Startup Exits Simplified: Tim Grassin’s Proven Tactics

Everyone, how's it going? My name is Ehan Isaacs. I'm the head of growth for the Founder Institute. Thank you so much for joining us today. This, I believe, is our first global event for Asia. We do a few of these a year, try to bring the different audiences together. I'm really glad to be here today. We have an exciting AMA session today with Tim. He was supposed to do this last week, unfortunately got sick, so we're very grateful for him to take the time out and join us today. So really excited for today's session. We had about 500 people between the two events sign up. I think we'll get maybe about 100 people live. We're at about 69 people. I wanna go over some housekeeping stuff before I kind of kick it over and we start doing the AMA. As you know, this platform is called Airmeet. It's not the most intuitive, so I just wanna go through some basics. On the right-hand side, there is a bunch of different buttons. The first one is there's a chat button. Please use that to communicate with everyone. Let us know where you're calling in from. I'm based in Dubai, UAE. Tim's in Bangkok, Thailand. So I think I see some people in from India, some people from Poland, so Portugal, awesome. Underneath that, there's a Q&A button. Please use that to field questions to me where we will start to bring up audience questions pretty soon, in about 15-20 minutes, after we do some introductions and some intro questions. And lastly but not least, at the bottom there's a bunch of emojis. Feel free to use that to just show your reactions. Perfect, I saw one heart emoji. Um, yeah, I think we're good to go. Yeah, oh, the last thing is if you're doing this on a mobile or it's not the best experience, try to join in from your laptop or iPad. Or tablet.

Perfect. All right, cool.

Let's get started. Tim, thanks for joining us.

Thanks, Ayaan, appreciate it.

Awesome. Yeah, then I hope you're feeling well. I'm just going to read out your bio and then maybe I'll kick it over to you to add anything to it and then we can just jump straight into it. But yeah, so everyone probably already knows about you. If not, Fahima, can you just put Tim's LinkedIn in the chat and then I'll broadcasted, but Tim's a 3-time exit founder and currently the CEO of KubeGrade, an enterprise SaaS startup automating Kubernetes cluster management for mid to large companies. With a proven track record of scaling startups, including growing TendoPay, its acquisition to Tonic Bank, Tim specializes in founder-led sales, go-to-market strategies, and innovative scaling playbooks. He's also the host of the Next Big Wave podcast, of founders in Southeast Asia. Awesome, Tim, thank you so much for joining us today.

Appreciate it, Ehan. And as you mentioned, I was a little sick last week. Well, actually really sick. I'm 90% better, so if my voice breaks at some point, I apologize. It's not intentional.

Yeah, no worries. Hopefully everything goes smoothly. I just broadcasted Tim's LinkedIn if everyone wants to go and connect with him. Tell them you heard about us from F5, and yeah. Okay, let's get things started.

I have a question before we get started. This Airmeet is F5 portfolio company or not? Looks really good. Just curious where it is.

No, no, no. I wish if it was F5 portfolio.

It's not.

It's a platform we started to use during COVID because they had, as you know, it has this virtual networking lounge. So we were using that a lot, and then we just adopted it as our main.

That's good. Looks— yeah, I like it.

You know, it's very nice, but it gets a bit clunky at times. Okay. But yeah, it's a pretty decent platform. All right, I guess for the audience here, before we open up for AMA, what I'd like to do is just go back to the genesis. Can you just tell me a little bit about your entrepreneurship journey? You've gone through a number of acquisitions. Maybe can you just— let's talk about the first startup, the exit, the second startup, and just at the high level, just so the audience know who we're talking about. I read your bio, but it's just always better to—

Spanish, uh, but yeah, I think it's a good thing because, uh, people mistakenly think I built 3 startups and sold them all. Um, the journey is more of a roller coaster than that. And actually, the first companies that I was successful with, uh, were service businesses, not startups specifically. And so on my track record right now, I have one full service company that I built, an agency That was my first build that allowed me to finance the rest of my ambitions. The second one was a productized service company. So, kind of a first step to tech businesses and productizing a lot of different processes and services. That was in the ad space, so ad tech. And the last company that I built prior to what I'm doing now, that was a full tech company, a fintech business in the Philippines called TendoPay. And again, with that one, we pivoted a bunch of times. So very rocky sort of journey. And in between these 3 companies that I sold, there are a lot of different products, ideas, projects that I sort of seeded and tried out and failed at. So my LinkedIn is the clean version, but in between there's a lot of like debris from, you know, my carcass or carcasses from the startups that I tried and failed at. So that would be the track record. And originally, obviously, just like anybody else, I didn't, go to school to build a startup, and I think anyone who goes to an entrepreneurship program will tell you that's not good enough to build a company. And most people who do go into entrepreneurship have had some sort of professional role before. In my case, I studied finance, I wanted to be in investment banking, and I worked in finance for a little while before I realized it was way too sort of structured, hierarchical, and like not really built within the type of paradigm that I'm comfortable in, which is every action has a reaction. And in a big corporation, every action you take will barely make a dent into anything, and you won't really see the repercussions of your work. And that was not good enough for me. So I very, very quickly pivoted into building something with my own hands where I had full control over the output and the outcome. And that's how I got into entrepreneurship, essentially.

Okay, awesome. So first startup was, um, focused on services, you exit that. Second was quasi product and services, and now you're on your third or you're on your fourth?

I'm on my fourth. So I only talked about the ones that I sold so far. The one I'm working on right now is as product as you can imagine. It's a dev tool, so it's very, very technical in the Kubernetes space, something that I didn't even know about 5 months ago, uh, before I got introduced to it by my now co-founder Caleb, who's a veteran in the DevOps space for the last 15 years. And this, like, you know, as much as my last company, the fintech, was indeed a full-on tech company, there was a lot of manual labor, a lot of financial auditing, a lot of financial sort of, you know, number crunching in the background. In this case of this coup-grade company, it's purely, purely software, and we're selling to software developers. So It's as tech as can be.

Okay, awesome. Maybe let's double-click a little bit on the CubeGrid, and then folks, while I'm asking Tim, please dump your questions in the, um, the Q&A portion so I can—

we can start collecting them.

Um, but, uh, Tim, so you've gone through 3 companies, 2 exits, you're doing the 4th one. Can we just— how did you come up with this aha moment? You're like, hey, I realized that I want to do this thing for CubeGrid? Like, what was that light bulb moment where, you know, you're like, hey, I'm willing to go through this entrepreneurial journey again?

Because that's not—

again, yeah, because some people, they, they're just like, hey, I got one or two in me and then I'm done.

And I mean, we all think that way until, you know, you go through a year of consulting, and that's what happened to me, and you kind of get bored and you want to build something again. So what happened after we sold TendoPay, which was about 2.5 years ago to Tonic Bank that you mentioned? Well, we went through an earnout, and in this case, it was a year and 3-month earnout, 15 months. And during that earnout, you're kind of working for a corporation again, which is the exact opposite of what I'm built with, like, which is entrepreneurial fiber. And I realized very quickly, I'm not going to work for that bank after the acquisition goes through and the earnout is over. So I packed my bags, moved away from Manila where I was based and decided to go to Bangkok, a place that was sort of on my bucket list to live in. I really love coming to Thailand every time I do. And my wife being from South Korea, it was very close to home and we wanted to stay in Southeast Asia. And during, you know, the post-acquisition period, most people don't have an idea immediately. And like, it's very rare to have back to back to back ideas. And I did 3 back to back ideas. This time I told myself, let me take a break. Let me take as long as it takes to come up with a new project. In the meantime, I did, I started a podcast. I was very active on LinkedIn, posting about a lot of different playbooks that I had developed for TendoPay and for other companies in, in, in that were, you know, operate operatable in Southeast Asia. And during that time, I was also consulting with a bunch of founders in Southeast Asia. So I probably worked with 20, 25 founders in the last year, which allowed me to kind of come up with new ideas, open my horizons into what was out there. Because as founders, one thing we realize is that there's businesses in every corner of the planet. We just don't know about most of them because we're not exposed to them. There's no need for us to know about them. And in this case, this idea came about because Caleb, whom I had known for over 5 years, we met in Manila, He had been working in this agency of his for 10 years plus servicing, you know, hundreds of startups, Series A and Series B companies with their DevOps needs. And he realized very quickly, maybe like 4 or 5 years ago, that Kubernetes was taking over. It was representing 90% of his workload. And because Kubernetes is fairly new as a technology, as much as it was born 10 years ago, you know, fast adoption has only happened in the last 3 to 4 years, especially at the enterprise or mid-market level. And there are a lot of problems coming to life because of this fast adoption. And one of these problems was upgrading components within a cluster. So making sure your cluster health was at par and making sure that all of your compliance needs were met on the cluster level. And so he developed a tool at his agency just to solve for that because it was a very time-intensive, very labor-intensive sort of task that only humans were able to do, even though they had developed scripts, et cetera, it was still not good enough. So he built a tool for his team and then realized that this was a tool he could bring upmarket, sell out of his agency, and in this case, spin out and build as a standalone SaaS. And as he had this idea to spin out the product, he visited me in Bangkok, asked me for a consulting session as a friend because he wanted to, he'd only built agencies in his life and never brought a SaaS to market. So he asked me for a bunch of advice. And then a couple of weeks later, phone rings and he asked me, look, you've been looking for a project. I think you'd be awesome to partner with. You've ran multiple companies, you've exited them, you know how to fundraise, you know how to build a product and bring it to market. I'm really good at tech, but I don't want to do any of that stuff. Should we partner up? And for me, it checked off all the boxes that I needed. So a solid co-founder that I knew outside of work and trusted and respected and was an expert in his field, uh, a growth market. So, you know, Kubernetes is growing at a 25% CAGR for the foreseeable future. It's an enterprise sales, uh, company, meaning we're selling SaaS to enterprise, and that's my bread and butter. And it's a product that comes with existing traction. It was built out of a need in an agency. It has implied revenue because within his agency, he can associate revenue to it. And for me, that was a sort of a given, like I had to work on this. It was a perfect, perfect next project for me.

Awesome. No, thank you so much for going through that. So let's just summarize that just so, because we talk a lot about this at FI in the curriculum. You know, you were sipping mojitos, you exited, you were chilling, and then what happened is you've identified, well, first of all, your co-founder identified a problem, built a solution, got revenue, got on it, and then came to you and be like, hey, let's look at scaling this up together, leveraging each other's experiences. And that's one of the core things we advocate at Founder Institute is that, hey, you know, as you're going through this ideation process, go talk to customers, validate the idea, and also go find a co-founder. And you kind of achieved all of that within a few months. Obviously, you're a serial entrepreneur, so this is like a muscle that you've used several times, but for a lot of new founders, it's super early, and they're going through this, they're going through their own mistakes and all that. Awesome, thank you so much for sharing your latest journey, I would say, on this front. So we have some questions coming in, I'll start to field them in about like 5 minutes, I just wanna do a couple more. So yeah, folks, please start dropping more and more questions in the Q&A, and then we'll get to them. One of the things, because most of us Our audience is here early stage. Again, this is not your first rodeo. You know, let's just talk a little bit about creating value. So what, and because you've done the agency, you've done product, you've done services, you've done hybrid, and now you're doing enterprise and mid-market. What's your like two cents of how you, how do you go about creating and delivering value to your clients at the early stage? You're an early stage startup, you're scrappy, you don't have all the resources as maybe some of your competitors and stuff, but, You know, you've got, uh, you, you've got, let's say, the tenacity to kind of go in and speak to customers. Uh, what's your two cents on like how do I go about creating and delivering value to those customers or prospects?

Yeah, I mean, the, the main thing, and I see people making this mistake a lot, is they're building based on a hypothesis that they have, uh, a personal need that they might have, rather than sort of surveying the market and making sure they fully understand whether or not that market has a need. So at the end of the day, like, all I do is spend time with potential customers, sit down, pitch them an idea, listen to their feedback, and iterate based on their feedback. Meaning if they do see an immediate need, I'll sort of expand on that, and I'll try and understand what about what I just said made them tilt so hard and is it really a problem that they would pay for, et cetera. So like, you know, you always talk about surveying and interviewing your prospects or your potential clients and trying to understand and building for that. Everyone knows the concept. I haven't seen that many people do it properly. And to me, that's really like a key way to build is just identifying an ICP I wanna build for. Especially with like an original hypothesis and just expanding on that. And I never go to a potential customer with like a survey form, et cetera. I do everything sort of relational based. So I'll ask them for 15 minutes of their time, have a couple questions, sort of like wanna direct the conversation a certain direction. And then based on what they, on how they react, I try to pick up on, you know, visual cues as well, not just what they say. but like see how they react. Like, are they excited about what I said? Are they turned off? Does it make them think about something? If it does, I wanna figure out what do they think of? Like, where did they go back to? Like, were they thinking of a problem and how they solved it? Were they thinking about another tool that they used? I wanna map out exactly how they think about the problem statement that I've defined and understand how I can potentially solve it for them in that. Is what you kind of call development partners as well. Is right now, now that we've sort of validated a lot of different things, we're a little bit later stage, but we still utilize the same, the same strategy by going to like 2 or 3 high potential customers and saying, hey, we know that you need this, you've identified it, you've mentioned that this is something that you would pay for, can we build it together? And In exchange of you sort of sitting down with us and really walking us through exactly what you want, from like features to look and feel to, you know, UI, etc., we wanna sit down and build it for you essentially. And in exchange, we'll give you like a year, a year of free service or whatever it is. And that, like, to me is like continuous iteration with your ICP, with your ideal customer profile. Which a lot of people forget to do. And like people get caught up in one validation and then start building like crazy. And it's kind of, you know, you probably see this at F5, people start building features, they get excited because they feel like working on something makes them feel better, makes them feel active, makes them feel less guilty. I'd much rather spend a ton of time doing nothing, just thinking, spending time talking, engaging with people. Than building because at the end of the day, I feel like I'll build something a lot more solid, a lot more needed.

Yeah, and I think just one thing to add that especially in the age of AI, like feature parity is there. Like I can literally go onto Replit and build a new product with like 6 prompts and I can, like it'll be janky, but like I can build feature, I can ship stuff. So it's no longer about just having strong features. It's about going in and doing what Tim is talking about is, just really co-creating the product with your customers to make sure that it's like a really good fit and then it gets really, really sticky, right? Um, I guess on that note, Tim, so I have two follow-up questions. One is, how many customers or prospects did you interview, or would you say is the right amount before you're like, okay, I see this being, uh, like product-market fit, or I just see some traction on it, right? That's, uh, the first one. And the second thing is like the whole AI, well, obviously it's no longer a trend, it's AI adoption is here. What is your thoughts on like how AI is being adopted across these different SaaS products and where would you kind of see that trajectory going? So I guess two fully loaded questions, but yeah, I'll—

Yeah, yeah, yeah, totally. So in terms of numbers, it's really hard to quantify. In our case, and this is a very specific and unique case, is we are building something that was used in an agency. So 100+ clients were using this tool unbeknownst to them, right? So Caleb's team was using this tool in the background. It's a command line interface, so the clients would never see it, but the engineers working on their DevOps were using this tool. So we had validation from that point. Then when it came to me and validating the product, 'cause I don't wanna just trust someone that, hey, they have this tool, it's working, and it brings value. Like, that's great. I trust my co-founder and we're really good friends, I'm not gonna jump into a new venture for, you know, potentially 5 to 10 years just based on something he told me. So once I was kind of interested and intrigued by the project, I reached out to 12 CTOs that I knew quite well, and it's a purely random number. I just went through my LinkedIn, my WhatsApp, et cetera, and started looking at people who would be relevant to talk to. So I talked to 12 CTOs and kind of walked them through the problem statement. Try to understand how big they were, how many clusters they were using, what difficulties they were having, how many DevOps engineers they were using to manage these clusters, what was their monthly cost to run these, to, to run these engineers, etc. That was kind of validation from the client side. And then I knew I was going to raise a lot of money for this product just because, you know, go-to speed to market, etc., are quite important. And in order to do that, I reached out to 7 different investors in Southeast Asia that I knew to ask them their feeling about the industry, uh, if they knew anything about Kubernetes in general other than, you know, the, the industry trend, but like more specifically, had they worked on dev tools, did they know anything about sort of cluster management, their familiarity with AWS, Google, Azure, and their, uh, and their Kubernetes offerings, uh, their network. So would their network be some, some people we could tap in the future if we wanted to find clients and get doors open. And overall, the response was really, really good as well. So for me, just having a handful of people I trust overall was good enough. But in the case that you don't know your potential clients, you might have to go a little bit deeper in terms of how many people you question. But that also begs the question, should you be building for people you don't know at all that you don't have a network in? In my opinion, and I might be jumping the gun here, is that whether it's you or your co-founder, you should be building something that answers a need that you've identified, not a need that you're thinking is there. So something, you know, from your previous company that you were struggling with, or you knew a team was struggling with, and you know that other teams are struggling with, you could build from that. Or, you know, something that you have sort of a competitive advantage or knowledge on that others might not have.

Yes.

That's kind of the first question. And the second one was, is AI taking over? So, you know, I'm reading the news same as you are. I've been sort of staying on top of AI trends since the last 2 years, probably a little more than that. And as of recently, all the, you know, big companies are laying off engineers because they're realizing a lot of the junior and now sort of mid-level engineering tasks can be automated and replaced by AI. In our case, the beauty is that DevOps is a very sort of grunt work type of space, and there is no— currently at least, there's no AI that can sort of do what we're aspiring to do. We're actually using AI ourselves to sort of enrich our compatibility matrix, which is one of our modes, which is really having a full database of every single component that runs on Kubernetes. Making sure we understand all of the, all of the versions, all the version compatibilities between the components and the different Kubernetes versions, and then all the dependencies between these components. And there are tens of thousands, right? So we're using AI to sort of scrape and enrich our databases, but our databases are mode. And right now AI cannot do what we do in terms of, you know, analyzing clusters, running all the components through compatibility matrix, and then assisting with the upgrades of all the different components on all your different clusters, whether it's on one or multi-cloud or on-prem, on-cloud, hybrid, etc. So it's a lot more complex than a lot of the different, you know, engineering tasks that are being replaced by AI at the moment.

Yeah, I guess that's where the Dijentic stuff comes in versus actual workflow automation versus RPAs and stuff.

I mean, yeah, Dijentic stuff is something we use Constantly, and especially in my team, like in the go-to-market, I'm building a lot of Agentic stuff, whether it's, you know, content creation, marketing, sales, customer support. We have a ton of stuff in the works right now. It's very exciting to be honest. Like I don't wanna, again, answer a question you haven't asked, but what I'm really excited about right now is that every new employee that I hire, whether they're, you know, already very well literate with AI or they're willing to be trained, Every new employee needs to manage their own agent, meaning every new employee is like hiring 10 new people. And that's the way I'm building this company.

Wow. Yeah, that's a very powerful statement. And I've done that internally with the team as well. I'm like, guys, like you need to be using all these different tools and you need to be able to figure all of this out to get more output out because that's the reality and that's how we'll be efficient. We're a small team and stuff like that. I love it. Okay, cool. We've got a bunch of questions. That's kind of— should we—

Just to add to that, I had an interesting debate with a founder because I'm in a founder community. Maybe you've heard of them, Iterative, out of Singapore. They're an accelerator and there's a really, really good active community there. And one of the founders was kind of complaining that she was interviewing a prospect and she could feel that her answers were, you know, AI generated. And she felt like she was cheated because, you know, the person was answering too well. And a lot of us had a different opinion that, maybe she shouldn't make the prospect or the applicant feel like it's cheating to use AI, but instead sort of highlight the fact that AI will be used and necessary and to be open about their process on how they're leveraging AI to lead a better interview, et cetera. So very exciting times 'cause some people are still against and they feel like they're hiring cheaters, whereas others see it as a pro and they feel like, hey, I wanna hire people who understand and leverage AI.

Yeah, perfect. No, I appreciate you sharing that. Yeah, being more transparent with AI with your prospects and seeing, I think also your prospects seeing that you're adopting some of this stuff maybe as an early adopter and just giving them that visibility could cause like a little bit of, like it could strengthen the relationship as well, right? Okay, cool. We have about 120 people live here. So folks, there's a lot of you, start fielding your questions in and there's also an upvote button. So what I'm doing is I'm literally sorting questions up by upvotes just so I feel them properly. So a lot of questions here about funding, Tim. I'm going to show this one by Nasser, all the way from Amman, Jordan, asking about fundraising and equities and like about rounds. I know this is a very detailed and tough to answer, but maybe do you want to talk about your experience of like how you approach fundraising and how much equity you tend to give and Or like, maybe what's your frame of thinking around this?

Yeah, well, first off, I love Jordan, spent 2 months in Amman 8 years ago, it was awesome. So cool. Yeah, fundraising is a toughie, because it really depends on your profile as a founder. So I'll tell you about 2 different stages of fundraising for me. One is fundraising for TendoPay, when I was brand new to Southeast Asia, and kind of had no track record, in the startup world per se. And the second one will be the story of how I'm raising money for Kuberate at the moment. And those are completely different stories. And it's not just because I had an exit. It does help, but it's not necessarily the, the reason, because I had two exits before raising for TenderBit. So when you're just starting out and you're new to a region and you have no reputation, no name, you're gonna basically lead fundraising the same way you do any sort of sales. And for better or for worse, it's pretty much one of your only options. But essentially, you're gonna have to do a lot of cold outreach. That's number one. And right now, like, we didn't have this when I was fundraising for TendoPay, but now there are databases of investors that are really, really well put together for by region, by sector, by stage, et cetera. So cold outreach will be not like a big, big, uh, uh, sort of playbook, and it's not gonna work very well, but you have to do it. The second thing is you're gonna have to network like hell, whether it's virtually or in person. So I try to go to every single startup event that I can, and I try to get like 5 minutes of FaceTime with every single investor there just to be on their radar, just so they've met me, they've heard my name, so that when I do use the cold outreach strategy, it's not as cold. They've heard my name, they might have spoken to me, they might remember me for something. So try to be memorable. The third thing is doing every single pitch competition you can imagine. And now there's like pitch competitions online, offline, everywhere there is. And I'm assuming you're talking about pre-seed, seed stages, by the way, because later stage, it's a completely different ballgame. But yeah, essentially you're gonna wanna have to be everywhere all the time and put yourself out there as much as possible. and it sucks. Like when we raised for TendoPay, not only were there no VCs in Southeast Asia, so to speak, there were maybe like a handful of VCs. So all of our fundraising efforts had to go through angels and we literally had to scrape LinkedIn for angels that were in the region from India to Japan and all of Southeast Asia and essentially send cold outreach via LinkedIn. Find their emails, reach out to them, try to get them on calls, you know, constantly evolve our messaging, constantly evolve our deck, be very, very flexible on terms. And that's just the sucky part about being a first-time founder. If you're lucky, you'll be sort of introduced to a variety of different programs, like FII might be one, Iteriv might be another, Antler are great programs. All of these programs that offer you, a bit of, a bit of funding for a little bit of equity, especially if you're kind of unfortunately nobody in the scene. Uh, a lot of these services will help you, you know, build a reputation for yourself and sort of provide the financial backing that you might need, help you find a co-founder, etc. But it's very, very tough, and it's the same for everybody unless you're in a hot zone like, you know, San Francisco where every single coffee shop that you go to, there are founders just like you, and there are investors that are looking for founders just like you. If you're in Southeast Asia, if you're in the Middle East, you know, we're all on the same boat. It's a struggle, and you just gotta find every single resource you can. Thankfully, with AI now, you can build huge databases of people to reach out to, to programs to, to apply to, and just, you know, do your, do, do your work and try to get in. Now, things change a lot once you either have an exit or build your personal brand. And I'm a big, big believer of building your personal brand. I started about a year and a half ago, and LinkedIn is honestly the best place to do it, is to just build yourself a niche, build an expertise. And I'm talking about startup related. So if you're technical, if you're marketing, if you're a salesperson, like any any niche or any skill or expertise that you have, build yourself a strong brand around that. And in my case, I was talking about GTM strategies, GTM motions, playbooks, et cetera. And also a bit of like the life or behind the scenes of a founder, talking about all these different stories. And I managed to build a strong following of people in my industry. So founders, but also investors who were, literally following along with my journey. And most investors have a mandate to, you know, keep track of interesting founders, people who have something to say and expertise, because at the end of the day, they wanna deploy capital. They just have to trust you enough to deploy that capital. And so when it came for me, after a year and a half of putting out content, creating a podcast, actually inviting investors onto my podcast, building relationships, starting conversations at networking events. I would now be somebody like people would recognize me and ask me to have a discussion with them about GTM, et cetera. And all of a sudden, when I started raising for KubeGrade, every single investor that I reached out to, they had already seen my face. I literally blasted my own face with every single one of my posts on LinkedIn so that when I reached out to them, they recognized me and were willing to have a conversation with me. And that was huge because it's not easy for founders to just knock on the door of an investor and get someone to answer the door. And that, for me, personal branding is really what helped me get there. So you get kind of two different stories.

Awesome. No, thanks for that too. I think you covered a lot of different, uh, pieces, a bit of advice there, which is super helpful. All right, let's, uh, because we just want to be cognizant of time and we have a few questions to go through, So Max from Munich is asking, what's the best GTM in early stage, early sales strategy for B2B SaaS companies? Imagine at pre-seed, seed level. So maybe what, when you were advising your founders and coaching them, how would you go about it? Again, I know this is a generic question. Try to give your best.

Yeah, I'm trying to think like of a specific playbook that worked, 'cause that like you could go any number of directions. The first thing is, you know, people think of GTM as just like the method that you're using to access your leads. I think the first part of GTM is understanding your ICP properly and defining who your ICP is and creating a persona around that. So get as narrow as you can. In our case, for Kubegrade, we're targeting, you know, mid to large enterprises that are using Kubernetes for over a year and within those enterprises in the US, by the way, we're only targeting CTOs, head of platform and head of DevOps. So really it's not that many people left in our, you know, in the pie that we're reaching out to. So pretty niche sort of ICP and then figure out where your ICP lives and that's important because where are you gonna sort of encounter them? Where are you gonna be able to make an impression on them? Where are you gonna make them read about you? It's gonna matter a lot.

Sorry, I'm just gonna jump in. Can you just— not like physically live.

Yeah, no, no, no. When I say you're not knocking on the door in person, where do they live is where do they spend time virtually on a day-to-day basis. We just call it where do they live. It's just like, I guess, an image version of living. But yeah, where do they live? So are they reading industry magazine? Are they going to conferences? Are they spending time on LinkedIn? Are they listening to podcasts? Are they reading newsletters? That's kind of where do they live other than actually doing the work. And based on that, we're gonna devise a strategy on how to reach out to them on a sort of multi-level methodology, not just a single channel, but multi-channel overall. And in our case, we realized that CTOs, head of platform, et cetera, they listen to a lot of industry podcasts, they read a lot of newsletters, They spend a ton of time on LinkedIn and they go to events. So our strategy is built around that. It's like, so our, my CTO is writing a lot of content around Kubernetes in general, and then specifically how our product solves certain problems, uh, how our product solves certain problems. I myself, I'm targeting investors, I'm targeting more commercial CEOs, et cetera. So I write about like the behind the scenes of building a Kubernetes startup. How like the ups and downs, sort of building in public as well so that investors get bought into the story and they will preemptively wanna give us money before we raise because they know a lot of eyeballs are on us. And so that kind of gives you an idea of like overall, who are you targeting? Where do they live? And then once you know where they live, how do you target them there? One playbook that I've used 100 times, and this works really, really well for B2B, is building an industry podcast. So when I built my, when I devised my podcast, uh, Next Big Wave, I wanted to interview founders because I thought it was interesting. But I was also consulting with founders, and I knew that if I can talk to 1 or 2 founders a week on my podcast, those are my specific ICPs, my target customers, and I'm going to spend an hour talking to each one of them, building a relationship, building trust, and helping them with certain problems live on a show. So really building trust. And after the fact, I can always either pitch them directly or they might want to directly ask me for help, etc. And that works in any B2B industry. So for the case of KubeGrade, we might build a podcast talking about Kubernetes in general and then have CTOs jump on the podcast and talking about the trends, what's happening with Kubernetes, what are the ups and downs. Where do we think it's heading? What is CubeGrade? We might slide it in there, et cetera. Or we might decide to just sponsor other industry podcasts. But podcasting for me is one of the sort of easiest low-hanging hacks. And by the way, when I build these playbooks, I built one for TendoPay as well, and it worked really, really well. People are very willing to come on podcasts because they feel they're gonna get exposure, they feel their ego being stroked, et cetera. So there's very little downside to building a podcast. The only upside is getting airtime with your prospects, which is a lot easier than blasting a bunch of people on Smart Leads or Instantly.

Just one thing on the podcast. I remember this is during COVID for one of my buddy's company, I was helping him out. We did this, we did podcasts and webinars and it was really good. I think we got a lot of solid relationships and then we had to hire 3 different people to help edit the podcast, break out the clips and all that stuff. All of that stuff can be done with AI for like $20 a month.

Oh, for sure.

Right? So it's crazy. Yeah, exactly. Well, not just like, it's just cleaning it up and then to distribute it. I forgot what the one was to go into the podcast.

Oh yeah, there's plenty.

Yeah, I think it was Riverside or I can't remember another one, but great, great. A lot of cool products. But one thing I'd add to this on the B2B SaaS GTM side is always remember if you're doing mid-market enterprise versus SMB, because those are a little bit two different motions. But everything that Tim said is sound. And I interviewed Mark Cosgrove from Outreach.io. He was the first director of sales and helped build out that machine, I think last week. And a lot of the stuff that he's saying is very similar to what you guys are talking about here. So I'll ask, we'll put it in the chat there, but highly recommend checking out that interview as well.

Cool.

Okay, let's move on. How are we for time? Okay, we got, we can do maybe 2 or 3 more questions. Okay, I like this question from Jake who's in Reno. I don't know how you're up right now, Jake, but I appreciate you joining us.

I saw a couple people in the US. I'm shocked as well. Thanks for being here.

Yeah, I guess they really wanna hear from you, Tim. So I really like this question 'cause you talked about it. This is like, how can I go and get a potential CTO or a technical co-founder if they're outside my network? So they're not my friend. Are you asking qualifying questions? Are you going through a specific strategy? What's the thinking around here at least?

Man, this is such a tough question because my answer is terrible for most people. My answer is do not become partners with someone you barely know. And it's crazy because most startups are built that way and You know, some works, 90% plus don't. And I'd argue that one of the reasons startups don't work is because you start building something with a co-founder that you just met specifically for the needs of this startup, whether you met, you know, through a networking event, through LinkedIn, you almost recruited them in a sense, or you were partnered together through a program that does, you know, founder matchmaking. You like, and I feel bad for my wife, but I spend way more time on my startup than I do my relationship. So my co-founder at some point is someone I spend more time than I do my wife. And I know I didn't marry my wife by, you know, finding her through a networking app just based on a few criteria that, you know, I thought it was going to work. I did meet her on a dating site, but I spent a long time betting her and spending time with her and making sure that she was the right partner for marriage. And at this stage, building the startup is your marriage already. So you're jumping from barely knowing them to marrying them. And the reason it sucks is because most people don't have a choice. I would say, even if you have an idea that is really solid now, date your co-founders. Like find a few people that you wanna date, spend time with, maybe discuss, you know, hack on different things, talk about, you know, industry trends, spend time together. And whether or not they have the qualifications— because you asked about a CTO, that's very tough. Because the same way, you know, I spend tons of time recruiting people and on paper they sound great, and when they— I hire them, they suck. That'll happen with a CTO as well. Like, you can't just evaluate them based on their CV, based on their LinkedIn. You might get a better sense if they're sort of an outspoken person and they write content, or if you're able to read code and you can spend time on their GitHub and kind of see what they're up to there, or if they're active on Hacker News or on Reddit or whatever. Try to find as much information outside of just a pure sort of static CV to see whether or not you'll have a personality fit, you see if they're liked, likable. All of these factors will come into play when it comes to building a business. And so, you know, I hate this answer, but I would have to say, for most people, it's better to spend time dating your co-founder and qualifying them rather than jumping into something based on an idea, based on like excitement. I've been through it, and I can tell you that this excitement of a co-founder where everything's going great, that eventually stops. And, you know, the sort of honeymoon phase of the excitement of building a project, once that dies down, you only see, you start seeing people's flaws and who they really are when, you know, you have adversity to sort of go through together. and you could have maybe figured that out by spending a lot of time as a friend, figured out, hey, maybe that personality fit is not right, maybe his ethics are not right, and you could ask a ton of random questions to figure out all these things, but figure out if they have the right moral fiber, if they have the right ethics that match yours, if they have the right personality in and outside of work, because like I said, you're going to spend a ton of time with them. So Sorry for that answer, but that's the only—

No, no, that's the best answer, to be honest. I remember when I was doing this, when I was at FI in 2016, we had like several mentors say like, hey, you're gonna be with this person for a very long time. Like start figuring out how that relationship, define it, set the right expectations, you know? What if your co-founder has different life stuff, you know, maybe they have to exit the company, like what does that look like? So I think you wanna spend as much time with them and get really comfortable. Start small, start with a small project. Maybe you give them a couple points in equity just to like, stay involved, and then like you kind of build up, uh, towards that. But like, to always start with the project, then go north from there, because you're right, on paper this could look like a great person, but when you actually start working with them, it's like, hey, I actually don't like working with this person because of so-and-so, right? Cool. Let's do one more question, um, and then we can break out for networking. I don't know, Tim, if you can stay for that long, but we'll definitely give the audience a chance. Okay, perfect. So Dima from Poland is asking, there was a few of these questions, is the closest one I found where it was like, when you're at the acquisition stage, like how are you finding those companies? Are they approaching you? Are you finding them? Like what's that process like? Maybe if you can walk us through because you've gone through that now a few times.

Yeah, so my first two businesses I was acquired by clients. Uh, so, you know, it's weird, but like, so the, the first business was a service business in the communication space, and I had a lot of Fortune 500 companies as clients. And for them, you know, there was a big expense to work with me on an annual basis. They had retainers, etc. And one of these companies just decided to internalize the service, uh, and they realized it would be better to buy our, our business unit than have to recruit for it and train the right staff. And on top of that, they were acquiring revenue outside of their enterprise. So in this case, it made perfect sense for them to buy us because they knew us, they'd worked with us for 3 years plus, and they just felt like we were the right partner rather than building it themselves. The second acquisition was almost the exact same thing. We were an ad tech business providing sort of services for North American ad agencies. And one of the clients that we had been working for a bit less than a year, they decided to move away just from ad placement and to do ad production as well. And our product was in the ad production space. And they knew there was gonna be a lot of synergies if they acquired someone like us, 'cause they could, they already had a ton of clients in the ad placement, media buying space that they could upsell to media production. And for them, it just made perfect sense to buy us. Not only they were acquiring the revenue from all of our other clients, but they were able to immediately upsell our product to a ton of different clients that they already have. Again, customer reached out to us, said, "Are you guys willing to sell? We've worked with you, we know your team, we know everything inside out. We just wanna see the numbers." worked out perfectly. And then the third one, we were raising our Series B, and because we were in a consumer lending business, we had to raise a ton of debt and equity to stay afloat for our operations, right? And so through that process, we couldn't make our, our debt investors and our equity investors align on terms. And we're talking, you know, multiple 8-figure sort of, multiple 8 figures in debt, and then 8 figures in equity as well. And we were kind of running tight on cash. We probably had like 4 months runway, and we still couldn't get everyone to align on terms. And one of our previous investors mentioned that, you know, there was another option, which should be a lot easier, was, maybe to get a bank to invest in us because they would be able to invest in us and then open their balance sheet so they, they could do both and they wouldn't have to agree with each other. They would just provide the terms that work for their equity and for the debt. And so we started talking to banks based on that investor's insight, and they introduced us to a variety of different banks actually that were looking for sort of a debt lend or a lending partner like ourselves. And it turns out that one of these banks was very eager because they were the first digital bank in the Philippines. They had sort of managed to get a ton of deposits as a promotional campaign because they were offering insane deposit interests. And so they had all this cash but no debt or no lending facility to make money on this cash. And so instead of investing in us, they offered to buy us outright. Offered us, you know, decent terms and said that we would have access to their entire balance sheet so we could scale as fast as we wanted. We had no limits on how much we would lend out, and that's how the acquisition happened essentially. But in general, other founders that I've coached, and I've invested in a few startups, and one of them went through an M&A 2 years ago, and for them, they use basically a small M&A firm that specializes in selling startups, you know, startups that have a few million in ARR, not more. Uh, once you start becoming bigger, you might want to go with bigger M&A firms, um, you know, big banks in the US or whatever. But these M&A firms, what they do is they literally go through a Rolodex of potential acquirers and they do the process for you. Like, they've already gathered all the information they need to build their sort of sales pitch and they're— they have a whole package for due diligence once the acquirer is interested, and they'll do the sales for you. They'll find the potential buyers, they'll put the deal together, go through the whole motion with you, and that's their job, and they get a cut of what you make.

Awesome, thank you so much for that. I think that was all helpful. That's a good way to end things because we've gone through the full journey of ideation to exit. I know it's a very short period of time, but I wanted to make sure that we cover as much as possible. Tim, this has been awesome. Thank you so much. I hope the audience, like all 100+ people who've joined live, got value out of this. Just before we wrap up, we'll do some open-ended networking with virtual tables. The way I like to end these is what's your one piece of advice for the founders on the call? Again, assume early-stage founders, ideation, maybe MVP stage, but they're going through this motion, setting up a company in 2025. Everything's against them. They got AI disrupting them. Investors are very bullish on them. What, you know, you're going through the process right now of building your company. Like, what's your last bit of advice you wanna share with the audience?

Yeah, so my advice is gonna be based on a question. So I've kind of been running through some of the, the chat, and this is a question that I get a lot and that I thought a lot about is like, if I pitch investors, are they gonna steal my idea, et cetera? Someone wrote it, and like, my piece of advice is talk to as many people as you can. If you're talking to people that are very, very smart, they're probably too busy working on a bunch of other stuff to think about stealing your idea. If you're talking to people who are kind of dumb, they won't be able to execute your idea. So don't worry about being stolen your idea. Talk to as many people, investors, other founders, potential clients. That's how you're gonna validate your idea, how you're gonna get better, or you're gonna improve and iterate on your idea. And that's how you're gonna get exposure to potential investors and clients. So don't be scared to put your ideas out there. It's not gonna get stolen, trust me.

Awesome, thank you so much. This has been awesome, I really enjoyed this. Everyone, yes, you will get the recording in 24, 48 hours, but this has been awesome. We'll send out an email with all of the details, including Tim's LinkedIn if you haven't gotten it yet, but we'll break out for networking. So I'll end the session, you'll see a bunch of virtual tables, most of them will be general networking. Tim will pop on a table or two just to say hi, but if he has the time, and I'll also be on some of the tables. But thanks everyone, enjoy the rest of your day. Hopefully we'll see you at one of these sessions again. Bye.

Thanks guys, appreciate it.