Lisa Kipps-Brown; Business Reimagineer

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Hey, how are you? This is Steve Sims. Welcome to another episode of the art of making things happen. The podcast, what would you call a 59 year old lady that likes talking to teenagers? I call her a unicorn. Now this young lady has decided to take a challenging path and all the different generations she usually speaks to, connect them together on automation, technology and selling your business. Lisa is a fun charismatic magnet. You’re going to love listening to her. She’s got a great point of view.

Hi, Lisa. Welcome to the show.

Hey Steve, thank you for having me

Now for anyone out there that doesn’t know the wonderful, beautiful Lisa Kipps-Brown. She’s a fellow speakeasy member. So a lot of people have seen over the events all over the planet, but I refer to her as a unicorn because I am going to ask you the question. First of all, that no lady ever likes to be asked. How young are you?

I’m 59 and I’m proud of it.

I knew you’d be strong enough for plus a fandom behind a microphone. So you’re gonna have to wait a few months to slap me, but so you’re 59 year old, young beautiful woman. And your unicorn is do you actually enable the communication between people basically over 50 with the younger technology crowd of, you know, the twenties and even the teens? How do you do that? And why is it important?

Well, that’s right. How I do it is that I’ve been a web developer since 1995 and I’ve opened, I’ve owned my web marketing and strategy business since 1996. So I’ve been working in the internet world, you know, back in the days of Alta Vista, if you remember that. So, I mean, back in the age of the dinosaur, except the internet dinosaur, except I’ve continued to learn. So I’m not a dinosaur. I keep up with things, but because I’ve been working in it so long, and because of my age, I’m able to relate with what younger people know and the technology and the language that they use. But I’m also able to, to relate to what people 50 and older know. And so I’m able to bridge that gap and use the analogies with older people that help them understand why they should do things. They don’t have to understand how to do it. They mostly need to understand why they need to do it.

Now let’s be blunt. You know what you knew, what you knew in the nineties about the internet world is irrelevant because let’s be blunt, you know, by 2001 is changed by 2001 and a half. He’s changed again. So we’re constantly evolving. We’re constantly changing that speed of change. And I was conversing with you a while ago on this. That seems to be what is terrifying people so much. And the fact they feel as though again, on a speeding train and that frightens them. How do you get over the fear?

You just have to jump in and do it. You know, you just have to immerse yourself in it. You know, I tell people, my husband is 73. He’s probably going to kill me for saying it, but he’s 73, but he literally understands how to use the internet better than a lot of 40 year olds that I meet and even people in their thirties. And it’s because he’s lived with me for all these years. And our kids because they grew up, you know, on the internet. So he’s absorbed it just by being around us. You know, it’s like if somebody moves to America from another country, they don’t understand, they don’t understand English. If they don’t, once they’re here, if they immersed themselves in the community, then they will become fluent at least to a certain extent. So that’s what you have to do. You just have to get out there and live it and try, you know, talk, learn, read, and mostly just use things.

You just have to get out there and live it and try, you know, talk, learn, read, and mostly just use things. Share on X

Now we all heard the statement, you can’t teach an old dog new tricks, the fear. And is there a stubbornness in now bear in mind mind? I’m 54. I’ve just turned 54. So I would say that I’m on that cusp. I think 55 is boomer. So I’m on that cusp of the generations. Do you think there’s not only an element of fear we’ve already established that, but do you think there’s a stubbornness of color? Well, I’ve always done it this way. That is ingrained in quite simply anyone over the age of 42.

Yes. I definitely think that. And especially with business owners who already feel like they’re successful, they’re like, Hey, it’s already working for me. I don’t need to change anything because I’m good. And what they don’t even think about is that two thirds of businesses never sell. And the one third of businesses that do sell, go for half of what the owner thinks it’s worth. Now, another fact is that 85 to 90% of the average business owner, 85 to 90% of their worth is tied up in their business. So if you figure, okay, 85 to 90% of my business is tied up or 85 to 90% of my net worth is tied up in my business. And I’m probably not going to be able to sell it. And if I do sell it, I’m only going to get half, you know, you’re shit out of luck when it comes time to retire, if you can’t sell it. And that’s all you got, you know, you’re looking at a hard life, a hard retirement.

So generationally, we’ve got a growing community and I’m going say youngsters, because we’ve got people like yourself that are young of mind that have always tried to embrace something to make their lives easier. Okay. And then you’ve got the old crowd and I know some youngsters that have got an old head and just don’t want to do anything, but we’ve got that stubbornness, the business owner. And I see this from coaching, the business owner, the thinks he’s got it sorted is quite often one of the most dangerous things out there. How do you get through to the older mentality? And again, that’s not relevant to age, but that older mentality of stubbornness and feel, which is a horrible cocktail, how do you use your skills? And I suppose most of them are communicative to get these people to be open, to change. What is it, the first things that you do?

One of the things that I do is I try to use a lot of analogies so that people can put things in perspective. So for example, when I was growing up, you know, all over the news was the generation gap, how parents and teenagers or whatever, you know, Oh, we didn’t see eye to eye. But if you think about it now, the technology gap with people growing up now and their parents is literally more like children and grandparents or children and great grandparents when we were growing up or when I was growing up, there’s a huge gap, the technology gap. So that’s one analogy that I use. And another is when you want to sell a house, pretty much everybody knows. If you want to sell a house, if you really want to get a good price, you’re going to have to update your kitchen and your bathroom.

The technology gap with people growing up now and their parents is literally more like children and grandparents or children and great grandparents Share on X

Those are the two major things, you know, have nice paint, this, that, and the other. And if you don’t, you can still sell it where you’re going to get rock bottom price, because you’re going to sell it to somebody who wants to fix her up or well that fix her up, or is your business. If you have not done anything to bring it into the modern age, because Steve, you know, nobody wants to buy a job. When someone buys a business, they want to buy a going concern. That’s basically turnkey that they can jump in and run it. And they don’t even have to run it that other people can do it. But unfortunately the vast majority of businesses, small businesses actually rely so much on the owner to run it, that they can’t sell it because it can’t be run without them, or if it can, it’s going to be somebody else who’s working all the time. And doesn’t want to

God, we’re building in some horrible little habits here. But do you think there’s also an element of pride and ego with the older community and the businesses?

Yes, definitely. Definitely ego pride. And when you mix ego and pride with fear, that’s very dangerous. And the thing is, the fear is legitimate because if you don’t understand the topic, you don’t know if somebody’s giving you the correct information and that’s the problem. Somebody who’s younger might be giving you the correct information, but they don’t know how to explain it in a way that makes sense to the owner. That’s one problem. But the other problem is that younger people who don’t have the life experience and don’t have the business experience, don’t know how to ask the questions to help develop really strategic solutions. So a lot of times an owner will end up with a half baked solution and then there’ll be convinced, Oh, this doesn’t work. So it goes both ways.

Who’s your client? Is it the younger mentality? And again, I’m keen to say mentality, not age, but is it the younger mentality that embraces technology getting into the older workforce? Or is it the older workforce being educated to the fact that they need new technology in order to be able to grow?

It’s actually a bit of both, you know, especially with employees, I’ve helped a lot of companies when the employees couldn’t get the owners to understand what they were doing and why they needed to do it. But at the end of the day, all of it is for the owner so that they can actually bring their business up today. And not only be more likely to sell it Steve, but also have more relaxing, have more time for themselves and make more money while they still own it. Because even if you don’t want to retire for, let’s say 10 or 15 years, you still want to be able to enjoy it. So if you can use automation and things like that to not work as much or nailed you’re in COVID, for example, if you have to lay off people, if you can use technology to help you be able to still run your business without those people and without you having to do it that time and peace of mind is worth a lot.

So how do you get clients to educate them on the benefits of technology when they’re already petrified of using technology? That’s gotta be quite a conundrum there.

Yeah. And usually what I do is I’ll start with one small thing that somebody needs. So it, it might be invoicing, for example, that’s some something that everybody can relate to. So, okay, well, let’s get you on a cloud invoicing system. Let’s set up recurring invoices, let’s set up the reminders, let’s set up automatic payments and all of that. So that all of a sudden you go from working hours a week, you or somebody working hours a week doing invoicing to nothing it’s done for you. And I’ll get, I’ll give you an example. My cousin actually owns a landscaping company. He’s probably, I don’t know, I’m going to guess 15 years younger than me. And he lives in a different state. We haven’t been working together, but I saw that he posted, he had just started using a system, an online system to do his quotes, his, his estimates, his invoicing and everything. He said, it’s saving him about two hours every single night. And he fought it forever because he’s old, even though he’s young, he’s old school, like a pencil and paper kind of dude. And his wife was like, Oh my God, we have a kid, we have a life. Can you please, you know, come into the current world? And she finally got him to do it. And he said, I can’t believe I waited so long. And I don’t think this is any coincidence, his business, top $2 million within a few months of making that change.

So do you use testimonials to grow your business or, or, you know, literally just introductions as referrals. How do you grow your business?

Usually referrals. Because when somebody that I’ve helped is able to talk to somebody they know and explain to them how that, how I help them. It just makes them feel more at ease. So introductions where else? Just people that I meet, because once I start talking with people and I just like to talk anyway, as you can tell. So, you know, once I start talking with people, just out of genuine interest, not like trying to make a sale, a lot of times, my curiosity will just open up conversation that ends up turning into work for me or work for somebody else. And that’s okay too.

Yeah. I’ve always found that referrals are best. You know, you get to walk through the front door with the credibility of the person that’s introduced you. So there is nothing better than getting a referral. It cuts out a lot of the middle ground of a basically you trying to sell yourself because they’ve already come in and established what you’ve done for them. That’s really good. So where do you see now? I love the fact that you go in and you take a small bite, the idea of going in as something like invoicing. There’s no one out there that doesn’t understand the invoice and run your own business at the end of the day. If you don’t have a client and you’re not being paid, you don’t have a business. So hitting it right where it hurts to start with genius. Brilliant. Love it. But what do you think is the next thing that really caused them to go? Oh, I never thought once you’ve got over the invoicing.

Yeah, well usually what I try to do is I try to find some kind of pain point that we can tie into what I’ve already gotten them to do. So let’s say invoicing. I might get, use that to move them in to doing some kind of email marketing, to nurture their clients, to keep them front of mind, because as I’m sure, you know, it costs five times as much to get a new client as it does to keep one. So being able to nurture them is very important. So once I’ve got them used to invoicing and the emails going out as reminders and automatic invoicing, then they’re more open to starting to tip toe into using it, to nurture their current clients. And it might be just sending out, you know, once a month, some kind of helpful, depending on the business, some type of helpful piece of information. Once I get them used to doing that, then I can start introducing sales funnels and showing them how they can use lead magnets to get people in and nurture them and get them close to a buying decision before they ever have to interact with them.

Once I've got them used to invoicing and the emails going out as reminders and automatic invoicing, then they're more open to starting to tip toe into using it, to nurture their current clients. Share on X

Do you ever find the youngsters looking at you kind of like almost in awe or kind of like a deer in headlights when you’re sitting there talking to them about building up the funnels and automation and the fact that there’s, there’s this beautiful lady of 59 young, that absolutely knows this shit. Yeah. Do you ever get them kind of a bit in all of that?

Yeah, I do. And it’s funny because a lot of times, if it’s somebody that I don’t know yet, when they first look at me, they’ll be like, yeah, you’re an old lady, whatever, you know? Okay. Yeah. You work in web design, whatever. And then we start talking and Steve you’ve known me long enough. I’m not the type to brag about myself, but just through conversation, it comes out with what I know. And they really are. A lot of times they’re shocked, but then they are able to learn from me. And I love that because we can help each other.

Now you wrote it, you wrote a book. What was it? A few years ago. Three years ago.

Yeah. Three years ago, Boomer Cashout. And I wrote that book because of this very topic.

Now, wait, what is your website? Give us, give a plug on that.


All right. So folks remember that Lisa has got an S in it not a Z and there’s 2 P’s in Kipps. You’ve actually got the book on there. Now you wrote it for these people or for this, subject matter. How’s the reception been on that book?

It’s been great. You know, to be honest, when I wrote it, I didn’t write it like expecting it to be a best seller or anything. I wrote it mostly for my clients and my prospects to get them to understand. But it actually has sold quite a few copies and it’s got a cup a couple of reviews on Amazon and they’re actually five star reviews. So the fact that I haven’t marketed it, I mean, I’m pretty proud of that, but mostly I wrote it, you know, to help people learn. And another reason that I’m interested in this topic and that prompted me to write the book is that have a lot of economic development clients. And I was on an economic development board. So I see these communities going out and trying to recruit all these big companies like they used to decades ago. And those companies are few and far between now. And I understand that if they will concentrate more on entrepreneurs and help the businesses that help start new businesses and nurture the ones they already have and keep them going and not closing down when the older people are ready to retire, that’s actually a bigger economic impact than a big company. Just moving into town, having all your eggs in one basket. So it was kind of a double angle.

All right, now I would be amiss if I didn’t mention the amount of work that you’re doing with both NASCAR and the U S vets. I know it’s not only a business, but it’s very heavily a passion project for you. So, and we’re going to go into that, but it’s very obvious from this conversation for me getting to know you, the, you don’t take the easy road you’ve always kind of looked around and go, well, okay, that’s a smooth piece of tarmac over there, booster that I’m going to go over here. And I fell on this.


You’re dealing with older folk mentality that is scared, proud, frightened of their business, dealing with youngsters. They’re looking at like, look at you. Like you should have been an extra in Jurassic park. And now you’re moving over into the vents where they’ve had foam structure and now they want to come out and develop their own business where they’ve not been allowed, freedom of thought and expression. Those are tough markets for you to be sitting in the middle. What is the challenges you find in working within the, in the, in the vet community?

Well, I would like to say first, I’m going to blame that on my daddy. Me being like that, my father was blind and he did everything. He rode horses, he shot guns. He even drove cars and boats, but I won’t go into detail on that. I mean, my best friend in high school didn’t even know he was blind and she’d been coming to my house for two months. I have this real streak of stubbornness and just this mule headedness, as he would have said that, I want to prove that something can be done. And I’m not saying it’s very smart. I would have made a lot more money by now if I hadn’t been like that, but I know that’s where I get it from naturally. So with the veterans though, you know, that is true, that they’re coming from a very structured environment, but I have met so many very successful veterans and military spouses that it was stunning to me.

And then I started realizing it’s a lot of it is because of the self discipline that they have, you know, and they, they know to set goals, they know how to plan for it, and then they know how to execute. And they also know when to pull back, you know, and the veterans nail, you know, they’ve been at war and deployed for 20 years now. So almost everybody who is veteran has actually been in combat at least once, if not multiple times. And they just learned so much from it. Another thing though, is that there’s a lot more support for veterans now than there used to be. So there’s a lot more support structure that helps train them. For example, the Rosie network is one, one profits that I promote and they’re out of San Diego. Her husband is Stephanie Brown is the founder. Her husband’s actually retired Admiral. She started that because as a military spouse, it was hard for her to get a job when she moved around. Plus it was hard for her to find that or no businesses to hire. So she actually trains and mentors, entrepreneurs, veterans, and military spouses. And she also promotes them through a national directory that people can use to to locate if they want to be able to use a veteran or military spouse own company.

Yeah. I’ve seen, you’ve been working with them. I know you’ve been working with those through the NASCAR team as well. So you have those in their workers. If anyone’s not heard of the Mozy network, do yourself and us a favor and go and check it out. It’s got some great people there. It’s got some great advice and it’s a fantastic community. So I’m big congrats on the Avon behind it and everyone putting it together.

Oh, I was going to say this hasn’t been a nails publicly because of Cogan. I mean, like in a big press release, but the Rosie network is actually nail the soul partner with Google’s veteran led back initiative where a business can go to Google and apply to get the veteran lib badge. So that will help people know that this is a verified veteran led company and they have partnered with the Rosie network. So the Rosie network could work, could verify these companies because there’s so much stolen Valor out there. So right now it’s under the, you know, it’s kind of low key because they haven’t made a big announcement, but if you go to the Rosie network, you’ll see information about it. So I’m really proud of that, that this little organization, you know, put together something like that for a big company.

Well, let’s call it out. What is it? The rosie network. What’s the website. It’s an org and it’s

Yeah. Hold on. I think it’s the Rosie network just a sec.

Sure, sure. We want to make sure we get this right. We want to support anyone that allows me to sleep well at night and potentially,

Yeah, that’s for sure. Let me see just a second. I’m sorry. You think I’ll go. Yes.

All right. Well, that was worth waiting for, so I appreciate you on that. Now, Dan, we’re involved in a NASCAR team that you’re very heavily involved with as well on may. So how long have you been involved in that?

Well, years ago, like in the early two thousands, I had a client who was the Daytona 500 winner that I worked with. And you know, did a lot of different things for him outside in and outside of NASCAR with his nonprofit. But nah, for years I didn’t work with anybody else. And then the end of 2018, I started working with Colin Garrett, who was a young NASCAR driver from here in Virginia, where I live. And initially I was just going to give them advice. And then I got, I sucked myself in and here over a year and a half later I’m working with them. But what happened is initially the racing for heroes, which is another nonprofit that combats veteran suicide wanted to hire me to do a national awareness campaign. So when I went out and I realized that they do free mental and physical health services, job placement Motorsports is therapy.

Every bit of it is free and they had no paid employees. Everybody was volunteer. And I thought, I can’t take money when I know it’s going to be coming from a program. That’s Why I’m just, that’s how I am. That’s why I have no money, Steve. So I called Collin’s dad, Ron, because Collins brothers are both active duty army. And they agreed to let me use Collin and all of his race cars because he races in different series in NASCAR, use them as the platform for their national awareness campaign. So everything I do for them is pro bono. Everything the team does for them is pro bono. And that’s how it evolved into us. Also promoting the Rosie network and veteran and military spouse owned businesses.

Now Colin’s quite a young lad. How old is he?

He just turned 20. Yup.

So again, do you feel that the fact that you have not, you know, stuck in the sand pit with a bunch of other 50 year olds, do you think that helps you

Definitely. And you know, it was a lot easier for me when my kids were here. They’re now 30 and 32, so they’ve been gone for years, but they actually both worked for me from the time they grew up in my business. But then from the time they were 15 own, they both worked for me. Like any other employee would. So just by me being around them, you know, as I said earlier, that osmosis thing, I was able to learn a lot from them and stay young without even thinking about it, just because I saw them doing things. So once they moved away, I did have to make more of a conscious effort to make sure that I’m staying up on things and, you know, hanging around with younger people. You know, I don’t want to try to act like a younger kid or anything, but I do know that you have to do that if you want to keep up with the times, basically.

Yeah. You got to challenge yourself. I used to live and it’s embarrassing, but I used to live in Palm beach and you know, I was in my forties and I felt like I was the youngest person there. And when you went out for dinner, you know, they asked you if you wanted to go at like six o’clock cause it was early bird special and the lights were up. So you do get old quick when you’re not in an environment where you’re being challenged by different energy levels. So you are very positive, energetic woman. And I, I had hoped it was because of the people you circle with. And I think that has got something to do with it. Now, your website again, was Lisa Kipps Brown,

Correct? Yes. That’s correct. Because I’m on your podcast. If they go to, they can get a free copy of my book, boomer cash out with the discount code, blue fishing.

Perfect. So if they go to Lisa forward slash Steve Sims with just one S then Lisa’s going to give you the code. The code is bluefishing, and you’re going to get a free copy of your book, correct?

Right. yes an actual paperback copy, not just ebook. They can have to book if they want it, but a real book that they can hold because I’m old and that’s what they want to do. They want to own it. I love holding books.

Is there something gratifying when you look at the book and your bookmark is halfway through the book?

Yeah. Paper, you know, all that, but we’re showing her HD. Yup.

You’ve been doing a lot more videos recently. I noticed that with your, your guest celebrity appearance of your cat, it seems to be that unless the video is on that, cap’s nowhere to be seen, but the cat, the video comes on.


Yeah. And I noticed that the funny thing was that when you first started doing the videos, the cat would pop in and literally just jump in front of the camera and then bugger off and you would carry on. But do you think that helped get you a little bit of attention by the fact you never knew when this guest to parents?

Yeah. It definitely helped that attention wise, but it also helped me because once Thumper pops in, I am less self conscious about what I’m saying, and I just become me, you know? So I’m still saying the same thing, but I’m just more relaxed, but, and everybody loves her. They’ve started a hashtag free Thumper and actually a named Monique for K. And she’s also a veteran who owns a business called the queen of spades. And she started the hashtag free Thumper and she’s advocating to pump her to have her own shed. So I don’t know if I can’t get Thumper to sign a contract though. So I don’t know if I’m gonna do it or not.

Does videos on what LinkedIn Facebook, when he did the videos?

Well, when I record them ahead of time, I just post them everywhere. But the live ones I’ve started doing on Thursday evenings at seven o’clock under the topic of adaptable entrepreneurs and having guests about different topics like podcasting and video and so forth that I do on Facebook live. And then I post it to YouTube and share the links and other places, Facebook page, Lisa Kips, Brown dot re-imagine the year.

All right. Okay. And what’s your YouTube? Youtube handle.

Well, YouTube is my company. It’s GlerinBR. And everywhere else, I’m just Lisa Kipps Brown.

Alright, perfect. So I’m going to give that final plug. Lisa Kipps forward slash Steve Sims. That’s me put the code in there, bluefishing, and you can have a hard copy with your hot chocolate and your coffee so you can understand what you need to be doing and why you need Lisa. She’ll be able to straighten you out. Lisa, thank you so much for taking the time. And I’d really appreciate the fact that you are just challenging the way you should be thinking and challenging yourself away from people being stuck into that age.

Thank you so much for having me, Steve. I’ve really enjoyed it. And Thumper also said, thank you.

All right. Look after yourself and see you around.

Okay. Thank you. Bye bye.