Why I Finally Raised $125K After 5 Years of Bootstrapping

Added: 2026-05-01

[00:00:00]After trying to bootstrap my own startup for the past five years to some varying levels of success, I finally decided to raise some money back in October and we ended up raising $125,000.

[00:00:09]And honestly, I was really embarrassed to talk about this on my channel because for so long I really talked about like [ __ ] venture capital, bootstrapping for the win. I was very binary, black and white about it. But as most things in life, as I kind of went through it all, life is a lot more nuanced and it's not nearly as binary and black and white.

[00:00:25]And that's why in this video I want to break down why exactly we ended up raising money after going 5 years with trying to bootstrap and going over a little bit about my experience about what it's like building without money with bootstrapping and building with money and some of the pros and cons that come along with it. So once again, just for context, I have been building apps for the past five or 6 years at this point. Since like 2021, I built over 14 different apps. And basically from 2021 to 2024, I was building completely solo.

[00:00:50]And then in 2024, I started building with my co-founder Mang Mang Duck on social media. And even then, we were bootstrapped until literally this past October. So October of 2025 or September 2025 around there. And that is when we decided to apply and get into Launch Accelerator. Launch is Jason Calacanis.

[00:01:06]If you pay attention to the tech sphere or tech media, tech news in any way whatsoever, you're probably very familiar with Jason Calakanis. You probably recognize him. And Launch is basically Jason Calakanis' accelerator.

[00:01:17]So, we ended up applying back in the summer because we knew a couple of people that went through Launch themselves. So, we were able to get letters of recommendations, referrals from them, whatever you want to call it.

[00:01:26]We applied and luckily we got in. And just because our friends put in a referral for us didn't mean we were guaranteed entry. We still had to go through the whole standard interviewing process. But I'd also be lying if I said a referral letter doesn't help. So if you're interested in trying to get out into any like startup accelerator or VC, referrals, warm intros are always the best way to go about it. Significantly more effective in any way whatsoever that we've seen. It's way more effective to at least at minimum landing an interview. And usually once you land an interview afterwards, it's kind of up to you. So back at that time in October 2025, we Andrew and I, my co-founder, we were kind of just stuck hitting the same ceiling over and over again. We were a bit of a product studio building a lot of different apps, seeing what worked, seeing what didn't. And we had a couple of apps that did okay. Like we had this app, A Monty. It's like an AI meeting recorder app. There's a bajillion of them out there right now. I think it peaked at around $1,500, $2,000 a month of recurring revenue. We also had this app as well, Perfect Interview, like AI interview prep, AI mock interview.

[00:02:19]Similarly, this peaked at around $2,000, a little bit over $2,000 a month of revenue as well. And at that time, we were just, it just felt like everything we were doing, we kept running into the same wall. And for me personally, I just felt like we were in the same motions over and over again, doing the same playbook, building similar products. And at least for me personally, I was just so tired and so frustrated of hitting this wall that I just wanted to do a complete absolute reset on everything that we everything doing. Literally, my mindset was everything that we were doing at that point, whether it was working to some degree or not, let's just do the complete opposite and shake things up. And that's when I opened up my mind to raising some money. And admittedly, my co-founder Andrew, he was much more down to raise money than I was. He kind of had to convince me. And to this day, it's like still a little bit of push and pull. He's very pro. I'm a little bit more hesitant about it.

[00:03:03]It's like the angel and devil on one shoulder, right? A little bit of yin and yang action. And if I'm being really honest, if I was a solo founder still, I don't know if I would have raised capital. But at the end of the day, I'm not a solo founder and I trust my co-founder Andrew immensely. Like literally, we trust each other so much.

[00:03:17]That's why we've been building together through all the highs and all the lows over the past 2 years or so. And a part of being in a partnership with anybody, whether it be a co-founder or like a relationship as well. Holy [ __ ] didn't think this going to turn into life advice. you had to compromise and meet in the middle somewhere. So, because I trusted Andrew as my co-founder and I know that he wanted to raise a little bit of money and at that time I was just feeling so frustrated of hitting this wall with the bootstrapping world. I was much more open to raising money. And I think a big reason at that time why I was so anti- venture capital, so anti- raising money in general. It doesn't even have to be venture money. It could be like friends and family or angel money. reason why I was so anti that was because I spent a little bit too much time on the internet like bootstrapping indie hacker Twitter where they talk so much about how raising money is bad.

[00:03:59]It's evil and I really really bought into that narrative and saying bootstrapping is the way to go, right?

[00:04:03]And there's a really big narrative and kind of point of view in the indie hacker bootstrapping Twitter world and tech media world at large where they hate on companies or accelerators like Y Combinator saying you're selling a pipe dream to these individual founders that they're never going to achieve. if they did bootstrapping and focused on bootstrapping and said they'd be so much more successful. And I really kind of took in that narrative and took in that mindset. Like for example, just look at this guy right here. He's pretty big in the Twitter space. Like if you look at his whole profile, what he has 200k followers, like literally multiple income streams, join Wine Combinator.

[00:04:33]Multiple income streams. Even right here, he says, "Yeah, ignore Paul Graham. If you're truly ambitious, you should want to have it all. Profession, lifestyle, family, health, hobby. Does not pick one or two out of five. Pick all five." basically a lot of people in the indie hacker space, bootstrapping media space, dunking on these YC VC people. And I think to some degree it is fair. But then what I realized is at the end of the day, yes, YC and all these venture firms sell a pipe dream to any founder. But at the same time, all these big bootstrappers and big figures in the indie hacker bootstrapping startup realm, they are also similarly selling a pipe dream to founders as well. It doesn't matter. It's the same dream, same flavor of a dream. Maybe one is more achievable than the other, but at the end of the day, everyone has something that they were trying to sell when they were trying to push this type of narrative. But then luckily, I just snapped out of it and realized, dude, there's no right way, there's no wrong way to build a business. You just need to do whatever it takes to build a business, whether that constitutes raising capital or not. And I think kind of going through the bootstrapping realm, what I realized is bootstrapping is incredibly difficult. Not in the building portion of it, but most of the time due to the marketing and growth portion of it because marketing and growth is really expensive. Like paying people to make videos for you on social media, paying for paid ads, paying for paid meta ads, Google search ads, SEO, all that stuff to do it really, really well at a high level, it costs money. So kind of transitioning into talking about my experience of working without money versus working with a little bit of money. I think bootstrapping really works when you have some type of marketing arbitrage opportunity where you can get a lot of eyeballs for a really low cost like having an audience which makes it seem like an even bigger skill issue for me because I have a decently sized audience on the internet and I still wasn't able to succeed with bootstrapping but my copium my excuse my reasoning whatever you want to call it for why I wasn't able to succeed that hard despite having a sizable audience on the internet was because a lot of the products that I built weren't always targeted towards my audience which is primarily developers. I never built a dev tool for good reason. I didn't want to sell that hard to my audience. So maybe it's on me for not wanting to take advantage of my audience and sell that hard to my audience. But it is what it is. With the recent growth of our app and also with the fact that we raised a little bit of money, we've actually slowly been building out our team. I actually have an intern working for me as a software engineering intern. And then we also hired somebody to manage our UGC social media marketing program.

[00:06:42]And as a result of growing, I really didn't want to do this, but we had to start introducing more process into our day-to-day operations. just creating better onboarding guides and tutorials for things that previously existed only in my mind and my co-founder's mind and instead making these shared resources that we can then shared to the rest of our team. We tried to create our various onboarding guides with just writing like a document or recording a video. But honestly, we just never really loved the quality of the product that came out and we weren't able to find any good solutions until we stumbled across the app Tango, which is a Chrome extension that you install into your browser. And then Tango automatically just takes like the real process that you just went through and creates a full-blown documentation step by step broken down based off of the real interactions that you just went through on your browser to accomplish said task. It's made new employee onboarding so much easier. And they also happen to be the sponsor of today's video. Instead of hopping on numerous calls throughout the day, we just use a Tango extension, actually accomplish that task once by ourselves.

[00:07:35]And then because Tango is actually able to create a full-blown documentation based off of the real process of us accomplishing the task, it makes it so much easier to make these quick onboarding tasks and tutorial guides.

[00:07:45]And then we can also go in and manually edit the documentation as well before we send it off. And it makes our lives working within our teams so much easier.

[00:07:52]If you want to try out Tango yourself, I'll include a link in the video description for you to try it out. And once again, thank you to Tango for sponsoring today's video. And like looking back in hindsight, I do think when we raised money, it was, you know, a bit of an emotional decision. It wasn't the most rational decision, but once again, in hindsight, hindsight is always 2020. I'm glad that we did do that because right now with what we're trying to build, which is called Yorby, you know, shameless little plug, but we're trying to create an AI social media marketer with a grand vision of basically this is a service that we run with AI that is running as a social media agency, a social media marketer that'll plan, analyze your content, post content, create content for you. We're slowly working towards that, but we have a little bit of progress on the way right now. And right now, we have a couple of features helping guide us to that ultimate end goal. This is probably, in my opinion, the first idea that truly feels venture scale. I feel like a lot of the other ideas kind of like that AI meeting recording tool that I built previously, Monty, or that interview prep tool, Perfect Interview.

[00:08:44]They were fun little tools, but they were truly never venture scale. They truly had no reason to raise money for that reason. But now for the first time with Yorby, it does feel like aha, like we're finally building something that could warrant trying to take a really really big swing and trying to go after it, you know. But now I want to transition away from why I raised money and to more so talking about my experience about what it's been like trying to build a startup without money and fully bootstrap versus now finally building a startup with some capital in the bank after raising a little bit of money. So honestly, in the beginning, nothing really changed. And honestly, nothing really changed until probably the past month or so. from October all the way until I'm filming this right now in April. Probably from October all the way through February, March or so, we really didn't spend any of the money. If you literally look at our bank account balance, it literally started at 125 and by the time it came around to March, it was at 125K as well. And the reason for that was because everything that we were spending with on Yorbi on our business, it was all based off of the money that Yorbi was already generating itself. So, we were running net even by strictly from whatever revenue that Yori was generating. It didn't actually make any real difference in how we operated and ran Yorby in the beginning until a month ago, which I'll get into soon. But despite not having any difference in how we actually ran Yorby, I think psychologically it left us feeling a lot more at ease. We just felt more secure psychologically knowing that we had some money in the bank. One of our good founder friends likes to call this courage capital. It doesn't really actually monetarily change your life that much or how you move and operate, but it just lets you, you know, walk around with your chest puffed out a little bit more. It gives you more confidence to take swings when necessary. And that is kind of what I wanted to get into. Starting in March and April, we felt like we had some semblance of product market fit because from December all the way through March, we were able to grow and scale to almost 7 8 grand a month of revenue. So then we realized let's take a big swing at this point in March and April and start spending a lot of money only on marketing. We started spending I don't know 8 10 grand in March and I think coming up in April for marketing. So only now are we really starting to take advantage of that capital that we raised, which has been really cool to do that because this is always stuff like that we always wanted to do in the past, but we just couldn't do it when we didn't have any money and we were just strictly bootstrapping. But at the same time, having money also has the downside of letting you kind of try to pay your way to win, pay to win when not every single game is necessarily pay to win.

[00:10:55]For example, I'm sure we have so many random subscriptions going on that we're probably not using to its fullest, but because we raised money, we kind of just forget about it or it's not super high priority for us, but we should definitely be more scrutinizing about it. And this kind of reminds me of Brian Chesky quote, the founder of Airbnb saying, "Funding is like food. You need some to survive, but too much of it is poisonous to you." And obviously we're not nearly at that size and scale of it being poisonous with a small 125 grand check in the grand scheme of things. But I do see how people stumble into that trap of, "Oh, we have money. Let's just spend our way out of it." I do think there's something to say when you're very capital restrained and restrictive about your capital. It forces you to be more creative and innovative about how you approach marketing, like more gorilla marketing tactic, getting your best bang for your buck in terms of CPM, CPC, whatever you may have, your customer acquisition cost. I don't think we've fallen too far deep into that spectrum quite yet, but I do see how people that raise even more money can fall into that spectrum and fall into that mind space. Raising money definitely also provides a lot more credibility when you're working with larger teams, small meds, B2B customers, enterprise clients because basically when you are going to YC, yes, you are raising some money from them, but what you're really getting is that YC stamp and it provides a lot more credibility to your business, legitimacy to your business to approach larger corporations and at least have a conversation with them. And we've had a couple of instances of that ourselves by having Launch and Jason Calakanis stamped on our startup as well. And I think one big thing that was living rent free in my mind about raising money that really made me detest and oppose the idea of raising money was losing control of the company that you built. I personally know a lot of people that have a lot of venture capital fundraising horror stories where they raise too much and because of how it all works out, they either get pushed out and kicked out of their company or they sold their company for even like $50 $60 million. But the way that the investor term sheet, what they call the prep stack worked out, they didn't get a single penny of that $50 million sale and they only would have made money if they sold out like a hundred million for example. That's really horrifying. and hearing those stories and also just hearing about it not even from people I know but strangers on the internet really made me horrified and really scared to raise money but one question that I always had in my mind was what is that point of no return and also like basically in what situation can the investors actually push me out of my own company and I actually asked this seemingly simple question to a good friend of mine who recently raised a decent chunk of money and he told me it's all about board seats so if you just give up one board seat and you raise some money as long as you and your co-founder it's like a 2v1 situation As long as you have the board majority, you're never going to be pushed out and it's your company and you can do whatever you want to do because that one board seat from like an external investor won't have a majority vote and they can't push either of you two out. Obviously, it can be bad if your co-founder teams up with the investor to push you out via a board vote or a board seat decision. That's pretty scary. But really, I don't think that stuff really starts coming into play until the series A or the series B realm. So, I think raising small chunks of money like little 125 grand check that my co-founder and I did, it doesn't feel like we're at that point of no return where we're too far gone. We are forced to play the truly venture game. I think right now because we're still so early and raise just a small amount of money, we can still play the game, the business, the startup game on our own terms. But I do think and I'm very aware of the fact that probably once you decide to raise even more, I think up to a seed round, you're probably okay. But I think once you start creeping up on the series A, series B realm, that's when you're at the point of no return and you really have to go for a truly like venture sized exit. But up until then, I think you're still relatively safe, relatively protected as long as you raise on decently good terms, and don't give up too many board seats during the process. But yeah, anyways, it has been quite a journey raising some money. Honestly, I felt like like I mentioned earlier in the video, I felt like embarrassed to talk about this just cuz I felt like so much of my content on the internet on my YouTube channel that you're watching me on right here was about not wanting to raise money. I was self-conscious and like borderline embarrassed to share this, but at the end of the day, like I want to document my journey and I also want to kind of admit that I was wrong in the past when I was super super anti-raising money. It is much more nuance. It's a tool. You can be successful with it. You can totally be successful without it. It's a bigger flex if you're successful without it in my opinion. But for us, for my myself and my co-founder, it just felt like we needed to shake things up and we wanted to do something a little bit different and take a bigger swing. And I think that's what we're doing right now, what we're building with Yorby, which we're trying to create as the AI social media manager or the AI social media marketer, whatever you want to call it.

[00:15:10]That's my story. A quick little update on my end. We would love to hear from you in the comments down below how things are going. Let me know if you have any questions or comments in the comment section down below. I'll try my best to respond to as many of them as I can. But that's all I got for today.

[00:15:22]I'll see you in the next one.