Business Innovators Radio - Michelle Pippin From $50 to 7 Figures – The Unconventional Path to Success

Episode Date: February 3, 2025

In this episode, Nina Hershberger talks with Michelle Pippin, an entrepreneur who started with just $50 and bootstrapped her way to 7-figure success.Michelle Pippin is a marketing strategist and copywriter who built a thriving online business after humble beginnings. She started out with only $50 to her name, working as a virtual assistant and doing “anything for money” to make ends meet. Over the years, Michelle has grown her expertise in business strategy, positioning, and content marketing, eventually launching a successful membership community called Women Who Wow.During the interview, Michelle shares the details of her early entrepreneurial journey – from her “anything for money” days to building an HR consultancy and transitioning into coaching and copywriting. She discusses the mindset shifts that allowed her to go from feeling like an underperformer to realizing her true success. Michelle also reveals the strategies she used to grow her membership to over 630 active, long-time members who continue to renew year after year.This episode is a must-listen for any entrepreneur looking to build a sustainable, profitable membership business. Michelle provides actionable tips on lead generation, positioning, and creating a membership model that keeps customers engaged and coming back. Whether you’re just starting out or looking to take your existing business to the next level, you’ll find valuable insights and inspiration in Michelle’s story.To learn more about Michelle Pippin and her Women Who Wow community, you can connect with her on Facebook or email her directly at [e-mail]. Be sure to mention you heard about her on this podcast!MegaBucks Radio with Nina Hershbergerhttps://businessinnovatorsradio.com/megabucks-radio-with-nina-hershbergerSource: https://businessinnovatorsradio.com/michelle-pippin-from-50-to-7-figures-the-unconventional-path-to-success

Welcome to Megabox Radio. Conversations with successful entrepreneurs, sharing their tips and strategies for success, real-world ideas that can put Megabox in your bank account. Here's your host, Nina Hirshberger. Well, welcome to today's show. I am excited. I've got Michelle Pippin on the call today. We have been trying to make this arrangement to have this show for a month. When I saw she was on my calendar, Michelle, I was so excited to have you on here.

As I'm looking at your bio, you started out with like 50 bucks, and you bootstrapped your way to seven figures. So this is the kind of show that I love getting into all those details. But the first, so welcome to today's show, Michelle. Thank you. And I have been so looking forward to this. honest to God, if you saw my to-do list since August, like every few pages you'd see, nine a show, nine a show. And so we've had a little bit of some personal issues, a couple of deaths and stuff.

So I've had a little chaotic end of 2024. So I was equally thrilled to be on here with you. And, you know, $50 was not me being frugal. Like, it's literally all I had because my husband is. is now and was then a public school teacher. And I was working for the city in the Department of Social Services, and I was pregnant. And I, you know, back then, my oldest is 26.

And so back then I was thinking, like, I want to make money. I have to make money, right? I'm married to public school teacher. But I didn't want to put my kids in daycare. And this is like no judgment on another woman who does daycare. For me, I didn't want that. And so back then, you know, you might have heard rumors of people working from home, but you didn't know anyone who actually made any real money from home. And so I took the $50 and I just went on my anything for money tour, which is a funny little, my first year is so funny.

But I did make $63,000 that year. And I, you know, turned that $50 into $63,000. And I still didn't feel like a success. And I like to say that because I think. think a lot of people in the digital marketing world in particular, but just online for any business, it's easy to feel like you're underperforming, right? Like, I didn't know I was a success that first year because I was still kind of just making ends meet. I didn't know how business was supposed to work. And I think a lot of people will look at somebody who's like touting, you know,

you know, six figures in six days or, you know, whatever. And they feel like they're losing at the game. And I just like to say that, like, I was winning and had no idea. And a lot of people here, it's like, you know, when you're in business, you're turning over sales, you're serving people well, you are a success and it can just keep growing for you. So what did you do for that $63,000 that first year? Oh, woman. It, like, it was my anything for money tour. And I like to say if it was almost legal, I did it. But I did things like I would, by the way, I used my, I didn't have a list, right?

So I used my wedding list. I just got married. So I used that list because they would know my name or my parents' name or my husband's name or his parents' name. And I basically, I knew enough back then. I don't know where it came from, but I decided to send out 10 letters. Basically the letter was, I'm having a baby. I'd like to work from home. Here are some ideas of things I could do for you.

Can we meet and see if there's anything that I can do, right? And then the next week, I would call those first 10 people and then send out 10 more letters. That was the whole strategy. And what I ended up doing essentially, I called myself an at-home secretary because the term virtual assistant hadn't been created. But I type water reports for embassies overseas, like as an aside, don't ever drink the water overseas. It's nasty. But I would type in as water reports. I would type up for different attorneys.

I would type up divorce depositions. I did resumes for people. I was kind of the public face for these panels called community advisory panels. They were chemical companies or plastic companies were required to host them in different communities. So I would take questions from the community. So basically anything that might would pay me for. I took donations for a political person and sent off a thank you letters, forging his name. anything that

anything that they pay me to do from home that didn't involve me being on the phone because, you know, I had a baby by that time. That I did that. Yeah, so the long list. And so, okay,

your one ends, and then you've got to figure out, okay, what are you going to do next? So now what happened? Well, I really, so at that point, I wanted to kind of get a little bit more official.

And because I felt like I was, I don't know how to say it. Like the money, I made $63,000 that year, but I was nervous about money a lot, right? Because I always kind of like I was eating what I killed, if that makes sense. And so one of my earliest mentors from college approached me about starting an HR company together. And so she had the HR experience. I happened to have an HR degree, but no. experience. And we essentially did for a couple years, we provided employee manuals for small companies. And this was like big business back then. And, you know, there's a lot of money being

made. But I hated the work that I did. Like, I'm just a, I'm more free to be, you and me, you know, very, very, like, hippie chick. So, you know, dot in every eye, crossing every T, going in and making sure the stupid signs were on the wall for the clients. Like, I hate that. hated the work. And so, anyway, I was young and foolish maybe, but I decided that I had known that when I quit my job after the first baby was born, I had $213 in savings, right? I took 50 of that to start the business. I had no backup plan. We had no credit cards. Like, it was really like my back was against the wall. And so after the HR company, I thought, you know what, if I put on back against the wall financially, I'm going to make it as a coach. But back then, you know,

business coaches, I don't know if they all lived in the same multi-million dollar house on the beach, but, you know, that was kind of the flavor back then. Like if you're going to be anything relating to business, you had to be a gazillionaire, right? At least that's kind of how it was. And I'm thinking maybe around 2005-ish at this time. And so I said, I'll be a life coach, which was interesting because I'm a really terrible life coach, but I'm an excellent marketer, which meant I got found out to be a terrible life coach really quickly. And so I did a little spin as a life coach,

but I was more like if you would say, you know, something to me that you were struggling with, you know, if you brought it up the next week, like I'm literally saying we addressed that last week. Like I can't deal with those anymore. Like move on to your next issue. And so not very great at life coaching. but I found that I was really great at marketing.

And I'll tell you what gave me the confidence to go into business strategy and copywriting. Because at my core, I'm a writer. I love to write. But I was mailing something off at the local post office. And lady in standing in front of me had, she owned a reptile company. They did like traveling reptile parties. And I knew that they were in our local like advertorial magazine. And so she and I were talking, it's a long line, and I had, like, this little scrap sheet of paper.

And I wrote down, like, I love business. I love small business. I was like, here, like, do this, say this. And I wrote stuff down, I handed it to her. And she was, like, grateful, but, you know, I never knew if I'd see her again at that point. And she saw me, like, a month and a half later, and he had tripled her income, her sale, based on what I wrote on that little scrap sheet of paper. And so by this time, I was kind of getting some confidence.

I started to read about business and figure even my anything for money tour was pretty decent, you know, for what, 1999 or 1998? So I started getting the confidence and I just put myself out there, not as a business coach because it really wasn't a thing so much, but more as like a copyright or business strategist. I got into the Dan Kennedy world and just really have never looked back. I started Women Who Wow essentially because I didn't like the, I don't know, I didn't like the pressure I felt like of the one-on-one business client. You know what I'm saying? And a lot of that I was writing for them and I really just wanted to write for myself. And so I started Wow to impact more women, help more women entrepreneurs make the money they deserve and know they deserve. without the one-on-one kind of appointment setting and, you know, all of that.

I wanted more time freedom. So what year was that, Michelle, that you started the win in a while? That would have been 2017. And I wasn't exactly, the only membership, honestly, besides like AAA or something like that that I was aware of, was Dan Kennedy. And at that time, you know, I'd already seen Dan, you know, Stella's company to go Glazer, change hands a few different times. And so I wasn't exactly sure the form that Women Who Wow would take. But honestly, we started with in-person four-hour meetings once a month.

And essentially, it was like a little small event. And within six months, we had women traveling to my hometown. Massachusetts, Virginia, from eight different states. And I just knew that I was on to something. And so at first, I started a digital component to the live event. And the live event, as an aside, like, you got a print invite to attend. And you had to pay, right? The invite was to pay and attend.

But people didn't come in off the street to women who wow. And I really did that deliberately because I didn't want, like, another women's organization of kind of like the wannabe entrepreneurs, you know, like they're not really serious. So I wanted it to be a different, I don't know, vibes than that. And so I did an invite only, and after about six months I did a digital component. And then probably in 2018 or early 2019,

I went full online. Because at that point I kind of felt like I was doing my outs. my West Coast in particular, my West Coast members that are a disservice, because they're not going to fly into Virginia for a four-hour meeting. And so they're kind of missing some of what's happening live. And so, and then since then it's been all online. We do have live events, but they're not like, they're not monthly, and they're not only four hours.

They're multi-day. And it's open to the whole team. Okay. So you transitioned within a very short time, actually, from live four hours once a month kind of a, and it was it an implementation kind of four hours? Was it like hot seats? Yes, we did do hot seats. It was not a lot of implementation, you know, a lot of my events back then, and somewhat now with a few events being the exception, it was kind of a Michelle show, right?

Like back then my approach to business, my perspective, right? because I had been in business for a long time at that point, and I had seen all of the BS being spewed about, you know, and I had reading Dan Kennedy, like, every day. And so it was very new. Like, I was talking to women who were not in the Dan Kennedy circles. And so it was really not a lot of implementation. It was I would teach on a topic, which I would then create a newsletter out of,

mail the newsletter to my, like, members. who were not coming to a live event. The people who came got the newsletter there. And so it was really like topical each month. And then we did hot seats. And then at the end of every meeting, I would say, who should be here, right? And they'd give me their name and their address. And we'd send them a print invite to pay to attend.

That's really how we grew. And so how many do you have now in your group? We have about 630 right now, and we're getting ready to do what I would call like a, not a member drive. We've never really done that. But I have had a couple of years where I've kind of just coasted. I lost my brother and only sibling in 2022 and then several people in 2023 and then in 24. And so it's kind of been a time of, you know, just not hibernation for me. I've still been active.

I've still had my members, but I haven't really done a big push. And I'm feeling the excitement of that, which is really, really exciting to me. When you come out of a period of deep grief, like, feeling those embers burning again and getting ideas again. So, you know, we, but we have about 630 active members. And how much do they pay? Well, I'm a firm believer in never raising my prices on my, people. So when I first launched the digital only membership, the fee was $37 a month. And now I never

charged by the month as an aside. Like I don't believe in that. So everybody has to pay annually for women who wow. So but it was only $44 annually. And so some people are, have been with me since the doors opened and they still pay $4.44 a year. But if people come in now, if they came in via a friends and family link, like if they come to me directly or somebody's like, hey, this is my cousin, this is my friend, then they can come in. It's $8.97 for the year. And that's like the lowest that we charge. I think on the sales page, it's $12.97 for, you know, people who just find it, which is

honestly not, it's not often that people come in through that link. They usually are saying so-and-so sent me to you. I heard you on this podcast. You know, something to that effect. So whenever I can, I'll give them the friends and family link. So now your membership, and we're going to get into the topic today. We're going to talk about six ways to get leaks to actually come to you. But it's very fascinating because membership, you know, and you're right, Dan is not, you know, he's talked about it for years.

But it's very difficult to keep members paying members, you know, continually year after year after year. So you're obviously doing something right. You know, I think when I'm doing right, if I'm completely honest, because I get asked about my membership all the time and I'm always an open book, right? Like, here's what I do, here's what I sell, here's what I require. So most people who try a membership and it doesn't work are they keep having to like open a new membership, right? Which is really just a digital course if it's not ongoing, essentially, right? but it's a, you know, most people are listening to kind of what everybody's saying.

So like they'll do a dollar trial and then they pay by the month. And you know what I'm saying? Like all of the, just like everything, right, in business, you've got to really consider who you're learning from. And so my first membership was $97 a month. I called it the coaching gym, right? That was the one I talked about with the Magic Jack, right? And if you do it authentically, right, if you include your members in like behind the scenes of your business, if they feel included, and of course they get value, right, it's easy to keep members.

But a lot of memberships are kind of like, they're like kind of bastardized a little bit, right? They're more like, I don't know, like libraries of digital content that you get a little bit of access to every month. month. And nowadays, like that digital content, that information, that is, you know, that's like the price of admission, right? You're getting that from AI. You're, you know, if you, I, I guess I travel in the currency of a relationship, really, and positioning with my market, really position, you know, and of course, Dan, he talks about this, but, you know, I, I maintain my positioning and I focus on the relationship. And I never am trying to charge, like, I look at the membership offers. out there. And I mean, I wouldn't pay it. You know what I'm saying? Like for, you know,

one group call and then, like, you get, like, you know, some, you know, basically YouTube video and that's really the membership or you get one worksheet. It's just, I mean, we have content. I do create intents. They are always free for my members. I sell them to outsiders. But my focus is on always, like, what can I do to best support my people? And I'm asking that all the time. So like two years ago, I think I gave content prompts every single day of the year, 365 days, right? Because I knew that they needed, the blank slate was keeping them from just having public conversation with their market, right? Forget the content marketing, just be in conversation. And like, I'm always asking, what do they need? And then I produce it,

and I included in membership. And also, my membership is the bulk of my income. You know what I'm saying? So a lot of people have memberships as like a sliver. And so they're always trying to get people to pay more, right? So it's like, well, you're in my membership and they look at it like, well, they're paying $47 a month. So maybe I can get them to pay $197 for this, right? And with, wow, they stay because everything's included.

If I think something up, they're getting it. And, you know, sometimes I have things that are not, obviously live events are not included in the cost of membership. Sometimes I'll do like Christian-based programs. And I don't include that in membership just because I went and went people who don't share my faith to feel, I don't know, like, that there's, you know, it's like a bait-and-switch or something, you know, so I don't include that in membership. But mostly everything is, and it's easy to keep members when you treat them like that. Do you have an ascension model? I mean, do you do any kind of one-on-ones with people that pay as a higher rate?

Yeah, well, I do have a women on a mission. It's full at this time. And, you know, for those people, I meet with them, I meet with them once a month, one-on-one for an extended session. So, you know, that is an option when it's available. So I have to cap that at 30 because I don't want to spend all the time on the phone. And so I do have that. I don't talk about it. It's really, you know, if I were to have an opening, I I usually have a wait list for that. I have the 40 strategy days every year. Most people who pay for those want to get inside my model, right? Which is totally, I welcome it, you know, and they want to create something like this on their own. So I do 40 of those a year. And I have, you know, live events. Like I do a big media event in New York City every year.

We have, like, the top, top media producers and editors, like, The editor and chief of entrepreneur magazine came, you know, for four years. We actually stopped inviting him because one of his writers also came as she did. She's done at least five stories on our attendees. You know, we really curate the list. So the media that we invite are top-notch and they do stories on us. So other than that, but there's no like real ascension ladder, right? Like I really celebrate when people come into women who, wow, try to get to know them.

I don't know everybody like I want this. but they also, Women Who Wound members actually have one-on-one with me. So it's a couple times a month. They can click and like schedule 10 minutes with me. We also do, I just tried something out and I've made it a core member benefit audio coaching, which I love, right? So it's like Facebook message. We can audio back and forth.

So I try to do what I can to be really accessible to my members. And a lot of people whose memberships don't work. Like, they actually do the opposite. They try to get them into membership and then distance themselves, so they'll pay more in some ascension model. And I just, you know, it's just not the way I've ever done it. But, and, you know, also, any membership, it's very much like the gym membership, right? So a few times a year I've had to, you know, I've doubted myself.

Like, oh, I should have never said this is a benefit. But most of the years, like 20% are using it. and but a lot of people who come into wow they're really driven women and you know I really set the tone and the culture of wow at the beginning and so they don't need a babysitter right they're not calling you with every brain part they have or audio messaging me but a lot of times like I might not hear from some of them in four months five months but when they need me when they're faced with like hiring this person or marketing campaign or whatever they're glad they have me in that in their back pocket.

Interesting. And so all of it's women, you don't really have men that kind of sneak in there? We have a few good men, right? If they come to a live event, we'll usually embarrass them. We'll play like it's raining men when they walk in. But you're not fine with me. There's one event that I've done. Actually, I did it every year, twice a year before COVID.

It's our working pajama party. And men can't come to that because we actually stay in a house together, or multiple houses together. And so I wouldn't feel comfortable with that. But yeah, there are a few good men, and they just come for the marketing and the mindset. You know, they have tried a lot. They've actually men and women. By the time they find, wow, they've paid a lot of money on expensive coaches or programs,

and they're workers, right? They did the work, and it didn't work for them. And, you know, they're feeling like what's wrong with me, and they're looking for a simple business model that's predictable, that they aren't chasing likes and share. They keep it more simple than that. So if I go back to you've got a calendar of, because you talked about you teach every month in those four hours.

So when you're teaching, are we talking about joint ventures and upsells and downsells, and down cells and, you know, lifetime value, all of those kind of subjects? Oh, yeah. Now, just to be clear, I don't teach every month anymore, right? So now I teach in intensive. So, like, I might do 14-day challenge or something like that. Or I might do a six-week focused on positioning. So I don't do it.

It's not the same as when it began, where it was once a month. So sometimes there's no live training for a month, and sometimes. Sometimes there's a lot of training once a week for six weeks, right? So we do have one, I call it the C4. So it is content, celebrity clout and cast report. So it's kind of like what's working now. So we do that the third Tuesday of every month. But other than that, so it's not I'm not teaching every month, just to be clear.

But when I do, yeah, I mean, some of it is I don't teach what I don't do. so I don't be joint ventures or affiliate, and I have nothing against it. I just like to keep things really sure with my market. So if I recommend you, for example, like, it's not because I'm getting a kickback. It's because I really think it's going to help one of my members. So I don't do any joint ventures, so I don't teach that. I teach a lot on content marketing, old school strategies, positioning, right, messaging, the things that I've been able to master and use for profit.

Interesting. Okay, so let's switch gears and let's talk about the six ways to get leads to come to you. Yeah, so it's not, it's like six of the gazillion ways, right? But, you know, I started realizing I was talking to actually one of my members on Call-in Day, and she is in insurance. And she was saying that she was struggling because, like, somebody wanted her to, like, do some cold outreach. And it hit me, I'm like, gosh, I would never do. Even when I was broke as a joke, and I have been broke as a joke, like using water instead

of contact lens solutions broke, right? And I never did cold outreach because I just didn't feel like I'd ever be good at it. Like, and it felt, wouldn't we all just want leads to come to us, right? Like, that's the whole goal. And so I just kind of put together like six different things that I do. Some of things are not new. They're like little hacks, like different ways. of doing what everybody else is doing to have leads come to you,

but also come to you in the right positioning, right? So, quick example, you know the strategy where somebody will say, they'll put something online, they'll say. I just finalize this like whiz-bang report of 13 strategies, drop an emoji if you want to copy, right? You know, something like that, right? And it tickles the algorithm these, like it does all the things. but and then they give them a link and usually the link will give them a firewall right like

give me your email and your name and I'll give you this free report right so it's kind of like so that's like standard but what I do is I will before the report is done so I use the same strategy because it does tickle the algorithm a little bit it gets some attention I know who's interested but I never have the link available I don't ever do immediate links And part of this is positioning, right? So I will say, you know, comments or message me, right, if you want whatever I'm offering. Say the old school playbook, comments or message me. And I'll get a bunch of comments and I'll respond to all of them.

And I'll say, great, as soon as the ink's dry, I'll push it over. And this little pause, right? This little, like, weight is really quite brilliant. I do it because I usually don't have it ready. When I'm doing this, I get the idea and I get excited. but the pause is, there's a lot of profit in that pause because what happens is, number one, you give them a pattern interrupt. You're not sending them to a page where they sign up. You're all the right away, not like everybody else messaging them, right?

Number two, it allows them to wait a little bit, to think about your report, you know, to wonder about it. Sometimes they're coming to ask you, hey, did you ever send me that report, right? Because they're so used to instantaneous. And right away, the positioning is there. Does that make sense? Like, they're waiting on you. It does. And, like, if you give them an immediate link, most people aren't even looking at it.

You know what I'm saying? So you've got to, like, it's just one simple strategy that any of us can do to get in real profit-based conversations with the social media. Like, I don't love social media. I'm definitely not the social media expert, but I use it to my benefit. So, like, that's just one. So it's like giving the free report is not at all interesting or new. but not following in the footsteps of everybody else. Don't give them that immediate link.

Let them wait a little bit, right? Let them think about it for a little bit. And then show up, even if it's a week later, the positioning is phenomenal. Hey, it's finally ready for you. Now they're thinking it took her a week to put this together. I'm definitely going for it, right? So anyway, there's one little tip of six of a million. But that's just one strategy.

And if anybody wants this report, I'm happy to send it over something. really happy to send over time. It's really the transcript of one of our C-4 calls. So just talking about what works to the members. That's fantastic. In fact, I am looking at the time. It's always not my friend because we could talk more and more. Maybe I need to have you on the call again.

I'd love you. If somebody's really interested, Michelle, Ian, even being part of your members, membership or in wanting to get that special report, what's the best way to do that? Honestly, like, if they're interested, come directly to me. They can message me on Facebook. It's where you can make place you can also write. I prefer, you know, I like writing just as much as like the audio messages. But you can message me on Facebook at m.m.m.

backslash women who wow. So it's women plural who wow. And that way you can come directly to me. Nobody's checking it but me. You could also just email me like literally at my Gmail account. I'm like B as in Barbara, Michelle Pippin, P-I-T-P-I-N at gmail.com. Wow. You must have a big team of people that help you keep track of all of this stuff.

Oh, Lord, I do not. I have zero interest in a big team. So I have a team of about four people that I rely on. One is full-time. It's my oldest daughter, ironically. She came in when she became a mother. And then I have two other team members that are large, well, one is very project-based. One is more routine, but he does more the back end for me.

And I hate busy. So if I ever get too busy, like, I'm going to fix that. I'm going to change something in my strategy and my system because I hate busy. And now I've got grandbabies, right? I want the time. And so I'm still valuing the freedom. Well, that's fantastic. That's exactly, as Dan would say, it's a lifestyle business.

It is. I remember the first time I had Gabby Bernstein speak at one of my events years ago in 2009, in York City. And he said the word, lifestyle business. It was the first time I'd ever heard about it. And I even know what it was. Like I wrote it down. And I was like, oh, my God, I'm going to figure that out. and over time I just I didn't do it all at once you know I had a thriving consultancy right

like and where I was copywriting and doing strategy and I just like over time allowed the membership to take over and one by one I fired my one-on-one clients right as I didn't do it overnight you know I didn't I don't have that pension for risk but I did it over time and anybody can do it well you you've you've mastered the art of having the members membership, keeping them forever. And I'm so honored and appreciative that you spent a few minutes of your time today, just even to chat about it. Yeah, the honor is all mine.

I was so looking forward to it. I really appreciated the invite and look forward to more. Well, we're definitely going to have to reschedule and have you on again. So, this is Nina Hirschberger. Until next time, what would Michelle say? she would say reach out to people and

pause for a minute before you actually send them something do I have that right? That's just one thing yeah but stay in conversation conversation brings the past and there's no need to get all salesing on people

right like everyone loves to buy they hate to be sold to see yourself make the offer because you know what it would do for them right? Make the offer because you know it would do for them on the other side Yeah, that's absolutely true. So thanks again, Michelle, and until next time. Thank you for listening to Megabucks Radio with Nina Hirshberger.

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