Ep. 2 Selling An Amazon Agency with Wendi Mathis Held
Legacy Branding host Laura Beauparlant interviews Wendi Mathis Held, the founder and CEO of In The Black Retail. Wendi shares her journey of building and successfully exiting her Amazon agency, True Hero, which was acquired by Channel Key in 2024.
Laura and Wendi discuss strategies behind preparing a business for sale, the importance of personal and business branding, and the emotional highs and lows experienced during the process. Wendi also shares her new venture and offers actionable advice for founders considering selling their businesses.
Tune in for rich insights and expert advice on creating a meaningful, impact-driven legacy brand.
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Wendi Mathis Held is passionate about empowering and inspiring entrepreneurs and professionals to reach their full potential and to create a positive impact in their industry.
She is the founder and CEO of In The Black Retail, a premier resource hub dedicated to helping individuals and businesses thrive.
With over 25 years of experience in the retail industry, she is committed to providing comprehensive strategies and actionable insights to drive success in today's competitive market.
In The Black, a retail coaching company, provides training and consulting to entrepreneurs, retailers and brands on how to optimize their performance and profitability.
Wendi has a proven track record of developing and executing strategic plans, managing key accounts, and building long-term relationships with clients and partners. She has a deep understanding of the retail process, from buying and selling to product development and marketing. She leverages her expertise to help her clients achieve their goals.
Wendi is also a co-founder of True Hero, a full service Amazon agency that was acquired in 2024.
True Hero grew premium brands on the largest Ecommerce platform for over 14 years. She continues this work as Sr VP of Strategic Accounts at Channel Key. Wendi is skilled in new business development, customer relationship management, and retail marketing.
She is a driven, creative, and collaborative leader who is always looking for new opportunities and challenges in the dynamic and evolving retail landscape and to help others do the same.
@wendijomathisheld -
00:00 Introduction to the Legacy Branding Podcast
00:42 Meet Wendi Mathis Held: First Guest on the Podcast
01:05 Wendi's Impressive Background and Achievements
02:26 The Journey of Selling a Business
04:34 Crafting the Story for a Successful Exit
09:27 Emotional Highs and Lows of Selling a Business
13:43 Finding the Right Cultural Fit
14:33 Red Flags in Negotiations
17:21 Post-Exit Identity Crisis
18:47 Building a New Business
21:43 The Importance of Mentorship
24:19 Advice for Founders Looking to Sell
24:57 Defining Legacy
27:01 Conclusion and Farewell
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Wendi Held: You're in the wrong room. If you're the smartest person in the room, you're in the wrong room.
Laura Beauparlant: If Welcome to the legacy branding podcast. I'm your host, Laura Beauparlant here to guide you through the journey of selling your business. And building personal brand that leaves a lasting impact on the show. We'll explore real life founder stories, expert insights, and actionable strategies to help you navigate the transition, avoid post sale crisis, and create your impact driven legacy brand. Whether you're thinking of selling, building to sell, or forget the other side, this podcast is your go to resource for making your next evolution, your best one yet. Let's dive in. Wendi mathis Held. I'm so excited to have you on the podcast. I have to let you know you are actually the very first guest.
Wendi Held: I love that.
Laura Beauparlant: Thank you so much for being a guest on the legacy branding podcast. So let me first start by introducing you to everybody who's listening. So Wendi Mathis Held is the founder and CEO of In The Black Retail, a resource hub dedicated to helping businesses optimize performance and profitability. With over 25 years of experience in the retail industry, Wendi has a proven track record of providing strategies that drive success. Wendi also co founded True Hero, an Amazon agency that was acquired in 2024, so just this year, and now serves as Senior VP of Strategic Accounts at Channel Key. She's passionate about empowering entrepreneurs to grow, scale, and exit their businesses successfully. Wow. That is impressive, Wendi.
Wendi Held: Don't know if it's impressive, but it sounds good. It sounds good. Coming out of you.
Laura Beauparlant: always nice to hear other people introduce you and the things that you've accomplished?
Wendi Held: Yeah, it is. And it really is. It's it's humbling, to think about what we've been able to do and accomplish. Sometimes you forget Laura Beauparlant: think that's a common problem with entrepreneurs is we don't actually stop to celebrate our wins. We just keep going. And then it's only when you do pause and you look back and you go, holy crap, look at the things I've done, but as you're going through it, you don't necessarily see it the same way as when you reflect back on it.
Wendi Held: I think that's so true. I think that is a
Laura Beauparlant: Yes. In all entrepreneurs, everybody I've met anyway. So the podcast is called Legacy Branding. It is all about helping founders successfully exit their business. Talk about all the pros and cons, how branding plays a part in that, how founders are creating their legacy around what they're doing, whether it's with their business or what they're doing after. And so I'm really excited to have you here as somebody who's recently exited your business and also started something new so soon after also a trait of many entrepreneurs, right? We're goers, we're doers. We're like, we can't sit idle for very long. So I'm really happy to have you here and have this conversation. So I wanted to start by finding out what was the turning point when you knew it was time to sell your business.
Wendi Held: So it's interesting. So I started the business and 14 years ago. Which is a really long time to own anything really. If you would talk to Mack Lackey, who is how I actually exited and was the person who encouraged, he's four to six years is really a
Laura Beauparlant: He's definitely going to be on the podcast a
Wendi Held: good length of time. Yeah, he's amazing, right? But we really started the business as a lifestyle business. It wasn't something that we really felt we could acquire. I came from the space. I, it was early, right? So we started in 2010, about in 2019. I had known Mac through another process. Like he had a company called mountain khakis. I represented that brand on Amazon as part of true hero. And I started having a conversation with him about mentoring.
Laura Beauparlant: Hmm.
Wendi Held: Really early before his exit DNA program. And we started talking about it and I said, Oh, you can't really exit an agency. And he's No, you can sell a phone book, like you can sell anything. And so that started the process of, okay, what does it look like to be able to sell? And like, how do I, so I really went from having a lifestyle business to creating scale, to be able to exit, which is why I'm passionate about it. Because I think there's a lot of people that are in that position where they don't really know if they can. And then once they realize, That there's something that they could sell, how to really stage it so they can maximize valuation. And so it was really, for me, it was having that conversation with Mac was my turning point. And then from there on, it was getting the business ready to sell.
Laura Beauparlant: What was the process from like that decision? Like having the conversation with Mac Oh, I could actually sell this business, a business that you hadn't thought that you could sell to actually selling it this year.
Wendi Held: I think we would have escalated how many years we were selling. Have it not been for a pandemic and not to, to oversell that piece of it or over talk about that piece of it, but it certainly plays into all of our worlds in some way, shape or form. Really the big things were Oh, we always had clean books. I'm a kind of a numbers junkie, but really making sure that we understood where the numbers were, where we needed to get to process is not my strength. I'm not an operations person at all. So really like honing in, like again, another DNA of
Laura Beauparlant: I'm laughing cause I'm like, yeah. Yeah. Like we're great visionaries, maybe not great operators, but I have a really great person on their team that. Was able to step into that operations role and create SOPs, all the different aspects that we have that made us a niche, gave us a little bit of a, an upsell. And so highlighting those and then documenting it. And so that whole, and then growing it. So if I, if it, to make it worth my time, like what my, not only my top line needs to be, but obviously what my bottom line needs to be. To make it attractive and then being able to craft that story. So it was really like really getting into that scale. Those years, but the operations for sure growing top line and then making sure everything was very tight when it came to numbers. Mac was talks about the phone call. If you're ready to sell, so we would call and give you like, the number that made sense. Are you actually ready to walk out the door? And honestly, I wasn't in 2019. I wasn't prepared for that, but by
Laura Beauparlant: Yeah. So you just said something. So you said, It takes time to craft that story. So can you tell me a little bit more about what you mean by that?
Wendi Held: Yeah. Definitely. So one of the things that I learned through exit DNA and it was talking about we're not going to sell based on EBITDA, right? So it's not just a valuation, just a multiplier of EBITDA. So being able to tell the story of what it looks like. Hey, if you purchase me. And being able to say, here's the things that set us apart. Here's our unique factors. Here's like the reason that. We do it a little bit differently. There's a ton of Amazon agencies. I've been doing it for a really long time. Like 2010, it was really early, but then how we craft that story. So I spent a lot of time on branding for sure. So people knew who we were. I wish I would have known you before, cause I can, you wouldn't really help me do that. So next company, next
Laura Beauparlant: company we're going to work with Laura on the branding piece of it. And so being able to really, I understand like how important that piece was. And then talking about, it's hard when you're in the business and to say, Hey, my expertise is forecasting and we've created this forecasting model and this process that was just day to day, but trying to figure out like how we were set apart and having lots of conversations. So really crafting the story of here's where my niche is, here's who I am. And if I were to partner with somebody like you. Channel key. Here's where you could take it. And that automatically shows them the story of being able to increase valuation. So they can get really excited about what they have. That's unique to them that can take what's unique for your company that you're trying to sell and be able to maximize that valuation. It's pretty impressive what we were able to do from an evaluation standpoint. And. Channel key is still really stoked about their purchase. It's a
Laura Beauparlant: win for everybody then, right? Everybody wins.
Wendi Held: it really is
Laura Beauparlant: right. what's so interesting about what you said and something that I've been really trying to share with so many founders looking to sell is that the brand is a really important piece. In the sales process that they don't always think about. It's usually the numbers or the books or those SOPs, the operations. But if you've got a brand that is distinguished, that's differentiated, that's clear on what, what it does, who it serves, it's got brand recognition. It's not a hot mess. It's not inconsistent. Like all of these factors. Help make the business sellable because when somebody comes and they want to buy you, or you have somebody, if you work with an M&A firm or somebody like that, how are they pitching your business to potential buyers? And if they don't know how to talk about your business and what makes you unique and different, how are they going to be able to sell it to the right buyer?
Wendi Held: So I think it's also really interesting just pulling out what you said. It's one of the reasons I always wanted to be in the room is that no one is going to sell your business the way you can sell your business. I can craft that story for our broker for M&A, I had a really great team that helped me get everything across the line and, protect me and our business, our family, but really no one can sell the company like you can your own company. No one can tell the story like you can tell the story and no one can feel the passion like the founder.
Laura Beauparlant: 100%. . So what would you say in that process where some of the highs and lows on an emotional rollercoaster level of selling something you've built, like you just said it, you're, no one's going to care as much, be able to sell the business as much or be as passionate about the business as you are. So can you share some of those emotional highs and lows? Wendi Held: So I think, so I come from real estate. I have my, I've done real estate since I was 18 and I come from a real estate family. And so I think about how you're looking at your house and you're trying to market your house and you're, it's such an emotional attachment if it's your own personal home and you think it should be this price and it's really the market saying it's this price. So when we first went to market, I was almost offended by the valuations that came out. And I had this talk with my broker, which actually Robert Taylor, he's part of Baby Bathwater too. And we had this whole conversation. It's okay here's the number I want to get to and then build. And like I said, we started talking about in 2019 and pandemic, we brought a really big client right at that time, which was great for the top line revenue. But it was just one of those things where we're sitting here and we're trying to figure out how we're going to get to this number so we can sell it at the price that made sense for me to exit the business. And so I think that was a low at first. You're like, Oh my gosh, now I have to wait. I have all this time. It's gonna take me two years to get to that point. And so that was tough. And it's a, it's very vulnerable, right? Cause now if you have a family business, which we did, showing everything. You have to show all of your numbers and you show all of your mistakes and all of your failures as well as your successes, of course. But you are literally
Laura Beauparlant: like, here's all
Wendi Held: my numbers and they
Laura Beauparlant: don't
Wendi Held: it's like you're standing naked in front of them being scrutinized.
Laura Beauparlant: That's the feeling. And being
Wendi Held: scrutinized, like judged
Laura Beauparlant: And they're not going to, yeah. And they're not going to tell you like, Oh, you did so good because
Wendi Held: So you're sitting there and at some point you get to see their numbers too, but it's still such a smaller view of what they're, I think they're seeing everything. They're like, they're looking at your taxes and your financials. And so was a, that was really hard to get, to overcome. At first, like I was very private about all the things is my company. I didn't have to share anything with anybody. So that was it. That was difficult. And a difficult obstacle, but then once you've shown it to a few people and you have some people that are interested, you're like, yeah look what I built, like, And then you're starting to, again, trying, crafting that story about, yeah, we had this one, one really tough year as post pandemic, but look what we did and like where we're projecting to go. And you're starting to see that and that starts getting really fun. We had, really close to a deal at the end of 2022, we walked away. And best decision ever was walking away and I'm still friends with that person. They're a lovely person, but it was, it just became this terrible fit. So I think not just getting past here's the number, but now is it a good cultural fit? If you were in a position like I am where I have to stay on for that earn out, which is very typical of agencies and any service company. That's not true for everybody, but I knew that was going to be part of what I was going to do. So
Laura Beauparlant: And I've heard some horror stories from people who've had to stay on for their buyout and they're like, It is terrible culturally, they are, it's just not a good fit for anybody. And it's years typically.
Wendi Held: it's years. So we took, I took a little bit less money and I have a really good cultural fit. Yeah. So I had heard a statistic, whether it's true or not but I heard it. And somebody had said that only 14 percent of people complete their entire earn out. Laura Beauparlant: Interesting. So what happens then? So if you don't complete your earn out, you just don't get the balance. Wendi Held: You don't get the balance unless you can negotiate out of it, but no, pretty much if you don't complete it then you're done. I am. I'm in such a good place because I really love the company that I sold to. I was very purposeful about it. We courted if you will, for
Laura Beauparlant: 9
Wendi Held: thing.
Laura Beauparlant: So I got to really.
Wendi Held: Yeah, I got to really know him. We we became colleagues shared some, mutual issues with each other, like as far as Hey, can you help me on this account? What's your advice on this? We could get to see how each other's brains worked. People are really important to both of us. So our teams were really important. I think that, no, I don't think I know that finding the cultural fit is worth some money. So it was worth it. For us to take a little bit less to be able to have that really like the vision is the same. Our morals are the same. Our cultural is the same, which, it's still, you're still merging because they took our whole team. So all true hero came. I think we, there was only a couple of people that , we couldn't take over. I think there was two out of our 25 people.., our teams are now integrated and I think it's, I think for an integration of two companies, it's pretty darn good. I think we've done a pretty darn good job and we're at what nine months.
Laura Beauparlant: So what was like the red flags that you noticed? So you walked away from this other opportunity that would have meant more money. Can you share a little bit about was it a red flag? Was there something said or done or how did that go? So that maybe another founder who's in that experience, maybe they're not getting the feels, but they don't really know what to look for.
Wendi Held: Yeah, that's, it's a good question. So we were really close into it. We did a lot of conversations. I think it's like dating. So everybody's putting their best foot forward. And then when we sat down to start doing the negotiation, we were with attorneys and you're sitting there and you're listening and you're listening to how they negotiate and you're listening to how they talk and how they treat people. Again, great people, not my culture. And so really saying can you visualize yourself working for this person? And I'm not the boss, right? I'm no longer the CEO. So can I respect this human enough to take direction? And is that person strong enough to be able to listen to some pushback as well? Do we have a mutual respect on how we do business together? And. I couldn't get there in that moment. I started seeing, I don't want to say true colors, but really true colors, like really like, how are you going to talk to people? And how are you going to treat my team? I'm watching how you're treating the people at this table. And if you're in treat them like that, then I'm not sure if I trust you with my team or trust you with my clients, it's not the way that I would do that. I really, I stopped the conversations right there. And I was like, I know we're really far into this process. I've learned a ton, but this is not something that I can subject my team and clients to. This is not the direction for me. Laura Beauparlant: It's like walking away at the altar, right? Like you've gotten to the wedding, you've got the Wendi Held: it really was kind of
Laura Beauparlant: all this money. If you think about that and somebody to have the guts to literally on the day of a wedding go, Yeah. I can't do this. Even though it's probably the hardest thing.
Wendi Held: It's so important though. I didn't see any