, “I know a lot of people and I have clients around the world but there’s only about four people in my life that I would say are my inner circle.” And he’s like, “The bigger your life gets and the broader it gets and you get out there that’s how your inner life will look. Be okay with it. Be okay with it.

And so as you reinvent yourself again you’re going to have more and more people leave you.” Which has happened in 2017, or 2018, I’ve had weird fights with people. I’ve had … All of a sudden these people that are just completely leaving my life.

Sometimes they’re fights, sometimes they’re just disappearing, whatever it is I think energetically as we move up there’s … Caroline Myss, who I don’t know her, I’d love to know her but I’ve been watching some of her videos online and I think she just said it so perfectly.

I mean, I had to watch the video like three times. I’m like, “Girlfriend, you just said it for me.” She said, “As you move energy, as you transition, as you reframe your life, and reinvent your life, think of it like you’re in a condo building and you’re literally going up another floor. So if you’re on six, you’re going to seven.

What happens when you move up a floor? You have different neighbors, you have a different view of life. The people that were on your sixth floor, they’re not bad people but you probably won’t see them anymore.” You know and it’s just this brilliant example of like, “Oh, that’s what’s happening.”

Melinda Wittstock:         It’s a lovely way of saying it because I think that’s true. As we grow, as people on like … Whether you call it a spiritual level, or whatever, but we just we grow, we learn, we get empowered, we get in touch with ourselves.

We get in to alignment with why we’re here. We start to … As we get older we start to think about legacy and all those sorts of things and with that clarity absolutely comes new people. You attract new people in to your life.

And I think what’s so interesting too as an entrepreneur is … And do you find this as well that you really do need to be around the right people? So the right people for you at different periods of your life may be different.

Heather Havenwood:     Oh, completely. I mean, there are still people I know from 15 years of being in this business. At the same time I find interesting how some circle back around or some disappear, you know? And as we energetically shift, the people in our life shift as well.

There will be people at events I’ll never see again. People that I’ve known for years, all of a sudden I’ll run in to and all of a sudden we’re connecting. We’ve never connected before. You know, our minds in the right place. I think that happens in all areas of our life.

And if you look at … I always kind of bring back to high school, which was just a weird time in my life. I don’t know about yours but in high school it’s the same thing. You know who you were friends with in Freshman isn’t always the same people your friends with in Senior.

You know, you grow up. That happens in entrepreneurship even more so than anything else. I think if you’re in a company things can get stagnant. When you’re an entrepreneur it’s in the conversations you’re having every day that change and alter who you are.

Melinda Wittstock:         Well, you can … As an entrepreneur you can go up, and down, and twist around the rollercoaster within the hour. Let alone within the month, or the year. I mean, it’s just constant change.

Heather Havenwood:     Yeah.

Melinda Wittstock:         And in a way you know … We joke on this podcast so much if you want a therapist, or you need therapy, become an entrepreneur because it’s the surest-

Heather Havenwood:     Oh, my God.

Melinda Wittstock:         Fastest path to self discovery… because you’re really testing yourself every day, every hour of every day.

Heather Havenwood:     Yeah, and also I think another one of that … Actually, my coach says this to me. She says, “The beauty of being a coach is that you have to constantly be growing yourself because you’ve got to stay ahead of your clients.” And she’s like, “The thing that you’re dealing with, your clients will start to deal with.” And so you’re like, “Oh, my God. My client’s dealing with that? I know I’m dealing with it. I better move this thing because if not they’re never going to move through it.” It happens every single time.

Melinda Wittstock:         Oh, really? That’s interesting. It’s like we kind of mirror each other.

Heather Havenwood:     [inaudible 00:17:07].

Melinda Wittstock:         Right. So we attract clients perhaps this energetic … This is interesting to think about it in terms of marketing and sales. Are we attracting the people that are mirroring us in terms of where we’re at in our own lives.

Heather Havenwood:     Completely. And I’ll do it third party so there’s a dear friend of mine who I’ve known for 15 years. He’s got a coaching group that’s just really powerful and he invited me in to sell to them how to start a podcast. So I’m now working with like five of his clients and I’m launching their podcasts.

And I talked to him. I said, “You, you need your own show right? You can’t have your clients having their own show.” He’s like, “I know, I know. The reason why, they’re dealing with the thing I have an issue about which is self-promotion. I know that. I know that.”

And I’m like, “Okay, look we’ve got to break through that for yourself if not you’ve got to stay ahead of that.” And he’s like, “But they’re dealing with it and so I know I’m dealing with it ’cause they’re dealing with it ’cause I’m dealing with it. It’s because of me. They’re dealing with what I’m dealing with.” I’m like, “Of course it is.”

Melinda Wittstock:         Oh, that’s so funny. I have such a similar thing as well because I was helping so many people with their personal branding and how to be authentic on social media. Advancing all these companies, and doing all this miraculous stuff for them but not doing it for myself. And I was like, “Wait a minute. There’s something wrong with this picture here.”

Heather Havenwood:     There’s an old saying for that, you know, the cobbler’s shoes or you know they’re really great at their creating shoes … I don’t know, whatever. It’s some saying like that. But basically-

Melinda Wittstock:         Well, it’s like the accountant.

Heather Havenwood:     Yeah.

Melinda Wittstock:         Whose finances are a mess, right?

Heather Havenwood:     Exactly. That’s what it is. So it makes you a better entrepreneur and when I started coaching again, quickly after the break up, months ago I felt really insecure about it. And my coach was like, “This is your number one way to get back to feeling confident about yourself. Is that when you … One, support the people but two, it forces you to grow faster.

When you’re actually supporting other entrepreneurs when you’re an entrepreneur. That is truly the best gift. And like I’ve said built so many other companies, I don’t know why my confidence was low.

A lot of it was because of the break up and all that stuff and that shifted a lot because now I’m seeing my clients just double their sales, and triple their sales, and so I’m doubling, tripling my sales. And so it’s kind of a symbiotic relationship.

Melinda Wittstock:         That’s so interesting you say that and when you’re referring to the break up. I mean, it was a big break up ’cause it wasn’t just a break up in your romantic, or personal, life. It was also a business break up at the same time. And so when your identity … Like your whole identity-

Heather Havenwood:     It was my whole identity. Yeah.

Melinda Wittstock:         Right? That’s hard.

Heather Havenwood:     It was hard. So it’s not like I had a break up and the next day I just go back to work. It wasn’t like, oh, I had my business altered but I go back home to I have my loved one. It was all gone in one day. Boom. It was just like whoom.

And it took me awhile to get my bearings to really figure out what am I doing. And I honestly say that it’s because of my coaches and I had good friends around me, just keep me centered as much as possible. And keep me aligned with that but it is, it’s very challenging. Not going to lie.

Melinda Wittstock:         When you have the wind knocked out of you like that. I mean, I think of … I was married for a long time but the relationship became toxic over many years, gradually. Kind of a lobster, right, gets in to the pan and the water’s cold and really nice and happy, happy lobster. But then, you know, before the lobster knows it the water’s boiling.

Heather Havenwood:     Right.

Melinda Wittstock:         And I had a relationship like that with someone who became extremely verbally abusive and, you know, had an alcohol issue right.

So that business that I was running at that time had very little chance of success because it’s so much the mindset that I was absorbing all this negativity. And being positive but forced positive through that.

And so I think when we’re in relationships that aren’t working it has such a big impact on our business. Or if we’re around friends who aren’t really that supportive, it has a big impact. So saying goodbye to the toxicity in your life is like a whole new lease of life and it’s so important.

So, I’m so excited for you because you’re stepping in to your power and on your own. Which is actually authentic Heather Havenwood, like on your own, which is awesome.

Heather Havenwood:     Thank you. Thanks for that. I really appreciate that. It’s been fun. It’s been interesting. I’m not going to … There’s a saying on my board, I’m staring at it. And it was perfect that I came across this card around the time. It says, “Detach yourself from your stuff.” But the word stuff is in quotes, you know.

Melinda Wittstock:         Hmm.

Heather Havenwood:     And that could be a lot of things. Relationships, business, and so when I’m going through the business divorce, and the lawyers, and stuff like that my lawyer finally looked at me and goes look, “This is going to be awhile. Just let it all go. Like act like it doesn’t happen. Just move on. Move on with your life now. Like now, just move on with your life now.” And I was like, “Okay.”

Melinda Wittstock:         Well, actually that’s such important advice. What’s interesting about the whole concept of letting go, or not being attached to the outcome!

Heather Havenwood:     Correct.

Melinda Wittstock:         In all things in life, the minute you do that … Like you genuinely do it.

Heather Havenwood:     I do.

Melinda Wittstock:         Suddenly, everything starts to fall in to place.

Heather Havenwood:     That’s exactly what happened. I just let it go. Like it’s all going to work out, or not, or doesn’t even matter anymore. I just completely … I kind of forget that I’m in the middle of it still. He has to remind me, oh I need this document.

Oh, yeah there’s a thing going on. I don’t even … I forgot. So the point is I’ve let a lot of things go but here’s what’s interesting about that where it goes everywhere in your life.

When I was going through the break up and all that process I’ve gone through my entire house like three times and I have let go of all this stuff, you know. I mean, of course I went through [inaudible 00:23:26] in the relationship.

That was already done but more like clothes, and this, and that and here’s where I came from, I came from, “Does this spark joy? Does this thing, this item, this situation, this relationship, this opportunity, does it spark joy?” It’s the same conversation I’ve said earlier, or the same question, does this feed my confusion or strengthen my clarity?

Melinda Wittstock:         Right.

Heather Havenwood:     It’s like, “Does this item, this person, does this thing, does it spark joy in my life? Does it add clarity to my life?” And if it really doesn’t it is sucking power from you. And it could be a trinket, okay. It could be anything in your space. It’s like get rid of it, get rid of it, get rid of it.

The more you do that, the more just people come in your life, or things come in your life, opportunities come in your life. Like, I met you through a mastermind. I never met you. You just popped in to my life, right? That’s how I look at it. You just like popped in.

Melinda Wittstock:         Yeah, likewise. It’s the same thing. You start to let go and you create the space in your life for magical things to happen and they start to happen. I love what you say about the clarity versus confusion.

Because part of the clearing out of that confusion is just clearing out the stuff that you really just don’t need. Being willing to kind of say goodbye to it. I mean, there is a real inherent confidence in being able to do that.

Heather Havenwood:     No, it’s huge. And I remember … My fiancée at the time went through counseling, thank goodness ’cause the counselor really helped us through the process … Helped me even tremendously more afterwards than the process and I remember …

It’s been now six, nine months. I looked at her recently and I was like, “I was really not happy in that relationship.” She’s like, “You were really not. I don’t think you realize how unhappy you were.”

Melinda Wittstock:         Well, yeah. That was like my experience too. I had no idea how unhappy I was. Friends, you know, I’d go back home. I’m originally from Toronto in Canada, I’d go back home and people would be like, “God, you know. What’s wrong?” And I’d be, “What do you mean what’s wrong?” Like I was so-

Heather Havenwood:     In it, yeah, you don’t know.

Melinda Wittstock:         You don’t know at the time and then the other really interesting thing was afterwards going back after being separated and all of that and it’s like, “Wow, you know, Melinda you’re back.”

Heather Havenwood:     Yeah, I’ve been getting that too. Like, “Wow, you’re back.” I’m like, “Where did I go?” Right. I have a friend I’ve known for 14 years and I said to him, “Was it that bad?” And he’s like, “Yeah.”

I’m like, “Okay, next time you just slap me. Like seriously next time …” No way I’m going to do that but you don’t really realize how … You just disappear. I’ve been giving my friends, my good dear friends, “Okay, next time seriously I need you to slap me around or something.”

It’s not going to happen again. I won’t get lost but you do see. Like you said, the lobster. We put a lobster in just cold water and you slowly heat it up. You have no idea that you’re in hot water. You just don’t know. That’s kind of where I was at too.

Melinda Wittstock:         Interesting. ‘Cause I think we have these relationships that can be toxic too in an entrepreneurial sense.

Heather Havenwood:     Oh, yeah.

Melinda Wittstock:         Like with clients.

Heather Havenwood:     Clients.

Melinda Wittstock:         Or the wrong investor, or whatever. And getting into alignment is so important. So many women, for instance, in the world that I was in for a long time around technology and raising venture capital money, and angel money, and that kind of thing is that women fall in to the trap of, “Oh, goodness I need the money so badly that they would take money from the wrong investor.”

And if that relationship is out of alignment for any reason, I mean, you could end up losing your company. And so it’s so important if you have the wrong clients.

Clients who don’t appreciate you, or undervaluing you, or you have … I don’t know under priced yourself or something like that. And it’s just out of alignment, it’s not working. Oh, my goodness that can be devastating for a business.

Heather Havenwood:     It can be. I think … Something I remember. I just want to share this with you because I can’t share a lot on a lot of podcasts but one of the things I really got to around 2008, 2009, where I’m sitting there on my friend’s couch.

Thank God I had some good friends. I was completely broke. I had nothing, right. I had nothing. I had no bank account. I had a cell phone and I’d pay it with cash, you know. So I had nothing.

And I’m sitting there on the beach and I’m just kind of this place like, “Who am I?” And this is a moment because I was brought up in a very Southern persona and I was taught, get married, have babies. Like, that was it. And my mom was freaking out when she found out I was going to be an entrepreneur.

Totally, flipped out. So here I am broke and it kind of around me family was like, “Haha! We told you.” You know, going on. And I’m by myself. No help from the ‘fam’ on any level and didn’t have a husband to fall back, all that.

So I’m sitting there going, “Who am I? Who am I? Who am I?” And I got really at a core moment. Like I really got it. Like who I am is an entrepreneur. Now there’s a moment … Let me explain this what this means ’cause it’s really powerful.

It’s like an athlete. When an athlete gets who they are, is an athlete, at a core level, it doesn’t matter what game they play, or sport. You’ve seen athletes move like Michael Jordan. He was MBA, then he went MLB, and then he went golf, or whatever.

He got who he is, is a athlete. You know, at a core level. So, when he … It doesn’t matter what game he plays. He’s unattached. That part about being unattached, it’s like, “Whatever. Fail, not fail. Win, not win. It doesn’t matter.”

[tweet_box design=”default” float=”none”]When I got clear, I’m an entrepreneur, I got that it didn’t’ matter what I created as long as I’m creating. As long as I’m being an entrepreneur. #WingsPodcast #WomeninBusiness @hhavenwood[/tweet_box]

So when I got clear, I’m an entrepreneur, I’m sitting on this beach broke, okay. I got that it didn’t’ matter what I created as long as I’m creating. As long as I’m being an entrepreneur. Think of a musician. When they get they’re a musician, it doesn’t matter one album does great, one album does not, one album … They don’t … As long as they’re creative.

Melinda Wittstock:         It’s not the outcome it’s the journey. It’s being on the journey. That’s a lesson I’ve really learned as well. It’s doing the things you love to do. It’s being aligned with your values, it’s being the person you are.

That you truly are and being in alignment with that rather than, you know, trying to live this life of somebody else’s life. Or life of should’s or lives of obligation rather just … Yeah, you mentioned the word joy before. I think that’s what that is.

Heather Havenwood:     It is joy and I … But I will say from a female perspective, it’s not as … It is lately now more but it’s still has this kind of connotation of … I mean, I was told a million times by men I was dating, by strangers, of like, “Oh, it’s okay. You’re pretty, you’ll get married.” Like that was this answer. Oh, I’ve had that a lot. I’ve had been go-

Melinda Wittstock:         That’s so patronizing.

Heather Havenwood:     I’ve had a guy, stranger on the airplane once, I told him what was going on in my life. Kind of like, here’s what my life looks like. What does your life look like kind of thing. Not trying to be a victim and he just patted me on the knee like a little girl.

And he says, “It’s okay hun. You’re pretty, you’ll just get married. Don’t worry about it.” It’s very patronizing. However, it’s interesting because I’ve even had men in my life who are my significant other say, “Okay, this whole entrepreneur thing. Okay, you can stop that now. You can …” They think it’s this fad. I’m like, “It’s not a fad.”

Melinda Wittstock:         It’s not, it’s not. It’s just who you-

Heather Havenwood:     It’s who I am.

Melinda Wittstock:         Exactly.

Heather Havenwood:     it’s your peace. Yeah, I’ve had men say, “Yeah, that’s really cute and all. Okay.”

Melinda Wittstock:         I’ve gotten to the point where I can only really hang around other entrepreneurs or creative people.

Heather Havenwood:     Oh, yeah.

Melinda Wittstock:         Who understand that because it’s like … God, I found myself saying … Describing non-entrepreneurs as civilians the other day.

Heather Havenwood:     Oh, that’s awesome.

Melinda Wittstock:         Because it’s true. Well, it’s very, very difficult I think for non-entrepreneurs unless they’re very empathetic to actually understand what you’re really going through when you’ve got payroll, you’ve got all these different … You’re only as good as the last sale you made. It’s a completely different attitude. All you’ve got really is you. You can’t just show up for work or complain about the boss. I mean, you are the boss.

Heather Havenwood:     You are. You are the boss.

Melinda Wittstock:         So there’s no one … If you’re complaining, you’re basically complaining about yourself, right?

Heather Havenwood:     Yeah. It’s not always … Almost every entrepreneur I know, almost all of them, usually are the black sheep. Entrepreneurship finds them. They don’t usually go find it. You know ’cause there are times … I’m not going to lie. There are times I wake up and I’m like, “Dude, why couldn’t I have just been a government employee. Get off all those holidays. Sick leave, two weeks pay.” You know what I mean?

Melinda Wittstock:         Yeah. I don’t even know what that’s like.

Heather Havenwood:     I don’t even know what that’s like.

Melinda Wittstock:         I have never had that because before I was an entrepreneur, I was a journalist and that was like-

Heather Havenwood:     Oh, forget it.

Melinda Wittstock:         You were only as good as the last story you did and in a really competitive environment too. You know, this was in my 20s I was on the Times in London. And you know you’re competing against 12, pre-internet, because I’m kind of ancient.

So, anyway, pre-internet and you’re competing with all these other national dailies. And if you didn’t have the story like heaven help you. The news editor would call you and get you out of bed at midnight and tell you to write the story or figure out and you’d have to call your sources in the middle of the night. I mean, it was brutal.

Heather Havenwood:     Wow. Yeah.

Melinda Wittstock:         So, having gone through that more over having written a story with Rupert Murdoch standing right behind me.

Heather Havenwood:     Oh, my gosh.

Melinda Wittstock:         Yeah, right.

Heather Havenwood:     Are you serious?

Melinda Wittstock:         Seriously. Because I was the media correspondent of the Times of London, which he owned. And so I was writing about things that directly impacted his business.

Heather Havenwood:     Oh.

Melinda Wittstock:         It was a really, really tricky job to have and to navigate especially in my early 20s. So nothing really scares me after that.

Heather Havenwood:     Right, I can see why you’re like, “Ah, nothing scares me now.” Yeah, well welcome to … When I hear … When I get clients, or women clients specifically, they reach out to me and they go, “I want to start a business, or I started this business, I want to make sure it’s going to be successful. Can you make sure?”

And I just kind of laugh. I can’t make that … No one can guarantee that. We can look at data. We can look at data and what people like and don’t like and there’s strategic, and there’ strategies to make sure that you’re on the right path, right? But there really is no guarantee.

You know, there is no guarantee and I like the football analogy, if I was playing in the Cowboys and if I went to my boss at the time, Jerry Jones, or whatever and say, “Hey, I want to play today but I don’t want to get hit.” He’s like, “Give me my jersey back dude. Get off my damn field.” You know?

Melinda Wittstock:         Mm-hmm.

Heather Havenwood:     It just happens. It’s just part of the game. It’s part of the process.

Melinda Wittstock:         This is why I really like agile methodologies in the start up world. Really, you know, test, try something, test, measure, build, constantly following, being in touch with your why, or your mission, being aligned with that because I think that’s pretty critical.

Make sure you got the right team. Making sure that you are actually enjoying what you’re doing and then looking at the data. Talking to your customers and it’s a work in progress.

Heather Havenwood:     I love how you … I love that about you, that you’re in to the data because it’s true. You got to test it. I don’t know if that lanterns going to work.

Melinda Wittstock:         Yeah, the more accomplished that I become the more I realize that I don’t know.

Heather Havenwood:     Yeah.

Melinda Wittstock:         I’m laughing at that but it’s kind of true. I don’t know. That might work, might not.

Heather Havenwood:     Might not work.

Melinda Wittstock:         But let’s just keep trying until it works.

Heather Havenwood:     Yeah. And I think that’s one of the challenges I think specifically women have a harder time because women don’t usually look at the data. Now, I’ve been taught to look at the data over time. You have too I think and you know ’cause that’s the best thing to look at. You don’t look at what I like, you look at, “Well, did they like it?” Yes, no, I don’t know.

Let’s try it again differently and see if they like that more. You start looking at the data and putting information in the data versus what do I like, or don’t like, or whatnot. So I think that’s important for women to get. Men get that … They just get that faster. They just do.

Melinda Wittstock:         Yeah. Interestingly though too, just even in terms of talking to customers, I’m always struck … And I quote this all the time but you know Reid Hoffman, who was one of the founders of LinkedIn and PayPal before says, “If you’re really happy with your product when you’re launching it, you have launched too late.”

And I think what he means by that is you really need customer input as soon as possible. Even in the earliest … Say in tech, and in apps, and that kind of product creation. That rapid prototyping process has to be free of attachment to outcome.

You go to test your hypothesis, your hypothesis, you may be attached too but you may become wildly wrong. And the only way you really know and get on the right track is if you involve potential customers early on in the process. So where I see a lot of women go wrong is that we have this perfectionist gene.

Heather Havenwood:     Oh, my gosh.

Melinda Wittstock:         So we don’t want to show it to anybody until we think it’s perfect but then we miss all that really valuable input from customers.

Heather Havenwood:     Oh, girlfriend. I’ve let all that go. You can’t … I can’t tell you how many times I’ve launched things, products, services, my podcast the first time, it sucked. But I launched it.

Melinda Wittstock:         Yeah, you just do it. You got to be Nike. You got to just do it and then you got to listen, listen to people. Right? But then the flip side of that though too, don’t you find, is sometimes we allow ourselves to be over coached.

Heather Havenwood:     Yes.

Melinda Wittstock:         We’re either not coachable, or we’re way too coachable and lose ourselves.

Heather Havenwood:     Yes, yes. Absolutely, and it reminds me the thing you and I talked about on my mastermind. Our mastermind on Monday, remember what we were talking?

Melinda Wittstock:         Oh, yes I do. You want to share that?

Heather Havenwood:     I will. I’m willing to share. So, I have this thing. So I’m in the middle of this contest with myself slash small group. We put some money on the tables. That’s kind of fun to put some money on the table, right. But it’s not a lot of money but it creates something. So, it’s 90 days, a video every day. Every day.

Melinda Wittstock:         That’s a lot. I mean, that’s a big thing to commit too.

Heather Havenwood:     It is. And the moment you miss one, you’re out.

Melinda Wittstock:         Oh, and there’s money on the table so you got to do it. You got to pull through.

Heather Havenwood:     There’s a group and they’re watching you. All of it, right, which is perfect. Which is perfect for me. However, I was on my mastermind with you and a couple of our colleagues there and I have this thing about being on camera in my space … Our space.

You know, information marketing, and helping people. I have this thing … I’m going to say it. Look, if anyone actually thinks Maria Forleo sits down all day and does Internet marketing you’ve got to stop and think no.

She has stylists; she has makeup artists. She’s got copyrights telling her what to say. You do not look like her doing Internet marketing all day. I’m sorry. You look like Melinda and I and right now you’re not seeing us. There’s a reason. You know what I mean?

Melinda Wittstock:         There’s a reason.

Heather Havenwood:     There is a reason ’cause we’re just chilling. You know what I mean?

Melinda Wittstock:         Well, I’m doing this podcast sitting here in my sweats because, you know, I went and worked out like right before. So I don’t have any makeup on. My hair’s in some scrunchie. So I’m not looking all that glamorous and a lot of the times entrepreneuring is not glamorous.

Heather Havenwood:     It’s not.

Melinda Wittstock:         I think there’s a lot of people that make it look that way. But then you are like, “Oh, God. If I have to do all these videos all the time does that mean I have to be … Have my hair blown out. Have full makeup on.”

Heather Havenwood:     Yeah.

Melinda Wittstock:         All that kind of stuff. And I remember all of us saying, “God Heather, just be yourself. Be authentic.” Right?

Heather Havenwood:     Which bothers me ’cause it’s scary to me because I feel like I have to measure up to the person that’s already out there. That’s where my head goes. And so I’ve been doing very well. You know, I’m out there.

I’m not saying my views are getting 10’s of thousands like her, which that’s fine, but I’m doing it. And it’s not perfect and I don’t know how to edit so they’re all just raw. And I’m sure in the future they’ll get better and I might eventually hire an editor.

I don’t know but I’m just doing what I need to do and focusing on the content. What can I give, what can I share, what can I add value. I’m focusing on that and just giving up … I have one on walking the dog.

I’m like, “This is me walking the dog. All right, let’s talk some business.” I’m just doing what I need to do. This is what life really looks like for me. I walk the dog.

Melinda Wittstock:         But here’s the interesting thing right now is that those authentic more vulnerable, less rehearsed, less produced, more raw videos actually do better. If you look at what’s really hitting on YouTube and particularly with younger people they like all the stuff that has terrible production values.

Often, there’s no lighting or there’s no … But people like that because I think we’re so … Our society is so canned in a way, right. There’s a lot of trust that’s been lost. We don’t trust government, or the media, or whatever.

And so anything that looks authentic, even if it looks authentic just because it’s kind of grainy or has bad lighting or the person’s not wearing makeup instantly there’s almost more trust.

Heather Havenwood:     Well, I hope so.

Melinda Wittstock:         So, I mean, I don’t know we don’t … And also, the other thing too, we don’t have to be like the other person.

Heather Havenwood:     Yeah, well that’s what … The reason I’m bringing that up is because it has what has stopped me from doing this four years ago, or three years ago, or whatever. I mean, I should have been doing this probably three, or four, years ago with video.

And I haven’t done it, you know. And it’s because in my head it had to be this Kim Kardashian freakin’ production. And girlfriend, I ain’t doing that. I mean, Kim Kardashian has two hours of makeup every day. Girl, come on. I’m not going to do it. I barely do like 30 seconds mascara. I’m good to go.

Melinda Wittstock:         Exactly. That’s what I say.

Heather Havenwood:     That’s what my life looks like. That’s how I look. That’s just … I’ll spend a little more if I’m doing a speaking gig but not much more. I think I’m ready to kind of come out and just be authentic and I’m doing my videos. They’re on YouTube, Heather Havenwood, feel free to say whatever.

Melinda Wittstock:         No, but that’s wonderful because you’re giving permission to other … You’re not the only woman who-

Heather Havenwood:     No, that’s good.

Melinda Wittstock:         I mean, I have this too so I’ve got to start the video part of Wings as well. And do I have to show up everyday in full makeup? I don’t have time to show up everyday in full makeup so I’m going to go through the same thing that you are going through.’

And you’re paving the way for other women just to kind of just be. You know, just be comfortable in our own skins and just own it. I think it’s wonderful. It’s inspiring.

Heather Havenwood:     I have a ton of high heels. You know, I do. I have a ton of shoes but I think I don’t wear them. I wear tennis shoes and yoga pants everyday, okay.

Melinda Wittstock:         Wow, that’s so funny. That’s what I have too. I’m looking in my closet, God, so many high heels ’cause that used to be my life. You know in New York, and London, and all that and being out and suits and stuff and now it’s mostly yoga pants.

Heather Havenwood:     Right, yoga pants girl. I’m telling you. We should create entrepreneur yoga pant line or something.

Melinda Wittstock:         Like I do yoga every day and it’s just … I don’t know. Yoga wear is stylish and-

Heather Havenwood:     It is.

Melinda Wittstock:         It’s easy. You feel comfortable, you know. Yeah, I’m wearing yoga pants right now so just to say anyone out there-

Heather Havenwood:     I am too. We’re like yoga’ed out.

Melinda Wittstock:         Whose in yoga pants let’s own the yoga pant thing. So, how did you become an online entrepreneur? What was it that says, “Okay, I’m going to go in to the online marketing space?”

Heather Havenwood:     Okay, so I didn’t know that, again, it just happened but I didn’t know it was happening. So here’s kind of my story just quickly. Started in Corporate America. I did very well in Corporate America. I was in B2B sales. I was very young.

The average co-worker of mine was male, 40. I was like 23, 24. I wasn’t even supposed to get the job. When I went in to get the job, or try to get the job, the guy laughed at me. I didn’t have my degree yet. He was like, “Oh, that’s cute. That’s funny that you want that. No, you’re in customer service. You’re a girl. You’re cute and you don’t have a degree and you’re like 20 something.”

And I said, “No.” And luckily he did the whole like, “Well, I got to ask my boss.” Kind of, you know, corporate thing and luckily she was a woman. It was the first time I ever ran across a woman in business. And she was a woman and she said, “Give her a try. I mean, worse thing can happen is we just put her in customer service.”

Well, I was there for four years in B2B sales. The average … Like I said my co-worker was men, 40 and I was 24, 25, 26. I started making $100,000 a year. Going to school at night and on the weekends so I was busting my butt. My B to B sales, which is all commission. One of those, you know, if you don’t make it you’re out.

And I ended up being there for four years and here’s the story, so I actually ended up number one in the country.

Melinda Wittstock:         Wow.

Heather Havenwood:     At a very young age.

Melinda Wittstock:         That’s amazing.

Heather Havenwood:     That’s why part of my book, “Beating the Big Boys” was in that tagline because that’s what it was like. I was beating the big boys man. I was beating, you know, everyone in the country and I was super-young.

And I wasn’t supposed to and that’s what happened so they fired me. So as soon as I got my, what I call, pat on the head. Congratulations from the president of division, or whatever, my boss fired me slash took all my accounts and gave them to my assistant who was 10 years older than me and a male.

Because he was a married with a baby on the way and I was young, and single, they fired me and gave all my accounts I had been building for four years to him. Hello. So that was a big slap in the face of woman thing going on.

I was very, “What in the world?” That’s kind of how it ended up being entrepreneur because afterwards a lot of my friends were like, “Well, just go and get another job. You’re good in sales. You’ll be fine.”

And I said, “I don’t know what I want but I’m not doing that again.” You know, I didn’t know what I was going to do Melinda but it was one of those moments where you’re like, “I’m not sure but it ain’t that.”

And what ended up happening, I was sitting on my girlfriend’s coach and an infomercial came on with her new husband clicking and eventually he went to get a beer thank God and he landed on this infomercial.

And this infomercial was like, “Do you want to control your life? Do you want to make more money?” And I’m like, “Yeah.” You know, that’s all you have to say to me. So I wrote down the location, I go to this seminar, the next day at 1:00, they’re obviously pitching a three-day, $3,000 event on how to buy and sell houses.

By the way, this is 1999, 2000, okay. 9/11 had just happened so I’m there, sitting there, I don’t have $3,000 and then they said the magic words and they said, “For your spouse, it’s $1,000.” And I punched the stranger next to me and I was like, “Yo, can I be your spouse?” And he’s like, “Yeah, that’s cool.”

So we go to the back of the room, different last names, no ring, different credit cards, whole nine yards and of course they took my $1,000. They were happy to take my money but they knew I was lying. They knew I was lying and they said, “What’s your deal?” They were kind of like poking at me. “Who are you? What’s your story? What’s going on with you?”

I actually ended up working for that company and traveling the country from 2001, right after 9/11, 2001 for four, or five, years. And that’s where I learned copyrighting.

Melinda Wittstock:         Oh.

Heather Havenwood:     ‘Cause if you go in to room of strangers and in 90 minutes you got to pull $3,000 out of them if not you’re eating Ramen noodles that night or you’re eating Ruth Chris, it depends. You learn quickly the art, and science, of sales and marketing quickly.

Melinda Wittstock:         Right, right.

Heather Havenwood:     And then I started getting in touch with … I started getting introduced to Dan Kennedy, [inaudible 00:48:25], John Carlton, copyrighting, how to buy and sell houses, how to flip houses, all these things. That’s how I got in to the business so in 2003 and four I went to Big Seminar, which was done by Armand Moran and then Alex Mandossian.

I got introduced to Corey Roodle, I got introduced to all these people that were the beginning of internet marketing. Matt Bacak, I’ve known him since 2003 and four. Went to the same seminar with him. Russell Brunson, I’ve known him since 2004. Again, met him at Big Seminar.

We all kind of started together. So it was a natural progression because the seminar business was like, “There’s this whole internet thing. We got to figure it out.” You know, so I started going and learning.

I actually ended up getting my master’s degree in online marketing believe it or not, 2010. I met Ryan Deiss in like ’04, ’05, when he was just a dude named Ryan. That’s how I kind of fell in to it. Literally, fell in to it and then my first business on line was zero to a million dollars because a guy came to me who was a lawyer and he knew how to buy and sell houses and things but he didn’t know this Internet marketing.

He didn’t understand how to put butts in seats, how to create a seminar, how to create a room. I produced over 450 events at that time and so he’s like, “I don’t know how … I know how to buy and sell houses. I know how to teach people to do that but how do I do this other part? This whole marketing thing? How do I create a product? How do I create a seminar?”

So I created all that and his job was to do the content. So we went from zero to a million dollars in one year. And before that I was doing consulting so that’s kind of the beginning of everything. And that’s what I do today.

[tweet_box design=”default” float=”none”]It doesn’t matter what the content is. You could be selling, or teaching widgets, or selling widgets. I don’t care. Marketing and sales is the same. #WingsPodcast #WomeninBusiness @hhavenwood[/tweet_box]

It doesn’t matter what the content is. I mean, you could be selling, or teaching widgets, or selling widgets. I don’t care. Marketing and sales is the same. How do you get a butt in seat, how do you drive traffic, how do you get a call? All those pieces of sales of marketing, copyrighting, that’s my expertise. So that’s what I do now.

Melinda Wittstock:         And so what was the calling to write Sexy Boss?

Heather Havenwood:     So after my bankruptcy and foreclosure, which was in 2006. And by the way, to connect the dots here, so we built the business from zero to million dollars in one year. That business is still viable today and then he’s still kicking it, that dude. But he came in one day … I left for a basic event and everything was gone. So he took bank accounts, money.

Melinda Wittstock:         Oh, my goodness. I’m so … Oh, how awful.

Heather Havenwood:     Yeah, so I came home after three day marketing event all excited to tell him about the newest greatest thing I just learned in that basic event and came back and my house was … My house was [inaudible 00:51:07] foreclosure within five days but it took 60 days to go through the process. And then I was in bankruptcy within 6 months. He just took everything. Just completely wiped me out while I was gone.

Melinda Wittstock:         Oh, my God.

Heather Havenwood:     So that’s what through me in to this, “Who am I? What am I doing? I live on people’s couches. I sold everything I had. Lived in my car.” Through ’06, ’07, ’08, takes awhile for all that to kind of transpire and then I had a good friend of mine, Joe Sugarman, who’s the forward of my book …

I moved to Austin ’09 and he looked at me … I went to go visit him in Vegas and he looked at me and I think it was like ’11 or ’12. He goes, “You’re like a sexy boss.” And I said, “What does that mean?” He goes, “Well, you’re a sexy boss because you own all areas of your life. You’re sexy as a woman, you own that femininity and then you’re like a boss ’cause you own all areas of your life.”

And he goes, “I think you should write a book and help other women.” And of course I was like, “All right, no one wants to hear from me.” That thing. I didn’t really write the book to make it what it is today. I wrote it for me.

You know, I wrote it to get my story out ’cause I was really ashamed. There was a lot of shame ’cause you got to remember my family was like, “This is stupid entrepreneur thing. Stop doing that just get married, have babies.” And then I’m like, “No, I’m successful.” And then I fall. I fell completely and I’m broke and they just had this like, “See, I told you.”

I was really ashamed and very, “Maybe something’s wrong with me.” I went through all of that and I was really ashamed and a friend of mine Alex Mandossian, at one point around ’07, said to me, “One day you’re going to write a book about this.”

And I think I pretty much said the f word to him a couple of times. Like, “No, I’m never going to tell …” ‘Cause I was so ashamed. There was no way I was going to share this story.

Melinda Wittstock:         Right, because it felt like it was about you. Like it was your fault and what’s so interesting is I’ve known entrepreneurs who … God, I’ve had all kinds of ups and downs financially and I’ve known entrepreneurs who …

Like one woman I know had like a $500 million exit but then her next start up left her living in her car. Okay, but then she came back from that to have an exit of like $200 million. So, right? This is part of the thing.

Heather Havenwood:     Part of it.

Melinda Wittstock:         So, when you hang out with other entrepreneurs you realize that everybody looks really successful around you but they’re not necessarily.

Right? Like they’re all struggling. So, when we compare ourselves to other people we know our own crap. We know all the stuff, all the stuff we are ashamed of, or judgmental of, or whatever within ourselves. But we’re comparing that to other peoples’ highlight reels.

Heather Havenwood:     Here was my intention, write the book and if one person buys it, it’s a success. That was it. That was my entire intention. I wrote the book in 90 days, everything. Whole thing.

Melinda Wittstock:         Wow.

Heather Havenwood:     90 days. Including the audible and then about a week, or two, after I launched it someone reached out and said Ryan Deiss just did a full blurb on you on Amazon. I’m like, “Oh, no really?” So all the stuff that you see people saying positive things about it, I’ve never did a launch with that book is what I’m trying to say.”

You know those launches where it’s like, “Launch. Yes, call your friends.” I didn’t do any of that. I just launched it. Got it out of me. I kind of birthed it. Like, boop, there it is. Boop. And then I had all this backlash. Here’s another thing I learned, don’t ask permission. Talking about being over-coached.

I did not ask permission. I did not go around and ask people for permission to write this book. I didn’t do any kind of marketing testing. I did it for me.

Heather Havenwood:     So I had men come up to me and say: “My wife doesn’t want to be a sexy boss.” Or, “I don’t like that.” They had all these negative connotations to it.

Melinda Wittstock:         They were threatened by it. Right? That says it all. “I don’t want my wife to do that.” Wow.

Heather Havenwood:     And what was interesting about that … Is that I didn’t ask for permission and then people start coming out of the woodwork telling me how great it is. Like the concept, not the book, but the concept of being able to say, “I’m a sexy boss.”

They can own that piece of themselves. And that was the intention for me. It was more about me owning that piece of myself. Is being okay with a woman, being okay with your charismatic energy. Think of [inaudible 00:56:32] chapter 12, Sex trains mutation. That book is about owning your sexual energy. The whole chapter is about that.

And that’s what Sexy Boss is about. And I’ll never forget there was a guy locally here in Austin, he did, he pulled me aside and he had this look. He was like, “Look, I don’t think women want to be a sexy boss.”

He said it like that. And, now, I was nice ’cause I was being nice at the time. That moment, I was being nice. I’m not always nice. And I look at him and I just smiled and I’m like, “Okay, well thank you for the feedback.” You know, or something like that.

But I wanted to say to him, “I know your wife. And I know who runs the pants in the family and it ain’t you. And I’m clear she’s a sexy boss and she’s the boss of you and the entire family and if it wasn’t for your wife you wouldn’t be here.”

Like I’m clear what that relationship looks like, right. ‘Cause I know his wife, his wife is a bad ass. So I’m like, “Okay. Yeah, you don’t know your wife very well ’cause your wife is a sexy boss my sweetheart.” But I just let it go. I think that people are threatened by it. People are threatened by when men, or women, own who they are.

They are threatened by that power because there’s a huge power when women own who they are on a feminine level. There’s power there. I think of Beyoncé. Now, here’s the challenge and with Beyoncé, musicians, and Madonna, and people in that space it is acceptable for them to be powerful. They’re musicians. It’s not always acceptable in the business world.

Melinda Wittstock:         Right, right. And sometimes I think women are afraid of stepping in to that power because they think they won’t be liked. We’re all so concerned about how other people see us. I think more so maybe than men because just relationships are important to us.

And so, particularly, what other women are going to think of us.

Heather Havenwood:     Oh, that’s been a big one for me ’cause I’ve had women come up to me and say they didn’t like it. And that to me stings more than a guy. It’s always stung more when women doesn’t like what my work … For some reason it just stings more than a man. I don’t know why that is. Men I’m like, “Whatever. You don’t know what you’re talking about.”

But I just hold women up in a higher caliber or something but I also know that part of them they have been taught to … Let’s just call it hide their sexuality and so here they see a women who just owning who she is on all levels. On the energetic level sexuality is an energy of sexuality. It’s called charismatic energy when you own that you’re more charismatic. You’re more powerful.

I’ll never forget, this is a great story, there’s a guy who you and I both know probably in the industry. He’s at my event and there was a time in my life that I wore turtlenecks and I wore real boxy big suits and flats. Knowing me now you’d be like, “What?” But I did.

And he said to me at this event … He called me out, publicly, in front of all these people and said, “You need to be wearing a skirt. You need to be owning who you are as a woman.” And I was so pissed. I’m like, “Who do you …” I was pissed. So the next day I came down in the seminar and 200 people and I wore a skirt, and heels, and a blouse. Okay.

And I was kind of like coming in going, “I’ll show you.” Or something. I don’t know what I was thinking really to be honest. And I walk in and he stops the whole seminar. The whole thing, 200 people, and stops it and makes everyone turn around and has me stand up. And he’s like, “You are more powerful today. You are powerful in that skirt. Own it.” And it was like, “What?”

Because in my view … where I grew up, being a woman was bad! You know, because you’re a woman in a man’s world Heather. You’re in business. You should act like the men. I was told that for a long, long time.

So here’s this guy, powerful guy, in front of this room going, “You’re more powerful today wearing that than you were yesterday. Be a woman. You’re more powerful being a woman than being a woman whose trying not to be a woman.” And it was just like, “What?” This is way before Sexy Boss.

Melinda Wittstock:         But this is so true. It’s like how to be authentic. Be ourselves and own the concept of feminine power, feminine strength.

Heather Havenwood:     Yes.

Melinda Wittstock:         Strength … Men do not have a monopoly on power and strength. Women can have those characteristics in a uniquely feminine way and I think this is where we’re headed.

And I think also the more evolved men are understanding that they, likewise, can be more heart centered.

And a little bit more intuitive and in touch with their feminine in a way. So we all kind of step up to being a little bit more balanced in that archetypal masculine, feminine sense.

Heather Havenwood:     Yeah.

Melinda Wittstock:         So, Heather, you know I could talk to you on this podcast for hours there’s so much to talk about. You’ll have to come on again but as we wrap up tell me just your vision? Where are you going? What’s the next big thing for you in the next year, five years, where are you going?

Heather Havenwood:     So where I’m going right now is I am really focused on helping more entrepreneurs become more successful, specifically females even though 60 percent of my clients are men.

So I’m really wanting to focus more on female entrepreneurs and helping them grow. Specifically, I have a mission in life to have all women to be self-sufficient.

Financially, because I know when women are self-sufficient financially they’ll make new choices in their life, relationships and whatnot. They will make different choices than they are in the moment if they feel trapped.

So that’s my big goal and big why. I’m focusing on marketing, coaching, and sales coaching. I feel like women need more help at sales. When you get sales, then you can market. Sales is the first step before marketing, believe it or not.

Get the sale, get the sale, then you get the money to get the marketing. That’s how I see it. And so I want to help more women get more sales and so I do a couple things, Chatbots, hold conversation around that. And then I also do Podcast launching and I just do hardcore marketing and sales coaching.

Melinda Wittstock:         Wonderful. So how can people find you and work with you?

Heather Havenwood:     A callwithheather.com. Callwithheather.com, that just goes right to my calendar. Get on the phone call. It’s just me. There’s no pre-sales person.

I really just want to have a conversation with them and connect. Heatherhavenwood is my main site and then my bot, which you and I have talked about, is askheatherann.com.

So this is my Optin. So I’m actually forwarding you to my Optin. Askheatherann.com and it’ll open up Facebook messenger and you’ll have a conversation with my bot and at the end of it you’ll get a free … Three free chapters of my audio book. That’s askheatherann.com.

Melinda Wittstock:         So Heather, thank you for putting on your wings and flying today.

Heather Havenwood:     Thank you Melinda. I appreciate your time. Thank you so much.


Subscribe to Wings!
Listen to learn the secrets, strategies, practical tips and epiphanies of women entrepreneurs who’ve “been there, built that” so you too can manifest the confidence, capital and connections to soar to success!
Instantly get Melinda’s Wings Success Formula
Review on iTunes and win the chance for a VIP Day with Melinda
Subscribe to Wings!
Listen to learn the secrets, strategies, practical tips and epiphanies of women entrepreneurs who’ve “been there, built that” so you too can manifest the confidence, capital and connections to soar to success!
Instantly get Melinda’s Wings Success Formula
Review on iTunes and win the chance for a VIP Day with Melinda
Subscribe to 10X Together!
Listen to learn from top entrepreneur couples how they juggle the business of love … with the love of business. 
Instantly get Melinda’s Mindset Mojo Money Manifesto
Review on iTunes and win the chance for a VIP Day with Melinda
Subscribe to Wings!
Listen to learn the secrets, strategies, practical tips and epiphanies of women entrepreneurs who’ve “been there, built that” so you too can manifest the confidence, capital and connections to soar to success!
Instantly get Melinda’s Wings Success Formula
Review on iTunes and win the chance for a VIP Day with Melinda