These 10 Mistakes are Killing Your Founder-Led GTM

You finally decided to rip the bandaid off. You're a B2B SaaS startup founder. You've tried everything else and it hasn't gotten you traction. So you start thinking, well, why don't I start doing some of this content stuff and see if that's going to be a way where I can actually build pipeline. That's a great mindset to finally arrive at. And I think it's worth applauding because it's a very tough thing to do. A lot of the founders I know don't want to be in front of the camera. They'd prefer to be behind the scenes in some way or in front of their customers. And all of this content stuff isn't really their jam. But taking that first step is a good way for founders of all stripes, but particularly B2B startup founders, to get an edge in the marketplace that their larger, more well-established competitors can't compete with and they can't do well. for those of you who are new to this channel everything that i talk about is about helping early stage b2b startup founders figure out how to get to product market fit every conversation that i talk about is how you can embed content into your outbound and gtm motions so that you can go from zero to one to growth to traction and if you're new to this channel make sure you drop me a subscribe so that you don't miss out on any of the episodes that i have coming out usually i'll put out a new episode every single week on a range of topics that will be relevant to anybody that's in that B2B startup space. Here's the thing. I'm all about helping people hit the fast forward button. In fact, the very first podcast that I launched was called Cascading Leadership and its mission was to give professionals and particularly professionals from underrepresented groups, the ability to hit fast forward on their career by sharing the stories of leaders across all industries who were members of the underrepresented community who had risen to director level ranks, VP level ranks, executive ranks in corporate America. And all of that was about sharing cheat codes that helped. young professionals, emerging professionals, or even mid career professionals get around that ceiling that they hit in their career. I've never lost that part of how I'm wired. So in this conversation, what I'm going to share with you are the 10 things that you need to think about once you decide that you're going to dip your toe in the water and start creating content as a B2B SaaS founder. And this is particularly important for founders that are in the startup space, and you're still trying to figure out how to get traction. Because the problem that you're dealing with right now, you're not having enough conversations. And without having those conversations, you're never going to get out of the learning loop that helps you move and get to product market fit. And in order for you to get to product market fit, you need to have a lot more conversations. And one of the ways that I advocate for having those conversations is embedding content into your process and matching the buyer journey, and the seller journey with content being the thread that stitches all of those things together. But here's the thing. Just hitting record isn't going to get the job done. You need to have a plan. And what I'm going to share with you are the 10 mistakes that I've seen founders make over and over again that stalled them out before they ever got started. So mistake number one is never developing that ideal customer profile. There's a reason why I spent an entire episode right here talking about why it's critical to spend time building that out and understanding that before you start hitting record and start. talking into a camera so i'm not going to beat a dead horse and recap that entire episode but the tldr of it is is that you need to get a deep understanding of who your ideal listener is who your ideal audience is map that out into a persona document and have it in front of you because that's going to inform everything else that you do after the fact when it comes to creating content so if you want to get more details into that check out the episode that is specific to creating that and let me know what you think. The second mistake that I see founders make all the time is not defining their problem set. So think about the problem set as the most common problems that your customers deal with that you help to solve. So before you hit record, before you start creating content, you need to have that well defined. And I usually recommend that you have 10 to 15 of those problems that you've mapped out that you helped solve for. And the reason why that's important is because those end up being the working themes for the content that you're going to create. So every conversation that you have with your guests is going to be about one or two of those key issues that you're going to be talking about. what's important is that when you bring your guests in to talk about those things you're not the one that's actually sharing expertise about how to solve it your guest is so i guess you can call that 2a as far as a mistake that is made oftentimes when founders decide to dip their toe in the water they're the ones that are doing most of the talking and they're the ones that are center stage when the reality is that you need the whole point of creating content and creating a content collaboration motion is to bring your icp candidates onto your show so that you can spotlight them and their expertise so second mistake make sure you define out your problem set now the third mistake that i see happen all the time and there's going to be some people that disagree that this is even necessary is that founders don't prime the pump what do i mean by priming the pump Oftentimes, when founders decide to dip their toes into content, and they decide that they're going to have guests on the show, they think that it's going to be as easy as saying, hey, I have a new podcast, I have a new YouTube series, I have a new this or that, would you like to be a guest on it? You're going to get a fair amount of people that will just say yes. But there's a whole segment of the population of your ICP that's not going to say yes right away. They're going to want to see that you have a legit content engine that's already in the wild. And when I say prime the pump, that's what this solves for. What priming the pump involves is you taking that list of 10 to 15 problem sets that you solve for and delivering your takes on it in short form or medium form content. So this is solo content with just you on the camera. And you're going to talk about the problem itself. You're going to talk about how it impacts the business. You're going to talk about the pain that it creates and why that's important to fix. But you're not going to talk about the product when you do that. You're creating a library to help your listeners, your audience, and your viewers go from problem unaware to problem aware. There's going to be a certain segment of your audience that has no idea that this is even a problem. And part of your job is to help steer them from problem unaware to problem aware to solution unaware to solution aware. And one of the ways that you can meet them on that journey is by leveraging the content that you're putting out to help do the heavy lifting for you. So if you're not priming the pump, if you're not creating that early bank of content. you're not going to have enough social proof to convert as many guests as possible into the show as you would like. So those are three things right off the bat that everybody needs to pay attention to. What are your thoughts on it so far? Drop me a comment and let me know what you think about the first three things that I mentioned. And if you think there should be something else that should be on the list so far that I haven't included, drop those in there as well. If you haven't already done so, make sure you give me a follow. so that way you don't miss any future episodes so the fourth mistake that i see founders make when they lean into content is not setting up their infrastructure properly yes all you really need to do to step into content is a phone or a laptop and a camera that's it you don't need a lot of equipment i certainly think that equipment discussion is important later on but it's not important right when you start but you have to do a little bit more than just that And one of the biggest mistakes is not setting up the proper infrastructure to help with that social proof and that conversion. So when I say infrastructure, what am I talking about? So some of this might sound really basic, but there are so many founders that I've seen that tried to execute on content, but they didn't have their ducks in a row to do it well. They didn't have their scheduling links available and set up. And those need to be separate from your standard scheduling links. You need to have a landing page established. that tells people about the show and gives them best practices and gives you the ability to look a little bit more credible than just randomly reaching out to people and asking them to connect. So those two things can save you a world of time and they seem pretty basic. So if you don't have a booking link, if you don't have a landing page, sort those things out first before you go outbound. The other thing that you need to think about as far as infrastructure is what does your outbound messaging actually look like? This is a content-led outbound motion, so you need to make sure that your messaging and the channels that you're going to use to go outbound and bring guests on have solid messaging that's going to get opens, it's going to get replies, and it's going to get bookings. So if you haven't sorted out what that needs to look like, you need to make sure that you do that as well. And then the last bit of the infrastructure side of it is you need to answer the question, who's going to be doing the outbound? Is this something that you're going to run on your own or are you going to offshore that or outsource that to an agency or some other entity to help you do that? Because you have to weigh where you want to be spending your time. And I can go either way in terms of if you do it yourself or if you offload it. Both of those are viable solutions. Just understand that if you're going to do it yourself, you're going to have less bandwidth to be interacting with your ideal customers and guests that you're planning on bringing onto the show. The fifth mistake that I see founders make is that they haven't established their playbook beyond the content piece. And even on the content piece, it's kind of half-baked. So if you want this to be effective and if you want a high conversion rate across your entire funnel, You need to be thoughtful about how it's constructed. So the infrastructure needs to be set up, but so does your whole strategy. I've seen way too many founders that go outbound with it and then bring guests and have them go right into record. the episode that's a mistake when you're thinking about your playbook when it comes to embedding content you need to have each of those stages mapped out and you need to layer in springboards that allow you to advance from stage to stage and this ties into what i mentioned earlier in this episode about how discovery needs to be re-framed as a process not a stage so what you're doing when you embed content into your outbound is that you're layering in discovery through the entire process so that means that when you go outbound the first step after that outbound is to book a prep session in the prep session you have some qualification items that are layered in there after the prep you book the show and in the show there are some qualification things that you layer in there to give you an idea of where this person is in relation to the problems that you solve for. After the show, there should be another stage that allows you to dig a little bit deeper and understand the market that they're operating in. After that stage, you should have a stage where maybe they get to see your product or you get intel from them on what they would like to see when they think about a certain solution or problem that they have. What would an ideal solution looks like? The point that i'm trying to make is that each stage in that playbook needs to be defined out and you need to have an idea of how are you going to advance from stage to stage right now especially if you're in a pre-product market fit startup you need to worry less about disqualification criteria because you don't really have enough under your belt to help you figure out what's a good prospect and what isn't a good prospect but in order to get to that point You need to have a playbook for the journey that that prospect is going to go on when you're actually taking them through that content collaboration process. So make sure you have your playbook in order. Otherwise you're going to do a lot of recordings and you're going to get stalled on how you advance them down funnel. The sixth mistake that I see B2B startup founders make when they try to embed content into their process is that they don't have an idea of how they align the buyer journey with the selling process. And this is critical because a lot of what we've been taught has to do with treating everybody in the marketplace as if they're ready to buy our solution right now. That's a mistake. And that's even a bigger mistake when you're an early stage startup founder. You can't treat everybody that way. Your approach and your mindset when you go outbound with this is to seek to understand before trying to be understood. And what that means is that every step in that engagement where you're going from prep to recording to all of the down funnel things, you need to make sure that you're going in there with a student's mindset. You're trying to understand what the customer world looks like and determine if there's a mutually agreed upon decision to move forward and solve a problem that they might have that you can directly impact. You're not going in there to pitch them anything. You're going in there to build a relationship, create great content, understand the customer world, understand their journey, and then potentially help them if a problem actually exists. So not mapping out what that looks like at each stage and how you're gonna advance from stage to stage is a big mistake that often leads to this stalling out. So now we've covered six mistakes that founders often make when they're trying to lead with content in the marketplace. What are you thinking so far? Does this resonate with you? Tell me what is the thing that stands out the most out of the six that I've mentioned so far and drop them in the comments and I'll respond to them. And again, if you haven't, subscribed to the channel make sure you do that so you don't miss out on any of the future episodes the seventh mistake that i see founders make all the time they cast a net that is way too wide so when you look at executing this motion what you need to think about especially if you're a pre-product market fit founder is think about the concept of a sprint And whether that's a two-week sprint or a four-week sprint, you need to think in terms of sprints. That means taking your entire marketplace and dicing them up into smaller, manageable chunks. And the reason why this is important is that you can look at these sprints as experiments that you're running across the market. You probably have a TAM, a total addressable market that's huge. You're never going to get traction targeting the entire market. You want to break it down by persona and segment and industry. and be really narrow with how you start and then building from there. Because what you want to do is you're looking for your first handful of wins, and then you can double and triple down into those segments and build depth in those segments before you expand out into other segments. When you cast a net that's too wide, it doesn't give you the space to do the analysis that you need to do to determine if... this was a good win or if it's a bad win and what were the factors that drove the win? Is there something specific in the industry or in that segment that made it a better opportunity than others? That's why you need to have a narrow net and work the sprint concept and have those debriefs where you're actually zooming out and taking a look at how things are shaking out. The eighth mistake that I often see is not building in a review process. Now, that review process can take a couple of different shapes. I mentioned in mistake number seven that you'd never have that retrospective of the sprints that you ran. That is one element of the review process that needs to be baked in to your content motion when you go outbound. The reason why that's important is that it helps you iterate. But there's another component of the review process that you need to embed into what you do, and that is reviewing the entire experience. from the guest's point of view. You wanna be continuously improving your process. And that includes how you go outbound, that includes how you do your prep sessions, how you do your shows, and having a well-oiled machine and tight process across those three stages are going to give your guests a great experience. And that's what they're gonna remember. That's what actually gives you the ability to reach back out to them at some other point. and ask them for more time. But if you're never asking them about how you could potentially improve or what you could do differently, that creates a problem where you have a lot of blind spots that are baked in. So one of the things that you need to be doing in terms of the setup of your show is setting up that review structure where people can give you feedback and then you can iterate on how you actually execute. The ninth mistake, and it's related to number eight as well. is never building out a referral engine. One of the points of actually using a content collaboration motion, a content process that's embedded into your outbound, is to create a content flywheel, but also a guest flywheel. You have an outbound motion that's already going, that's getting you guests in your ICP into your ecosystem so you can have those conversations. When those guests are done recording, if you're not tapping them for referrals to other peers in their network, who might have interesting things to say about the problems that you talked about, that's a missed opportunity. That's how you create a content flywheel and a guest flywheel so that you're doing double duty in terms of being able to bring guests in. And it's highly likely that a guest that's referred on the show is going to convert at a higher rate. And they might also convert down funnel at a higher rate than a guest that you go outbound and bring in from the cold. So make sure you bake in that guest referral process into your show process and your communications so that way you're building the flywheel and another channel for building pipeline. And number 10. We're at number 10. So let me know what you thought so far of the first nine mistakes that I mentioned. If there's anything in particular that stood out or that you're going to implement, make sure you drop those in the comments as well. If you haven't subscribed to the channel, make sure you do that because I'll have episodes out every week that cover topics that are relevant for B2B startup founders and how they can go from zero to one to growth to traction. So number 10, one of the biggest missed opportunities is not applying the principles that you get from content collaboration and long form content and applying that to other venues or other channels. So here's what I mean. The reason why I advocate for long form content as a go to market engine and a content flywheel is that you have multiple ways that you can reuse that content to get more traction in the marketplace and more eyes on your conversations and build brand awareness so that long-form interview could be part of a newsletter it could be part of a blog it could be part of a sub stack you could have additional content that goes out on linkedin those are all different channel opportunities that you can leverage off of that anchor piece of content to create inbound traffic so now you have a couple of outbound channels that are defined and you're also working on building your inbound engine as well but here's the thing you can apply the principles of long form content and apply it to your conference strategy. You can apply it to your trade show strategy. You can apply it to your local community networking events. All of these things, all of the principles that you're using to get guests into your ecosystem on a long form basis can be applied to any one of those other things. You just need to tweak around the edges in terms of the format. And it gives you a way to get in front of anybody that you need to get in front of. And It creates an environment where people start knowing you for a specific set of things and people actually want to talk to you. The whole point of all of this is to figure out a way where you can get in front of everyone in your TAM and have meaningful conversations and remove the ick factor from going outbound with typically salesy outreach. That's what this allows you to do. So if you're not leveraging the lessons from the long form execution of this playbook for your short form and other content pillars, that's a huge missed opportunity. So there's your top 10. Those are the 10 mistakes that I see founders make all the time when it comes to dipping their toe into the content creation process. So hopefully you found this useful. I'd be curious to hear about what stood out the most for you. What are you doing from a content perspective as an early stage founder that's paid dividends? Is there something that I missed? Drop all those things in the comments and I'll respond to them. It's a great learning opportunity for all of us to get those shortcuts and fast forward hacks to help us be more effective as we try to grow our businesses. So I appreciate you hanging out and listening and watching. If you have any questions, let me know. But otherwise, drop me a subscribe and follow and then tune in next week for another episode where I'll be covering another topic that's going to help B2B startup founders go from zero to one to growth to traction.

This episode is focused on helping early-stage B2B startup founders use content as part of their outbound and go-to-market motion to get more customer conversations, build traction, and move toward product-market fit. 

Founder-led content can give B2B SaaS startups an edge that bigger competitors struggle to match. But just hitting record isn’t enough. In this episode, Dr. Jim breaks down the ten mistakes that stall founders before their content motion ever turns into pipeline, from skipping ICP work to failing to build a referral engine. 

This episode addresses common content creation mistakes, highlighting the importance of deeply understanding the customer journey. Dr. Jim explains how embedding content helps gather crucial customer feedback, providing valuable business insights. By focusing on the entire customer experience, founders can refine their business strategy and avoid common pitfalls.

This one is for founders who know they need more customer conversations but don’t want to burn their TAM with generic, salesy outreach. Episode 

Chapters
00:00 – Why founder-led content can create a startup edge
02:37 – Why more conversations drive product-market fit
03:23 – Mistake 1: Skipping your ideal customer profile
04:12 – Mistake 2: Not defining your customer problem set
05:38 – Mistake 3: Failing to prime the content pump
08:02 – Mistake 4: Not setting up content infrastructure
10:23 – Mistake 5: No playbook beyond the recording
12:57 – Mistake 6: Misaligning buyer journey and sales process
14:51 – Mistakes 7–10: Narrow sprints, review loops, referrals, and repurposing

Website: www.cascadingleadership.comSubstack: https://substack.com/@cascadingleadership?utm_campaign=profile&utm_medium=profile-page Book a Call: https://cal.com/dr.jim-cl-gtm/30min-networking


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