Brendan Mahony - Why founders should look at building startups as a game and not a business!

I think you should really block out the noise. And if you have identified something that's interesting, and not only that, something that people will use or pay you to use, just pull the thread. Just pull the thread and keep pulling the thread and be patient. This is like such a patience game.

Welcome to the Undefeated Underdogs Podcast, where I unpack and narrate stories of ambitious people who turn obstacles into opportunities. My goal for this podcast is to create a platform to narrate underdog stories and maybe play a small, teeny tiny role in inspiring you. I intend to highlight the underdog mentality and make authentic conversations with people who play the long game, take action with a chip on their shoulder, and convert obstacles into opportunities. Buckle up as I'll be bringing some authentic founders, VCs, community builders, and content creators who got underestimated their whole lives, and yet they beat all the odds to become insanely successful. Now today I want to tell you a little bit about our awesome sponsor acquire.com. Selling a business is as tough as building a business. As someone who went through this process once, selling my own startup, I know the pain it takes to get to the end zone. This is where our sponsor shines. Imagine this, You're a founder who's built a solid SaaS product, acquired customers, and generating consistent monthly revenue. The problem is you're not growing for, for whatever reason— lack of focus, lack of skill, or just plain lack of interest— and you feel stuck. What should you do? The story I'd like to hear is you buckle down, somehow reignited the fire, get past yourself and the clichés, and start working on your business rather than just in the business. You start building an audience, move out of your comfort zone to do sales and marketing, and in 6 months you triple your revenue. The reality isn't as simple. Situations may be different for every founder facing this crossroads, but too many times the story ends up being one of inaction and stagnation until the become business, business becomes less valuable or worse, worthless. If you find yourself here or your story is likely headed down a similar road, I offer you a third option. Consider selling your business on acquire.com. Capitalizing on the value of your time is a smart move. Acquire.com is free to list and they've helped hundreds of founders already. Go to try.acquire.com/sharath and see for yourself if this is the right option for you. Now let's get into today's episode. Let's be honest, 90% startups fail. They either get shut down or get acquired. My next guest is Brandon Mahoney, the founder of Sunset, which handles all things from legal, tax, operational burdens when shutting down a company. It actually sucks when you go through the process, you know, because you started something It feels like your baby. And then at some point you have to wind things down and they make sure, Sunset, these folks, they make sure founders and investors avoid penalties, liabilities, you know, immediately they show path to like move on and literally like, you know, what the company's name is, they just sunset things and they've helped hundreds of VCs back startups. And VCs get their, you know, money back. And I think over $100 million in funds were redistributed in the last couple of years, if I'm not wrong. Brandon is also like a YC alum. He's a 3x founder, and I'm excited to chat about, you know, this is like so different from other, my other conversations because generally we have founders talk about doing awesome things, and this is about— doing the other part, which is not talked about, talked a lot about. So Brandon, how are you feeling? How's it going? Thanks for joining the show.

Thanks so much, man. No, it's great to be here. And yeah, feeling great. Feeling great. You know, it's beautiful in New York and yeah, nothing to complain here.

No complaints. Everybody's grateful. I think that's exactly what I'm wearing.

Yeah, I love it. Exactly.

So yeah, let's start like, you know, going in through Sunset. You know, I read the letter on the website. It was a very painful experience, if I'm not wrong. That's why you started it. So yeah, talk to me about like, out of all things that you have done as a co-founder at that time, you sold companies, you went to YC. And you were into product marketing. Yeah. Why going after such a— because I, my, one of my SaaS products got acquired and they did like a lot of due diligence. I hated it. So there is like a painful logistical operational things that, you know, generally we avoid. Right. So yeah, you were on a different role. So why Sunset? Why this problem? What excited you? To like, okay, this is where I want to spend my rest. I don't know, like 10 years or so.

Yeah. Yeah. Why'd I start a funeral home? Yeah. So that's a good question. Yeah. My mom's so proud. So yeah. So I guess, I guess a little background. I know you already, I appreciate, appreciate the intro, but yeah, went through YC, started kind of first company was like a good cash flowing business. Didn't really feel like it was going to be venture scale. We can talk more about that. I think that actually could have gotten a lot bigger, but was drinking a lot of the startup Kool-Aid at the time. So anyways, decided to sell that. We sold it to kind of a PE shop. Immediately started a second company, which no one should do. It's so dumb. Like, take a minute. I honestly don't know if we like, if I took a day between the two. But yeah, the second one just made so many Dumb mistakes. Oh my God! But the biggest, the biggest stupidest mistake we made was definitely—I mean, such a classic mistake—was we just built, like built in isolation for an entire. Yeah, by the end of it, we like came up for air. We had this whole like crazy product and tried to sell it, and everyone's like, "Yeah, what? What is this? Like this kind of sucks, and I don't care, and I'm not going to pay for it." And at that point, I was like, "Okay, I've been like doing the founder thing at that. You know, probably like." 5 years. And I was like, I'm so tired, I'm done. You've obviously started several entities. If you start a company, it's really easy. Like, go on Stripe Atlas right now, go on Clerky. It'll take you 10 minutes to start a Delaware C corp, cost you $500, and you're like good to go. And now they're doing all these things. You can like get an EIN quickly, you can get a Mercury account. Like, it's slick, it's awesome. Yeah. So if you're used to that workflow, You know, you're probably thinking, wow, okay, if I have to shut this down, it's going to be similar. It's not. It's really bad. So it took me— and also as a note, like, if you're the CEO especially, or just the general founding team, like, this works on you. No one's helping you because your company is done. So yeah, it took about like 7, 8 months. I felt horrible about myself. I was like, I don't know what I'm going to do with my life. I don't know if I'm a founder or if I'm any good one. I don't know if I'm ever going to start another company. And yeah, it felt like a huge failure. I felt really alone. And then I had to spend like months doing this absolutely awful, like awful work. Yeah. I mean, you're literally dealing with state agencies and like workers' comp and insurance and all your vendors. And everyone hates you. Like, lawyer, my lawyers did not want to talk to me at all. My accounts did not want to talk to me. No one wants to talk to you at all. Your investors are like, totally written you off. So anyways, thought nothing of it. Like, literally blacked it out, contracted for different startups, worked for a different startup. And yeah, during that time, I mean, I definitely had the bug, you know. So I was playing around with different ideas, but nothing was that exciting. And You know, I, during that time, I started getting texts from like YC buddies, like other people I knew just being like, hey man, company's not doing that well. I have no idea what to do. I know you wound down a company in the past, like, can you help me out? And so after like the third or fourth text, I was like, this is insane. Like, why is it so easy to start something and so, so difficult to shut it down, especially just like The business we're in, like you said at the beginning, literally the whole VC model is 9 out of 10 aren't going

to

work. That is how— and more broadly speaking, in the US, if you look at the statistics in a 10-year time span, like 80%, 90% of companies go out of business. And so that just felt really crazy to me. And so, yeah, just felt weirdly compelled to honestly help, just really help people, really help people in a very, very difficult time in their lives. And so that's kind of the origin story. That was really long-winded. No, no,

no, no, it's all good. I feel I've kind of— thanks for that answer because I picked a couple of things I want to like go and dive a little deeper into. Let's talk about Sunset. You know, let's talk about Toybox. Started like 2018, sold it to— sold it 2020 and raised a bunch of money. So talk to me about building as a first-time founder and going after VC, the whole experience. Do you have any tips and like You know, any insights that you can provide as a first-time founder for listeners who are first-time founders that, you know, people that should avoid or like you should really focus on certain things?

Yeah, definitely. Firstly, definitely apply to YC. Like, you know, even, even just the process of filling out that, they'll, they'll tell you this too, but it's totally true. Just filling out the pro— filling out the application, whether or not you hit send, it's actually a really useful exercise. They just get down to brass tacks, right? Of like, What do you do in a sentence? That's actually— this is a tangent, but that's actually probably one of the best things I learned from YC. In YC, I don't know if they still do this, but you're in a batch, and in that batch there are little subgroups. And so every week you meet with your group and your partners, and you go around a circle, and you have to give a one-line sentence what your company does. And you do that every single week, and every single week are Ours was like, for Toybox, even today, like, it's really hard to say it in one sentence, which is not great. And it was humiliating. It was absolutely humiliating and absolutely had like PTSD from those, from just like being in this small room and just them being like, what the hell does that mean? Like, what do you do? What do you actually do? And so with this business, I actually think it's one of the best exercises, especially for early stage founders. Tell me what you do in one sentence. If I do not understand it, no one's going to understand it. You can't sell something that you need to be able to say it in one sentence. So with Sunset, like, yeah, we help companies shut down. Great. I could tell that to your grandma and she would know exactly what it is we do, right? I can be a little more specific. I could say we help venture-backed tech startups shut down, right? So now whoever I'm saying that to, they can disqualify or qualify themselves as well. But anyway, so that's kind of a side tangent. But yeah, the kind of first-time founder, I'd say the biggest areas, maybe the biggest learnings that I have going into Sunset, maybe that's a different way to frame it. So one of them is obviously like, can you actually say what you do in one sentence? The classic thing that everyone tells you is like, are you solving a real problem? Which is totally true. I mean, that's just like boring advice. Most advice you hear, I've listened to all the podcasts, guys. We've all listened to all the podcasts. I've read all the books. You're going to hear the same advice over and over again, and you're going to be like, cool. And then you're going to ignore it, and then you're going to do the wrong thing. And then—

Even after listening?

Yeah, totally. Yeah. You can listen to it like 100 times because you're like, cool, that's the same boring piece of advice that I've heard a million times. And then you're going to screw it up, and then you're going to be like, now I get it. And I've done that about a billion times. So You know, it is what it is. I think it's important to do that. But all my advice is like all the boring— like, for— you talked about fundraising. Let's get into fundraising. I've had a lot of founders come up to me and ask, what are your strategies? How do you fundraise, especially in this climate? So for Sunset, we raised back in December. People are like, how'd you actually do that? It's such a difficult climate. Honestly, the answer is really, really simple. It's just build something that makes money or that anyone is using. I have no strategies. I'm not a good fundraiser. But if you have something that people pay you money for, investors will want to put money into your company, most likely. If there's like, if you know, if you do an okay job storytelling, sure, there's a bunch of minutia, but at the end of the day, Like, that's it. And so if that's it, just like forget the fundraising thing and just actually try and make money. Just try and sell whatever it is that you want to sell. But I feel like I'm like going all over the place. So maybe you can hold me in a little bit.

You go, you be you. That's the whole podcast. Like this is a conversation.

But yeah, that's, so that's kind of my biggest thing. And then in terms of actually like, how do you go and sell something? So One, I think that is the only skill that matters in this game. If you're trying to be a CEO, obviously a CTO, different thing, but selling is the only thing that matters. It's the only thing I would practice. It's the only thing I would care about. You don't really understand. I feel like you don't really understand that. I didn't even fully understand it until Sunset as well, because Sunset has been far more successful than my previous companies and has been growing a lot more. then my only job, the only thing I do is selling. I sell employees on why they should join me. I sell investors on why they should give us money. And I sell customers as why they should also give us money and use our service. The only thing I do is sell. That is it. And that's how we started this company. So the other thing, so main learnings from Toybox, Contrast days, Contrast, the company that we shut down.

Mm-hmm.

So, you know, I love YC, but like, there's a lot of Kool-Aid. And there's a lot of advice, and I won't single out YC, but there's a lot of startup advice. So a few pieces of advice that I don't necessarily agree with. One is, I feel like a lot of times, people try and massage and craft and perfect this idea before they start anything. And what I mean by that is like, it's recurring revenue. The TAM is monstrosity. It's, it's like XYZ, it's using ABC, blah, blah, blah, blah, blah, right? And you have to have that like perfect message. And then if it doesn't check one of the boxes, right? It's sort of like, it's sort of like dating, right? Like you all have that friend who's so fucking picky and is like, oh, I need them to be this, this, this, this, this, this, this. And they have all these little checkboxes and know what? They're single.

Yeah.

It's the same thing as a founder, right? If you're going to go out there and be like, oh, it needs to be like a quadrillion, trillion, million, billion dollar market already and like XYZ, I'm not going to do it. And so I really believe that. I really, really did. And I think the industry, I think the ecosystem makes founders, especially first-time founders, believe that. This company, right? This is the weirdest goddamn company. We are so weird. We are like, think about it. All the companies we work with, they're going to business, right? Yeah. So first question I get is, okay, so recurring revenue? No, we're transactional. The other question I get is, do any of them have money? The other question I get is like, how big is this market really? Like, can you actually Scale this thing? Is this just a services business? Is there actually tech? Like these are all the questions that investors and they're great questions, right? Don't get me wrong. They're great questions that we've been starting to answer. But old me, a younger me, would have never started this company because at the front I would have asked myself those questions. I wouldn't have had the answers or I would have assumed the answers without actually going out. and trying anything and trying to get money from people. And I would have never started it. But our business, I think, is a really good example. I don't know how big this thing's going to get. And maybe all those people are right. Yeah. But like, we've got a, like, we have a real company on our hands. And I think you should really block out the noise. And if you have identified something that's interesting and Not only that, something that people will use or pay you to use. Just pull the thread. Just pull the thread and keep pulling the thread and be patient. This is like such a patience game. I feel like everyone wants to like get a quick buck and I'm on such like a little soapbox diatribe. This is like, I'm, this is awful. So

I love that answer for, for, for various wonderful reasons. You're so authentic. It feels like It's not fluff because some founders I just talked to, fluff is a bad word. They're very kind of way far ahead, like, you know, in their journey that they're in this moment, but they're like, their mind is somewhere else, right? Yours is, it feels like you're pretty chill. That's the right word. Like pretty chill. You know what you're doing. And I have like a bunch of kind of like follow-ups from that. One of the questions I have is how do you even get investors on board? Because this is again, yeah, for this, for Sunset, it's such a, like I said, in your words, perfectly described. So weird.

I'll tell you. And it's, that's my answer to before. The only way I got, I bootstrapped this company. We were generating hundreds of thousands of dollars in revenue. And then I went and raised money. It's that easy, right? And fundraising is really hard. Fundraising, even at that stage, like it was pretty quick. We have amazing people on the cap table, incredible operators, founders, super well-known folks. And I'm very happy, but even still, like, I think we had a great hit rate, but I think I still probably talked to about 80 or 90 investors. And I think we've got about 30, 35 of them on the cap table. So almost 50%, which is great rate. But again, like, it's a brutal game. And that's literally That's me going out with real paying customers. Like I said, hundreds of thousands in revenue generated. And even still, that's, that's kind of hit rate. So that's another thing. Like everyone says it, but like this game is, you're, you're just going to punish yourself. It's just a game of being punished every day. Like it is, it is, it is just people telling you you're an idiot.

Rejection. You're like, you're the wrong, wrong guy for the wrong reasons and you know whatnot. You're giving permission for other people, including yourself, to double down on the doubt, right? So they're like weird ways startups work. So let's, I think we should talk about Sunset. I think the biggest thing is how do you even find customers? It is so weird. I know the fact for the fact that We all know 90% startups die, but nobody talks about them. Everybody wants, how much is your MRR? How is your ARR going? You've reached 4 million customers, 10 million customers. You hired this incredible, you know, executive level, or you got like sunny side, like you go to this, you know, offsite and whatever it is, it's all like on the bright side.

Yeah.

But what you're dealing with is the sad part. Like, how do you even go find not sad founders, but founders who are feeling terrible about themselves and ask them money? It's like, it's like the—

You're making me sound like a grave robber. No, no, no,

no. I'm not, I'm not sounding like that.

No, no, no. I'm just, I'm just joking. It's, it is the reality, right?

Like, it's, it's a reality in I think traditional typical marketing doesn't work in my opinion, right? You can't put content out saying that, hey, your startup is about to fail all the time.

That's— Yeah, people don't love that.

People won't love that. So what does your marketing strategy look like? How are you finding customers? How did you generate like that thousands of hundreds of dollars? What is your approach?

It's a really good question. So I'll actually elongate this answer as well. I'm sorry in advance. Yeah, go, go, go ahead. It goes back to your original question, which was, what are some of the other learnings for first-time founders? So like I mentioned, second company that I built didn't work out, just built in isolation. No one cared. This company, I was like, I'm never doing that again. So I wrote up a blog post. It was like my personal story about shutting down, had like a little catchy title. And I posted, YC has like its own forum. And I posted in there and it got a ton of comments and traction. And I said at the end, like, hey, if you ever want to chat, like I actually have like a little team here of like lawyers, things like that. I didn't have anything. I had no idea how to shut down companies. I had no lawyers, no tax, no team, no nothing. But I was just like a little bit at the end and like, here's my Calendly link. So I think we got about 25, 30 calls, and I think I closed like a few grand in sales, like just off the bat, just asked for money. And that's how I started Sunset. And that's how I understood, like, is this even worth pursuing? Is there a willingness to pay? Things like that. But that kind of goes into your second question, right? Which is around distribution. So it's the classic meme. And it's the most true meme, which is just like first-time founders focus on product, second-time founders focus on distribution. The only thing I cared about with this company was distribution. Like our product, like just now is our product getting really good, but it's been like, uh, and really good in terms of like the technical aspects of it, right? Like the actual technology and the app and the whole thing. Like up till now, you know, for the first I don't even know how many companies. We were using spreadsheets. I didn't even build anything because why would I, right? Why would I, why would I go and automate this when I don't even know what should be automated? And so, and again, this strategy doesn't work for all companies. I understand that. So, you know, whatever. So I had those same questions you had at the beginning. So I was like, I really need to figure out how distribution works. And my hypotheses ended up being pretty accurate. Luckily. But yeah, we get all of our, at least currently we get all of our leads through channel partners. So VCs, accelerators, law firms, accountants, and just other founders. And so for us, it's an interesting, it's a very interesting distribution strategy where you're kind of talking not to the, yeah, you're not selling necessarily to the end consumer at first. Then they kind of come, they hear about you from one of those folks. And then you actually have to talk to that founder and explain them what we do and try and understand their situation and then actually, you know, sell to them. So that's how that works.

So it's a lot of word of mouth if I'm understanding it right. And it's just one year ago you started this. It's not like you're in this like for a long time. Any Interesting insights that you've learned in the last 1 year. Uh, I also wonder, why have you applied for YC, or you have, you want to go to YC through this? You just want to stay as it is? Curious on that, on that front as well.

See, I started this, so I started this full-time a year ago. Um, I started working on it, uh, almost 2 years ago. Uh, was, was doing that blog post, those first couple of customers, that whole thing. That was, yeah, that was, sorry. Is there background noise or is it okay?

No, it's all good.

Okay. Um, yeah, those first, uh, I still had a job, so I still had a paycheck. A lot of people say that as well. It's very hard. I'm not great at that either. So I think for some folks, they can do a good job at that. It wasn't great, but anyways, um, yeah, it started about 2 years ago and then I'm still, I lost the question.

What wasn't good that you just mentioned about paycheck?

No, I think there's pros and cons. So it was awesome that I had a paycheck and like started testing this product out.

Right. So you're doing this on the side?

Yeah, I was doing it on the side. So that's such a nice way to relieve the stress. And it was very helpful for me because I think I sometimes in my earlier self would prone to pivoting if I didn't feel like there was attraction really, really quickly and not giving things enough time. And so by not having the pressure of like, where's my income coming from and like the return rate, like how many months left, that was super helpful. But it's just hard, I guess I just meant it's hard to balance that, to like actually focus on those 2 things at the same time and do a good job at anything. But But yeah, I lost the original question. Yeah.

Yeah. The question is like, have you thought about going to YC? Because you've done that before. That's one thing. The other thing is it's been one year. It's not like, so you're still early in the process. So you kind of, I'm assuming you're learning new things, finding new insights, talking to customers and all that. So anything that you want to share in the last one year being full-time or even like in the last 2 years experimenting and then going full-time. that you've identified that you can share with us?

Yeah, for YC, it's a good question. Again, I think it's amazing. I think especially if you haven't gone through it, it's honestly one of the most life-changing things you can do if you get in. I was super shocked we got in, to be honest. I really was. But yeah, It's like, it's the Harvard, right? The ability to say that you went through that on podcasts when you're talking to other investors, when you're talking to employees, like, it's, this is the way the world works, as unfortunate as it is, but it's an incredible badge that follows you for your entire career. And secondarily, the network is just unbelievable. So, which also follows you for your career. So, you know, it actually, I've gotten a lot of, during that hiatus, like I got all my jobs through the YC community.

Hmm.

And so it's pretty incredible. And then also, you know, if you're building a startup, I think my biggest advice on going through YC though is they let folks in like without an idea. They let folks in with really early ideas. Like, my advice would be really have something that you have high conviction in before you go in and maybe some early traction. Because I think it's such a pressure cooker that it can really incentivize you to pivot and not— like, again, this game is so long to make anything work. You need so much time. And you're not going to get there in three months, and they're going to tell you outlier stories of folks that did, and their stories for a reason. Most it doesn't work like that.

Right. Maybe reality is different.

Yeah. Just just don't listen to them.

Yeah.

They're toxic. They really are. I think they're really toxic for for founders.

So,

but anyways, YC is fantastic. Highly recommend it for this one. I felt like. I had already gotten the value from YC. And yeah, I don't know, we just raised outside of that. And I just at that point didn't feel like it was worth going through it again. But maybe that's a mistake. And then on your second question, yeah, I think, again, I think one of my biggest learnings is, so our first company did pretty well, but it was nothing like this. And The second company did not do well. And it just is so goddamn hard no matter what. And I think no one— I think people talk about that, but it didn't— again, it was another one of those things where like you hear on podcasts, but you don't actually internalize until you're there. It's just like, it's just all different types of suck, right? Like when it's not working out.

Yeah.

And no one cares. Like that's awful. Like that shit feels terrible to your core and really like you wake up just questioning and upset and, and I've been there. It's just, it's, it's terrible.

Yeah.

When things aren't going really. Yeah.

Yeah. It fucks with your mindset. Like, oh yeah, there'll be a lot of self-doubt and, you know, you, you just can't be confident anymore because something's so bothering too. Like, go anyway, go ahead.

No, no, I totally agree. But what's funny is like, if it's going well,

you're top of the

world, really hard. Really hard. Yeah, it's not, it's not that fun either in many ways. Really? You know, no, it's really, it's really fun. It's really, really fun. And again, I'm, we're not, we're like, we're doing, we're doing well. We're not like, you know, whatever. But like, yeah, you're, you know, you get customers who might be upset with you. You have yeah, you're you're just trying to you're trying to figure out like okay, do I hire this person now? Do I hire this person later? Like oh shit, I hired way too late. Like we're currently way understaffed, and it's hard to hire people, and that's really challenging. And like building the the whole thing is just like so hard. Whichever way it goes is basically what I'm saying. It's just like right, you're it's never you always think. God, if only I could get to a millionaire, if only I could get to $2 million, whatever it is, life will be good. And then you get there and you're like, shit's harder than it was before. You know, this is the game.

Oh man,

it's the most

fun

game. It's the only— it's the game that I love the most. It's the game that I always want to keep playing. And it is a game. But yeah, it's—

Have you— so now that we're talking about startups as a game, in your experience, do you think people can bend the rules and play the game. I'm sure there are like some incredible people or incredible founders who did that before. At least in your experience, you've gone through YC, Y Combinator, you've seen like so many peer founders of yours. So more curious on how to bend this game that works for you. Like, how do, how do you, how do people do that? How do founders do that? Just following traditional rules because you also kind of are in a way bending the rule of saying, hey, I'm not going to build traditional way of building startups. I'm going to do my thing, right? So in a way I'm talking about founder mode, but so is there— is now that everybody's talking about founder mode, but it's got into our heads, right? Literally on my head. So yeah, talk to me about like, how can founders bend the game to work towards them?

That's a good question. I don't know. I don't know the answer. I don't, I'm not nearly good enough or successful enough to, I think, answer that. But again, I think it goes, okay. I think, I think here's the analogy. I'm a designer by trade in college. was like a studio art, like fine art major. And when you first get started, you copy shit, right? You copy everything. And that's how you learn, right? You copy what everyone's doing. You draw the little spheres and the triangles. You do, you're looking at still lifes, you're looking at the previous masters. And look at like, go look at like all the famous artists and look at their early, early work. These are incredible. Like, you look at a Picasso, okay? And you're like, God, what the— like, what the fuck is that? Like, that's crazy. It doesn't even look like— how, you know? Go look at— go look at his early work. These are unbelievable craftspeople. These are people who can draw, paint the most realistic, beautiful things you've ever seen in your entire life. And so when you look at that kind of crazy looking contraption, you might think, wow, like they don't actually have any skill or something along those lines, right? Not the truth. You have to start doing the copying and then over time you build your own language and you build your own style and you build your own design patterns. And I think every game, and especially this game, works exactly like that. And When you first start out, you're going to read all the books, you're going to read Lean Startup, you're going to read, watch Alex Hormozi and whatever the hell you're going to do, and you're going to copy. And there's nothing wrong with that. And you should copy. You should copy, copy, copy, and keep trying to copy. And over time, you're going to learn what works and what doesn't work and what totally sucks and what's awful advice and maybe what's good advice. And you're going to make your own style. And I think I'm still really early in what is my style, but I think I have started to forge that path a little bit after just putting in the years of this job. So that would be my answer.

For whatever reason, it's so comforting to hear that answer as a founder because it's kind of hopeful that you still have Basically do your thing and have least expectations when you do things, especially trying in the beginning, even at whatever stage, like VC-backed, whatever it is, you're still a work in progress. I think you should remind— founders should remind about we're all work in progress quite a lot of times, and it's not necessarily on your first attempt you should do or you should crack the code. I think when you're in— what you're saying is Cracking the code is something that will happen naturally once you started copying the code. Like once you copy, copy, copy, that is so comforting. I don't know if you answered that question with intention, but it's so comforting that, okay, you still have a long time to go do your thing. And I think you seem to have— So I spoke to Andrew Gazdecki. I think I can relate you to him because—

Oh, that's nice. He's the nicest guy I've like ever met.

He is so calm, just like you. It's like no distractions, nothing. So calm. And I feel you've gone through such a painful experience, made you calm. Is that right? Or are you calm by Generally by nature, I'm curious because he is like way calm. And I asked him and he said it was a very deep personal story that he explained. He lost his mom at a very early age, one of his parents if I'm not wrong, and that shook him hard. So his point of view is everything that's happening won't cause me that much pain. So he keeps that perspective always. It's like if shit goes wrong, it's not that shittier or it's not that level of pain that he experienced. So that is super helpful because you have to remind yourself as a founder, if you go through some horrible times. So I'm curious, like, is the painful experience of shutting down your second startup made you way calmer? You seem to be like in peace. Like,

I'm not, I'm totally not. That's a facade if it is. I appreciate it, but no, I think, I think—

Have you cultivated any habits or anything like that to help you?

I was going to therapy for a long time. I'm actually not right now, but that's one. I, yeah, okay. There's some things to talk about here, I guess. Let me think. So I think there's maybe one. Okay. So another thing, and I still struggle with this actually all the time. But it's like the hustle culture, number of hours, commitment level. I recently got married. I have a partner. She's great.

Congrats.

She has— she runs her own business as well, which is fun. And we've got a dog. We live in New York. We have friends. We have family. Our siblings are having babies. Like my first startups, we would work so much. We would work 100-hour weeks. And look where that got me. You know? Perspective. The outcome is not nearly as good as the outcome that's going to come from this one. And this one, yeah, do we work a lot? Yeah. Do I think about this company? Pretty much 24/7 for sure. But like, I go out to dinner, I hang out with friends, I see family, I go to the gym every day. It's again, it goes back to this patience thing. This game takes so long, you're not going to figure it out. You're not going to get there tomorrow. You know, you're, you got to buckle up for years. And the only way to do that is to not, not like try and burn yourself out in the first, in the first like 6 months, you know? And that's what we did. So I would say that's, that's kind of a big one for me.

Love that support system, right? In a way, it's like, I hate the word work-life balance. There's nothing, in my opinion, work and life when you're into startups, it's all the same. But at least having a line where you can like say, hey, I have to have My own life is really important. Let's talk about,

I think, I think actually another, I'm sorry, my last, my last point of that too is like the line of, like, it's really interesting. The line of work I'm in, all I do is talk to founders who, with companies that are going out of business. And these founders are in a really tough spot and I've been there before and I deeply empathize with all of them. And I talked to them later on, they find new jobs. And they've started another company and they've raised some money or they've traveled. Or once you've gone through it yourself, you know how painful it is, but you know that where you are on the other side is, you know, I'm so glad where I am today. And then I'm also seeing probably like the most amount of founders shutting down that like anyone's hopefully ever going to see like in any portfolio or anything like that. So That also, I guess, brings some solace of just, yeah, like to your point about Andrew, like what's the worst that's going to happen here, right?

Yeah. Hmm. Yeah. Yeah. It's all about, I think, having that mindset and patience is the name of the game. It's like, so it takes so long.

It's all boring advice. It's all like boring. You know what I mean? Like it's all the same.

But I think the most impactful advice is always boring and obvious. That's why people miss it.

Exactly

right.

Exactly.

Let's start off. So given you took hiatus, second sort of shutdown, you picked this. Do you have any other ideas that you wanted to work in? If you were to go back to the times like 2022, that's where things got down. You're working, you're consulting, hustling. Do you have any ideas you want to share? Like if this, if Sunward Sunset wasn't like a reality now, what would have, what would have Brandon, you know, worked on?

Oh my God. I was working on crazy stuff. I don't even know. You should, you should talk to my wife. I won't bore you with it. Crazy stuff. No, I think actually I don't really do this as much anymore, but actually a tactical tip, which is so also stupid and boring. But I didn't used to do it and then I heard about it and then I started doing it. It's actually very, very helpful. It's hard to, it's actually sometimes it's not, I think supernatural for most folks to identify problems in the world and especially remember them. So literally I just have a notes app on my phone. Like I heard this on some podcast or something, but yeah, one of these founders, they just like have these giant notes app and anytime they hear a problem or something, they just like write it down. And I started doing that. And I don't, I wish I could remember. I mean, it was, I think it was after, like I mentioned, it was like after one of the— I got a text from a buddy and then I just, I already had this Notes app and I just wrote it down. And I don't think I came back to that idea for another month or 2. But that's kind of a tactical tip of just like get in the habit of anytime, like they can be the dumbest. You want me to pull it up? Like what really dumb ideas do I have in here? I'd love to hear it. Awful. I'll tell you what I was working on, because then you can see how stupid this shit is. I love tea. I don't drink coffee. And so, I found that tea, like tea bags suck. They're like super messy. It's hard to get like the actual concentrate you want. Either it's too strong or too light. You know, they have things as tea concentrate, but it's like, you won't really buy that anyways. I thought of this company called Teat, like

oh my god!

And it was basically a squeeze bottle with like a little teat at the end of tea concentrate. And so I was super bored, and I was at my job, and I mean, you ask my wife. I like bought all this tea. I was making all these concentrates in in our kitchen, and I was like playing around the logo and all. Yeah, it's like you know once you get the bug, you got the bug, and you're just gonna keep doing dumb shit. But like that that's what I mean. Like You just have to, you have to play. It's just a game of playing. And I played with it. And I was like, this is so stupid. Why would I ever do this? But like, I got, you know, like, you gotta go.

Hmm.

You just— that, again, that's the big learning with Sunset and all these other things. It's just like, don't write things off at first glance. Just give it a little shot. And have fun. You know, it's like the whole The whole point is fun. I'm having a lot of fun with this company. So yeah.

I love that. I think again, reassuring. It's so reassuring to hear that just show up and play. And I think when you do that for multiple times, one of these shots will make it, right? Like if you go after the basket so many times, it means one of the shots will make it. Like, you know, so. Yeah. But

come back to me in a few years. But yeah.

Thank God you're not building that or else we would've talked about tea bags right now.

I know. That is insane.

I'm curious now that you have that Notes app open, any weird startup ideas that you want to share? Like something that, man, it has potential, but it's so weird, like Sunset. Take your time.

Sorry, I'm just going through them now. Let's see. All right. Some, some that I really, these are really weird. Have you guys used Paperless Post recently?

Yeah.

Pretty bad.

Yeah.

Don't think it's great distribution-wise. I think it'd be very, very hard. Right. I don't know. I don't know how you go about distributing that, but I think it's a really, I think, I think the whole like e-card, e-invite. especially with AI and personalizing the cards and the messages and the videos and potentially incorporating things like payments into it. I don't know. I think there's like actually something really interesting in that space. There's a ton of money that goes there. So that's one that I was, yeah, using Paperless Post for our wedding invites and it was a horrible product. And I was like, there's something interesting there. I have some other ones that are too weird. That I want to share. Coconut whipped cream can. That's one kind of dairy-free. So I love, love coconut whipped cream. So if someone can make that. Yeah, I don't know, man. I have, I have some automatic car cleaners, like car washes for future self-driving cab fleets. Those cars are gonna get dirty. So yeah, I don't like— who even knows? Yeah, that's what I mean though. There, I have terrible, terrible ideas in here. Wire cutter for puppies. When we got our puppy, I was like, what the hell do I buy? I have no idea. So I would have loved like a wire cutter for just dogs. Tons of money there. I think you could crush. I think you could crush. I think you make a ton of money there. Yeah, I've so, I have so many other things in here that are just out there. I haven't looked at this in a while. You know what I'd actually love? You still Yeah, good,

good.

But my last one, that's really— what's, um, what's the show on Netflix where like the 5 guys will like revamp someone? Like they do the house and the— do you know what I'm talking about? They like restyle them and the—

No, I'm not big into any of that.

Anyway, never mind then. Okay. Oh, good. We're done with that.

Man, do you still have that habit of writing problems even now after After sunset?

It's funny. I've been doing it a lot less. I think I just wrote one down pretty recently, but you should actually, actually, you really should do this. Even when you're running your own company, we encountered so many goddamn problems running our own startup that are now huge companies.

Whoa, I'd like to hear that.

Yeah. So we basically how the product worked is like, think of it, it was a tool for digital agencies. So it was really hard to get feedback from a website on like a Waiter asset that you created that was hosted from your clients. So we made a really easy like Chrome extension. There's a tool called Jam out right now that did the same exact thing. Yeah. We were like toy box with that before Jam existed and you just like leave sticky notes on a website. And then, so we had to build a ton of integrations. With project management tools, tons, Jira, like all these crazy tools, and they it was such a pain in the ass. Such such such a pain in the ass. Finch, Merge, all these companies that are like raise monster rounds, like that is literally what they do. And we we were doing that, like we were encountering that problem years ago. Sales tax is becoming like really hot right now, like as products you see a lot of them. But again, we had huge issues with like sales tax for SaaS subscriptions. Again, this is like 2018, things like that. I mean, the list just goes on and on. We like things like CommandBar.

Yeah.

All these types of tools we were building in-house or like trying to figure out how to do them. And I just like, we just were, you have your blinders on. And so I do think it's actually a really good habit to do even when you are. And this is a good reminder and inspiration for me to keep doing that. So

yeah, yeah, yeah, I love that. Well, Brandon, it's been awesome jamming with you. Ideas and like really—

Man, sorry for just like saying crazy shit for an hour.

No, no, no, it's all, it's all good shit though. That's the, that's the part, right? People should hear about this and founders should learn about or kind of take in the boring ideas or the boring problems and boring advice and actually take it seriously. So appreciate you for joining the show. Any closing thoughts before we wrap up?

No, I mean, I think if you're a founder who is struggling or trying to figure out what to do, I'm always around to chat. Like, we're not a salesy company, but, you know, I think a lot of founders don't know how the different options available to them and when you should start thinking about those different options. And it's usually earlier than you think. And things just get really complicated if you take your bank account to zero and if you don't start a little earlier on trying to raise that bridge or trying to find a home for your team with an acquihire or try and sell your assets, things like that. There's a lot of things you can do with enough time to avoid a pure shutdown. So again, that would be my only thing. If you ever want to chat and you're in that situation, Always happy to, you know, founder to founder.

Love that. Love that. And we're going to keep all the related links in the show notes anyway, so that, you know, listeners can reach out to you directly. But that's been like a blast. I wouldn't say blast. It's been like a very calm, really like, you know, calm conversation. I'm so glad we did this. I'm so glad that I didn't expect this. I'm so glad. We talked a lot about like, you know, the things that people should pay attention to. So appreciate you, Brandon. And

thanks so much for having me. It was a lot of fun.

For folks listening, just play the game. That's it. There you go. Nothing more. Nothing more. All right. Cheers. And stay tuned for more founders like Brandon to hop on and share their advice and their journey and their lessons. So take care.

Thanks, man.