This SaaS Founder Thinks That Your First Customers Are Also Your Investors

Lindsay Tjepkema: When you have the number one right person in the right seat it can make all the difference and when you don't, it can be tough for both sides. It can be frustrating for somebody who's in the wrong seat or who's not aligned with where you are, and where you're going and that can be really frustrating too. People talk about how important hiring is. I think that's, it's magnified. It's absolutely amplified in a startup. Voiceover: Welcome to SaaS Origin Stories. Tune in to hear authentic conversations with founders as they share stories from the earlier days of their SaaS startups. We'll cover painful challenges, early wins, and actionable takeaways. You'll hear firsthand the dos and don'ts of building and growing a SaaS. As well as inspirational stories to fuel you on your own SAS journey. Here is your host Phil Alvez. Phil Alvez: Today I have Lindsay Tjepkema from Casted. Welcome to this show, Lindsay. Lindsay: Thanks, so much. I'm happy to be here. It'd be great. Phil: Yes, so the first question that I like to ask our guests is, tell me a little bit about your product, your SaaS product, and what problem does it solve? Lindsay: Sure, so we are a marketing technology platform. We're a SaaS product made specifically for B2B marketers to empower them to both maximize and also measure the power of their rich, creative connective content much like this, their audio and video content to say, how can you get more out of it, how can you drive real value for the business. In short, that's what we exist to do. Phil: Walk me through a user case. Let's say, who is the ideal user of the product and how he would use the product? Lindsay: Sure so we are made for B2B marketing teams typically the decision maker is like a VP of marketing and then their team of marketing managers, content marketing managers, people on that team that already have a podcast and, quite often are also doing some other video content as well. Some webinars, some virtual events, but have a show like this. They typically use our platform to not only get this show out into the world, to disseminate it out to Apple, Spotify, Google, and YouTube, but also get more value out of it. To break it down into bits and pieces and clips and key takeaways and amplify it across multiple other channels and also understand who is engaging, how they're engaging, and how it's driving business revenue. Phil: Makes sense. That's awesome, and so how did you come up with the idea? Lindsay: I had a lived experience, so my background is marketing. I was a marketer, a B2B marketer for 15, 20 years before starting Casted, and was like many of our customers, I was running a show, my team and I were doing a podcast, and I was just really shocked at the fact that something like Casted didn't already exist. That you create a podcast, and you publish it on some hosting platform and then you have to walk away and share a link on social media hoping that people will engage. I was really shocked that there was no way to take that content that was a podcast or it was a video, and use it in other ways easily without the help of other teams or agencies, or vendors. I couldn't create a clip easily, I couldn't get a transcript easily, I couldn't do other things with that content that I saw a lot of value in. I knew I was leaving a lot of value behind on the table that I just couldn't unlock. I also couldn't share with my CEO or my CMO what value it was delivering to the business. A number of downloads don't mean a whole lot to a CEO, but how's it generating revenue? That challenge turned into a real roadblock for us, and I said,"If I'm having this problem and our brand is having this problem, I'm sure other people are too." That just ballooned into an opportunity that I couldn't walk away from. Phil: You had a job, you saw that there was a huge need because your job was hired to do it, basically, because you couldn't do everything they want to do because there wasn't a tool that did that. You have to maybe be using different tools and you felt like, "Okay, this should live in my podcast hosting platform. That's where I should be able to do all of that." You found the need. What did you do? Did you quit your job and went with your SaaS? Did you go and raise money? Walk me through the process, like now you know and you feel that pain yourself. What's the next step to starting your company? Lindsay: Yes I was feeling the pain just as you mentioned. We were doing a mix of one-off tools and point solutions, some manual work, and some can just not doing other things that I knew were important. The first big step to doing what ended up being starting Casted was I actually talked to a venture studio here in Indianapolis. I talked to Scott Dorsey, who started Exact Target, grew it, and sold it to Salesforce. He and some partners are running a venture studio here in Indianapolis called High Alpha. We were talking about this need and this challenge and this opportunity in the market and what's next for B2B podcasting and what's next for content marketing in the world of B2B. I said, "Hey, yes, B2B podcasts are huge, but that's just the start. That's just the beginning of something so much bigger. Here is really what I envision, which is now today something I call amplified marketing, which says, start with content like this. Start with podcasts and video content. Use that as the center of your fully integrated marketing strategy. Bring it out across multiple channels, and understand the impact that it has on the business. Oh, by the way, in order for that vision to come to life, this SaaS platform needs to exist." The more he and I talked, the more I realized, yes, this is a company. He was excited enough about it too to say, "Why don't you start it as part of the Venture Studio?" That was the first step in this direction of leaving my job and stepping foot into this role as founder and CEO. Phil: What is a Venture Studio? Sorry. Lindsay: Sure. Phil: Now very familiar with that. [laughs] Lindsay: Basically I was able to leave my job and come start what is now Casted with the nest, if you will, the support that surrounded me as a founder with more resources and with more expertise than I would have on my own. Becoming part of the Studio, we had a little bit of startup capital, and then I had access to Scott and his other partners who have started and grown many other companies so they have that expertise. As well as some of the studio resources, like how to get things started from a finance perspective and a business incorporation perspective and recruiting and some support in just getting the business stood up so that I could focus on the vision of the company and with my co-founder getting an MVP up and going. That's the concept of a venture studio is. Other iterations of it look like an accelerator or something like that, but the studio is a little bit more intensive, and it let me make this leap in a way that really made sense for me. Phil: It's basically a version of the incubator. Lindsay: Yes, I would call it my own words. I don't know how they would define it this way, but it's more intensive, and more long-term than an incubator. Phil: Makes sense. How hard was it for you to quit your job? Of course, you met Scott and he's like, okay, come over you have all this structure. I'll give you some money, but I'm sure that money wasn't enough to replace your income. [laughs] Lindsay: It was terrifying and exhilarating all at the same time. I am solving a problem that I had and in a world that I'm very passionate about, B2B marketing is all I've ever done. I know this world, I love this world. I've grown up in this world and feel very passionate about what needs to happen from here forward to disrupt the status quo that we've all been dealing with and a lot of the problems that we as B2B marketers have been dealing with. That, I'm hugely passionate about. That's a no-brainer. Leaving all I had known as a marketer, then marketing leader to come to be a first-time founder and CEO was a little bit scary. To create something that never existed before that's a little daunting. Yes, it was one of the hardest decisions I've ever made but at the same time, it was a no-brainer because I always say once I saw it, I couldn't unsee it. I couldn't not do it, if that makes sense. Phil: Yes. I think I see a lot of people, like in your shoes where they see something and as you say, you get afraid of making the next step. You still did. What tips do you have for people that maybe are thinking about taking the next step, like going on their own? It was your first time being CEO, your first time being a founder, what conversations you had inside your head that help you go and like, keep going? Lindsay: To me, I already knew it was a good idea. I already knew that I had this potential partnership with Venture Studio, so I already, there was already a path forward for me, and for Casted, and for this company. As I was still saying, "Am I going to do this? Is this what's right for my career and for my family and for my personal life and my professional development?" On the question I asked myself that I would advise other people to do the same is, "What if I don't?" I think we quite often say "What's going to happen when I do? How's this going to work when I do?" You have a choice and one of those choices is to not do it and to stay in your role and do something else. The thought then of somebody else doing it, instead of me seeing this company come to life and what it does, whether it was successful or a failure, like I couldn't bear the thought of somebody else doing it. I wanted to build this thing. Even though that felt really risky and pretty scary and daunting on many levels, I just couldn't bear-- There came a point where I couldn't bear the thought of not doing it. Sure I could keep doing my job. I could keep down the path that I was on, but the what ifs of, "What if I don't do this? What if I never see this vision through? What if I never pursue this dream? What if I never pursue this opportunity?" The regret that would go with that, I don't think I could have lived with very well. Phil: Yes, I think that's a great way to see and to think about opportunities. Am I going to be more frustrated if I do it and fail or if I never do it. [laughs] That's basically you're thinking, and you're like, I guess I'm going to be very frustrated if I never do it. I'm doing this and I think that's a great way to make decisions. Why do you think you were the right founder for the product? Lindsay: I am weirdly passionate about this problem that we're solving in this company that we're building and this solution that we've created. I am uniquely prepared for it. I spent 15 years as a B2B marketer, large companies, small companies, agencies, global, local, everything in between bunch of different verticals and industries. I know B2B marketing and I especially know B2B brand building and B2B content marketing. I know it so well that I know what needs to change and I know I can empathize with our customers because I've lived their lives. I've been in the manager's shoes, I've been in the specialist shoes. I've been in the marketing leader shoes and the VP shoes. I've lived it on so many levels that I know so deeply what's broken and what can be fixed and how it needs to be fixed in a way that makes sense for the marketer and for the team and for the brand. I have a vision and something I'm really excited about for how I think it could be looking forward. Not just what does the software need to be, but what does the next generation of B2B content marketing need to look like and how do we get there? I think that you need that level of conviction and that level of understanding of the world that you're stepping into. If you're going to jump into the founder's seat. Phil: I agree with you. I believe being a real industry expert, knowing the industry inside out, it's really going to set you apart because now you're not relying on other people to know. Of course, as you build your product, we're still going to interview our customers and stuff, but you understand your customers in a way that's so deep because you have 15 years of experience. Who built the first version of your product and how it was, how long did it take? Walk me through the process because it is usually pretty hard to get something out there. Lindsay: Yes. I have, excuse me. I have a co-founder who heads up the product side of the business and originally we had another co-founder as well who head up the revenue side of the business. The three of us together did something that I would recommend for all startup teams to do, which is I spent the first five to seven weeks just talking to people. Talking to other marketers like, Have you experienced this? Would you do a podcast? Why, why not, have you, haven't you? What would you want to see in a platform? What kind of challenges have you seen? Just to overcome some of my own biases and check some of my assumptions and start to understand too, what would people want, what would people pay for? Took a ton of notes, and those notes turned into two things. One was a set of ideas that we could start to prioritize for our MVP. Two, is it became our earliest version of our CRM and our prospect list, because we had people that were excited and said, hey, if you do build that thing, by the way, let me know. I'm really excited to watch this come together. I really think that that's a good place to start. Then you get people who are a little bit bought in either literally or figuratively. Then we made sure that we were able to hone in on only the one or two features that were the most important. That's where we started. Then we built on it from there. It took us about 60 days to sign our first customer and about a hundred days total before we had a product in the market. Phil: That's awesome. You guys spent seven weeks in product discovery, and even though you had a co-founder that was the product person, now at this point, everyone is doing product discovery because you guys are working together to figure out what's our MVP? Of course, there was so many ideas, how did you guys got together? It was like, this is the only thing we are going to build, because 60 days to build that first version, that's pretty impressive, especially for a small team. I expect guys to have points for a lot of conversations to figure out what are those two features that guys have to do. How was the process? Lindsay: Like I said, I came back with tons of notes. Pages and pages and pages and pages of notes. Similar ideas got plus one and rose to the top. I got super excited. The platform that we have today, three and a half years later is what I envisioned from day one and obviously we're still growing and it'll be something different and more and bigger and more massive five years from now, but what we have today is like where I thought maybe we could start, but my co-founder was like, "Less. Okay, cool, but less, what's one thing we could remove? Okay, less, less, less, less." Until we got down to the very bare minimum. Where we started was clipping and sharing of B2B podcasts, and then we added hosting, and then we added transcription, and then we added premium transcription, and we just kept adding to it from there. We just quickly asked a bunch of questions to get to the root of what's the fastest thing we could build that would add the most value that people would pay for. Then how can we have a nice solid roadmap from there to keep people excited about what's coming next? Phil: Yes. You felt like, okay, clipping sharing is a big enough pain that even if you don't have any, all the other things in my vision people are going to start using because it's so hard to clip and share podcasts right now. That's where you guys started. It's something that people are going to use even if we don't have other features. Let's talk about the first customers. I love it that you are interviewing people and put them in a waitlist and they become the first few customers. Let's talk about, how many of those people sign up and how it was getting their first 10 customers and then get getting your first 100 customers. Lindsay: Goodness. I think when you're in this early stage, and I still definitely put us here, is you're learning from every single conversation. You're learning from every win and every loss. The earliest customers are different than the ones you'll get later in that-- You mentioned your first 10, they're in many ways investors. They are a totally different breed of customers than you'll be working with, or you'll be acquiring years down the road, a hundred customers later. These are the ones that see the roadmap and they're like, "Okay, I get it that you barely have something to log into today, but I see the value in what you're building. I believe in your ability to get it there. I have enough of a need, or at least enough of an interest to join in on what you're doing to pay you some money or to join your pilot or whatever, however, your business is formatted because I want in and I want to be able to help shape the roadmap to get out of it what I want." I think that it's really important for our founders to know that those earliest customers are going to be a different breed. They're going to, like I said, basically be a version of investor. Phil: Let me stop you here before I talk about a hundred customers because I think that's very valuable. I agree with you. Those first 10 customers, they're the investors. They have to buy into your vision. How did you find them? How did you find those first 10, before we talk about the next 100? Lindsay: Those conversations, I'm telling you those reaching out to my network and then asking who else I should talk to and being really clear that, hey, look, I'm not trying to sell you something if you end up being excited enough about what this company that I'm building is doing. Cool. Of course, I'd love to have you as a first customer, but let's talk first about what you would want to see what you're seeing in the market. Do you align with this vision? Some of those turn into very like cut and dry conversations and of course, I tried to keep them warm later, but some of them were-- Hey, keep me posted about this. What you're doing is really cool, or I really love this. I love how you're approaching this. I really want to see you succeed. Those are the people that you just got to keep close and keep informed to keep in the loop so that eventually when the time is right they'll jump on board officially. Phil: Yes. If I'm understanding right, being the space for so long, you build a big network and at this point, you're leveraging your network and you're talking to people about your product. This is how you're bringing and how you're finding those who you're calling the investor customers. They're coming from your network. Lindsay: Yes. My network and then their networks, and then their networks and just being really bullish enough and bold enough to ask for more conversations and to ask for more introductions. I think that you have to be really approachable. If you say that you're not going to try to sell something, don't lie. [laughter] Lindsay: You are trying to sell something. I just really had good conversations and said, "Hey, I'm a marketer just like you. I'm building this thing because I see a problem. Here's the vision of it. How does this land with you? Does this resonate? What would you want to see? If you had a magic wand, what would this look like to you?" End it with like, "Hey, if you're interested, I'm happy to keep you in the loop. Otherwise thank you so much for your time," and don't try to close them if you promise that you were just doing research. Quite often if you're talking to the right people, and if you talk to enough people, those hundred conversations turned into the first very small handful of customers. I think that's how you got to walk into it. That's the expectation that you need to have for those discussions. Phil: Nice. Let's talk about now the next hundred customers, and maybe as you're putting together a little bit of more official marketing channels, what little channels were and how they work and how did you go about that? Lindsay: We have always set out to be our own best use case, so we started a podcast and started conversations and started some content marketing and built a set out to build a strong inbound engine and just do a good job of sharing thought leadership, casting a vision and like I said, being our own best use case. That followed up with some good outreach and some follow-through on those initial conversations. Really capitalizing on the customers that we were able to bring in and say like, "Hey, let's bring them on the show. Let's bring them on the podcast. Let's talk about what we're doing together." That engine starts to rev and it starts to really speed up on its own. It was not magic, [chuckles] with that, it absolutely was accompanied by a ton of work and outbound a lot of founder selling, a lot of outreach to people that we knew needed to be customers and that we could really help serve. Just using that content to prove the value that we could deliver and to get people excited. Then following through with like, Hey, this is something we really think we should do. What do we need? What needs to be true to make it happen? Phil: It looks like it's a mix of content marketing and outbound. That's how you guys went about. Did you spend any money paid or was more like organic? Lindsay: More organic. We didn't do paid. Just a little bit until much later. Phil: Did some of your podcast guests end up becoming customers too? How did that go? Lindsay: Yes, and then also the other way around. We highlighted existing customers on the podcast. I am a big proponent of your podcast being a way to build relationships and to establish and strengthen connections. What I am not an advocate of is saying, "Hey, bring people on that you want to sell to, and use it as a lead gen to say like, 'Hey, come on my podcast, I'm going to sell to you.'" I think that's your guests will know that and feel it, and your listeners will know it and feel it too. If you're talking to someone and it leads to a really natural conversation and you build a good relationship, and afterwards you follow up and say like, Hey, I feel like there was some interest here. Do you want to keep the conversation going? There's definitely opportunity to build relationships there but not as a primary reason to do the show. Phil: Yes, for sure. That would be weird. Come here and then let me say something before you go. [laughs]\ Lindsay: It happens a lot. Phil: Yes. Could you share like a failure of the early days of your company and how you guys overcome? Lindsay: I think ongoing, we're failing and learning all the time. If you're not feeling and learning, you're not growing. I think the importance of staying really close to customers doing everything that I just mentioned, having those conversations, knowing that you don't know everything, but that you need to stay close with your customers in the market because they're the ones really who matter. The answers are not in my head. They're in the heads of our customers and are and in our market that's really important. Anytime that we or any business have been a part of starts to forget about that, that's when you start to go down a rabbit hole and maybe it's the wrong way. Then just the ongoing importance of making sure that you've got the right people on the team and in the right seats as you go, like startup life and the specific stages you're at as you grow as a startup are different. Bringing someone in from a really large company into a startup, there's going to be some bumps. There's going to be different expectations of a person that comes from really large company jumping into a startup of what resources you'll have available, what head count you'll have available, what budget and time you have. I think that's been a learning too. Making sure that you're really intentional about bringing the right people in, making sure that they understand where you're at, what you're able to offer them, and what you expect from them, and how you're able to work together what you need from each other and making sure you continue to have the right people in the right seats. That is so important. Phil: Did you guys brought someone from a big company and was like strange, the person maybe was in the wrong seat? Lindsay: No, I just think all throughout the company in different roles and then throughout my career as well, when you have a number one right person in the right seat, it can make all the difference. When you don't it can be tough for both sides. It can be frustrating for somebody who's in the wrong seat or who's not aligned with where you're going. That can be really frustrating too. I think that's just a learning from all of the roles that I've been in, how important people talk about how important hiring is. I think that it's magnified, it's absolutely amplified in a startup. Phil: For sure. The startup, everyone counts, to say there's no way, nowhere to hide. Everyone's important. If someone doesn't show up to work, it's noticeable, but it's also unavoidable that you're going to make a mistake in hiring as important it is. I think everyone is telling you that's so important because everyone had made a mistake and was super hard to overcome and to walk through. Could you maybe share some of your thoughts on how to go about when you realize you just made the wrong hire? Lindsay: Oh man, I don't know about that, but I think to me before you make a hire, making sure that everyone's aligned on why that hire is being made, what's expected of the role, what is possible even with the perfect person in that role versus what's not, there's no such thing as-- You are 100% right that in the startup everybody makes an impact. Everybody has the ability to really, truly make a noticeable impact on the business. Yet no one is a silver bullet. No one person can or should be the hero. Make sure that as a leadership team, you're really aligned on what that role is. Who would be the right person in the seat? What is the seat, where is the seat on the bus? What is the budget for that role? Especially now things are all over the place in the market, in the hiring market. Alignment from a leadership team, alignment with the hiring manager and alignment with the goals of the business for what's possible for this role are super important, and with your board too, make sure that, especially for some of your senior hires, this is what we're hiring for, this is what we expect. Are we all aligned here before we bring someone in and we think they're doing really great and you think that they're not achieving this unrealistic goal that you thought they would or vice versa. You think you're doing what that they're doing, but within the team it doesn't feel like a fit. That alignment even before you open a rack and even before you start interviewing or definitely make a higher, make sure that alignment is there. Phil: For sure, what has been the biggest challenge to date? Lindsay: Oh man. Starting a business right before a pandemic and trying to grow it through a recession. I think that's been the hardest part. Truly we started April, 2019 announced our seed round, closing our seed round right before the pandemic, raised Series A March 2021. Here we are in the midst of a recession and it's been really tough. It's been really tough for marketing budgets and that's our customers. It's been tough trying to fan the flame of this next generation of B2B marketing amongst people that think that it's really great and it's really resonating with. They don't have always budget suspense. Budgets are coming and going and trying to grow a team and nurture a culture in the midst of, we were all in office hybrid before hybrid was a thing, and then we were all remote in the midst of a pandemic and now we're hybrid on the other side of it. That presents its own opportunities and challenges too. Man, I think to sum it all up, trying to be a first-time founder in the midst of the last three years has been quite a roller coaster for sure. Phil: For sure. The market's definitely weird. I was listening to a book and I think was Intel founder that said, in crisis bad companies die. Good companies survive, and great companies improve, and so you were able to go and raise money 2021. I know evaluations were going lower. Investors are worried about investing in companies, so how did it make that happen? Why do you think? Because even in my own consulting firm. We had a lot of customers that couldn't raise the next round then they have to really reduce the spending and you still were able to make it. How did you do it? Lindsay: I think what's really important is that the vision that you cast and the passion that you have for what you're going to build, then especially we were raising series A being able to show the track record of success and saying, look, these are the great logos. These are the great customers and brands that are on board with what we're doing. This is the success that we've had thus far. This is why we have reason to believe that it's going to continue. This is what we see as the opportunity moving forward and how we are seizing our opportunity to be the first mover in this space. The other side is just having a ton of conversations. Raising money is hard and it takes a long time. It takes a lot of conversations. It takes just relentless optimism and passion about what you're doing and unwillingness to accept that there will be any other way and we'll see what happens with the recession in the mix now but I think that's regardless of what happens with valuations and what happens with the markets those things are foundational. Phil: For sure. Thank you for sharing that and let's touch a little bit, another point that you talk about, you say marketing budget goes down in recession and it looks like it's the first people go cutting off it's their marketing budget. What's your opinion of that and how you think companies should handle? [chuckles] Lindsay: It's funny, I had just entered the job market in the 2008 recession I had just graduated from college and I didn't quite understand what was happening then. All I knew was that I was this scrappy kid right out of college that didn't know any better and was like, sure, I'll work all the hours and do all the things with no budget and no teammates. Now here I am leading a company later in this recession, and I've seen it happen in many ways, shapes or forms over the years where marketing gets cut first and it makes sense. It's a big spend for any company, it's always a large portion of whatever budget the company has just in its nature, and in some ways that makes sense to be prudent and to make sure that your marketing dollars are going, are most likely to be going to the things that are most likely to drive the business forward. On the other hand, we also hear about this and have absolutely seen it to be true. Many businesses shoot themselves in the foot by cutting marketing budgets too severely to take care of the right now problem at the cost of tomorrow's opportunity. I think in short, make sure that you're focused on the things that matter. You're focused on the things that are going to create long-term connection and are going to not only attain, but retain the customers that you need to grow on the other side of this thing. Phil: Yes, I think like at the end of the day, if we can track marketing better, it's going to be easier to keep going because when the recession comes that it's all the initiatives that you don't have a way to show ROI that very quickly that it's being cut down. I think a product like yours where you're looking about, okay, where is the revenue coming from, how is this working? It helps because at the end of the day, like in my own company, I'm like, okay, what's working? This, this, this. What are experiments? Okay, we are doing experiments, guys. We're going to do what's working. In America, one can actually put more money on what's working. I like, okay, move all the money on what's working, experiment later. That's why I think it's important for marketers is to be able to understand and be able to show what's working and what's the experiment because, at the end of the day, market is also a lot about experimenting. Lindsay: Yes. It's almost entirely an experiment because things and things will change, what worked yesterday probably won't work tomorrow or maybe it will, we don't know. I think that being willing to be nimble being bold in the actions you're going to take, being confident enough in the things that you're going to base your strategy on and giving things time to play out and say, okay, what do we think that this influenced? How do we think that this made an impact? How do we know that it's working or not and where are we most likely to reach the people that we absolutely need to reach in a meaningful way? Phil: For sure. Maybe even like, because it's all about experiment maybe you have to, even as you reduce, you have to think about what, I still have to be doing a little bit of experiments because if I stop doing out together, it's a problem. If you could go back 2019 and you start this company and meet yourself, you have just one hour with yourself, you have one hour talk about business, maybe going to have another hour to talk about other stuff, but how you going to spend your hour that you're going to talk about business with yourself? Lindsay: Believe in the vision, it's real. I'd say that, and I would say some of the things that we've already talked about, like be really intentional about how you grow about the customers you bring in the team that you build, the product that you build, and be bullish and take action and move fast, but also be intentional and cautious and make the right decisions follow your gut. I think that's another thing that we don't always listen to enough as founders, as people in general, because I think that we are and should be data-driven. We talk a lot about being data-driven and how data should influence our paths in business and in marketing. That's absolutely true but you know what else is data? Your gut, your instinct it's based on your entire life. It's based on your entire career of experiences and lived moments so your gut, your instinct is a computer in many ways, and so rely on it to make decisions. Phil: Yes, for sure, because I feel like you're gut basically it's your mind working the background, making those decisions. It's just not out of nowhere. Sometimes one thing that I like to do is like, I'm going to go in a walk or somewhere and not think about the problem I have to solve because I know that I'm actually thinking about the problem in the background and a solution's going to come. [laughs] Lindsay: If you overthink it, you're going to put yourself in a rabbit hole and you're not going to make your best decision. You have to take care of yourself. You have to step away literally and figuratively. Take a walk, go get some fresh air, and sleep, and that clarity provides a lot of wisdom. Phil: Could you share, like, guys-- three years in the market right now, right? Lindsay: Yes. Phil: Could you share like the first "Oh shit" moment that comes to mind? Lindsay: I don't know I think when you inevitably you're going to have some customers turn, and I think when-- I don't even remember the first time that happened, it was a while, but the first customer that we lost, it was like, "Oh no, this is a real thing, we're not just going to grow forever, there's going to be times that we lose customers." That was scary and it was sad. I think everybody who was on the team was like, we were in mourning about it and it was like, "Oh gosh, this really sucks. People aren't just going to stay forever." Then immediately you get into what do we learn. What can we do better next time? How much of this was us? How much of this was them? How can we learn from it but that was probably the first bubble burst. Phil: [laughs] I think your guys' reactions, it shows that you really love the problem. They're really trying to build something to be there for the long term that's a great. What book do you recommend for early SaaS founders? Lindsay: So many. I'm a big reader. I love audiobooks and real books. There's two ends of the spectrum. One is Dare to Lead by Brene Brown. I love her so much. Then another one it's called, Venture Deals. It's called Venture Deals by Brad Feld and if you're going to be venture-backed, if you're not going to be venture-backed, then you don't really need it but if you're getting into the world of venture capital, I remember in the earliest days it was a really helpful book for me to understand some of the terminology and just what I was getting into. Yes, two ends of the spectrum. One is like venture financing for beginners, for beginning founders and the other one is Dare to Lead, which is making sure that you're building and growing a team from a place of wholeheartedness and in real, genuine leadership. Phil: That's great. Let's go deeper like learning about venture, because I think I do the same every time I'm going to a new thing, I find a book about it, then I learn a lot of stuff. What did you learn about venture and from the book and now from being a venture back company for three years what are some things that you learn and that you think you wish you knew when the things started? Lindsay: One, jumping into a venture studio, this was where we started, so it wasn't really a choice of like, "I don't know, I've been bootstrapping it this long, maybe I should go-- Maybe I should get some venture capital or not?" A lot of people have to make that choice, but for us, we got on this path from day one. I have talked to many other founders and I think it's important to know that it's a very different path. The opportunity to accelerate is real and it's awesome, and you can grow a lot faster but also the expectation and the bar is set a lot higher for how much you're going to be able to grow. It takes some of the things off the table. Some founders have the ability to say, okay, this is how fast we're going to grow, this is how slow we're going to grow. This is the pace at which we're going to take things. Venture changes that, and like I said, it's a real beautiful, amazing opportunity to accelerate. That comes with the bar set really high, and I think that's really important to know before you get into it. Then I would say also just the people that you partner with really matter. The people that provide that venture capital, the investors, you got to make sure that you really like. I love our investors and they believe in the vision and we align on the opportunity ahead. That's really important because you hear great stories and also horror stories all the time about investors that come in and don't align. Then it can be really tough and it can be a lot of pressure. The importance of finding investors that believe in you, that share the vision and that see the same opportunity ahead that you do as a founder. Super important. Phil: Could you share some of your target growth, like being a venture company? What's the percent of growth? What is the churn? What are some of the numbers that you could share about like, that very high bar that you have and that you guys are trying to achieve? Lindsay: Well, I would, but I think it's changing, especially now with the recession, right? Two, it's different for every company and every industry. I think super broadly speaking, people are talking about 1X, 2X, 10X, 50X growth. I mean, that happens in venture. It's not a matter of like, can we grow by 20% next year? It's like, can you double, can you triple, can you quadruple next year? I mean, that's the difference. It's exponentially different. When you get venture capital fuel, it's expected that you're going to fan that flame. That rapid growth becomes an expectation that I'm assuming, I mean, like I said, I've been venture-backed all along, but when that's not on the table and when you can grow at a different pace because you're bootstrapped, it's just different. It's a completely different set of-- It's a different context. A different set of accelerators and levers that you need to pull to get to where you need to go. Phil: I think it's a different game and you have to like the game. Lindsay: Oh my God, you have to be obsessed with the game. [laughs] Phil: It feels like you love the game being venture. It is just like you choose your journey, it shows yours. That's the game you were playing. Could you share sometimes or we're not going to get to that projection side. How did you handle, how did you change, what did you make it to make sure you got there or you didn't get it? How did you manage the expectations of your investors? It seems like they're very happy and you guys have a great relationship. I think that's all about managing expectations too. Sometimes you just don't get where we think you're going to get. How you do that? Lindsay: Especially right now, especially in recession times, right? Somebody told me early on, and I absolutely believe this to be true as well, is that you have to be super duper open with your board and with your investors. I agree with that. I think that, good news is easy to share and bad news doesn't age well, right? Now that doesn't mean every time you have a close a prospect, "Say thanks, but no thanks." You don't call up your board say, "They said no." When you see trends, when you start to see patterns, when you have something, when you start to feel like, I don't think we're going to hit that number. I don't think this person's going to work out, I don't think this customer's going to stay. I don't think dot, dot, dot. It's important to use those as opportunities to lean into your board, not hide from and say, "This is me as a leader being confident in my ability to see down the path and around the corner. Here's something that I think I see that has me concerned or excited. Here's an opportunity down there that I think that we should pursue, which possibly means an investment in a different area or a change in what we're building or what we're growing to." That's what your board is looking for in you is for you to have a command enough of the business and what's happening and what could happen, good or bad, and bring them into it. I always tell them like, "Help me see around my blinders, help me see my blind spots because I'm super passionate and I'm seeing things from this perspective. You as a board and as my investors are seeing it from the outside in, you have other data points from other portfolio companies and from the market that I don't. Where are we heading and what do we need to see and what do we need to do together?" I think that seeing it as a partnership is super important. Tapping into the collective wisdom of your board is also important. Remembering that as the founder, it's on you to communicate what's happening in the business. Otherwise, they don't know or they don't know until it's too late, right? To either fix what could be broken or to capitalize on an opportunity. Phil: I think that's like in addition to their money, one of the biggest values that they're going to bring, right? In your board, they have experience. They have seen stuff. If you can, instead of being afraid of them, leverage them and say "Guys, I have a problem. Come here. Help me. What's going on? Can you help me?" I think that's the right approach. Let's talk about the future. We talk about a lot where you come from and about the origin story, but how do you see the future for your company and where you guys are going? Lindsay: To me, the entire company is built on this vision for what the future of B2B marketing should look like, right? The entirety of my career has been leveraging a playbook for B2B marketing and content marketing that has since become outdated. It's all built on written content and blogs and algorithms and those things all have their place 100%, but they don't take into account the opportunity for connection and for creativity and for building relationships and establishing trust that comes with content like this podcast and video content. If you don't put that at the center, you're really missing an opportunity. In order to put it at the center, you need to be able to use it across other channels and measure its impact on the business. That's what Casted does. We're introducing to the world this methodology called amplified marketing that I really think is that new playbook that the world of B2B marketing needs. To me, that's the future. It is introducing and really starting and growing this conversation around amplified marketing and then pointing to Casted is the way to make it happen. I think that we can become a big successful company that delivers a lot of value to B2B brands around the world and hopefully is a really great company to work for along the way. Phil: Like HubSpot introduced inbound, you're trying to introduce amplify marketing. Is that correct? Lindsay: That's literally exactly the words that I use all the time. I'm a HubSpot junkie and they're a customer of ours, and we're a customer of theirs and we're great partners. They changed my life. It's not an overstatement to say that they changed my life by introducing inbound marketing. My career was different because HubSpot introduced something called inbound marketing. My career took on a, went down the inbound marketing path, and I became a different marketer because of it. They had a bunch of agency partners that they called inbound marketing agencies, and to us, the opportunity to say, "HubSpot introduced inbound and built an entire category around it and also built this partner ecosystem. Casted is also going to introduce amplified marketing as this category and as this methodology provide a lot of value to a lot of companies in this methodology and in the platform that we created." Also, we're building a partner network of amplified marketing partners that actually just rolled out this week. Yes, very similar to that approach to the world. Phil: Yes, I think for like other founders, you can always think about what, because you can learn from other companies and you can replicate it in a different market. That's basically what you're doing. Everyone knows the HubSpot success, and like I say, it's life-changing. Now you're like, let me do this again, but in here and I think that's again why I like to do this show because when people are listening to you, they can learn from you and they can apply the same thing now in other market that maybe they are the industry expert. Lindsay, thank you very much for taking the time to be with me on the show today. I think there was a lot of golden nuggets here for our listeners. Lindsay: Thank you so much for the conversation. This was super fun. Phil: Thank you. Voiceover: SaaS Origin Stories is brought to you by Dev Squad. To find out more about how we help entrepreneurs launch new products and help larger businesses plug in a ready-to-go development team, visit devsquad.com. Add us to your rotation by searching for SAS origin stories in Apple Podcasts, Google Podcasts, Spotify, or anywhere else podcasts are found. Make sure to click follow so you don't miss any future episodes. Thanks for listening. Remember, every SaaS hero has an origin story.