How To Build a Startup in 2026 | 10 Lessons That Save You Years

If you're looking to build a startup today, there are certain rules that have completely changed because of AI. But at the same time, there are certain rules that because it's just business, they just haven't changed. In every inflection point of growth that I've had in my companies, I've learned key lessons that my mentors taught me to acknowledge and identify early on, or I just made mistakes and then had to learn it the hard way. Either way, there's certain mistakes that founders are still making today even in the age of AI. Even with the new rules of building companies. So in this episode, I'm going to walk you through 10 of the most important lessons that I've learned in building companies. I'm going to break this down across the zero to one stage, the one to a 100k ARR stage, and then the 100k to a million I'm going to give you a bonus one of how to get from a million to 10 million, and the key lesson that I learned there. When you learn these lessons, you may still make these mistakes, but knowing them, knowing these lessons will actually help you identify that you're making one of these mistakes and course correct that much faster. And when you learn these 10 lessons, it is my sincere hope that you're able to build a successful startup today in 2026. INTRO. WHAT'S UP, EVERYBODY? WELCOME TO MY CHANNEL. I'M TK, the managing director of TK Capital. TK Capital is a holding company of a portfolio of software and advisory companies. And on this channel, I share everything that I'm learning as I'm operating these companies and working with other founders that are following the same principles that I teach in this channel. So if you're new, be sure to hit the subscribe button and that bell icon, where you'll get notified every single time I drop an episode with the TK energy. Also, if you're part of this community, welcome back, my people. It's really awesome to see you over here. I'm going to share these 10 lessons with you. I'm going to break it down into the revenue stages, but you might be wondering who is this TK guy and why is he credible in sharing his lessons and why should I care? So quick background on me. I started my career in SaaS. I started a company called ToutApp. ToutApp was backed by Andreessen Horowitz, Jackson Square Ventures, Founder Collective, and a number of other prominent VCs in Silicon Valley. I lived in San Francisco. We pioneered the sales engagement category. We built out that platform, we scaled it, and we sold it to a market leader called Marketo. I then joined as a SVP of strategy at Marketo. Marketo was then owned by Vista, a private equity firm. We did a 2-year transformation, and then we sold it to Adobe for $4. 75 billion. After that, I started another company, Unstoppable. It's one of my portfolio companies. It is an advisory and coaching business where we work with founders on their go-to-market strategy. It's an incredible company, and I've been running it for the last 6 years. And then I started TK Capital. TK Capital is my holding company, and it's a portfolio of this advisory business and also a series of software companies that we're building and growing based on the principles that I teach and have been teaching on this channel. So everything I share with you comes from actually being in the trenches and in growing these companies. And I'm just going to be sharing the 10 most important lessons that I've learned. So if you're excited to dig in, go and smash that like button for the YouTube algorithm. Let's go through the first stage. And by the way, as I said in the beginning of the video, I split this up into each of the stages along with the bonus one. So each of them have about three lessons learned for each of the stages, and I'll just work through those. Let's talk about the zero to one stage. This is where you've got an idea, and you're just literally just trying to get to one. One being one customer, a dollar of revenue, the zero to one. Now, on average, this stage, believe it or not, even in the AI era, can take up to 3 years for something meaningful. And that's okay. But there's three lessons that I've learned in every company that I've started, and I learned it the hard way in the first few, and then I really started to apply it for the subsequent companies that I started, and it's helped me actually move a lot faster. The first lesson learned is focusing on who instead of what. Baby TK would always focus on the idea. What is the idea? What is unique about it? The mature TK, HoldCo TK, really thinks about who. Who is this for? And this is one of the things that founders that I meet, I always try to sell them pretty early. It's like, "Hey, I get it that you've got a really cool idea, and right now you can apply it in a lot of different ways, but who's this for? And who has an urgent important problem? " The sooner you start asking who is this for, do they have budget, is it urgent problem, is it an important problem, the faster you can actually understand if this is a real problem that you're solving, and you're going to get to the one stage. The second lesson that I learned is being in stealth. There are very, very few cases where being in stealth helps. Maybe like 0. 01% of companies need to be in stealth. The rest of the companies, you don't need to be in stealth. It's actually a waste of time, and in reality, if you really think about it, you're just lying to yourself. You're afraid of putting yourself out there, and that's why you're making You're saying you're in stealth. And that applies for 99. 99, whatever, percent of people or founders that are going through it. Usually, the core reason that someone wants to be in stealth is they're afraid that someone is going to steal their idea. But if you play it forward, it's like, "Okay, well, you stay in stealth, and then you announce it, and then you tell everyone cuz you want customers, and then someone bite codes it. Great. Like, what was the use of that? " That's actually not the

scenario. The scenario that really happens is you stay in stealth, finally you gather up enough courage to tell people, and then you realize no one wants your product. And you've now wasted 8 months of your time, or maybe longer, because you actually stayed in stealth. The third lesson is the one more feature trap. This is probably more true today because of bite coding, but this has been true in SaaS and in software forever. The one more feature trap is where you're like, "Hey, I just need to add this one more feature to my product, and then everyone's going to buy. They're going to look at it and they'll be like, 'Oh my god, I'm going to buy. '" And this usually roots from a few different places. One, people you're trying to sell to say, "Hey, if you had this unique feature, then we would totally buy. " And then you build it, and it takes months, and you go back, and or takes days because of bite coding, and you go back, and they're still not going to buy. They're lying to you. Another reason it comes is, kind of tied to this whole stealth thing, you're just afraid. And so instead of doing the hard work of getting it out there and trying to sell it, you say like, "Oh, now I suddenly need to code," which is your comfort zone. I'm an engineer, I get it. So you stay in your comfort zone and keep building more features. The reason this is bad is because the complexity of your product goes up. You have more features. So the next time you're on a demo, you're now showing them 18 features, and believe it or not, the more features you show, the less likely you are actually to win a deal because people get overwhelmed, and they're like, "I really don't want to learn all this," and then they move on. So that's the third lesson where don't stay in the one more feature trap, get your product out there, figure out what the core loop is. So that's the zero to one stage. Let's go to the next stage and the next three lessons that I've learned for getting from the one stage to 100k in ARR. 100k of ARR is pretty magical because if you're doing 100k, that's like 10k MRR. And depending on how you're structured, I don't know if you raise money or you're bootstrap. If you're bootstrap, 10k is amazing. If you raise money, 10k might feel like, "Okay, well, we got a long way to go," but it's still a milestone. But a lot of people make a little bit of money and then don't ever get to the 100k ARR because it turned out to be a thing where people like tried your product, but not enough people stuck. And therefore the churn kind of killed it, and you never really reached 100k ARR. So this path of going from one, where you got some customers, maybe you convinced your mom and your uncle to buy it, and you're like, "Cool. " By the way, that doesn't count as one. You know, ideally it's people that like, yeah, are in your ICP, and you now can go after more of that ICP. But the 100k ARR, there's some lessons that I learned as I've gone through this multiple times in my companies. And when we start new companies as part of our HoldCo, we also think about very deeply. The first one is capped to warm. I've made this mistake multiple times, and remember, some of these mistakes, you're still going to make. What's important, and the reason to watch this video, is to recognize when you're making them. It's not to prevent you because sometimes you just got to go through the suck to really learn it. And even though you know you shouldn't be doing something, you might still do it, but the key is to course correct faster. The reason I've been successful in my startup journey is because I had people around me, mentors, coaches, investors, that helped me course correct faster. And so that's what I'm trying to do for you. Okay, so capped to warm is where you're just trying to sell to your warm network, and you're staying there. There's a couple of things that go wrong here. One, if you're just selling to your warm network, people that already know you, they may not be buying because your product can survive in the market. They may be buying because they just like believe it or not. And so when you try to sell to a stranger, they're like, "No, I don't want this. " And you're like, "But my friends bought it. " And you're like, "Yeah, I don't care. " So the quicker you go and try and sell it to people that don't know you, the more successful you're going to be. And the quicker you go out into the cold, the faster you can grow versus just staying in your warm network. So I know it's a comfort zone for you to stay in your warm network, but you got to get out of it in order to get to the 100k ARR. The second lesson learned on this one, on this stage, is hiring one sales person. I see this very often, founders and CEOs make a little bit of money, and they're like, "Okay, cool, there's something here. We need to sell more. Cool, let's hire one sales person. " And then there's like a subtext and I see people saying, "Oh, they have a Rolodex. " And so there's a few things wrong here that I learned. The first thing is never hire one sales person. If you're only hiring one sales person, and they don't do well, which they likely won't because you're so early, you shouldn't be hiring someone. You should be doing more of these sales, but if you just hire one, you don't know if they are the problem, or your sales process is the problem, or the market is the problem, because you just don't even have enough revenue to have conviction. Hiring one is always bad, you need to hire two. But also, at the same time, if you hire two, your burn goes up at this stage, and now these sales people are basically starving cuz you don't have enough pipeline, and you're telling them like, "Oh, you got to do outbound and kill your own. " And they're just like, you're going to get the worst sales people. Because any good sales person is also kind of like an entrepreneur, they'll never join you at this stage. Very, very unlikely. So you're actually going to get the shitty sales people that no one else is hiring, and therefore you're going to lose anyway. So don't just hire one sales person, and just net try to avoid hiring a sales person until you get to at least 100k ARR. Because if you can't get to 100k ARR doing founder-led sales, you just don't have enough proof points to really know if this thing's going to work, and you won't really get the good sales people anyway. And definitely don't hire one as you get past 100k ARR, hire two. That way, you know, if one's not going to work out, and that's fine, but one will. And then hire two more. The third one is hiring an agency. This is super, super attractive, right? Like it's like, "Oh, I'll hire an agency and they'll

figure out my sales and marketing for me. " Guess what happens when you hire an agency? First of all, they're on a 3-month retainer, 25k a month, then they want ad spend and they're like, "Look, we need at least 5 to 10k of ad spend so we can go test different forms of messaging. " And what they're really doing is spending a bunch of money to try and guess at what product market fit is. And you could do that, but they're likely going to fail because you just can't spend enough money to get to product market fit fast enough that way. What you're better off doing is owning the marketing yourself and doing founder-led marketing and just getting more inbound leads coming in and that way, as you get inbound leads coming in talking about the problem that you're solving, you're having these conversations and you're converting to revenue, you get to 100k of ARR and then you can hire an agency because by that time you can say, "This is who I'm targeting, this is our message, this is our sales process, I want more attention. " And then an agency can actually do their job really well. But if you're hiring an agency to figure out product market fit and your messaging and your positioning and your ICP for you, it's a losing game. You're going to lose the battle. And two of these kind of go hand in hand. Basically, the hiring a salesperson and hiring an agency, underlying lesson is you cannot outsource go-to-market. If you try to outsource go-to-market at this one to 100k ARR stage, you're going to fail. You just uh literally are going to fail. I [snorts] would love for you to prove me wrong. So, if you just got your first set of customers and you want to go spend 80k on a salesperson at one salesperson and then 25 * 3 is 75k on a marketing agency and you want to prove to me that you can get to 100k ARR, please do that and let me know. But, I take no liability on this, by the way. Like I recommend against it because it never works. Ever. So, that's lesson number 1, 2, and 3 and 4, 5, and 6. Before I go to 7, 8, and 9 and 10, let me pause here. Are you starting to see the power in this? Each of these stages, the zero to one, a one to 100k ARR, and then 100k to a million ARR, and then a million to 10 million, they bring different types of problems and therefore there are different lessons to learn. You may still make these mistakes and that's okay because you're in it. But, the key here is to recognize when you are making the mistake and course correct. You're starting see the power in this. Can I just get a yes in the comments below? And also smash that like button for the YouTube algorithm. It just loves you when you do that. Also, this episode is brought to you and sponsored by Instant. Instant is a demand acquisition platform. It serves founders and CEOs and CMOs across different revenue stages. And its entire goal is to get you inbound leads and inbound leads that fill your pipeline. So, if you're in that stage where you're really trying to figure out, "How do I generate demand? How do I actually get inbound leads and warm conversations and net new people in my ICP to buy my product? " You should absolutely check out Instant. You can go to useinstant. com or you can follow the link in the description below. And be sure to thank those people. They're sponsoring this episode. Now, let's go to lessons 7, 8, and 9. This is the 100k to a million ARR stage. And the million ARR stage is really cool. I remember for ToutApp, we got to a million ARR and with six people and we were cash flow break even, which was like pretty crazy uh even in those days. And even today, like I think there are rumors of more companies like that, but I don't meet that many of them. But, there are rumors of like even the one-person 10 million ARR company. We'll see. But, the 1 million ARR is like a very, very exciting stage because you got you think about it, you have 83k coming in every single month. Now, to get to that 1 million ARR from the 100k, there are some key lessons that I've learned. The first one is don't just rely on outbound. Now, my last company, ToutApp, we pioneered the sales engagement category, which means that we pioneered outbound. But, back then, outbound was kind of like a channel that no one else was doing or you had to do it manually and we automated it, so therefore we got a lot of yield. Back then, the response rates were insane with outbound. But today, outbound is just like a 1% response rate. And then you add on AI spam filters and you have AI SDRs sending even more emails, so now everyone's just kind of desensitized to it. Today, relying on outbound doesn't work doesn't just work. And I see this across the portfolio companies that we operate where if you just do outbound, it's just like a loser's game. Yeah, you have to do so much volume, it just doesn't work. What works a lot better is marketing if done right. If you are doing inbound, if they are coming to you and then you're then nurturing them and prospecting into that account, that works really, really well. So, don't just do outbound, make sure you actually do real marketing and you drive for inbound leads and then go into them and convert them to revenue. That's the best way to do it. Don't just rely on outbound. The second lesson I've learned is being cheap with ads. I feel like along the way I still happens today, people are like, "Oh, we don't do any marketing or we don't run any ads. It's organic only. " And what they sometimes don't tell you is like, "Oh, yeah, but we also did a press release about how we raised $100 million and that got us a whole bunch of impressions. " Everyone's doing marketing. And they're also kind of lying about like how much marketing

they're doing. So, don't believe them. Don't be cheap about ads. Ads are actually one of the most effective ways to grow when done right. There are certain variables to look at. If you work with the right agency, then they'll do it in the right way where they'll look at impressions, they'll look at leads, they'll look at pipeline, they'll look at revenue, and they'll look at how much it costs to acquire a customer and how you can accelerate that. And there's lots of companies and founders that I've met through Unstoppable where they are doing ads properly. So, don't be cheap about it. Advertising is necessary. You can't just rely on spamming people and organic. You need ads, especially to go from the 100k to a million ARR. So, start baking that in. The third one, and I've seen founders do this, is only relying on Google Ads. The best way I can describe this is if you are only doing Google Ads, you actually don't have a business, you just have a very limited time arbitrage on Google search. That's it. Because all you're really saying is like these people are buying right now and Google right now charges me $10 a click or $20 a click and I can convert them for $299 a month. Well, I'm just going to bid on that. But, pretty soon your competitors are going to catch on and the bids are going to go up and you no longer have a business. Don't just rely on Google Ads because you'll have a short shelf life and the algorithms will catch up and your competitors those bids will go up. Build a real business. I have a proper go-to-market strategy in terms of proper marketing where inbound's coming in, doing outbound, doing events. You should have a robust strategy as you're driving towards a million in ARR. Don't just rely on Google Ads. And I've seen this more than once, which is why I included this as a lesson learned. I hated Google Ads, so we never did it. We did a ton of social marketing and even today we do mostly social. We do inbound organic. We do social. We do very little Google Ads and outbound for growing our companies. But, you know, for every company's different, every ICP is different, so you'll just have to figure out which mix works best for you as you're going from the 100k to a million ARR. Now, I did promise you a bonus one. You get to a million ARR and you're driving to 10 million. The biggest lesson I learned as I got to a million and drove to 10 million. And you know, I've been part of companies that are upwards of 450 million ARR. The biggest thing that I learned is like it's funny cuz some of the rules and lessons invert as you go into later stages. So, if you think about the zero to one, you were thinking about who versus what, meaning who do I want to serve instead of what's my idea? The same similar lesson applies on the 1 million to 10 million in a different way. And that's what versus who. I phrase it a little bit differently just so I can explain it. In each of these inflection points, if you really take a step back, a lot of the things that I'm telling you is, "Hey, you still need to own founder-led go-to-market. think about who am I serving? getting outside of your network and getting the messaging and positioning right. " No one else can do it aside from the founder at these earlier stages. Once you get to a million and you're driving to 10 million and if you want to do it in a rapid clip, you have to start asking who. not what do I need to do, but who do I need? Who do I need around me? And this was something that at that point where Baby TK was at a million ARR with six people and we were raising our Series A, the biggest piece of advice I got in the first board meeting we put together, our board member was like, "Hey, we need to get some people surrounding you. Like it just can't be you guys. It can't be the six of you. And we need to start asking who do we need? " The credit goes to him. This is Greg from Jackson Square Ventures. Incredible investor. He was really great because he really surrounded me with the right people at that time. He got me introductions to major CEOs of either post-IPO or pre-IPO companies, major companies. Like they were just showing up to my office and I was so young at that time I didn't even know how to appreciate that. But then also, we spun up recruiting for getting in the right VPs. We hired a VP of customer success, VP of sales. It was interesting because my first inclination was like, "Well, I'm at a million, I want to get to 10 million. Like let's figure out the VP of sales. " But, I met Jason Lemkin from SaaStr and he was like, "Hey, listen, I know your business. What you shouldn't do is hire a VP of sales, you should customer success first. " And he was right. I hired a VP of customer success to protect the revenue we had and then hired a VP of sales. And I surrounded myself with the right advisors, mentors, coaches, and that really made a difference in my trajectory. So, at the 1 million to 10 million, you should really start asking who. Again, just like in the zero to one phase. Except phase, it's who am I serving? What's my ideal customer profile? And what do I need to do? But, in this phase, it's not what do I need to do, but it's who do I need around me. As you're going from the million to 10 million. And that's why this is so powerful. All right, so let's recap. On the zero to one phase, the three big lessons are ask who do I serve instead of what's my idea? Don't stay in stealth. Don't fall into one more feature trap. On one to 100k ARR, you want to make sure you get to selling to strangers as fast as possible. Don't be capped to warm network. Uh don't just hire one salesperson and don't hire an agency to figure out your product market fit, they will fail. They'll still get your money, they'll be fine. You're going to fail. 100k to a millionaire ARR, don't just do outbound, especially today outbound has a 1% response rate

do full marketing, do inbound marketing. Don't be cheap with ads, once you have your organic marketing working, scale with ads, and also don't just rely on Google Ads because that's not a real business, that's just an arbitrage opportunity that will disappear. And then, bonus, once you get to a million you're driving to 10 million, stop talking about what do I need to do, I start asking who do I need around me, because it's impossible for you to do everything even with AI. And it's impossible to just have AI do everything because if that was the case, Anthropic wouldn't be hiring a head of go-to-market for 400k, or hiring more engineers at 750k. It just wouldn't be realistic there. If you got value from this video, please smash that like button for the YouTube algorithm. Also, this episode is sponsored by Instant. Instant is a demand acquisition platform. Instant helps you get inbound leads that fill your pipeline. You can be up and running within minutes. You just plug in your website and it figures out everything for you from your offer to your messaging to your lead magnet all the way to the nurture emails to turn leads into real opportunities. So, go to useinstant. com to check that out. Also, link in the description below. Also, I drop an episode every single Sunday with actionable strategies and tactics from the trenches from operating my holding company and all the portfolio companies that we have and are continuing to build out. So, if you haven't already, be sure to subscribe button and that bell icon where you'll get notified every single time I drop an episode. And lastly, remember everyone needs a strategy for their life and their business. When you are with us, yours is going to be unstoppable. I'm TK and I'll see you in the next episode. Also, if you're in the stage where you're figuring out more of your marketing, whatever stage you're in and you just need more marketing, check out this video. In this video, I walk you through what's working in 2026 today in terms of B2B marketing. Take care, everybody.