The #1 reason mid-market B2B startups fail — Lindsay Tjepkema names what nobody says out loud

Welcome back to another episode of the Bridge the Gap podcast powered by Revenue Reimagined. We have a special guest with us today. We have Lindsay Chepka, who is a three-time founder, 20-year B2B marketer who now helps founders grow their businesses through story, thought leadership, and building authentic, human-centric brands. That is not mass emails. That is not just cold dialing, spraying and praying. That is being authentic and building a human-centric brand, which we're going to talk about today. We don't have AI Dale here. We have real human Dale here today. Lindsay, welcome to the show. Thanks for being here. I didn't tell you that I'm actually AI now.

Oh, I like it. A spoiler, just a plot twist. All right. Do we have to prompt you properly to get the right answer?

Yes, please.

Okay, Dale, this is your test. What is the AI prompt? This is tough. This is tough. Lindsay, thanks for joining us. Amazing resume, and I love the human-centric brand part of it. A lot of our founders and customers and companies that we're talking to, they're struggling with top of funnel, and we call it like stabilization because we're kind of identifying their ICP, their buying persona, their value proposition. Of those three, where do you believe the customers are failing the most, and what are a couple things they can do to change it up today?

Okay, give me those three that you listed again.

Ideal customer profile, buying persona, and value proposition.

Oh goodness. Okay. Well, I mean, obviously it can fall apart with any of those, but I think it all starts with your "who." If you don't have your who figured out, what are you doing? If you're trying to build something for everyone, if you don't have your ideal customer profile figured out, I think that's where it all starts.

Yeah, it's so. We talk about that a lot, right? ICP. What is the proper ICP? Who are you selling to? And I think a lot of people, certainly that we see, and I'm curious your thoughts, confuse your ICP and your BP. Your ideal customer profile and your buyer persona are two very different things, at least in my opinion. Are they different to you? And if so, what are the differences?

I don't know if I'd say they're very different, but I think it's important to call them out. So, ideal customer—like, I would always say, here's who we're talking to. Here's our total addressable market. Who could buy from us and be very, very happy? And then if you're talking about ideal customer profile, that's a little bubble within it, saying, but ideally, the ones that we're building for specifically—the one that this is absolutely designed for—are these people. And I think your buyer persona is okay. Within anyone who does buy from us, this is who's making the buyer decision. It might not be the user. It might not be the person who initially finds you. But they're the one who's actually going to be buying. That's the way I think of it.

So I'm loving this part of it. And one of the things we've been asking a lot of guests—not really founders or people that are running it—but how often should people be pressure testing this ICP, buying persona, value proposition? Because I can tell you in the past it's been like, I don't know, couple years seems fine.

Couple years seems fine? I mean, maybe if you're like Eli Lilly or something, you're like a massive company. But especially for startups, if you're talking about growing, it's going to change. It's going to evolve. I mean, let's say even your company stays completely the same. No pivots, no bumps in the road. Look how much just the world has changed in the last few years. My word. I mean, like, while I was a founder of a venture-backed company, we went through a pandemic, and like, everything—from how we buy, what we buy, where we work—like, it all changed. So the answer to your question in my mind is constant.

I was talking to somebody yesterday about the same kind of thing, and she was talking about like, how often should you think about brand? How often should you talk about messaging? How often should you talk about ICP and pressure testing things? And it's like, think if you, as a human being, thought that you could just think about your personality one time, go figure it out, and just be like, "That's done. I'm going to go live my life now. Figured out my personality." Like, you're constantly getting feedback. You're constantly responding to how the world is interacting with you. And as a leader, you're going that much further to actually get intentional about it monthly, quarterly, yearly to say like, "You know, I'm reflecting on what the world is telling me." The same exact thing goes through your business. You got to be constantly taking feedback and understanding how those people that you are designing your business for are responding to what you're putting out there.

Adam, you have to change your personality. That's it. That's what I get out of that conversation.

It, I, I, I do. Lindsay, let me ask you a question. So I want to tie this to I can. A lot of founders, when it comes to changing their ICP, letting go that CRO who hasn't helped close a deal in six months because they're afraid that, you know, something is better than nothing, scratching a product that just isn't performing. A lot of times we're talking with founders, and we hear the word, "I can't. I can't do that. I can't make this change." I know you have very strong feelings on the word "I can't." Talk to us about how and why founders should shift their mind to "I can" versus "I can't."

Wow. It's almost like you teed this up because I have a show called "Actually I Can." I may be the one of the two of us that does a little bit of show prep. Well, I appreciate it very much.

Okay. So my whole thought process there is that, as anyone—as a human being, but I think especially my experience as a founder and talking to and working with a lot of founders—is that as your business scales and your business grows, your job changes so much all the time. And unless you've actually been there, you might think you understand, but you don't. The pressure, the amount of pressure on you to figure things out, and all of the voices—not only in your head, which seem to multiply, but also around you. All of the, "Hey, you should do this. You need to do that. Don't do that." To your point, like, you absolutely can't do that. If you're not careful, will completely dilute that magical vision that started everything in the first place.

And so to me, this whole "Actually I Can" conversation that I've started is like, what got you here was something that is nothing short of magical. Founders are crazy. Founders are a little crazy. You have to be, right? You have to be. And it's, you're adventurous, and you're not risk-averse. You're a risk taker and you're a dreamer. Like, that's what got you here in the first place. And if you listen to all the real or perceived voices that tell you you can't do something, you're going to be just like everybody else. Like, best case scenario is mediocrity. So you've got to really, really protect that vision and surround yourself with people, affirmations, and just self-grounding to be like, "This is what we're doing, and you know what? That's all good advice. I'm going to pick and choose what I actually absorb and really make myself believe that actually I can see this thing through."

I love it. That's amazing. Yeah, when you were saying that, it reminds me of Eric Thomas. He's got that mantra: "I can. I will. I must." And it was like, that was kind of going through my head as you were saying that. As someone that's building an organization, when they get these pieces of doubt in their mind, what's a couple things they can do to get the doubt out of their mind? Like, what are some actionable things that they might be able to do?

Okay, so this is where we get kind of "woo-woo," but it's not woo-woo because it matters. I think the worst thing you can do is just keep moving forward and not pay attention to it because, again, you'll dilute the magic.

So to me, it's journaling. Ironically, I have mine right here, and I have like hundreds of notebooks behind me because when you—let's see—there's a book called "The Artist's Way." Even if you're not an artist, even if you don't think you're creative, it's really important because it talks about the importance of journaling. Three pages a day, handwritten. Doesn't matter. Nobody sees them. There's no format. There's no magical way to do it. But it forces you to check in with yourself. It forces you to tap into that magical founder vision—the concerns, to talk yourself through the challenges that you're facing—because we know this: like, more often than not, you already have what it takes. You already know the answer. There's just head trash or other people's voices in the way.

So one: journaling every single day. Whether you want to spend five minutes or three hours, every single day will help you see the patterns and actually listen to yourself.

And then two is surround yourself with good people, which is so much easier said than done. People who don't have their own motives and their own agendas.

What you're doing with your business, but that really are there to listen to you and to support you and will hear you out and just kind of ask you the tough questions about what you're doing. So many people don't ask the tough questions. And it's funny, so this morning we're on the phone with a VC firm out of the UK. And I think one of the things that we really honed in on—and Dale could gut check me here—but that I feel they appreciate it is we are going to come in and ask the tough questions. There's a lot of people who are just going to show up and be like, "Oh, you're doing this. Let's do a little tweak of that and like your team's perfect and everything's wonderful and here's your pretty slide deck." And like if that's who you want, like I would rather walk away from that business. Because my ethos at the end of the day is like we want to extend your runway and decrease your burn and I can't do that by blowing smoke up your ass, pardon my French. We have to be very honest with one another. But you work with a lot of founders as well. How many of them really want to answer those tough questions and how do you shift the ones who don't to understand that they really need to if they want to get where they're going to get?

I think most of them somewhere in there really want to. I think the only ones who don't—99% of the time they're afraid. I mean, that's the thing. There's so many voices around there, there's so much pressure that they feel like they've there's this perception that they're in so deep that they can't possibly switch tracks or—because if they have to answer the tough questions themselves, they've got to go start tough conversations with somebody else. Whether that's using the example of like letting go of that chief sales officer that just isn't performing, or maybe standing up to the VC that they desperately need money from but they know it's not going to work, or they're bothered that's kind of pushing them around. They know. They know they want to answer the tough questions. They don't feel like they can.

And so to answer your question about how do you get them there, I think it's helping them to again tap into that like what got you here in the first place. It's like this is about so much more than that tough conversation. And your vision that you believed in enough to start this whole thing deserves to have you get through the mud. Like you got to believe in that. And I think most people that I work with will get there. Sometimes it just takes a little bit more time. And then on the other side it's like, "Gosh, I wish I had done this sooner," every time, right?

That—one of the things that you talk about is developing a personal brand for the founder and creating this thought leadership space, like this movement. We talk about this a lot with our clients because we talk about if you want to ever get to a repeatable stage in your go-to-market, you have to have somebody. Like people have to find you, they have to understand, they have to have awareness of what you do, what your ethos is, why you started it. Like a lot of questions I like to ask sometimes is like, "What's your origin story?" Like, "Why did this thing come up when you start pushing this button?" Because we struggle with this all the time with our founders. Some of them will take it on, but I'd say 90% of them are like, "I don't want to do LinkedIn. I don't want to do social media. I don't have time to write content." Like, what do you say to those people? And like how do you convert them?

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I run into that a lot, too. There's a lot of people who feel like it's braggy and like, "Oh I don't want to go talk about myself," and it's like, no, your business needs you to. You're the only one who can tell these stories like you're the only one.

Okay, so how do I get them to come around? To me, it's actually something really tactical. Because yeah, most founders don't have time to sit down and write or create a blog or to spend ten hours a week on LinkedIn. Like, they just don't. So to me, something tactically that's worked for years—and actually led to me starting Casted—was record it. Record it. Like founders spend so much time talking. Record it. Get somebody to—I do a lot of things where it's like I'll talk, we'll talk, and then we'll take me out of the conversation and we'll get you and then that's stuff that you can share and that you can use and that you can repurpose and that we can turn into stuff. You don't need to become a Pulitzer Prize-winning writer. You don't need to become LinkedIn famous with your posts. You just need to find a way to capture and share your thoughts because they matter. They are the only thing in a super noisy, crazy space that the market is turning into. Your voice and everything that you guys just said about your unique perspective and your stories—that's the only differentiator you actually have. And so take that, capture it, talk to some of your customers, and maybe that turns into a podcast, maybe that turns into YouTube stuff. Maybe no one ever sees the videos, but that's a really easy, efficient, and effective way to get started.

Well, and I think so I love all that and I the way I like to describe it with founders sometimes is like, "Well, if you don't do this and you want top of funnel, like you're not going to get there. Like no one else will tell that story like you do." And so if you believe one of your problems is top of funnel, here's a solution. Whether you want to take that solution or not is completely up to you. I will not force you, but you're saying one thing, but you're doing another. Like talk is cheap. Talk is cheap.

And I think with the advent of AI and especially how prevalent it's becoming, everyone feels that there's just this magic button, right? They could just all do the exact same thing. And Lindsay, I'm going to read a quote that you sent when we specifically said, "You know, what is a topic that's really important to you?" because it speaks to this. You know, at its core: "Businesses don't achieve long-term success by doing what everyone else is doing, hitting the AI button. They transcend by being brave, establishing human connections, and holding space for creativity. There is no growth hack or tech stack for success. You have to get brave and audacious and human."

How do you as a founder or someone who coaches founders, how do you get people to resist the urge to hit that easy button and go say, "I'm going to go send out ten thousand emails this week and, you know, we're going to get a 0.1% response rate and like that's good enough, man. We booked two meetings, but we pissed off nine thousand nine hundred ninety-eight other people."

Yeah, exactly. Okay. So I think there's the people that I work with—they already start with kind of have that foundation of knowing that that's probably not the way. Like early in discovery conversations, if people are like, "Yeah, but what's the ROI when like when you do a when we work on this and I do a LinkedIn post, how many sales am I going to get?" I'm like, "We're probably not a fit." But the people that I work with and that do are like, "Okay, but like AI, like we can AI this." I'm like, "Well, there are certain ways that you can use AI for sure that we can make this whole thing more efficient and be a lot more effective and do some really cool things and really maximize our time. But what I do is I point to—I have a conversation. And I'm like, "Tell me about the most iconic brands you can think of. Like Salesforce, HubSpot, like Apple, right?"

Mm-hmm.

Some of the new upandcomers like Drift and all the cool things that they did when they came onto the scene and created this cult-like following still around a chatbot. No, they got purchased by Salesforce. That's a whole other story. RIP Drift brand. But then we talk about it and say, "Okay, name—tell me the brands that you think are really iconic." And then I ask them, I'm like, "Do you think did they get to where they are by following someone else's playbook? Like, did they do what everybody else that came before them did and they were just really, really good at executing someone else's playbook? No. They wrote their own. And so what are you going to do? Are you going to get really, really, really good...

At AI prompts and that's how you're going to become an iconic brand? Are you going to chase down the market? Are you going to be the one person who finds a magical playbook from some other brand and you're just going to be super good at implementing it and that's how you're going to become a billion dollar business?

But that last one that you just said—listen, I spend on consultants all the time. And we actually don't use the word consultants, but this is the exact reason because founders are doing it too. Dale's smiling because he knows exactly what I'm going to say. The 1995 playbook, the $1,995 playbook that I used at company one, two, and three is not going to work at company four. Listen, our playbooks certainly have a structure, don't get me wrong, but there is no playbook that is plug-and-play. Boom, Lindsay, here's my playbook I used at Revenue Reimagined. Use it and it's going to scale your business. Founders need to understand the same thing. You can't copy Outreach's playbook, Salesforce's playbook, Gong's playbook. You're not Gong. It ain't gonna work, right?

Thank you so much for saying that because there are obviously things that you can pull from. There are things that I do. I mean, especially now that I'm working with clients—I'm not working for a brand. I'm not just thinking as I go. I had to turn around and be like, "How do I package this up in a way that other people can understand other than me just coming in and being like, I don't know, we're going to do stuff and it's going to be great."

You have to have a way you can talk about it. But the thing is, it's not one-size-fits-all. And here's the thing: people want to see and want to know how working with a consultant, a fractional, an adviser, somebody is going to go. They want to know what the product is. They want to know what the beginning, middle, and end is going to be like. And so the more structured the sale is—like, here's the playbook, here's how we're going to get started, it's going to take X number of days, and then here's an example of the blueprint that I'm going to give you—that feels good to buy.

But you have to ask yourself: who's going to benefit from this? It's the person selling the thing that made it really easy to buy. As the person who's buying the thing, you've got to ask the tough questions and say, like, how are you going to customize this to me? How does this framework adjust? How do you toggle it to different scenarios? Because certainly I've got a lot of nuances that are a whole lot different than your existing clients. How does this flex to fit?

And backing to the conversation we had earlier—if you're modifying your GTM strategy call it every three months, you're pressure testing it. So if Gong had built out a playbook or someone built out a playbook, you're only pressure testing it maybe a year ago. Like, that's not relevant. And what stage were they in? Like, there's a lot of variables or dimensions in that conversation or strategy that you are not taking into account.

Yeah. And so when you're trying—that's why we don't just give strategy. That's why we have to execute because our philosophy is we can give you a process, we can give you messaging, we can build out the best process, but until we go pressure test against the market, the market's never wrong. The market's always going to give you feedback if you listen to it. And you always are going to have to iterate over that feedback.

And so when we get that question like, "What's our ROI? How are we going to do it?"—it's like, well, how many iterations are we going to have through the process? Because we're not going to get it right the first time. Even though we've done it a lot of times, the success is in the journey and not the end result.

Yeah. And there's so many variables that you're going to adjust for along the way. The market will tell you. That's so true. Not just in new sales, but I was having this conversation with a founder the other day who's struggling really, really bad with churn and leaky bucket. They're a small to medium-sized business, call it $150-ish per month, annual contract, but allows people to bill monthly. So they always get this: "Well, Lindsay, even though I have six months left on my contract, I dropped from five people to four people. So I need to reduce a seat."

Yeah. Now that's a whole separate conversation about what to do. But when you see people churning at the end of their term and not renewing, what's the market telling you? Generally speaking, I'm a big believer—and another founder said this to me yesterday—if we're building a product that's so good that people love it and can't imagine running their business without it, they are not going to churn. Now, you're going to have out-of-business churn. Like, you're going to have certain things that happen. But when people start leaving you in mass for a competitor, you have to be willing to say we have a fundamental problem. Is it a pricing problem or is it a product problem? But it's a problem at the end of the day.

The market will tell you what your problems are—whether you are looking at top of funnel, whether you are looking at mid-to-bottom of funnel, or whether you're looking at renewal and post-close. The problem is most people don't want to listen to the market. And I find—and I'm curious if you see this as well—a lot of founders take their product very personally, which is great. That's what makes them amazing founders. But it's almost like, "Oh my god, you're telling me my kid is ugly." I'm not telling you your kid's ugly. Your kid is fantastic. But your kid needs to go to a little bit of training or something to get a little bit better. Are you running across that?

Yeah, absolutely. It's rough. Founders deserve help. Yeah. Of course. Of course. And I think it goes for founders. It also goes for investors. Anyone who has skin in the game. And I think that getting everyone aligned to listen to the market together and hear the same thing and then be like, "Are we all hearing the same thing? Can we make sure we're all hearing the same thing?"—that's so much easier said than done because, yeah, the founder—it's their baby. I've been there. I have felt it. And investors and other stakeholders literally have invested in it and need to see a return. And so it's—I actually had an investor tell me one time like, "Lindsay, you have to remember our priorities are not aligned."

And that just smacked me in the face. And I was like, "What do you mean?" Like, we all want to see this succeed, but succeed meant something different to me as wanting to see the vision through and carry forth this vision versus an investor that was like, "No, I need to see a return like no matter what that return looks like."

And so yeah, I think that listening to the market—obviously that is truth. And doing—we were talking about how often do you pressure test it?—that's yet another reason to do that as often as possible and make sure that all of the stakeholders around the literal or virtual table are aligned on what the market is saying.

So, how do you do that from a—sorry, Dale—from a super tactical, super actionable point? How do you pressure test anything as a founder? Like, whether it's messaging, whether it's product—like, what can a founder who's listening to this right now walk away and go pressure test one thing? What's the one thing they should go pressure test right now?

Goodness. Talk to your customers. I mean, it's amazing how many don't. But I digress.

I know. I know. I think, yeah, especially—there's lots of different founder personas and I think some it's more natural than others, but you have to. And not just the happy ones. Especially not like the ones that don't like you very much.

Yeah. You'll get in an echo chamber and you won't be able to decipher what's real and what's not real. You know, one of the interesting things that I find, whether it's working with your board, investors, or just the people in your organization and what we do with a lot of companies we work with—you have to establish expectations and make sure that the expectations are the same. You just talked about what success is. Like, we all want to be successful. Great. Success means different things. Like, you probably wanted to get to a point of selling the company, but what the profit margin on that or what the return on that may not have been what, when you got funding on it, was what the investors wanted for success. Like, if you get a five-X return, maybe that's success for you but not success for the investor that said, "I wanted a ten-X return on my money," right?

So aligning those expectations and getting like pure definitions—not like, "Okay, we all want to be successful," but—how do we define it? I always say set those expectations early and often, make sure they're time-bound, they're measurable, like everyone knows what they are. And then revisit them like almost weekly because that one percent off that you get on a weekly basis over a quarter could have you so far off base that it's really hard to recover.

You got to do unnatural things in the business to recover to that place.

Yeah, yeah. I actually, this is kind of an aside, but in support of your "one decision" thing. Can one percent? I was in a talk that I gave last week. I was talking about these one-degree decisions. A plane that takes off in San Francisco headed for Washington DC, if it is off course by one degree when it takes off—just one degree—by the time it gets over LA it'll be off course by just six miles. Ultimately, it will land in Baltimore, which is not Washington DC. Safe landing, which especially these days is a great thing. I'm flying on Friday. Dale and I are flying next week. Yeah, we like safe. Ironically, I'm going to Baltimore in a couple weeks, so I'm there with you. But if I'm on that plane, I'm going to be like, "Cool, Baltimore seems lovely, but I needed to go to Washington DC." So yes, you're right. Aligning our expectations of where this plane is going—again, easier said than done. It's probably easier within your executive leadership team and throughout your organization than it ultimately is, sometimes, with your board and your investors, because those goalposts can change and they can shift. But the least you can do is have alignment of what good looks like, what success looks like on a regular basis within your organization. Easier said than done.

And with that, we are just about at time. But we wouldn't be who we are if we didn't throw some rapid fire your way. So, ten words or less—we may have had someone yesterday who probably went 654 words on one of these questions. Good thing no one knows when we actually record these.

Early bird or night owl?

Early bird. How early?

I get up at 4:55.

Oh, okay. That's early. You win. There we go, Lindsay. You win.

If you weren't in tech, what other profession would you be in?

Interior design.

Nice, nice. And she's good too.

Favorite guilty pleasure snack.

Ice cream, which I can't have dairy anymore, which is really lame. So a good non-dairy ice cream is a big treat.

What's the most used work emoji in your Slack?

The shrug. That one's my favorite. We don't use a lot of emoji in ours, but we tend to text much more than we Slack.

What's the one thing you do to unwind after a particularly long, stressful day?

I have the three best kids and my husband's amazing. So I live with the four greatest dudes on the planet, and so just time with them. They still snuggle up with me even though they're like teen and pre-teen, just all piled up on the couch. I have a 13-year-old. He cuddled with me last night. It's very rare that he's like, "Dad, can we just hang out and watch TV?" And I love it. Yes. Anytime right now, I let drop whatever I'm doing, running to the couch.

Yeah, yeah. That's neat. Let's wrap this up. Dream vacation destination.

Scotland.

Have you been?

I have. Nice.

Awesome. It's amazing. First place that came to mind was Scotland. Nice.

Lindsay, thank you so much for joining the show. Thanks for sharing your insights. Where can people find you and learn more about what you're doing? Feel free to shamelessly plug your podcast.

Okay. All right. This is when you give me the tickets to my dream vacation, right? Just after we stop recording to Scotland.

Okay.

I'm super active on LinkedIn, so if you can figure out how to spell my name, you can find me there. And then humanbrandswin.com is a website where I'm constantly changing how I talk about what I do. Lindsychma.com talks about speaking and how I do that. And then my show, as you mentioned, is I Can. I love it.

Lindsay, thank you so much. Have an awesome day.

You too. Thank you.