LeeAnn Marie Webster is someone I’ve known over 5 years, but never had the chance to learn her origin story, aka how she got to this point in her business, until today. Turns out we have more in common than I thought! Join us as we discuss how our past experiences shaped who we are today, trusting our gut, and being comfortable with taking risks in life and business. It’s up to ourselves how we respond to risks and failures, so why not take a shot and use feedback to propel yourself even more forward.
Resources
Transcript
Erin marcus
Welcome to this episode of the Ready Yet?!?! podcast. I’m very excited today to introduce you to my guest, but also because I realized I’ve known her for years and I don’t know, as I put it, her origin story. So we can all learn this together. Right? So, Ms. Leeann Marie Webster.
Leeann marie webster
Hi, thank you. I’m so excited to be here and I can’t wait to connect and learn more about everything.
Erin marcus
Well, we met – it’s gotta be like a good five years ago. I think I met you during what I am now calling Erin’s Year of Failure.
I’m pretty sure I met you during 2018, which is now forever to be known as Erin’s Year of Failure when I was just figuring out what I wanted to do next. And didn’t quite – none of it was working. I’ll just call it that.
Leeann marie webster
Been there, been there.
Erin marcus
I met some really cool people, which I still know today, but why don’t you give everybody a little bit more formal introduction of who you are and what it is that you do?
Leeann marie webster
Sure. I’m Leanne Marie Webster. I am the creator of Email with Heart and I help entrepreneurs to build, grow and nurture their email list without being cheesy or sleazy.
Erin marcus
Yes. It’s the cheesy not sleazy part that matters.
Leeann marie webster
Everyone loves that.
Erin marcus
Yeah. It’s so true. It’s so true. And now it’s all in the direct messages, right? They’re like, well, I didn’t do it by email. So I’ll just do it in your DMS.
Leeann marie webster
Oh my God. Yeah. And the reason I actually came up with that was because I found when I was talking about email and you know, I’d meet someone at a networking event, tell them what I did. When I said email, without adding that little caveat on there, a lot of times I could see their face go like, oh…
Erin marcus
In a former life, I worked with families with aging parents and I would help them through the downsizing process. And all the time I would get this follow up from my clients going, oh, I thought you were gonna be the, throw it all away lady, like you weren’t gonna let me keep any of – No, that’s not how we do this. That’s not why we’re here.
Leeann marie webster
Right, right.
Erin marcus
But I think it’s so true. I think it’s one of those topics that is interesting to me because you meet people who don’t get it at all. And they give everyone a bad taste in their mouth. You meet people on the other end of the spectrum who are so worried about doing the wrong thing, saying the wrong thing. Someone won’t like me, that they end up not saying anything at all.
Leeann marie webster
Yes. Yeah.
Erin marcus
Yeah. And then there’s this beautiful place in the middle where we all get to talk to each other.
Leeann marie webster
Yes,
Erin marcus
And help each other and grow our businesses.
Leeann marie webster
Exactly
Erin marcus
And do all the things that we actually really set out to do. So I have a question, because like I said, I don’t know your origin story. Where did you come from? How did you get here? Did you jump off the corporate cliff? Were you pushed off the corporate cliff? Did you ever have the corporate problem?
Leeann marie webster
Oh my gosh. I’ve been in and out of it. You know, I always like to say that as a small child, I dreamt of being an email marketing expert.
Erin marcus
The astronaut, the ballerina, the veterinarian, the email marketer. Well, here’s the thing when I was a small child, there was no email marketing.
Leeann marie webster
Really we did not exist when I was a child either. And I’m older than I look. So yeah. My path is a little – I’m an attorney by training. I don’t know if you know this.
Erin marcus
I don’t think I knew that – we would’ve been having completely different or no conversations.
Leeann marie webster
Yeah. See, I call myself a recovering attorney because, you know, I come in peace. So I did practice law for a few years and then I’m originally from Ohio. I moved to California originally to practice entertainment law because I was unhappy with my practice and I thought it was because of what I was doing. And so I kind of had this like, oh, you know, maybe if I change the area in which I practiced, then I will be happier.
Erin marcus
Subject matter. Totally get it.
Leeann marie webster
I just don’t like practicing law.
Erin marcus
That had to be a brutal realization. You know, I talk a lot to a lot of people, myself included, who had fantastic careers. Fantastic corporate careers with all this time and money and effort invested in it. And to walk away from that, like that’s the conversation you never wanna have with your mother. But as you know, some people lose their jobs and find entrepreneurship. Some people are weird enough to leave fantastic jobs. But the similarity you’re talking about is the time, the money, the investment to be the thing.
Leeann marie webster
So, I quit practicing. I ended up getting into – it was when I moved to California to practice entertainment law, then I realized relatively quickly that I didn’t want to practice law at all. And I didn’t pass the California bar the first time I took it. And so thankfully, no one will hire you in California if you haven’t passed the bar yet because the bar passage rate is so low. So that ended up being a blessing because during that time when I took it and then I had to retake it, I realized that I didn’t wanna practice and I would be strong enough to walk away from it. And so I did that. I got into court reporting sales, which is selling to the legal industry.
Erin marcus
That’s quite a business. It’s one of those businesses you don’t know exists.
Leeann marie webster
Totally, totally. But it can be quite lucrative in sales and even being a court reporter, if you have that technical skill. And so I did that and then I was really good. I started doing training and I rose up in the ranks for that. And then of course I was like, meh.
Erin marcus
I’m doing fantastic. This is boring.
Leeann marie webster
Exactly, exactly, exactly. So I went – let’s see. So first I left the court reporting sales to go, – sorry, this is gonna be a long answer to your question, but I promise it’s a good journey. It’s a good journey.
Erin marcus
Very interesting.
Leeann marie webster
I went from court reporting to working for – I discovered coaching by the way in late 1998. You know, before anyone really knew what it was and I was in California and I did coach training through Coach U and so I left court recording sales to open a division called Professional Development Services for Spirion, which was a fortune 500 company. And I worked in the legal division, and had court recording. That’s how I kind of made that transition. And so I did that for about a year. And that was really cool cause it was like the backing of this big company and in coaching, which was new and exciting. And after a year I was like, oh snap, like, you know, I’m way ahead of the curve. And people are not hiring coaches, especially in the legal world.
Erin marcus
They’re still having a hard time. I mean it’s 30 years later and they’re still not really getting that. It’s hard.
Leeann marie webster
Totally. So, that’s when I was like, huh. I literally was talking to a friend. My friend said, you’re great to be around. Can we just figure out a way you can have your business and people just pay to be in a room with you? And I was like, how do we do that?
Erin marcus
That sounds fantastic!
Leeann marie webster
I was single, which I still am. And I created a singles business doing events for singles, which ultimately became speed dating. And I was the first person to do speed dating outside of the Jewish community. And I had the largest speed dating company in Southern California.
Erin marcus
But what you’ve really had, even though some of them were jobs, is an entrepreneurial journey that was just sometimes housed within a company.
Leeann marie webster
Yes. For sure. For sure. For sure. Yeah. it was because I always was in a place where I was either creating a new position. That’s always been my kind of thing. My jam is creating, and I love doing that because then no one could tell me, well, you know, Susie never did that.
Erin marcus
Right. No one can tell you you’re wrong. No one can tell you what to do because they don’t understand. I’ve had the same thing. It finally clicked to me that I’ve always been an entrepreneur. It’s just sometimes it was within a company. So I have a question for you because one of the biggest challenges I see with entrepreneurs is a lack of confidence. How, or did you even realize why? Cause I don’t know why I have it. So I’m still waiting for someone to explain it. Where does the confidence come from to continually walk into place after place, after place, willing to change the rules? You don’t have to answer, because I don’t.
Leeann marie webster
We’re gonna open a can of worms potentially. I’m gonna give you the snippet answer and you can tell me if you want more. And it’s coming to me just because I’m literally, I don’t know if you know this part about me either. I’m literally working on a one woman show. And it’s gonna be like if Tony Robbins and Tina Fey did a show together. So like motivational, autobiographical and funny. Hopefully.
Erin marcus
You’ll be fine.
Leeann marie webster
And, literally yesterday I was working on one of these stories and it hit me yesterday as I was working on this story that this is one of the reasons I’ve been so successful. I think it comes from this. So when I was four,my brother, Danny, who at the time was 12, was killed in a car accident.
Erin marcus
Oh, wow.
Leeann marie webster
What I see now that happened – because my four year old self, of course, didn’t know. And what happened was everybody went into their own world and had to go take care of themselves. And you know, this is 1973, there’s no counseling or let’s get therapy. Like, you know, none of that is happening, especially in Southern Ohio, you know, in a, in a smaller town and with no resources like, you know. And my parents divorced when I was three. So there was a lot of chaos packed into those two years. And I think as I look back and by the way, it took me 40 some years to look back and catch this, that at that moment, everyone went on their own and I realized I was on my own and I had to fend for myself and I had to, to do what I needed to do. And it’s like, when I look at, you know, how on earth did I walk away from a good job? How did I move cross country? How do I travel all around the world by myself?
Erin marcus
You never didn’t take care of yourself.
Leeann marie webster
That’s right. Cause I knew I was the one who was gonna do it. And, it turned out I’m also smart, which helps a lot. And so just along the way, there’s been every now and then the right person just stepped up and was like, Leann, you’re smart enough. You should go to law school. You’d do really good. Okay, I’ll go do that. And then like something will come along –
Erin marcus
It’s so true. And I’ve heard this side several different ways. There’s no such thing as a successful entrepreneur who hasn’t overcome something dramatic. It really is true. And it doesn’t always have to be insidious or malicious.
Your parents weren’t trying to neglect you by any sense of the word. Right? And my version of that (for people who don’t know) came more in a health crisis, my first operation was at 24 hours. I had three life saving operations before I was two. And then I got my face ripped off by a dog when I was five. So I have 110 stitches in my face. So the bottom line to that was no one was allowed to touch me. No one was allowed to touch me. There were very few people who knew how to take care of me.
But you get that survival instinct, right? And then of a myriad of parents divorcing and decision making and money or not money and all the different things that just happen. And you realize you’re on your own, and I don’t wanna say that any more than you did in a – It’s not a woe-is-me thing. It just is.
Leeann marie webster
Well, it’s a tremendous gift with the upbringing that I had. I wouldn’t, I wouldn’t wish it on somebody and I wouldn’t change it because I learned lessons very early on that have served me like crazy through my life that have given me a will and an instinct and a gut. You know, I have one of the most amazing gut instincts ever, and I know part of it is my brother, because my brother isn’t on this planet with me and he’s guiding me and he can help me, you know, go here, go there, talk to them, and to be able to tune into that –
Erin marcus
But you listen to it, you listen to it because at the end of the day, what you know, and I’m projecting here because I feel, you know, I think this way about – because people will comment to me – one person put it so well. And as a writer, you’ll appreciate this. I’m perfectly comfortable out on the thin branches.
Leeann marie webster
Oh, for sure.
Erin marcus
I’m perfectly comfortable because at the end of the day, what I know is I will always be okay because it’s always up to me to be okay. When we talk about personal responsibility, people usually start out with a downside of it, like the guilt and the weight of it. But if you keep at it, you get to this empowered side of it.
Erin marcus
Loving what you’re learning here and interested in, more check out our free Facebook group and join us at Conquer Your Business community to find even more tips and tools designed to help you get out of reaction mode and into conquering your own business.
Leeann marie webster
Well, it’s that knowing that deep knowing that it doesn’t matter what happens. It doesn’t matter what happens. I’m already okay. It’s already good. And I’ll flourish in another way. I mean, the business thing is so interesting because with the speed dating business. So I ended up by the way, going from zero to 20,000 email subscribers, to build that business, and this was before there was Constant Contact.
Erin marcus
You were doing a lot of this manually.
Leeann marie webster
I had an Excel spreadsheet with 20,000 names and I had this little piece of software that would BCC every 10. Anyway, I brought it up because I ended up taking on a business partner and then we had this bad divorce. And so I ended up selling the company to her and, and I mean, phenomenal, that’s a whole other story. I won’t even drag you into.
But here’s why I’m bringing it up. I had started the company and started the speed dating and then I brought her in and together we built something that we couldn’t have built alone. I know that for sure. And we were on national television and we were, you know, it was a thing. It was amazing. And I remember sitting with her when I had made the decision that, my original request was I was gonna buy the business from her, like take it back to me, you know, and do this. And, she was not having that. And I just remember sitting in a meeting with her one time and just watching how she dug her heels in. And she was so attached to it. She was so attached to it. And I just remember thinking that will never be me. Nothing will ever have a hold on me like this because I will recreate. This is amazing. And it’s awesome. And there’s all, there’s all this stuff with it and it’s incredible. And I can do it again. I can do it again and I was able to walk away and, and it was like –
Erin marcus
So let’s fast forward a little bit. You’ve been in your current – am I missing? Am I skipping decades here?
Leeann marie webster
No. The only thing that was in between. So when I left the speed dating, I did go into marketing and business development for international law firms. So I kinda went back into the corporate world for a little bit, but then on the law firm side, I did that for seven years. And then my current business I’ve had for 10 and a half years.
Erin marcus
This is the other similarity that I think helps me immensely. And I see that you’re doing it as well. I have what always felt like these random experiences that on paper have nothing to do with each other, but are exactly what I needed to learn in order to do what I’m doing now, which is truly the first thing I’ve ever created on purpose. Mm. Like I’ve created other things, but I always got my job. I always got my next opportunity by doing a good job and being presented an opportunity. Mm. This was the first, you know, my business now, conquer you business, what I’m doing now was the first time I really took a long time to decide what do I want to do? Not what’s in front of me, but what do I want to do? And I don’t know that I could ever be doing as well as I am and be having as much fun with it as I am. If I didn’t have this crazy random background.
Leeann marie webster
Yes. I agree. A thousand times. Yes. A thousand times, yes. It doesn’t seem like it makes sense, but I can stitch together the why. And like you said, the pieces, you know, the first year of my business, what I started doing in this business, I’m, you know, 180 degrees from that. And what I learned in that year, I now see it was the pieces and the building blocks that let me go to the next thing. And then the next thing and the next thing.
Erin marcus
I never would get to multiple six figures in less than three years if Erin’s Year of Failure didn’t happen first.
Leeann marie webster
Right, right, right. Yes.
Erin marcus
You need – and this is the whole thing about failure. And I can tell, by the way you’re talking about it, it’s not failure. It’s just information.
Leeann marie webster
Just learning.
Erin marcus
It Didn’t work. Failure to me is like giving up. Most of failure isn’t very loaded for me emotionally, because what I know to be true is that most things don’t work. So it’s not, you know, failure feels big and heavy, but the truth of it is most things don’t work.
Leeann marie webster
That’s true. Yeah. That’s so true. I was talking with someone about that the other day. Cause she’s like, oh, you know, I did this thing and she did like a webinar or something and she’s like, you know, only like 10 people showed up and I was like, girl, I’ve had nobody show up.
Erin marcus
Yeah. I mean, and you just plan for the fact that next time you’ll know what not to do.
Leeann marie webster
Right. Right. Well, I mean, all marketing is like that. Right. All business owning. But also I especially think all marketing is like that. It’s just, we get so attached to it, it’s gotta work this way and gotta do this way. And this has gotta happen. And we get attached to the gurus or whatever, the other people who, you know, say like, well, I just sent out one email and then I made a hundred thousand dollars.
Erin marcus
That’s my favorite thing to rail against. I sent out one email and made a million dollars. I’m like, yeah. But you sent out a million emails that made $0 first.
Leeann marie webster
Right. They don’t tell you the shit that they did.
Erin marcus
But that doesn’t look good on Instagram. Hey, I sent up my 432nd email that –
Leeann marie webster
Nobody did anything. Right. Exactly. Exactly. And not that you need to send 400. I mean, ideally, you know, my business Shortens the (email marketing) learning curve, but you still have a learning curve and there’s no getting around that. There’s still gonna be things that work and that don’t so just roll with it, go in knowing that. And then, you know –
Erin marcus
And like you said, find the people who can lessen your learning curve. I watched so many people stay stuck, stay in frustration. I’ve had a conversation with someone who was also a business coach and she literally told me she didn’t wanna hire me because she was a coach and she didn’t want someone telling her what to do. And I thought about that for a second. And I’m like, all I want is for someone to tell me. If someone has already done what you want to do, hire that person.
Leeann marie webster
Right. Right. Fast, fast. Right. And plus, can we have a little integrity moment here that if you’re coaching someone and you’re training your thing, you need a coach to help you with da, da, da, and you don’t have a coach helping you with your thing. I think there’s a giant integrity issue there.
Erin marcus
And I used to say, and someone pointed out my error and I agreed with him. I used to say, I had a hard time with people claiming to be able to teach you something that they’ve never done themselves. And then what they said to me was yeah, but look at all the basketball coaches that have never played basketball. So, okay. So that was a valid point, but there’s gotta be a huge level of understanding.
Leeann marie webster
I hear that. And I agree with that in the sense of yes, and not necessarily the best basketball player makes the best basketball coach. I’ll give you that for sports. And if in the absence of doing it well for yourself, you need to be able to have done it well for other people. And so there’s a lot of people that don’t have either one of those categories. They’re taking the fake it til you make it a little too extreme.
Erin marcus
And we all have to start somewhere, but there’s ways to get started. In integrity and going back to what it is, you know, as we wrap this up, we’ll have to do like seven more episodes because now more questions instead of less questions. I always really liked your approach to what you teach people because there’s another reason why not just that it’s the right thing to do. But as someone who’s a little weird, a little different, you know, people notice by doing things the way you’re talking, I get to just be me.
So tell us a little bit how to get a hold of you, sum up what it is that you can do for people, talk about your one woman show. I mean like all of it, give it, however much you want to share.
Leeann marie webster
The easiest way to get ahold of me is to go to my website, https://leeannmariewebster.com. And that’ll show you all the email stuff. There’s nothing public about the one woman show yet because I’m literally in the beginning phases of it. In fact, I can’t even believe I mentioned it because I gotta be honest. There’s a part of me. That’s like-
Erin marcus
And now it’s out in the universe!
Leeann marie webster
So yes, it’s happening! June 24th, 2023. That is the date in Chicago. I got the date. I’ll be ready by then.
Erin marcus
That’s how you start, reverse engineer it from there. Perfect.
Leeann marie webster
That’s right. So there’s, that’ll get you all the information on that. And what I’m about. Let’s see, is it the whole reason I started email was hard. The whole reason I do what I do is, is actually in line with what we’re talking about. I really wanted people to, I wanted to change the conversation around email. I wanted people to remember that it’s about building a relationship. It’s not about building numbers and just tumbling people with messages. And you know, let’s, especially as coaches, as speakers, as authors as, as you know, consultants and entrepreneurs, as people who are in this personal service industry, let’s take that time to, to leverage this mode in a way that, that honors everybody, I call it honoring the inbox. It’s really like, let’s, you know, let’s use this as a connection tool with our tribe so that we are building that relationship and, and building it into one that’s long term. That’s not just like, here, let me go sell you this. And you’re gonna buy from this right now. And if you don’t buy that amount, like no, let’s, you know, build it as something that will serve us long term. And by the way, it’s probably a lot more fun that way too. because then you’re not trying to like, how do I manipulate this message?
Erin marcus
You get to choose: do you want to create a relationship and have that be the way you run your entrepreneurial journey, the way you run your business? Or do you wanna go for numbers games?
For those of us who wanna choose that and I’ll share my stat with you, because I’m very excited about this. I recently had an open rate on one of my emails at 47%,
Leeann marie webster
I love it. That’s amazing. Amazing.
Erin marcus
So here’s the deal. I Highly recommend people reach out to you. Growing your email list, growing your audience, you can’t get a more important part of your business. I teach a lot that your marketing gets planned first. Yes. Before client fulfillment marketing gets planned first. Because without it, you don’t get the client fulfillment part.
Leeann marie webster
Right, so right.
Erin marcus
So you might as well make it something, you enjoy doing something you get good at doing. And I know that you have a variety of ways that you help people do that. So thank you for sharing your story. I knew it’d be interesting. I had no idea where this was gonna go. This was phenomenal. I seriously look forward to maintaining, growing the connection and I’m excited to share you with my audience as well. So thank you.
Leeann marie webster
Thanks. It’s been a lot of fun.
Erin marcus
I hope you enjoyed this episode of the Ready Yet?!?! podcast. I truly enjoy bringing these stories of success and inspiration to you. Please join us in our mission to empower entrepreneurs, to be in charge of their businesses and in charge of their lives. By sharing this with anyone, you know, who would benefit from our tactical and motivating advice, leaving us a review and letting us know if there are any particular topics you would really appreciate hearing about see you next time.
