Dating With Online Marketing Success With Heather Havenwood

In this podcast episode, Matt Coffy interviews “Chief Sexy Boss” Heather Havenwood about her online marketing success journey and how she’s using her relationships, acquired skills, and mindset to run highly successful dating and coaching businesses.

Matt Coffy: So we’ve got Heather Havenwood on today on the podcast. Heather say Hi.

Heather Havenwood: Hi!

Matt Coffy: So this is kinda cool. I have a lot of people telling me I should podcast with you because they said you are very unique in that you have a different slice of the market. You do some email marketing, you do some coaching, you have a dating site. Talk to me first about the dating site cause I’m just fascinated with these people who built these dating sites cause I’m upset I didn’t do it first.

Heather Havenwood: I understand that dating is a very different market so let me explain to you how I even got to that place. So I started in business online in what I call the dark response marketing business back in 2001 doing real estate. Teaching people how to buy and sell real estate. I was in Florida, you’re in Jersey I see so we’re get on pill from coming to New York to buying property in real estate and stuff like clump payment and that kinda thing right so I spent almost seven or eight years doing that. In that time frame, I travelled the country and I was learning what I call dark response marketing where you get in front of a room of strangers and you talk to them and communicate with them for 90 minutes and then you have them give you $3000. How do you do that? So I learned this whole process of dark response marketing and then this thing called Blow Up Time of 2005 and 6 and 7, I’m sure you remember that. And during that time, I lost everything and I also had a business. Shocker right? I did. I lost everything. Bankruptcy, foreclosure. Everything went gone overnight. And I ended up living in my car with me and my dog and myself and that was my only bill and I just kinda had this hard look on me and life and like I don’t know what to do here, I thought. Out of this gravy train that just completely went off a cliff. And I just didn’t know what to do and I had all this skillset so it took me a couple of years. I’m kinda sharing the story in a condensed version. That took me a couple of years to come and get out of the mindset of poor me. Okay I’m ready to kick ass again kinda thing?

And what happened is that a friend of mine she said to me hey you should be getting into the online world. And I said well, I don’t know because one, I don’t want to teach people online marketing when I’m broke. That would just sound weird. Like you can make money online, I’m broke but you can. And then I didn’t wanna teach real estate for obvious reasons. Real estate was gone. So they said why don’t you go onto the dating business where you’re teaching men how to talk to women. No one could ever question you on that. And it was true right? I was a female and I was dating men and they were usually older men who were divorced and I thought oh well, that’s true. So I started I took all this stuff I knew about marketing, dark response marketing, email marketing, conversion, opt-ins. All that stuff. Copywriting, branding, and put it into my business on and onlydateyoungerwomen and I did have some help. Perry Belcher and Ryan Dice did publish me at the beginning and so Perry Belcher was my first. He did my first sales letter. He helped me out completely and got me kinda launched and then I took the business and ran from there. So that was in 2008 or 9. So that business is still live today. Now from that process now I’m a coaching business I have a summit business I have a local business. It kinda goes on from there. When you learn how to make money online like the world opens up. So you can just go oh I can go down this niche. So it started to open up different worlds and then that’s why I have the dating business today. So that’s and

Matt Coffy: So that business to me a catalyst or maybe it’s a jumping point for a lot of other things because then you start. Are people paying recurring revenue on that?

Heather Havenwood: No they aren’t. I think that really works is what I call, you know what I mean? Because getting someone to do a recurring on a dating product, relationship product is I won’t say an easy thing. Some people do it but the model like 4-5 months and they fall off. That’s a full model. But this is interesting because I think when someone’s in that space of what I call the dating niche they’re in some kinda pain is what I call it. They had a divorce or for my guys, a divorce and they want to get back in the dating world but they’re like I don’t know how to do this. I’ve been married for 20 years, I got kids. How does this work? So they have a lot of questions and then that’s where I come in. but the dating industry is very different. You probably heard a lot of guys over the years they’ve been paying doing really well in the niche. It’s a broad niche too. The one thing I like about it when I got into it is it was international. And that was akey thing for me because I just got burned by the United States government. And so I kinda had, I want something that’s not connected to the oil prices. The mortgage prices. I want something that’s so unconnected to that and I know that sounds kinda weird but I did. I didn’t want anything connected to the government. So dating is an international conversation. I have clients from all over the world.

Matt Coffy: I do like the fact that your varied and so have you done speaking engagements?

Heather Havenwood: Yes.

Matt Coffy: It seems like maybe Success Magnet Seminar was one of the places where you started getting your established.

[clickToTweet tweet=”‘When you learn how to make money online, the world opens up’ @hhavenwood” quote=”‘When you learn how to make money online, the world opens up’ -Heather Havenwood”]

Heather Havenwood: Thanks for asking that. Success Magnet Seminar that was fascinating. I haven’t been in the speaking business for many years and I kinda went in a hole and that was my coming out party. Me and Joe Sugarman hosted that event. It was fun. It was awesome and that lineup was just ridiculous. John Vincent, Joe Polish, John Carlton, Joe Sugarman, myself, I’m blanking on somebody. And what’s interesting about that Matt is when we put it out there, people thought it was a lie because the lineup was so awesome. They didn’t believe it. And so what happened is the turnout was pretty small. It actually weren’t that great, it was like maybe a hundred fifty people. Well who’s in the room is even better. It’s amazing copywriters like Carlin, Matt. These guys are like really awesome copywriting business owners themselves and the room much less on the stage, and it became this intense small little mastermind the whole weekend. It didn’t become this big seminar what we thought it would be. And so it’s really fascinating. So you can get the CDs, sorry that’s old school. You can get the videos on you can buy them but what was fascinating was people were literally call me a week afterwards, they go oh my god, we didn’t think it was real. It was real. All those people hung out at the room all weekend. I’m like they didn’t, you missed it. So it was awesome. I really enjoyed it. but what I learned from that, now that I already know this but kinda reiterated that is that copywriting is the key. What I call the power of the pen, nowadays power of the Macintosh keyboard, I guess, is the key to entrepreneurship. When you understand the power of selling with your pen or selling with the concept of how to get the message to market to a product or service, you can create anything. And that was reiterated there.

Matt Coffy: Interesting. So how did you and Joe Sugarman team up?

Heather Havenwood: He’s a dear friend of mine. We’ve done business together for a long time. I’ve known him 2005? 2006? He was the foreword of my book. He’s just a dear friend. He’s now my mentor, I call him my friend and a mentor. He’s a mentor to me. So much through my troubles when I was building myself back up and still am. That’s how I see it. He’s just a great guy. He’s amazing.

Matt Coffy: So it’s interesting that you give the guy like Joe and then you’ve got Carlton and Joe Polish. You’re gonna start to see some of the larger frameworks that are out there as well in the copy world. They’re the big dogs which puts them in a whole different place.

Heather Havenwood: I think that’s why people didn’t show up cause they really thought oh please. That’s not real. It was real. It’s no longer gonna happen ever again. It was pretty high standard. So I’d like to redo the Success Magnet Seminar again with the same concept obviously not gonna have those people back, maybe one or two of them but having all these guys in one room, it was really cool but that weekend because it was kinda small event and the people in the room were so awesome. A lot of the guys decided to hangout and sometimes they did like speaking and they leave and they didn’t. They all like oh this is cool. We’re just gonna like hang out. So they all like just hung out at the back of the room, chilling, talking to people. It was just so open. Everyone was just like, it was like a big hangout mastermind. It was awesome.

Matt Coffy: So you’re barely well-known for also some coaching. Can you tell us a little bit about the coaching strategy that you work with so for instance I say I’m a small business. Are you coming in to help them with the email marketing piece, are you coming in to help them with the marketing in general? What’s your main diagnosis and what’s a typical customer look like and what would you provide them?

Heather Havenwood: That’s okay. That’s a great question because there’s  a lot of coaches out there and I get it. what I work with them a lot is what I call teaching them and educating them and coaching them on how to be from a mindset and the vision of how to be an entrepreneur. I know that sounds really weird but sometimes people come in with I have a product proposition, I want to sell it but they don’t understand marketing and understand how it works and that when they understand how a business works from a marketing perspective, I think that they are stronger entrepreneur versus just handing it over. I think a lot of entrepreneurs just want to hand it over. Oh I don’t want to deal with marketing, here whoever you are. Here’s the baton and guess what happens. No one’s gonna take care of your baby like you. So you have to understand how marketing works on all levels. Even if you’re handing over the baton of the buildout of the site. You can’t hand over the strategy. You have to work with them. You can’t just let all that go. You have to be able to understand it and be the one who’s the visionary of that. So I work with them on that. I also tend to work with a lot of them on the email marketing side. And they always wanna hand that over and I’m like no. You’re not allowed to for like 90 days. Until it gets to this point with me where I feel you can get it then you can hand it over because once they understand it, then they can hand over so they can what I call watch the other person. You know what I call train them versus feel like they just hand it over their entire list because the list no matter it’s a customer list, or opt-in list or lead list, is the business. Doesn’t matter if you’re selling widgets or you’re an agency or if you’re selling dentistry, the list is the business and you just can’t hand that baby over. It is the baby and so I worked with him a lot on how to communicate. How to talk to. How to email. How to do that process text messaging I’ve been on it right now. How do they use that information that what I call medium and so that they can make more money with their current customer list.

[clickToTweet tweet=”‘Copywriting is the key to entrepreneurship’ @hhavenwood” quote=”‘Copywriting is the key to entrepreneurship’ -Heather Havenwood”]

Matt Coffy: Interesting. I get the fact of this whole business of trying to put together the right pieces for businesses we’re going through a lot of changes in how we deliver stuff with the agency business that we do today because we’ve sort of migrated from wholesale and we’re doing more retail now. We still do wholesale but so on the retail space there’s a lot of openness on to provide a great service and great value to the end user. And the challenges, what do you do? What do you provide from a marketing perspective and have you standardized on any platforms that maybe you can give a hint to our audience on what you like and what you found to be successful on a specific platform level?

Heather Havenwood: Like a software platform? Well a couple of things. I’m gonna talk about text messaging. If you’re a small local business, or a local business or a big local business, what I mean by that if you’re advertising on radio, TV or doing native ads, may I suggest that you say in your advertisement either verbally or TV or whatever, you can text or call this number. Let me explain to you why. And what I’m learning from my business, we have a local weight loss company here in Austin Texas and we started saying from the beginning hey, you can text this number. Oh my God. People loved text because one, they want text versus call because it’s like I don’t want to talk to anybody. But they will text you back and forth all day to schedule stuff, to have a conversation, ask questions. They’ll text our system all day long it’s crazy and they love it versus picking up the phone and having one conversation they just love the text messaging plus we’re increasing our leads and what’s interesting is that Mastermind this weekend was I talked to a guy that he works at this huge law firm that spends millions of dollars a year on advertising and we have this conversation and says it’s funny you say that because we have this law firm who’s been out there for a year and calls day 1-800 whatever? He said, they didn’t have that number text enabled and so we text enabled it and all of a sudden we were getting all these leads and we didn’t even tell people it was text available. Then we changed our message that you can text or call and it was like this floodgate. It was a 400% increase so people assume that your phone number for your business is text messaging is available so that’s a big one. On podcasting like right now, I used text message and I’d tell you if you wanna know more about me you can text the word SEXY to 7200 and when you text that I’m gonna get your information, I also get your email address, stuff like that and then I can now communicate to you. Text is a huge one. That’s a big one. I use a company called Those are the ones out there. That’s a big one but as far as software and what I called a personal annotatement channel I think email is not dead it is still very viable and a local business should be emailing their client list at least once a week. Now my dating list, I do sometimes 1-3 times a day. But that’s different. So you have to look at the particular kind of market but minimum once a week if you’re in what I call normal internet marketing funnel, once a day minimum.

Matt Coffy: Any platforms you specifically like? I’m just curious.

Heather Havenwood: For text messaging, for email, I have my own server on one so that’s a different world as well as AWeber, I definitely still use it cause it’s a closed system and Infusionsoft for some tagging like all the kinds of segmentation piece.

Matt Coffy: Cool. We’ve been experimenting with radio ads to text landing page.

Heather Havenwood: Yeah? Is it working?

Matt Coffy: It’s just different and I think that we’re trying to embrace bringing in new strategies when we talk to clients but that same conversation starts happening every five seconds which in most of the businesses that we work with, I just want phone calls and traffic. We do have to do the paper book, and SEO, and social media marketing. The email marketing has been a bane for us just because we have not, it’s a full-time job meaning that it’s not easy and that’s why I was asking you, we use active campaign, and we’ve used Infusionsoft before. So I mean we run a lot of campaigns for our customers but it is one of those things where it involves copywriting, landing pages, conversion strategies, A/B testing. It just goes on and on and on forever.

Heather Havenwood: It does.

Matt Coffy: And we’re really chopping it to bit to try and solve to find the better mousetrap there. Well let’s go back to your story and again I don’t wanna burn all of our days on platforms.

Heather Havenwood: Oh no that’s fine.

Matt Coffy: So you got the book Sexy Boss it’s up and running. It seems like that was something really helpful obviously was part of this I would think. How did you get in touch with Bryan and obviously he’s been involved with you to some degree.

Heather Havenwood: So Bryan Dice was a part of Sexy Boss. That’s okay. And I’ve been around awhile, I guess I’m old. I’ve been in the online internet marketing going back to seminars since 2003. Ryan was just a geeky guy and I think when you’re going to these seminars in 2003 and 4 like Mike will say Hey Mike. I’ve just known everybody because you were around the time when they were just normal dudes. Perry Belcher, lived in Austin Texas and they’re also down the street from me and it’s kinda like you run into people at events. I think it’s, I’ve been around awhile. I’m old I guess? That’s how I know them. they actually were the ones that came up to me and wanted to publish me with the dating business and then Perry did my copy with that and we worked with him and actually the product itself, the original product is actually me and Perry Belcher which is so funny. It’s actually a really funny, funny product. It’s him and I talking. It’s really funny. A lot of people don’t know about it unless you know who Perry is. So that’s how that happened and then they gave me over the company cause they went into a different direction. They were adding new products and changing management and they stopped doing that model publishing others so moved from that they’re still friends so Sexy Boss actually came out from Joe Sugarman. Joe Sugarman was like you’re like a sexy boss. You should write a book. So here we go we write a book and he was the foreword to that book and that was my story. It was me coming out about my story because I think with online marketing we assume everyone’s successful and they’re all hanging out together. it’s all not true. So I went through a massive personal, financial, whatever bankruptcy everything downfall. And it was my story of sharing what happened and how I overcame that and how I’ve moved away from what I call from bankruptcy to sexy boss very transformational development.

Matt Coffy: Has that provided you with stage do you think?

Heather Havenwood: Yeah it did. It provided me with branding. People call me Sexy Boss which is a great brand and I love it but at the same time it created a platform for me to be out here and start speaking about not only my story but being an entrepreneur, but marketing and I hadn’t really done that. I’ve been kinda behind the scenes for many years and so it’s been my platform to come out and say okay, I’m ready to coach people now and teaching marketing because I have now started a business from scratch, from nothing and built it so I have this great lifestyle and now I could teach it from a place of yeah, I make money online and I teach you versus I only make money when you give me money to teach you which I hate that. So it’s like I wanna go, I wanna have these other businesses and it’s a Ryan Dice model, he’s got a bunch of businesses and he teaches you. And I like that model and I was like, I wanna show people, look I have these businesses that I succeed and fail every day and I teach you. so that’s how that came to be.

Matt Coffy: Two Austin questions then one other question then we’re gonna wrap it up cause on our thirty-minute mark. Alrightey, believe it or not. So Austin, love it?

[clickToTweet tweet=”You’re a better entrepreneur when you understand business from a marketing perspective @hhavenwood” quote=”‘You become a stronger entrepreneur when you understand business from a marketing perspective.’ -Heather Havenwood”]

Heather Havenwood: Love it!

Matt Coffy: Wanna ask you if you know a couple of people in Austin.

Heather Havenwood: Okay.

Matt Coffy: So one of my favorite guys in the marketing world who owns AppSumo so you know Noah?

Heather Havenwood: Yeah. I mean cross paths not, dear friend.

Matt Coffy: Yeah. He’s a great guy. He actually set me a FitBit. He and I ever meet in New York at one of these meetings and he’s like oh dude you gotta get a FitBit.

Heather Havenwood: That’s funny.

Matt Coffy: Cool. Is Anton still there? The Club Anton’s?

Heather Havenwood: Oh no. It got moved. Austin’s in this.

Matt Coffy: It’s in the next phase.

Heather Havenwood: It’s in the next phase. Anton’s got moved so in my world, it got killed off because Anton’s is just the name but it’s like the location and how cold it was and all that. So yeah it got moved. That is a big huge tower there. We’re still building the tower.

Matt Coffy: So the last time I was in Austin I went to Anton’s and I got to get on one of those musician guys.

Heather Havenwood: Oh well, then you love Austin.

Matt Coffy: So I went backstage and I met with Steery Von’s old band an Chris the drummer, Tommy Shannon the base player and Reese the keyboard player and hung out with them and kind of met the owner, it was really an interesting experience and I was just curious if it was still there. That was all my Austin questions.

Heather Havenwood: Okay. Well Austin’s great but I have this, there’s this t-shirt that says, I heard Dallas is great please go there and please don’t come to Austin. I kinda have that shirt going on. Please don’t come here. Stop.

Matt Coffy: Go to Portland.

Heather Havenwood: Yeah go to Portland, go to Dallas, Houston, Wacko. I heard Wacko’s nice.

Matt Coffy: I could ask you a lot more questions but I wanna ask you one final question. What makes a successful person like yourself? You’ve got a lot of energy. You’ve got a lot of stuff going on. You’ve turned it around. What do you think is the catalyst for your success?

Heather Havenwood: That’s a great question. Wow, I didn’t think about it. Well, drive. I think it’s the internal drive to be better who I think I am as constantly drive, drive, drive. The other thing that helps me is a coach. I think left to my own devices and staying in my own head will be a dangerous place for me to be. So for me having to coaching outside myself helps kind of what I call hone that drive to something better because I’m a type A personality.

Matt Coffy: No.

Heather Havenwood: I know right? I’m a type A and so when I take things on, I take things on. I’m a performer too. they call it performance. It doesn’t matter who it is. Elton John. If you see how he is personally, he’s a performer and then he’ll go what I call into a hole. Sting does this. They perform and they go into a hole. That’s a lot of entrepreneurs. They wanna perform then they kinda wanna go behind the scenes because they are a performer. That’s usually type A personality. I’m the same way so I think having a coach in my life, keeping me on track helps me really. That’s what kinda pulled me out of my bankruptcy and all that cause I was definitely going down the leg. I’m just gonna become my cab driver at this point forget it. forget life. I’m done. I’ll become waitress. I did. I tried to become a waitress. I really suck at waitressing though because another person comes into your table saying ya’ll, you got everything. You good. I’m out. I’m leaving now. I’m not coming back. I don’t come back and then oh wow, I forgot, they wanted ketchup.  And I’m like pshh, you already said you were good. I’m like that person. So I got fired.

Matt Coffy: So Heather where do we find you? where is your next or what are the things that you want to tell me the audience that’s listening right now?

Heather Havenwood: Sure, thank you for that. So they can text the word SEXY to 7200 and they can opt in and they get three free chapters of my audiobook, Sexy Boss if that interests you or you can go to the and you can click on work with heather and we can have a conversation for your in working with me if that suits you or if you’re like what’s this dating business thing. Just throw it out there, and if that kinda interests you as well.

Matt Coffy: Awesome. Heather it’s been a pleasure talking with you. I can hardly keep up. Let’s try and circle back maybe as we through our year at some point to connect and see. We’ll have another discussion. I wanna go deeper at some point on that email strategy but it’s been awesome talking to you and we’ll catch you soon maybe one day in Austin.

Heather Havenwood: Yeah absolutely. I’m here. I live downtown. Love to show you around, the bars, the awesome bars and the amazing music are slowly being demolished so come early come now, come come cause there’s so awesome here. The music scene here but it’s starting to become less of that because of the big money coming in. yeah come on down.

Matt Coffy: Alright. Thank you.

Heather Havenwood: You’re welcome.