Today’s guest is Heather Havenwood, the chief sexy boss at Heather  Heather is a serial entrepreneur and keeps stacking one new business idea on top of another.  The first thing we talk about in this episode is how Heather keeps track of all of her businesses.

We spent some time talking about some new technologies that you can use to engage your customers and keep them coming back to visit you and your company on a regular basis.  She is a truly engaging guest and you’re going to get tons of take-home value from this episode.

Here are just a few of the things you’ll learn today:

    • What the mindset of a serial entrepreneur sounds like.
    • How the basic principles of sales are the same, no matter what industry you’re in.
    • Understand that we as humans haven’t really changed which means our motivations to buy haven’t changed much either.
    • Why systems are the breakfast of champions for any sustainable company.
    • What systems mean for a consistent customer experience.
    • What a chatbot is and why you might want to pay attention to this technology.


Narrator:         Welcome to The Sustainable Business Radio Show podcast where you’ll learn not only how to create a sustainable business but you’ll also learn the secrets of creating extraordinary value within your business and your life. In The Sustainable Business, we focus on what it’s going to take for you to take your successful business and make it economically and personally successful.

Your host, Josh Patrick, is going to help us through finding great thought leaders as well as providing insights he’s learned through his 40 years of owning, running, planning and thinking about what it takes to make a successful business sustainable.

Josh:                Hey, how are you today? This is Josh Patrick. You’re at The Sustainable Business. Today, our guest is Heather Havenwood. I’m not really sure what businesses to introduce her as because she has like a ton of them. She is a Top 50 Must Follow Woman Entrepreneur by the Huffington Post. She calls herself the chief sexy boss. She has a book How Female Entrepreneurship is Changing the Rule Book and Beating the Big Boys.

Others call her an icon creator or a wizard behind curtain. I like wizards behind the curtains. So let’s bring Heather in and we’ll have a little conversation today.

Hey, Heather, how are you?

Heather:          Thank you, Josh. Thank you. I’m definitely a chief sexy boss but I’m not chief technology sexy boss. That’s some technology. I’m not technology officer at all, right?

Josh:                Right, right. The technology gets more challenging.

Heather:          It does, right? I’m like, “I’m the sexy boss but CTO I am not.” I am like, “That’s not me, right?”

Josh:                Right, so.

Heather:          In some big company, we just call some dude over like Tony. “Tony, help me fix this” but it happens. Sorry.

Josh:                You know, those things happen. I’ve had it happen before and it’ll likely happen again. So tell me, you have like a zillion businesses, how do you keep all of them straight?

Heather:          Honestly, it’s building blocks. So I started one, started another. I’m kind of a serial entrepreneur. I’m actually in the process of selling two of them so that’s exciting because I’m actually looking at my plate like “Look at all this time.” They all kind of fall into the same genre for me because I’m really good at the marketing side. It’s interesting, Josh, because I have this view that it doesn’t really matter what you’re selling, you’re still selling, right? It doesn’t matter the medium, you’re still selling. So it could be in front of a person. It could be at a brick and mortar. It could be online.

My expertise and what I’m great at is like what’s still selling. So that’s why my clients– I have a big coaching program with coaching clients. And my clients are all over the board. I’ve got a Hollywood producer. I’ve got a bridal company. At the end of the day it’s still principles that sell. So I usually help them with those simple principles.

And it doesn’t really matter what kind of company you have – a tire company. It’s time-tested principle because at the end of day, Josh, even though technology has altered and it’s changing every day, if not six months, we as human beings haven’t changed for years. And why we buy, why we don’t buy, why we move towards something versus why we don’t move towards something hasn’t altered. So that’s why I’m able to have so many different companies. I just take these time-tested principles and place them in different types of “businesses”.

Josh:                Okay, so I get that it’s all around marketing for how you run your business.

Heather:          Yes.

Josh:                But let’s talk about operations.

Heather:          Yup.

Josh:                Goodness.

Heather:          Yeah, and I get it.

Josh:                It’s great to get the business but you’ve got to deliver it so if your strength is marketing, who handles operations for you and how do you go about doing that?

Heather:          So I have two main strengths. It’s sales and marketing which is kind of combined and then operations and the systems of the operations. So I love building the system such that it’s a consistent deliverability. And my supplement company and local business, here in Texas, I was the one doing all of the systems. And the deliverability, we actually had a doctor. So the doctor was the deliverer, I guess, you’d say “deliver in front of the patient.” And I was dealing with all the marketing system and the operations systems. Because customer service is a system from the time they touch your company on some level outside, to internal, to all the way through the sales process. That’s just one big system.

Josh:                Okay, so systems happen to be one of the five things I think create a sustainable business.

Heather:          Very.

Josh:                And my question around systems is, “How do you establish them?”

Heather:          I’m just going to take one because it’s just easier, right?

Josh:                Right.

Heather:          One of the things, when we first started the supplement company and the local weight loss company is, I was the one there every day answering the phones for about three months. I didn’t want to do that so I was like, “As fast as I could get the up and running, the better” and I handed it out. But I knew that I had to set the system. I had to set how do you answer – the scripts, a lot of technology, Ring Central. They can talk anywhere. I set up Mindbody – all the different systems, so that when someone enters the information, which could be done by not someone very technical then what is the communication that happens with the client on a technology level – through text messaging, through e-mail marketing. Now, like chatbots but that’s a whole other conversation.

So what are all the things that I can control? As a business owner, what are the things that I can control such that the “human” end of mix is controlling very little? And that’s what I did. And so eventually I quickly within, I’d say, two months, I was hiring like, “Okay, here we go.” And they didn’t have to know much. They didn’t need to know the product. There was very little training. The training was, “This is how you answer the phone. This is how you make an appointment. Everything else is done. You’ll learn the rest later.” So we were able to hire pretty fast.

And I think that’s a key piece because it’s interesting that in Texas right now– well, after Harvey, I’m not sure. But before Harvey, the market here for finding a good employee was hard. They had options. There’s a lot of jobs here. So we had to be able to get people up and running really fast and to a point where they enjoyed the business really fast. That was a really big issue for us. We didn’t have like people wanting the job. It was more like, “Okay, I kind of want the job but I have five other offers.” So we’re like “Wow!”

So we had to really look at what are the systems we have in place such that people will leave easier. We also had a lot of turnover for a good six months until we found some really good people. So we had to have a system set up – this is a big one, that businesses don’t do. The system’s set up such that people could leave and it doesn’t hurt the business.

And usually, with a small business owner, we only have like three of us for a while. Then, it went to four and max five. And that’s not a lot. Usually, that kind of business, they make everyone personal. And so, when one person leaves of that pie, oh my God, things collapse. And I set the whole system up such that people can come and go. And as soon as they leave, there’s a big wall that happens and they can’t take any of the system with them. Much like a big company does. But now, technology is such that small businesses can do that.

And that’s my number one thing I see with small business, when I walk in, there’s like two of them or three of them max. I start to look at, they’re using their personal e-mail and like all their docs are on their private cloud server. I’m like, “What are you doing? You’ve got to act like a business so you can control the system.”

Josh:                So here’s my question about systems. Why have them in the first place? I have my reason but I’m curious why you think having systems is important. Maybe you’ve touched on it a little bit but what’s the number one reason you think systems are important in your business?

Heather:          As a business owner, number one word – power and control. This is two words. It’s really control – power and control. But I got to a point where we had, at any time, we pretty much were recording. Every time any of our employees answered the phone, all of it was recorded through Ring Central. It’s easy. All e-mail communications through any kind of customer service at all ever was recorded. All text messaging with the customer was recorded.

So we could control the flow, so if we had a problem with the client, it predominantly protected us. And it protected us from or with employees. It also protects us from clients. Like, “Well, we said this.” And we’re like, “Well, actually, here’s a recording.” So it actually protected us from– I mean, seriously, it protected us from situations where like, “Oh.”

I mean, it sounds small but before we started putting this in place, the company was just a chiropractic company beforehand. And before I got involved, it already had two employees come and go and stole a bunch of money. They had stolen the Yahoo main business account that everything went through and they wouldn’t give it to us. They stole the Facebook accounts. I mean, I’m sure you all heard of this kind of stuff.

So it’s control and power. I don’t know if you worked for a big company before, but I started with big, big company, Southwestern Bell, SBC Global. It’s huge. From the moment you walk in, they give you a little badge or whatever they give you now – a chip in your hand or something, they pretty much know everything that’s happening in your communication. And if you get fired, either nicely or not nicely, you’re cut off – in seconds.

Josh:                Right.

Heather:          Every data. All data.

Josh:                Right.

Heather:          And it sounds easy to do in a big company but there’s a reason why do that. So small companies need to be able to do that. They could do that nowadays with the technology. I use Google Drive. It’s a Google Business. It’s a Google Business, not just Gmail but a Google Business you can set up. And then I use Ring Central. And then we use Mindbody and some other ones. And like I said, every time, any interaction, any transaction, any communication was touched by an employee or a customer, it was on some level recorded.

Josh:                Okay, so I’ll give you my reasons systems are important. To me, it’s all about consistency. It’s consistency of service from your employees and consistency of service that your clients get. And the only way you ever get that is through having great systems, at least in my opinion.

So I want to pivot for a second here because you mentioned a thing called chatbots.

Heather:          Yeah.

Josh:                I have no idea what a chatbot is.

Heather:          Oh, they’re super cool. So first off, I’m a little novice. I’m still learning myself. I’m still part of a community. We’re learning about them. I’m actually about to get my Heather Havenwood ChatBot delivered to me in the next 24 or 48 hours. I’m super excited now. So it’s so weird.

Okay. But let me explain it this way. If you go to Facebook, and nowadays you can go to a business page. Okay, there’s a business page [inaudible 00:10:18] on and then you can communicate with the business.

Now, that hasn’t been a major thing yet in the last year. People go to business pages but they don’t think, “Oh, let me communicate with the client or communicate with the company via messenger.” They don’t think that through. What chatbot is doing is chatbot is saying, “Hey, you know what, instead of calling us or e-mailing us, chat with us.” And what it’s going to do, it’s going to have you to have the ability to have a system so that you can actually walk through a conversation with somebody.

So, example, you reach out to [inaudible 00:10:53] spa the other day and it said, “Text the word FACELIFT to this spa.” So I go in there and put “Facelift” and all of a sudden this chatbot pops up. And when I say a bot, think of an animated cartoon. So instead of just text, it says, “Hi” which we all know it’s in automatic. Instead, what pops up is a woman. It pops up and goes, “Hi”. And it’s a cartoon but it says “Hi.” And it goes, “What’s your name?” and I say, “Heather.” And it goes, “Hi, Heather. What kind of service would you like?” “I’m looking for a facial.” “Facial, great. Here are some options.” It literally gives me these options all inside of the communication with Facebook. And they could even say, “Click on this to go on our site right now. And here’s a code of 1, 2, 3, 4 for 20% off.” You can do all of that within a chatbot.

Josh:                So it seems to me that using a chatbot is really more of a sales tool for millennials and probably not so much for baby boomers.

Heather:          I disagree with that. And we don’t have stats yet so this is more a feeling. I don’t have like stats to go against that. But what’s interesting about chat because the person I’m communicating with, he’s a baby boomer so he would be like, “What are you talking about?” He loves it. He’s like all over this.

The guys that I’m working with that are developing this stuff out called real technology is about the fact that we, as human beings, don’t want to just deal with just text, we want to actually have some kind of communication with somebody. Now, people are always going to have a phone call and, of course, that’s going to be way better for they call it order demographic, I guess. And that’s never going to replace it. But what it does do is can sift and sort the conversation for you.

So I’m going to get one for my podcast. And I wish I could tell you the exact terminology it’s going to be at but I don’t have it yet. I’ll be getting it delivered tomorrow.

So what that’s going to do, it’s going to help me get their name, get their e-mail and maybe learn something about my particular customer. And then I’m going to be able to get that data and be able to potentially send them offers based on that data and get them onto my podcast. It’s interesting. It’s kind of revolutionary. But here’s the key you want to learn. The key of it is that, I think, and this is what we’re kind of banking on, is that it’s going to replace e-mail.

Josh:                Well, here’s my challenge with all these sort of instant messaging activities with small businesses, I don’t sit in front of my computer all day waiting for a message. And if one comes in, it might be several hours before I get back. So that works fine with e-mail. It doesn’t work fine for instant messaging.

Heather:          Correct.

Josh:                And a chatbot seems to be kind of an instant messenger sort of thing.

Heather:          It is. You’re absolutely correct. I went to this mastermind and this gentleman I was talking to whose client is– he didn’t say the name of the client. He wouldn’t say. But he said, “I work for a very large, large, large law firm.” That’s what he said. And he goes, “We’re the ones– do you see the commercials? I work for the company that has the commercials that say, “Do you have mesianlioma? I think I’m saying it [inaudible 00:13:45].

Josh:                Mesothilioma, that’s–

Heather:          Yeah, yeah, that one.

Josh:                The form of cancer.

Heather:          Okay, yes. So he’s the one that he helps them put all these commercials out all over the place and it does the online data that drives them. He said, “You know what they found out? That they had an increase of conversion when they made the phone number textable. So call 1800 blah blah blah to see if you qualify, if you want to talk to somebody. They said, “Call or text the same number.” They had this massive inquiries. And they found out that people had been texting the number. Because what texting does is it kind of creates this barrier. It’s like, “I want information but I don’t want to talk to anybody.”

Josh:                Okay. So I get that but, again, instant messaging, texting, all that sort of stuff seems to be the type of communication that requires an immediate response. And for most small businesses, they’re not in a position to do immediate responses.

Heather:          So the person who’s ever answering the phone – if it’s an 8:00 to 5:00 business and someone’s answering the phone every day, that’s the same person doing the text messaging.

Josh:                Okay. Again, I mean, I’m a little bit obnoxious about this but I’m thinking about my own office. We have five people here. We do have somebody that answers the phone but she’s often off doing something else. And there’s lots of times where she’s not here. So, again, we’re going to have somebody who contacts our business, potentially, and they’re not going to get a response for hours or even maybe a couple of days. They’re going to be really frustrated.

Heather:          Well, then it might not be the technology for them.

So when we did a weight loss company, again, what I did is when I started pushing at our advertising, I put, “Here’s the phone number to call or text.” And our market, by the way, in weight loss is women. Women over the age of 45 or 50. That’s our market. That’s our money. Our money’s in there. We had some 20s. We had some 30s but not really. Our money came from women over 45. They’re the ones with the cash.

So we found that the women– essentially, women love texting. And so, women would be like, “Hi, I saw your ad. Hi.” And they would have this whole conversation with our assistant. And now she would say, “Hey, do you mind if I call you?” She tried to move it quickly from a text to a phone call so she can have a better conversation. But we had a huge increase of people. And we still do – everyday. They actually wanted to text because women really like texting. It’s not a man thing. It’s way more women than men. That’s [inaudible 00:16:07].

Josh:                That’s true. I understand. I know lots of men that text also.

Heather:          So it’s also consumer based. This particular business that we’re talking about, it’s a very consumer business, B2C. It’s a very B2C business. So if you’re a B2B like an accountant, which is more B2B, it might not work, right?

Josh:                Oh, it actually works great. And I do this all the time where I go to a website and there‘s this little thing that brings up a chatbox and I’ll start talking to somebody. And if they don’t respond within 30 to 45 seconds, I just leave.

Heather:          Correct. So it’s the same person. Whoever’s doing that can also do the phone calls and also the text messaging.

Josh:                So the real thing is, it’s probably very effective–

Heather:          It is.

Josh:                But you need somebody there who can immediately answer questions.

Heather:          Absolutely.

Now, what’s cool with the chatbot is that you don’t have to have that person because the bot takes them through a process and kind of takes them through a sales process.

Josh:                Okay. So that’s–

Heather:          And it ends it for them.

Josh:                So that’s the difference then? Okay.

Heather:          Yeah, it ends it for them. It basically says, “Thank you.” If it could tell you’re done and any more information, you need to go to the website, call, or e-mail or call a different number, or text a different number. The bot gets data from the customer and basically kind of passes them down a process.

Josh:                And then the data can be passed off to somebody in the sales organization?

Heather:          Yeah. There could be a time delay. So then that could be a time delay of a day. Like, “Hi, I see that you chatboted with our [inaudible 00:17:25] Wilson a day ago. How can I help you?” You see, that’s in a day later and the process is still good, the system is still valid.

Josh:                Okay. So that’s where the difference is between regular chat and chatbot is a chatbot is run by a computer system.

Heather:          Yes.

Josh:                And it’s a much better way of going around doing that.

So, Heather, I want to talk about one more topic which is the future of sustainability in an entrepreneurial business. So what would that mean, in your opinion?

Heather:          So I’m actually part of an organization here that is all about sustainability. It’s actually a venture capital firm here in Austin. I’m a volunteer for that. I’ve been with them for three years and my intention is to help businesses be created that are sustainable in the world of sustainability. What that means, in their world, is more green things that are helping the planet -sustainable in such a way that it’s helping things – people, technology, systems such as sustainable over a period of time. That’s a little different sustainability but that word distinction is kind of a green word in that world so I’m not sure if that’s exactly what you mean.

Josh:                Well, sustainable in my world is how to make your company economically and personally sustainable. And often that includes green sustainability especially if your marketplace is millennials or your employment force is millennials.

Heather:          Correct.

Josh:                Because for that group, sustainability is a hugely big deal. And old people like me need to learn that. And one of the things that I like to see people do more, talking about sustainability, is become a benefit corporation. I don’t know if you’re familiar with BCorps or not.

Heather:          It’s a corporation, I’m assuming, that’s giving part of the money to a fund raiser or a charity?

Josh:                No. No. It’s actually a form of corporate formation where instead of legally just being involved with making money, it’s called a triple bottom line company. What triple bottom line is typically people-planet-profits. So you often will see ESOPs today (employee stock ownership plans) become a benefit corporation. Ben & Jerry’s became a benefit corporation. In Vermont, the larger ESOPs are all benefit corporations. And it’s a way to prove that your business is actually sustainable from an environmental point of view and sustainable from an employee relations point of view. So you often will find that the top-rated companies on Glassdoor, for example, will be BCorps.

Heather:          Got it.

Josh:                So it’s a piece of sustainability that I think is really important for here. And economic sustainability doesn’t have to happen without having planetary sustainability. Both can happen simultaneously. And hopefully, they will more in the future.

So Heather, unfortunately, we are out of time. And I’m going to bet that people would like to find out more information about what it is you actually do and how they might contact you. So if somebody wanted to do that, where would they find you and what would they be doing?

Heather:          Thank you. Thanks for having me. I really appreciate it, Josh.

My name is Heather Havenwood and you can find me at And if you’re interested in having a conversation with me on how I can help your business in the world of marketing and sales and systems with that, you can go to and we can have a conversation and see if it’s a good fit.

And again, my name is Heather Havenwood.

Josh:                Okay. And Heather, where should they go again to find you?



Heather:          Yeah.

Josh:                Okay, great.

Heather:          It’s simple. I think it’s simple.

Josh:                You know, I like that.

And I also have an offer for you. I have a free one-hour audio CD. It’s called Success to Sustainability: The Five Things You Need to Do to Create a Personally and Economically Sustainable Business. It’s really easy to get it. All you have to do is take out your smartphone. Don’t do this while you’re driving. I ride a bike and I don’t want to be run over by texters so wait until you’re out of your car and text the word SUSTAINABLE to 44222. That’s the word SUSTAINABLE to 44222. You’ll get a form, give me your name and your physical address, and we mail those out to you. And if you don’t happen to have access to a CD player, which I find more and more, just send me an e-mail at and I’ll send you the audio file.

This is Josh Patrick. You’re at The Sustainable Business. Thanks so much for spending some time with us today. I hope to see you back here really soon.

Narrator:         You’ve been listening to The Sustainable Business podcast where we ask the question, “What would it take for your business to still be around 100 years from now?” If you like what you’ve heard and want more information, please contact Josh Patrick at 802‑846‑1264 ext 2, or visit us on our website at, or you can send Josh an e-mail at

Thanks for listening. We hope to see you at The Sustainable Business in the near future.

Topics: sustainable business podcast, Sustainable Business, systems, creating business value

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