Sexy Boss with Heather Ann Havenwood

Sexy Boss with Heather Ann Havenwood

Heather Ann Havenwood

Heather Ann Havenwood is a serial entrepreneur whose early career accomplishments include starting an online publishing company and taking it from zero to a seven-figure revenue in less than a year. She is also a prolific author—with titles ranging from dating to podcasting to entrepreneurship—and has been named one of the Top 50 Must-Follow Women Entrepreneurs for 2017 by Huffington Post.

Heather joins the podcast today to share insights from her newest book, Sexy Boss: How Female Entrepreneurs are Beating the BIG Boys While Changing the Rule Book for Money, Success and Even Sex. Listen in to hear the important lessons she learned from the struggles along her entrepreneurial journey, as well as her advice for female entrepreneurs to help them become a powerful force in the world.

If you enjoy the show, please drop by iTunes and leave a review while you are feeling the love! Reviews help others discover this podcast and I greatly appreciate them!

Listen in:

On Today’s Episode We’ll Learn:

  • The critical lesson entrepreneurs tend to learn the hard way.
  • What Heather learned after going from a million dollars in sales to being broke and bankrupt.
  • Why business focus can be both good and bad.
  • What Heather means by “sexy” in the context of her book.
  • The stereotypes attractive women face.
  • Mistakes to avoid when following Heather’s “sexy” advice.
  • Tips for being a great podcast guest.
  • Advice for women weighing entrepreneurship against a traditional job.

Key Resources for Heather Ann Havenwood:

Share the Love:

If you like The Brainfluence Podcast

  • Never miss an episode by subscribing via iTunes, Stitcher or by RSS
  • Help improve the show by leaving a Rating & Review in iTunes (Here’s How)
  • Join the discussion for this episode in the comments section below

Full Episode Transcript:

Get Your Full Episode Transcript Here

Welcome to the Brainfluence Podcast with Roger Dooley, author, speaker and educator on neuromarketing and the psychology of persuasion. Every week, we talk with thought leaders that will help you improve your influence with factual evidence and concrete research. Introducing your host, Roger Dooley.

Roger Dooley:    Welcome to the Brainfluence Podcast. I’m Roger Dooley. Our guest this week is one of my earliest Austin friends. When I first moved here I attended and spoke at a few digital marketing events, and one of the first people I met was Heather Ann Havenwood and I’ve enjoyed seeing her progress both as an entrepreneur and as an author. Heather Ann is a serial entrepreneur who earlier in her career started an online publishing company and took it from zero to seven figures revenue in less than a year, and she’s got a story about that that I think she’ll tell us.

Heather Ann is a prolific author with titles ranging from dating, podcasting, to entrepreneurship. Her newest book is Sexy Boss: How Female Entrepreneurs Are Beating the Big Boys While Changing the Rule Book for Money, Success, and Even Sex. She also has a book about how to become a great podcast guest so be sure you’re taking notes.

Welcome to the show Heather Ann.

Heather Ann:      Thank you. Thanks for having me, and you’re correct. You were one of the first people I met as well when I moved here to Austin.

Roger Dooley:    Really? Wow, that’s interesting.

Heather Ann:      Yeah, it was like 2010.

Roger Dooley:    Well you probably were here the week before so it seemed to me like you were an old timer in Austin.

Heather Ann:      No, not an old timer, but I came here around ’09, ‘010.

Roger Dooley:    Well, that’s just about when I started so yeah I guess so. Okay, well that’s really interesting to know.

So, Heather Ann, one thing that most people probably do not know about you is that you have been a body building competitor. That’s got to take tremendous discipline, both for working out and dieting and so on. Tell me about that experience. What’s it like?

Heather Ann:      So, it’s very challenging. I still do it to this day. I work out four or five times a week, and back in 2015 my 40th birthday I got in a tiny little bikini and asked people to judge me. So, as I’m having cake that day I got in a tiny little bikini and I asked people to judge me and got all tanned up.

Roger Dooley:    That’s bravery.

Heather Ann:      It was bravery. I had a really good time. But, it was hard for me because, you know, I don’t know, I think it’s just getting older or whatnot but it was one of the most challenging things I did. So, I haven’t competed in a while and I would like to compete again, but I still workout five days a week.

Roger Dooley:    Well great. Good for you.

Heather Ann, the foreword to sexy boss is written by the legendary copywriter Joe Sugarman, and he’s the same guy that sold millions of Blu Blocker’s, sunglasses that is, or glasses. I’ll tell you my Joe Sugarman story. I had already developed my persuasion slide framework for thinking about just about any kind of persuasion problem whether it’s online conversion, or in person sales, or just about anything else, and it was loosely based on BJ Fogg’s behavior model, BJ Fogg from Stanford, and after writing and speaking about it I decided to actually write a short book to expand on the concept and while I was researching that I found a direct mail error book about copywriting by Sugarman that said “Your advertising copy should be like a slippery slide. Once the customer starts down it it’s inevitable they’ll get to the bottom.”

Now, my framework is a little bit more detailed than that but I was really happy that a smart guy like Joe also thought a slide was a good metaphor for that process. How are you connected with him?

Heather Ann:      Obviously I’ve known him, I started in the information market industry since 2001, and what that means is I’ve traveled the country with so many different people and produced over 450 events, and so I think I met him … I was trying to figure that out the other. ’05, ’06 maybe? I’m not sure. At an event, we just kept in touch.

And then in ’08, ’09 I just stayed in touch with him, we’re dear friends, and 2013 he actually was the one that coined the term “Sexy Boss”. It was actually 2012, I’m sorry, with a book in 2013. He coined it in 2012 and he looked at me one day while we were having salad together in Vegas and he’s like “You’re like a sexy boss.” And then I think he went and got some ice cream. He’s really adorable, but he’s also very connected. He’s so smart and so intelligent. He actually helped me create the sub-headline as well of the book as well.

He sent me his books in ’07, ’08 right? So, here I am bankrupt in ’07, ’08 after my first million dollar business and I’m sitting there and he called me to see how I was doing, and he sent me this huge box and the box was all of his books, and I read all of them, and I have one right here sitting next to me called Triggers. This is one of my favorite books, and actually one of my opt-ins on one of my websites, if you opt-in you get three free chapters of my audio book, but you also get four chapters of the audio version of Triggers. There was some guy over the years that actually interviewed him, there’s 30 triggers and he interviewed Joe on all 30. That’s one of my opt-ins is actually part of that. You can’t buy that audio anyway, you can’t buy it on Audible so it’s kind of a collectors item.

Roger Dooley:    No, you know, I think that there are so many people who are younger than me at least that don’t recognize that there’s been great copywriting around for years and years, and what makes a good headline hasn’t necessarily changed that much. You know, people think that this is like a new science of creating click bait and stuff that people will read, but wow, if you look at some of the work of the ad greats this stuff is timeless, and I think Joe’s stuff falls into that category.

Heather Ann:      Oh, he absolutely does. I mean, he really taught me. I love the slippery slide slope, that’s actually in his Ad Week workbook, you can get that at Amazon, and he talks about that. You take someone to the top of the slide and then you drop them down, remember the ’80’s when we had the slides that went right into the pool? I don’t think they have those anymore, but that’s what I grew up on and I just love that analogy because it’s true. That’s what good copy does.

And if someone is thinking to themselves “Oh, well I don’t need copy.” You use it for everything. Email marketing, email communication, texting, I’m done dealing with chat bots. Chat bots is this whole revolution with Facebook Messenger, but everything I was taught and use every day with copywriting I’m using in chat bots because part of the process is we want people to stay engaged like a slippery slope.

So, it all goes back to copywriting and in 2013, in October of 2013 right after I launched my book Joe Sugarman and I did an event called “Success Magnet Seminar”, and in that event it was me and him were the headliners, and then we had some other amazing headliners, I think that they were more headliners. Joe Sugarman, John Carlton, John Benson, and Joe Polish were all the speakers there, and what was interesting about that event Roger is that I had a lot of people who called me, text me, or emailed me later after the event and said “Yeah, I saw that. I thought it was not real.” Because the lineup was so incredible you know? They just said “Oh, that can’t be real.” Right?

So, they didn’t go, but who was in the room was not only those guys but all of their followers. So, in the room, like the people who were participating in the room, like the attendees were like Harlan, and Neville, all these other amazing copywriters. They all were there because they all want to see their guru’s you know?

So, just the people in the room were amazing. So, I had a good event., which is where the event is.

Roger Dooley:    Yeah. So, Heather Ann the title of your book Sexy Boss seems like it’s either brilliant or disastrous these days. After Harvey Weinstein, and Me Too, putting the words sex and boss in the same phrase will make some people cringe anyway, but sometimes zigging when everyone else is zagging is a good thing. Have you had any blow back in the last few months?

Heather Ann:      I haven’t had blow back, but I’ve had people say that to me like “You need to be careful.” Or whatnot. And I understand that. I completely am sensitive to that. At the same time, if you read the sub-headline it really is about women empowerment, and the sexy boss is owning who you are as a woman and understanding that there’s two elements. The sexy is a charismatic energy. It’s the feminine and masculine energy together, it’s the feminine energy and owning that. And the boss is just owning all areas of your life.

And if you think it’s sexist, well then I guess you think Grow Rich by Napoleon Hill is sexist because if you read that book chapter 12 is called “Sex Transmutation” and what he’s talking about is charismatic energy, and he calls it sexual energy right? And that’s a time tested book that was wrote in the ’30’s.

Roger Dooley:    Yeah, and still hits the best seller list from time to time, which is just amazing.

Heather Ann:      Yeah. So, my book is about my personal story of how I went from zero to a million dollars in sales in a business, very successful, and the next year I was completely broke and bankrupt and then how I-

Roger Dooley:    Why don’t you tell that story Heather Ann? I think we’ve certainly got a bunch of entrepreneurs among our listeners and it’s a great tale, both the start, the middle, and the finish.

Heather Ann:      Yeah. So, Joe Sugarman is the one who taught me everything happens for the best, not reason but best right? And when he speaks he’s actually really the person that kind of helped me write the book or have the courage too. When he speaks all he does is the whole presentation to the very end he talks about all of this failures. Now, everyone knows if you listen to him he’s the CEO of Blu Blocker’s sunglasses right?

So, the point is that failures, we learn from failures. So, what happened for me was I was in the information marketing business for many years in 2001, and then 2005 I had a coaching client approach me and say “Hey, I’m a speaker and I teach people how to buy and sell houses. I’m really good at that thing, but I don’t know how to market myself. I don’t know how to position myself or brand myself. This whole internet marketing thing, what’s that?” Right? “How do I get people in a room? How do I get butts in seats? How do I put a program together? I don’t know how to do all of that, can you do that?” I said “Yeah. So, okay, let’s partner.”

So, I did all of the marketing, and sales, and branding, and messaging, and we went from zero to a million dollars in one year. That business is still viable today, he does very well, it’s just that I guess he got greedy and he kicked me out of the business and took everything and I was emptied the bank accounts and he’s still kicking it today and doing well.

So, I though got thrown into bankruptcy and foreclosure within 60 days, and bankruptcy within 6 months because he had left me with a lot of the debt of the business, and I was so focused on that one business that I didn’t have any backup. I didn’t have something else going on. I dropped everything else and focused on that.

Roger Dooley:    Which is a reasonable thing when you’re achieving a lot of success.

Heather Ann:      Mm-hmm (affirmative). It is achievable. I’ve learned quickly though that, one … Here’s my lessons. One, always have a lawyer, write your own contract. Number two, maybe don’t do business with lawyers because he was a lawyer. And then lesson number three, yes focus is key, and driving something up is key, but always understand that markets change, and a lot of people that had business focused on Google, or Facebook, and one change on Google or Facebook and their whole business would collapse.

So, yes focus is good, but only one basket’s not.

Roger Dooley:    Right. Yeah, definitely, and that’s really been sort of a watchword of what I’ve been doing in my entrepreneurial efforts, not so much lately, but certainly earlier I always tried to have both within a company multiple revenue ideas or streams so that if something went bad, and things did go bad.

I started my entrepreneurial career with a mail order company that I co-founded. We were selling computer products to the earliest owners of home computers, and I bailed out of a really good corporate job that I really liked because it started as sort of a side gig and it started to get traction.

So, within a couple of months of leaving my cushy corporate job and becoming an entrepreneur with a limited income and certainly no guaranteed income the company that we were focused on, Texas Instruments, pulled out of the market completely. They just said “Oh, we’re done.”

Later on, a few years later we had to cope with the bankruptcy of another giant supplier, TI didn’t go bankrupt they just pulled out, but Commodore Business Machines went bankrupt and they were a huge factor in the consumer marketplace until they weren’t. You never know what’s going to happen, but in each case we did have already some other revenue streams going so that it didn’t kill the business.

Heather Ann:      Right, versus all just on one product, or in our case one media right? Or just one product. It’s a really critical lesson that I think a lot of entrepreneurs just don’t learn, or they learn the hard way like I did right? That markets change. Markets do change, and they do drastic change, especially online so that’s a big one, or you just have bad business partners, which there’s not much you can do about that.

Roger Dooley:    Good contracts, because I’ve had not the same experience as yours, but a couple of experiences where clearly a better partnership agreement, or contract, or whatever up front would have made a world of difference and saved me some grief, and difficult negotiations, and in some cases quite a bit of money.

So, that’s something that I think the thing is Heather Ann that when you’re starting off a business maybe sales are zero, it’s like there’s not a lot going on so how important can all of this stuff be?

Heather Ann:      Yeah, that’s kind of what happened. You’re just excited to get started and you’re just like “Oh, we’re going to make money but don’t worry about those contract things we’ll just get going!” Or there’s nothing to really put in contract about because there’s no money yet. Exactly, that’s happened to me and some of my friends as well, but also when it happened I remembered something that one of my mentors said. They said, I was definitely crying when I was talking to this person, I was in tears, I was very much into victim mode. Poor me, what happened to me, I’m smarter than that, why’d this happen to me. I was very much in a victim mentality at the time and he goes “If you don’t like to get hit then get off the field. Welcome to entrepreneurship.”

And I’m not saying that everyone has to go through what I went through but it is a part of it. You have to understand that you will get what I call hits. It’s like being in football. If I was a Dallas Cowboy, because I’m a huge fan, and I went to my boss Jerry Jones and said “I don’t want to get hit today.” He’d say “Then get off the field and give me back my money, and give it all back to me.” So, “Give me back my uniform and get off the field. If you’re not willing to get hit then you’re not willing to take the ring of the Superbowl.” You know?

And I think it’s the same conversation with entrepreneurship is that people come to me, I don’t know if they come to you Roger, but they come to me and say “I want to build this business but I want to make sure that this idea will work.” I’m like “Well, good luck with that. I have no idea. We can look at stats. We can look at data. We can look at we think it will work based on this information but do we really know? Do we know what’s really going to happen tomorrow? No.” So, that’s entrepreneurship.

Roger Dooley:    Right. And I think hopefully most of our listeners won’t have a business partner drain their bank account and disappear, but I guarantee you that anybody who has gone through a business formation process and growth process is going to have some pretty serious episodes where it seems like the whole world is crashing, and being ready to deal with that and not necessarily letting it stop your ambition I think are the important pieces.

So, Heather Ann when you use the word sexy probably most people think of actresses, or swimsuit models, or something like that, but why don’t you expand a little bit on what you mean by sexy in the context of your book?

Heather Ann:      Sure, and thank you for the opportunity to say that.

So, in the context of my book sexy is owning who they are as a woman, and owning that feminine energy. And so going back to the book Think and Grow Rich in chapter 12 “Sex Transmutation”, what he talks about is there’s a charismatic energy. So, I’m going to take someone that’s not me add to the equation, 007, we’ve all seen the movies of 007. This charismatic guy who walks in the room and he’s all like dapper right? And we’re like “Oh, who’s that?” There’s this energy about him, he just has that swagger. That’s the confidence right? And we’re attracted to that as other human beings. We’re attracted to that confidence on some level.

And that’s what I’m pointing to with women is that women are just now allowing themselves to have presence and walk into a room and go “Yeah, I know what I’m doing here. I belong here. I have a presence here.” That’s the energy, that’s the sexy. We call that in men’s world “Oh, that’s charismatic. That’s sexy.” But when a woman walks in the room and she has that same “I own it.” We sometimes call her a B, and I want to reframe that.

However you did something really interesting. In the world of artists, like music artists or musicians it’s okay to be sexy. I’m thinking of Beyonce, she owns that. You think of Pink, she rocks it. Madonna, they’re like power houses. But there is an okay to be allowed there because they’re musicians, or actresses. Jennifer Aniston, and on and on. Sometimes even politics.

But when it comes to business lots of times women are told “Okay, that whole charismatic sexy, you need to just bring that down.” I’m like “No, no. There’s an energy to that. There’s a powerful energy to that that you can really bring that confidence in all areas of your life, not just being a musician or an artist.” And that’s what I’m bringing to and pointing to.

And the reason I bring that up so powerfully is because I was at a point in my life that I was constantly trying to hide that. People would say to me “Heather, you’re sexy in a burlap sack, can you tone it down? Can you put a big old turtleneck on you?” It’s not because I have boobs guys, it’s because I have an energy. I don’t want to hide that anymore and so I want to be able to own it, and I want to give other women the permission to own power, own their own energy.

And again, this is time tested success principles. Think and Grow Rich, Napoleon Hill, chapter 12, read it, he talks about it, I’m just adding a spin to it and focusing it on women specifically.

Roger Dooley:    Yeah. You know, I think for years in business women who are in sales have used that a little bit more. I think its perhaps been just helpful in connecting with customers for the first time whether they’re pharmaceutical reps connecting with doctors, where there’s been a tradition, not so much these days I don’t think but probably 10 or 15 years ago, most pharmaceutical sales reps, not all. I had one friend who was a middle aged guy, many of them were relatively younger women, and they tended to dress, not inappropriately, but they didn’t try and hide the fact that they were women either, and certainly I think I’ve seen that in real estate too. If you look at many successful real estate people they seem to be owning that persona.

But when it comes to managing a business that seems to be a different area. Has that been your experience?

Heather Ann:      Yes, absolutely. There’s these specific niches that I think society has allowed that. You know, real estate, realtor specifically. Actor/actresses, artists, but there’s this whole other world, you know, lawyers are starting to. There’s this whole other world called just being a business woman and I’ve been told many times by other people “Tone it down.” Or blah, blah, blah.

I remember, just to give you an idea, when I was going through the bankruptcy and all of that stuff and I was kind of coming out of it and I went on an airplane, I don’t know where I was going, it was probably an event, and I sat next to a stranger, a gentleman, and I was kind of just sharing my life. Like “This is what’s going on in my life.” You know, “And this is where I’m going, and I’m building my life back.” And I’ll never forget it. He took his hand and he kind of just patted my knee and he said “Don’t worry sweetie, it’s okay. You’re pretty. You’ll get married.”

Roger Dooley:    That was very empowering.

Heather Ann:      Right. There has been a lot of that in my life. I’ve had not only that stranger, but that’s just to give you a snapshot. I’ve been told that a lot like “Okay, you’re pretty. That whole entrepreneur thing, you can stop now because you’re pretty and you need to get married and have babies.”

Roger Dooley:    Sort of, yeah, “Go to college, get a degree and you’ll find a husband along the way.”

Heather Ann:      Right. I was bred to be a MRS degree. You know what that is?

Roger Dooley:    Right, the Mrs degree.

Heather Ann:      I’ve had men in my life who I was in a relationship with that said “Okay, that whole entrepreneur thing, you can go ahead and stop now.” It’s like a phase you know? “You can go ahead and get a job now.” I’m like “No, I don’t think you get it. This is who I am.” And people have their own view on that, whatever that view is.

Roger Dooley:    Well, you’re breaking a couple of stereotypes there. Not just the stereotype of a female who is in business, but I think that for most people a traditional job is sort of the acceptable thing and being an entrepreneur is kind of weird. Although, these days with Shark Tank and so on I think entrepreneurs are getting a better name, but certainly a few years ago that was not the case.

Heather Ann:      Correct, but it’s also personal. So, it’s a very personal thing. I think I’ve finally got on my journey who I am. Who I am is an entrepreneur, and when I got that’s who I am on a core level it doesn’t matter if I have a business or not right? So, it’s like an athlete. When an athlete gets who they are as an athlete it doesn’t matter what game they play sometimes. Maybe they’re Michael Jordan, he played NBA, then he went to baseball, then he went to golf. It didn’t matter. Who he is is an athlete.

So, it’s like that and when you get who you are at a core level it doesn’t matter for me as a business owner, as an entrepreneur, I can create something, it can work, it can fail. I’m not attached. I’m not attached to the outcome as much. Do I want it to be successful? Yes. However I just build another business from zero to 1.5 million in sales and sell my company here in Austin. That business is going through a transition and my ex-business partner is going to take the business over. I’m starting something from scratch again.

So, I think that that’s a very powerful view to come from when you get who you are, versus trying to be a business owner, trying to be an entrepreneur, and trying to make one thing work versus just giving that’s who you are if that’s who you are.

Roger Dooley:    Yeah. You know, Heather and I suppose a few readers might look at the title, and skim a few pages, and then go out and buy some new stiletto’s and a push up bra or something. Are there some mistakes women should avoid in trying to follow your strategies?

Heather Ann:      Yeah, so leading with sex is very different than owning who you are as a feminine woman. So, going back to my days I used to travel the country and I would literally wear turtlenecks and really big, huge, boxy outfits. Try to cover up that I was woman. Try to cover it up because I want to be smart, I want to be intelligent, and that’s what happens a lot. I hear that a lot from women.

Versus around ’08, ’09 I had a person that you and I both know probably in the industry, he said “You need to wear a skirt.” Now, when he said that to me I was really mad at him. I was like “Who do you think you are?” I was very mad. So, the next day I came to the event in a nice skirt, and heels, and a blouse, I looked like business, and he pointed me out to the entire event, 200 people, and he goes “That is more powerful. You being in a skirt, owning who you are as a woman is power. You’re constantly trying to cover it up.” And that’s when I got it. He wasn’t trying to be sexist he was just saying own yourself, own you’re a woman, wear a skirt. I’m not saying a really high one, but the point was when you own who you are, whatever that is, there’s just power in that.

Roger Dooley:    Well I think that’s a really good message. That must have been a defining moment for you Heather, when a light bulb went off in your head.

Heather Ann:      Especially having 200 people turn around and him-

Roger Dooley:    Yeah, that would be kind of strange too. Having your appearance and clothing commented on by somebody.

Heather Ann:      And for a very long time until I finally understood what he was trying to say, you know? He wasn’t saying that I was weak because I was a woman, he was saying you’re weak because you’re trying to cover up you’re a woman. When you own you’re a woman and just be comfortable in that that’s when you’ll get your power. I think that’s what Sexy Boss is all about.

Roger Dooley:    So, you used the word entrepreneurs in the title, or the sub-title of the book. If you were talking to somebody, a woman who was weighing an entrepreneurial opportunity versus a job that presented reasonable prospects for pay and promotion, how would you advise them to make that decision?

Heather Ann:      I would say take the job, and I mean that in the most loving way because honestly entrepreneurship is challenging. It just is. Anyone who tells you it’s a dream is lying to you. It’s fun, there’s a lot of opportunities, but it’s not stable right? So, there’s a lot of ups and downs sometimes, it depends on your business that you choose, and if you’re looking to build a family and whatnot sometimes having a corporate job would be better.

You know, there’s so many times in my life personally Roger, you probably don’t know that, that I have like “Oh, be great if I just worked for the government and I made like $150,000.00 a year and I got all of these things called holidays off and stuff. [inaudible 00:25:33] and they do like sick pay stuff.”

Roger Dooley:    Yeah, leave work at 5:00PM and not think about it.

Heather Ann:      Right!

Roger Dooley:    Yeah.

Heather Ann:      There’s this thing called happy hour at 5:00, that’s really weird, that would be kind of fun.

So, there’s a lot of stuff. The other day it was President’s Day and someone goes “Are you going to work?” I’m like “I didn’t even know it was President’s Day. It’s a Monday for me.” You know?

Roger Dooley:    Yeah, didn’t even notice. I’ve done that even for more major holidays because not everybody celebrates President’s Day but I’ve been working on a Monday, and “Gee, nobodies answering my emails. What’s going on here? Oh, gee, today’s a holiday in the US.”

I think that while you were talking it occurred to me that one way to answer that question is if you have to ask the question about this entrepreneurial opportunity versus a job maybe it’s not the right entrepreneurial gig for you because really I think if you’re going to be successful as an entrepreneur you’d have to have such fire in your belly for that particular opportunity that you wouldn’t really too seriously consider a job, unless, I mean obviously at some point the pay and the prestige and whatever might be worth it, but by and large if you don’t feel compelled to do it, that the world needs you do this it’s probably not the right thing.

Heather Ann:      Absolutely. I have clients all of the time, they’re like “I want to be an entrepreneur.” And I’m like “Do you have something that you really want to do?” I honestly believe that entrepreneurship finds the person, a person doesn’t find entrepreneurship. Every person I know that’s really successful in our world, in the entrepreneurship world they always have this story right? That they’re like “Oh, I’m going along and then this thing happened and now I’m an entrepreneur. I don’t know how that happened because my family, they’re not entrepreneurs, they’re all working for the Army.” Or something. It’s usually some kind of story like that.

One of my friends Doberman Dan, that’s his name, that’s what he calls himself, Doberman Dan, he was a police officer for like 10 years, and looking at him now because he’s such an entrepreneur and so kind of ADD I’m like “How in the world were you a cop?” He’s like “I don’t know. I didn’t do very well.” So, he laughs about it, and knowing an entrepreneur, he’s a copywriter too on top of that so you’re like “What?” It’s super strange.

Roger Dooley:    A cop-ywriter.

Heather Ann:      He’s a copywriter, was a cop.

Roger Dooley:    Yes. Yes.

Heather Ann:      And I worked for Corporate America for five years, so I think we all start where we start and entrepreneurship kind of is that it finds us.

Roger Dooley:    Right. It takes you over. I know it took me over. I had really in the early part of my career never thought about being an entrepreneur. I mean, I had this sort of vision of a corporate progression, of working for maybe one company, or maybe changing companies once or twice and just moving up that ladder and so on, as was typical a long time ago, but then I got bit by the bug and I haven’t really gone back.

Heather Ann:      I’ll tell you a quick story Roger if you don’t mind about that.

So, when I was starting the process of becoming an entrepreneur, this was when I was 28, 29, and I didn’t really know what I was doing yet, but I was like hanging out and stuff like this. My mom called me, god with her she’s no longer with us, but she called me and she goes “I heard that you are trying to be an entrepreneur.” I’m like “Hi mom. Yeah. You know, well, starting some stuff.” “What are you thinking?!” She was just livid right?

Roger Dooley:    Yeah, something on the level of hearing that you were trying out to be a stripper or something. “Oh my god, are your serious about being an entrepreneur?”

Heather Ann:      She seriously was mad, and then she called back a couple of days later and she goes “I just want to let you know that I found you a job as an assistant at a manufacturing plant in Hope, Arkansas. They pay $8.00 an hour and they have benefits.” Now, what you’ve got to understand, I’m sitting in Orlando, Florida at the time, traveling the country, traveling the world with millionaires right? And I’m making some good money myself and my mom tells me this and I’m like “Mom, really? You want me to move to Hope, Arkansas which is tiny and you want me to drop everything I’m doing for $8.00 an hour? What are you talking about?” You know what I mean?

But I know she’s just wanting to keep me safe, and she was scared as all get out for that whole entrepreneur thing, and I understand she loves me, but you can get that’s how my family looked at it. This whole thing that Heather is doing, I have been doing it for 15 years but they still look at it as “Well, one day she’ll grow up.”

I don’t know if I ever will Roger, but now you understand.

Roger Dooley:    Right. That was actually about the same age. I was probably about 29 or 30 when I launched my entrepreneurial career so maybe there’s something built into our wiring there that you hit that point in the corporate world and start looking elsewhere.

So, let’s change gears for just a minute Heather. You’ve written a book about podcasting but from the perspective of the guest, so that’s kind of an interesting idea. Most people, there’s probably a zillion podcasting books out there but they’re all how to start one, how to host one, how to produce one. What are just a couple of insights that you could share on that end of it?

Heather Ann:      Thanks for that. I love guesting, which is what I’m doing now. I love guesting because I get to share my personal story, I get to add value. How I view it is that I’m in your home. This is your party. This is your home. I’m a guest in your home and I’m adding value to your listeners. That’s my job. That is literally my job when I’m here.

And what happened is I started my own podcast in 2013 called The Sexy Boss Show, and it failed miserably. I did five episodes. I didn’t know what I was doing. The intro music is super cheesy, super bad. Super bad. I call it, it’s in the graveyard. I stopped that because I was like “Well, that whole podcasting thing doesn’t work.”

So, then in 2015 I had a friend of mine who had a podcast and he kind of reached out to me and said “Hey, do you want to be on my podcast?” I’m like “Oh well, that sounds cool. Do I have to do anything?” “No, just show up and talk to me.” “Okay, cool.”

So, I did that, and then about two, three weeks later I had someone on my website email me and go “Hi, I heard you on this podcast. I’d like for you to coach me.” And it became a $5,000.00 coaching client. Now, my little head went off like “Wait a minute. I didn’t travel. I just kind of talked about some stuff I was doing and then I got $5,000.00. Okay, I can do that.”

So, that’s what happened. I started focusing on podcasting. Up until right now I’ve been on about 300 since June of 2015, and I was on 150 before I even started my first show. I came from the view “First give, give, give, give, give.” You know, how can I add value? How can I make someone else’s great? How can I promote your show? How can I just give first?

And I did 150 shows before I said “Okay, now I’m ready to create my own show.” And not everyone has to do that, but that’s how I chose to do it, and then I love, love, love being a guest. I think it’s a lot of fun. I meet great, amazing people, and I give value, I always promote. You know, I always promote their show. Why wouldn’t I? It’s about me. Why wouldn’t I do that?

And I think there’s a huge value add there and so, yeah, I love guesting and so I wrote a book about it in June 2017 with my partner Rob and I lay it out. I lay out exactly what I did because I realize a lot of people say me “How did you do that? How did you get on so many?” First of all it comes from a particular mindset right? Because I give first. Number two, I never say no, meaning it’s rare I say no. I’m not picky.

Roger Dooley:    Gee thanks.

Heather Ann:      What I mean by that is-

Roger Dooley:    I’m kidding you Heather.

Heather Ann:      If someone doesn’t say “I just started my show, I don’t want you to come on until-” I’m like “Don’t worry about that. I want to add value to you. Why would I not do that? Add value to you and to your listeners.” So I’m not picky in that way right? Some people are like “Well I want you to have 10,000 downloads before I ever come on.” I’m like “No.”

Roger Dooley:    Right, yep.

Heather Ann:      And then the other thing is I come from that view is when I approached you, yeah? Is that I have it that this is your party and I want to add value first so I come from that view. It’s like how can I add to you and to your listeners? That’s why I’ve been on so many.

Roger Dooley:    Well, it’s really great advice. I was speaking with a sales outreach person the other day and surprisingly enough this strategy is not dissimilar to what you’re talking about where doing cold outreach so often it’s all about “I, I, I, me, me, me.” And “Here’s how you can help me.” Which is not what most people want to hear. You know, I’ve literally had outreach people say “Hey, I’ve got this new product and I really need more exposure for it so can you write about it or have me on your podcast?” Whatever, and given that there’s absolutely nothing in it for me.

Even if they had said “This is why your audience will find my product interesting.” Then suddenly “Oh okay, hey, that makes sense.” But in one case the person didn’t even say what the product was. It’s like “Well, why would somebody act on that?”

Heather Ann:      It takes a lot to produce a podcast. People don’t understand that.

Roger Dooley:    Well yeah, actually guesting is probably a lot better deal than hosting and producing because that takes time and money.

Heather Ann:      But I always promote. You know, I always promote, I will promote this show and a lot of people don’t. I don’t know if you’ve had any guests not do that but I always promote. I’m going to promote your show. Why would I not? I mean, you’re promoting me, why would I not give back? That’s just crazy.

So, I’ll promote your show. I’ll promote it on LinkedIn. I want to add value to you. I’ll put it through Twitter. I’ll do that whole thing. So, I’ll put it into recur, what would I not? I do actually promote more of other people’s show than I promote mine.

Roger Dooley:    Great. Well, I think there’s a good lesson there for our listeners regardless of the kind of outreach they’re doing whether it’s podcast or something else, think about the person that you’re dealing with and show how you can add value, and you’re much more likely to get a good response.

Hey, we’re just about out of time. Let me remind our audience that we’re speaking with Heather Ann Havenwood. The one and only chief sexy boss, and author of Sexy Boss: How Female Entrepreneurs Are Beating the Big Boys While Changing the Rule Book for Money, Success, and Even Sex. Heather Ann, how can listeners find you?

Heather Ann:      Thanks for having me Roger, I really appreciate it. So yes, they can find me at, and we were talking about bots a little so I’m going to give you a URL right now and it’s going to open up, when you put it into your browser it’s going to actually open up Facebook Messenger and go through their whole bot process so you can experience it. It’s called, again, go to and it’s a chat bot, super cool. Go through the process and you’ll get three free chapters of my audiobook.

Roger Dooley:    Great. So there’s a Heather Ann chat bot in existence now?

Heather Ann:      There is.

Roger Dooley:    Oh very cool.

Heather Ann:      One only. So, goes there, or go to and if you’re interested in having a conversation with me I like to be accessible and open. There’s a click the button called “Call With Heather” and you can get on there, and get on my calendar, and have a conversation.

Roger Dooley:    Great, well we link to those places and to any other resources we talked about one the show notes page at And there will be a text version of our conversation there too.

Heather Ann thanks so much for being on the show.

Heather Ann:      Thank you Roger for having me, its been a lot of fun.

Roger Dooley:    Thank you for joining me for this episode of the Brainfluence Podcast. To continue the discussion and to find your own path to brainy success please visit us at


Join 23,647 smart marketers like you.
Better results, less money! Get my newest, best ideas free!

Leave a Reply