Ep 160: Feelings Check-In on winding down a startup and 'Founder Mode'

[00:00] The Feelings Check-In is a podcast for people who love to listen to two women overshare about the challenges of building a business, navigating careers in tech, and trying to have a personal life. I'm Natasha Hoskins. I'm Dina Burke. And this is Boys Club. Wait, is it just Boys Club? It's just Boys Club. The Boys Club podcast? No. No. [00:20] Just boy stuff. [00:22] I went to church on Sunday. As I've been doing, as we have talked about, which is... [00:27] new and old thing for me to be doing. - A new church, right? [00:31] New church. Took a long break from church. Now we're back and... [00:35] We're seeing how it feels. But I take little notes when something hits and there was, I don't know if I can do it justice. But anyway, he was talking about this idea of how certain people process their emotions and that there's two different types of people. And one was a differentiated person and one was a fused person. [01:05] uh, [01:06] know the limits of an emotion and see that there's an emotion that's coming up, there's a feeling that's coming up and that it is, you can ride the wave of it. [01:15] and know that there's some part of that emotion that [01:19] speaks to your life and that is important and that should maybe result in an action and it's like an invitation to go into that feeling but it's not the truth of the world and that like a fused person it's a hard time seeing

[01:33] that the emotion is not the absolute truth and that it's, [01:38] they have a hard time seeing where the responsibility of that emotion lies. And it was an interesting distinction and basically that Fuse people have a hard time seeing who's responsible for that emotion. And [01:50] differentiated people have the... [01:52] maturity and emotional intelligence to observe that emotion, see where they're responsible to it, but also not let it like completely overtake them. And in... [02:03] the context of this podcast, I feel like one of the problems that we have is... [02:07] It's not exactly the same, but there are feelings that are just feelings that we're just moving through that aren't. [02:14] the thing and aren't used to them yeah we have a healthy relationship to that feeling and that emotion and we can observe it and talk about it but we know that it's not the absolute truth and we also know that there's many factors to that and that it's fine and then we go on this podcast and we get to and we love to do it but sometimes it's like i don't need to spend that much time with this feeling and i don't need to put it on main and talk about it and publish it out to the world but i don't know what i'm saying but i don't know what i'm saying but i don't know what i'm saying [02:40] We have to do this podcast. So I feel like one of the things that we want to try to do is to be like, okay, here are some of the things that we experienced this week. And here are some of the feelings that we had around those things. Yeah. [02:54] They're not the main character of the week, and they don't need a full spotlight on them. But it's an interesting sort of exercise in how do you have... [03:02] a differentiated experience of those feelings on this podcast does that make sense totally there it is there it is

[03:10] you [03:11] Hey, Natasha. So a question we get asked a lot is, what do you look for in a crypto platform? So let's talk about it. Well, Dina, I look for a secure, no fuss platform that I can dive into right away. That's why I love today's sponsor, Kraken. If you're waiting for the right time to get into crypto, Kraken makes it super easy and intuitive to get started. Plus, if you get stuck, they have an award-winning client support team that's available 24-7, along with a bunch of educational guides, articles, and videos to help you along the way. If you're ready to check out [03:40] Go to kraken.com backslash boys club and see what crypto can be. Not investment advice. Crypto trading involves risk of loss and is offered to U.S. customers through Payward Interactive, Inc. [03:53] okay so we're gonna start by talking about you had to do or are in the middle of doing something this week that um for a founder for in founder mode can be quite painful which is shutting down your prior startup yes yeah so for those who do not know i had a startup before this it was in a totally different industry it was in travel [04:15] I left my job, raised around the funding, built a product, worked on that product for several years. It was a travel product during COVID. It was tough. It was a TF. [04:26] time. And... [04:29] I ended up building like a little business, but the cap table was fucked. It wasn't a venture scale business. Like there were all these issues with it. And it was also like a major lesson and you don't. [04:38] The [04:39] I had such an unhealthy relationship with that business. I had so much of my identity and my self-worth wrapped up in that business. I think back to some of those days and I was like, wow, dark in how much...

[04:52] I thought my identity was this business and that my whole worth was wrapped up in it. And I thought about those investors every single day. I woke up thinking about them. I like... [05:03] felt an immense amount of anxiety and stress about my relationship to them and the money that they had given me and that they had invested in the company I just mean like that's part of it where it's like [05:14] They are taking a risk and hoping for a reward. And so that was, I just, I hear myself and you saying that, I hear myself being like, they gave me the money. They didn't give me the money. Right. They didn't give me money. They were making a bet. [05:27] They were making a bet. [05:28] And what happened with that business, the assets of that business were acquired by another business. And then there's like the shell of the incorporation that continues to exist. And it has existed. And there's like a few reasons why it's continued to exist that like we don't really need to get into. And it's not that interesting. But it's like administrative. And it's been now like four years. Like I was like looking at it. I was like, holy shit. I went and picked up my mail. And I had like three letters that are from the Delaware. And I'm like, I'm done. Yeah. [05:58] I just need to deal with the hard truths of this situation and... [06:05] Not that I haven't. All the investors know what happened and I've talked with all of them. But there's some admin that they have to do. And I feel this responsibility to them of they have to deal with this thing again. And it's nothing for them. It's like filing a loss on their taxes and it will be fine. [06:21] I've had some feelings come up around

[06:26] honestly, like just taking me back to those days. I don't feel any, like I met with my lawyer today, I met with my accountant today. And one of the feelings that came up was, wow, I have come so far. I would get so full blown sweating when I had a call with the lawyers. I'm going to say something stupid. I'm going to embarrass myself. I'm going to be exposed and they're going to know that I don't know anything about what I'm doing and that I'm an idiot. I remember feeling so stressed out about these little things. My main feeling today on the call with my lawyer was, man, I have grown. I was like, hey, I don't know how this works. I don't know about this. This is [06:56] I know this is what I said, this is the email, what do you need? And him giving a list of all the things that he needed and me being like, great. It was just such a different experience, that part of it. But what has felt tough is pulling up the cap table, looking at all these people's names, getting all their information together, and just really being brought back to that time in my life that was like, [07:14] really challenging and really good for me professionally expedited so much of my life. I'm really grateful for all that time, but I was, [07:21] so anxious and stressed out and having a flashback to that time and those people. And like I drafted an email to one of our main investors who there's some details of what needs to come together that they need to help with to wind down the company. And I like. [07:37] had this insecurity come up that hasn't come up in so many years where I texted you and I was like, can you look at this email? I just needed someone to look at it and tell me that it was okay and that it wasn't a stupid thing to say and that like it checked out and that the logic was there. But that felt like such a [07:53] 2019 behavior but I was like I'm back there something about it

[07:57] looking at all this paperwork, it's bringing me back to that. Anyway, it's been a really interesting experience winding down a company. The admin of it is just really annoying and expensive. I'm like, I'm on the call with the lawyer and he's like, yeah, well, you got to call your accountant. And I'm like, can't just one of you do it? [08:13] Wait, why does, why do you have to call the accountant? There's some filing of the last return and then also he was, you need to file with the Department of Finance as well. Like basically you have to have proof. A death certificate. Exactly. Basically. Yeah. Basically in order to get your death certificate essentially for your business, you have to have a letter that's saying like you're in good standing with the Department of Finance. That like you don't know taxes essentially. Okay. Okay. I have to call our... [08:39] our accountant this man named Adam who is just a funny guy just a funny guy and I sent him and I was like it's gonna be easier if we just hop on a call can you like oh he loves to hop on a call he loves to hop on a call and I love to hop on a call so we're we're a match made in heaven honestly our emails are just hey can you hop on a call hey I'm gonna call [08:58] Anyway, it's been interesting. There's people in my life today who have [09:03] absolutely zero context and [09:06] knowledge, [09:07] of that time in my life and what [09:10] I was working on and how much it meant to me and all of this stuff. And it's so [09:14] That's very weird. It's like a very, it feels... It's like you have a second family somewhere. Yes, I feel that way. Yeah, exactly. Exactly. So it's been cathartic. I saw this tweet from Gabby Goldberg the other day that was like, it's so embarrassing when you've been putting something off for three years that takes 30 minutes. And that's a little bit how it feels. Is there any part of you that's like, man, to be selling travel, that's so straightforward? We're in a business that's so...

[09:38] whatever the opposite of straightforward is. [09:41] and to look at a product that's legal and a contained thing. Yeah, I had this experience the other day where a mutual friend of mine sent me [09:52] a text and she said, "Hey, I have a friend who's starting a business that's very similar to Allcall." And she sent me a link and it's like a beautiful website and like this girl's [09:59] Totally cool and she was like I I [10:03] wondering if I can connect you with her so that you can... [10:05] talk with her about her business and what she's up to and give her any advice. And I was like, totally, please feel free. I would love to do that. And, [10:14] So she connects me and this girl's like, do you want to get coffee or drink? And I was like, we need to get martinis because I need to tell you, don't do this fucking business. [10:23] Like that's going to be the conversation. That's the most loving thing for you to do. The most loving thing to do, because I know so much about this industry. Don't be in that industry. So in some ways, yes, I'm jealous for a time where the nuts and bolts of it are, are, are, [10:37] clear and the path to [10:39] to whether it's working or it's not working is clear. I'm so envious of that time because that's not the business we're in today and it's totally different. But you don't know what you don't know about a business or an industry until you're in it. And I was so naive to the dollars of the travel industry. And now I get it and I have equity in a company that I'm like, that company's gonna win. And that's the only company that's gonna win. Like they figured it out and that's great. But it's just hard because I haven't met with this girl yet and maybe she has a unique take. That's really interesting and I hope so.

[11:09] talk to early stage entrepreneurs in that [11:12] industry, I'm just like, man, [11:15] I'm doing something that they are doing too. Like I'm making some mistake in this media business or in a bootstrap business or crypto business that some other founder who's been doing it longer than I have is looking and saying, [11:27] Oh my God, they're making that mistake. That's such a stupid mistake. And like, you just don't know it until you do it. [11:32] Totally. I do think in crypto though, since it's like more nascent as an industry that there's not a lot of people that can look at it and be like, these are the mistakes you're making. True. [11:42] I think it's a small crowd. Maybe that's why we landed here. We're like, nobody can tell us we're doing it wrong. [11:48] Oh, man. Any reflections? You were very much in the middle of it. I was very much in the middle of that. I have also done the same with my own startup. Yeah, I think like that moment for me winding down my first startup, I think my biggest feeling about it is the difference in how I felt in my own startup. [12:08] and the pressure I felt in the day to day of running that business and like catastrophizing what it would look like and feel like if I did have to shut down that business and if it didn't work. Yeah. The difference between that. [12:20] feeling in that moment of when you're running it [12:23] versus like the actual feeling of what it means to shut it down and to tell your investors that it didn't work and [12:28] they can take a loss in their taxes and the reality of doing that is so much easier [12:34] Like it's hard. [12:36] And it sucks. Like it really sucks. But you live to see another day.

[12:40] Mm hmm. Totally. And like you hang up on that phone call with the person who put the most amount of money in the company and they're having whatever reaction you're having. And then you go and you like get a cup of coffee. [12:50] Yeah. Yeah. [12:51] you're fine. Like, yeah. And I think that your life continues. Your life continues when you're in the moment, the first time founders, especially I think like it's life or death and it isn't. I know. I think the biggest lesson for me has been [13:04] I had that conversation four years ago. [13:07] And I should have just [13:08] Shut it all down. Yeah. Like when you're just... [13:11] do it all then rip the band-aid off don't let it like linger yeah like i let it like linger and [13:17] There's a few reasons for that, but like not good enough reasons. It was more of an avoidant. It was a decision made out of avoiding that part of it for some reason. But I did the hardest thing and then I just let this thing go for like forever. [13:30] And you're so right. Like you do it and the feeling is so horrible. And then afterward, it's kind of a major sense of relief. Honestly. I think also when you tried your hardest, like when you're like, I did everything I could do. Totally. [13:42] It is what it is. Totally. The other feeling that I have is, I don't know, maybe this will be useful for someone, but in reflection on the time that I was shutting down my first startup. [13:53] after I'm through it and it's years later and I'm looking back at that time. [13:58] There was a good... [14:00] six, seven, eight months there that I knew [14:04] It wasn't working and it wasn't not going to work. And then I just let it linger. [14:09] and kept it going and was trying like Hail Marys. But I don't tend to like go through life thinking about regrets, but I would say like, not a regret, but like if I was giving advice to myself at that time,

[14:22] from where I'm sitting now, I would be like, [14:24] similar rip off the band-aid thing where it's like when you know it's not working just cut your losses [14:28] Yeah, it's hard because you see founders doing that and you're like, just move on. Just move on. But then... [14:34] the story that everybody tells you is startups don't fail founders give up it's really hard to get that message out of your head that is true thank you that is true those are competing narratives both can be true both are true both are true it's tough it's tough seeing people out there grinding and there's also like so much yeah [14:57] survivor bias in this industry oh you just think of the one person [15:03] Brian Chesky. [15:04] Exactly. Yeah. We were like, well, he kept on keeping on when he was making those... [15:09] fucking cereal boxes for the gmc or what was it that's part of the lore right something like that yeah yeah i was like i think it was a salesforce conference yeah and then that's what keeps someone going [15:20] Yeah. That's what kept me going. [15:21] Yeah, totally. And those are [15:25] dangerous and false narratives. [15:27] Yeah. [15:28] Okay, on to the next feeling. There it is. We actually had more juice on that feeling than I thought. [15:33] It's time for a more open, inclusive, and transparent financial system. A system that serves nearly everyone, everywhere, all the time. That's why we love today's sponsor, Kraken. Kraken is a crypto platform that provides a super simple on-ramp to the world of crypto with a 24-7 support team. Crypto transcends physical and imaginary borders. No matter where you are, you can send funds easily and quickly to almost any part of the world. Plus, forget about waiting times and waiting lines. You can send, receive, and trade crypto anywhere near instantly.

[16:03] See what crypto can be at kraken.com backslash boys club, not investment advice. Crypto trading involves risk of loss and is offered to us customers through payward interactive Inc. No third party transfers available. Okay. Founder mode. Having said all that. [16:20] So there was an article that was published, a blog post that was published over the weekend [16:34] which is an elite... [16:36] startup incubator. Sam Altman famously worked at Y Combinator for many years. It's like cream of the crop. [16:44] Kermit the Crop. Airbnb. [16:46] Coinbase, DoorDash, Brex, Dropbox. I mean, basically in that era, Stripe, [16:54] Webflow, Zapier, [16:57] Oh, stripes a big one. They're all there. Gangs all here. 10s to the 20s. Probably before that, too. But I'd say that's really the heyday. Okay, so Paul Graham drops this essay over the weekend. [17:07] Not a long essay. It's a short essay. I recommend you read it. [17:10] to just have the sense of the zeitgeist. And the essay's called Founder Mode. And Twitter... [17:16] was a buzz [17:17] over it for many reasons. It goes on to talk about how there's [17:22] conventional [17:24] that [17:25] startup founders receive when their business starts to scale. They're a founder, they got something, and it's working, and they're starting to hire and to scale the business. And the conventional wisdom, your management consultants, your Baines and your McKinsey's would say, "What you do in that moment is that you hire really good people,

[17:43] and delegate essentially and like give them room to run and you let them do their thing and you as the founder give them the space to do that and [17:53] And Paul argues that that is... [17:56] not the thing to do and that there's something called founder mode which it's just like so memeable like it really works as a meme you had told me one time that you had a call [18:09] with an investor and they asked you how you planned to break through and win on the memetic battleground of Twitter. [18:19] And you called me and you were like so pissed You were like this is such a fucking stupid question And like I hate it And I'm honestly like [18:27] Calling something founder mode is how you win the mimetic battleground. He's won on the mimetic battleground for sure. It seems intentional to me. I think it is. [18:35] I'm giving him a lot of credit for that, but I feel like he probably deserves the credit based on who he is. Let's give him... [18:41] Let's give this man some more credit. He needs to hear it from me for sure. [18:48] Anyway, it goes on to talk about how that's not actually the thing that you should do and that founders should actually be across everything that's important to their business. [18:57] Which honestly, that isn't really revolutionary advice. That's like, yeah, founders should pay attention to what's important in the business. And there's all these examples that he pointed to where when you do hire people outside of the company, [19:11] that it's led to like these disastrous results because those people basically are good at managing up to founders and are ineffective at their job.

[19:19] So there's a lot of feelings and takes and thoughts that flow from this post, but that's essentially it. Is there anything else you feel like is? No, I feel like that's basically it. And it's got meme to hell, as you can imagine. And the main sort of take that I've seen is essentially we've rebranded micromanaging to founder mode, which is funny. [19:49] tells himself founder mode like I've seen a lot of that like when are you telling yourself like founder mode founder mode which is funny it's a funny way to yeah I think some of the takes in addition to that was like part of why there was a certain type of founder that like really celebrated this [20:05] blog post and it's because they're looking for license to [20:11] behave a certain way or they're looking for an excuse to behave badly an excuse to yeah [20:17] behave in a certain way that maybe they're already doing anyway so saw some of that [20:23] I saw one from Ray Han who is so funny on Twitter. Like, he's just really funny. Some of you guys need to worry less about founder mode and might want to consider found her mode. [20:36] really dumb but that's really dumb really good really dumb really good I think there's an easy take in [20:44] which is like micromanaging people [20:47] is bad and ineffective. And I think what, honestly, what this brings up for me more than anything is our take as like Boys Club is we're not scaling this business in that same way. So it's like we don't have a lot of...

[20:59] first-hand experience to draw on. But I will say the sort of small amount of experience that I do have with this type of thing is, I do think that... [21:08] before you hire for something [21:12] you need, you should, as a founder, you should feel it entirely yourself. You need to, I do think it's important to understand exactly what the shape of the work is and not just like what the scope of the work is, but all the areas of the business it touches and what it feels like to do that work before you hire for it. And I think that that makes you more effective at hiring for that role and more effective in managing that person because you have more empathy for what their day to day work looks like, and you can better support them. Yeah. [21:40] in moments where there's like some challenge so that's really tangential to this idea of founder mode but i do think that that's something like just as a management idea is something i think about a lot yeah that checks out yeah i was really struck by when i was reading and i was like wow we're really not a venture-backed business like this is so much about you've got 12 million dollars in the bank and you're trying to scale something that is product market fit and you have to hire 150 people in the next three months exactly and i felt a real sense of relief that that's not the [22:10] I was doing. You know what I mean? Yeah, I do. Okay. Well, founder mode. That is that. [22:15] That is that. From Idris Elba to Stripe to the Central Bank of Brazil, the sixth annual Stellar Meridian Conference in London has the range. Join policymakers, investors, builders, and more on October 15th through 17th in London to talk about how crypto is transforming everyday financial services right now. Tickets are going fast, so get yours now at meridian.stellar.org.

[22:45] two okay the first one is going out in brooklyn be like and then in quotes this is my wife this is my boyfriend nice nice that's great thank you should i fire it off yeah okay cool wow i didn't think you really you really laughed like that was a genuine laugh i love when that happens it feels true it doesn't feel true for you but it feels true it was it oh i didn't say that [23:11] Someone said that to me. Someone was like, hey, I'm Olivia. This and then this is my this is my wife. And I was like, oh, nice to meet you. And she was like, and this is my boyfriend. And I was like, okay, that's cool. That's totally cool. I'm, I'm not scandalized at all. I'm just surprised. It's not common. As common as one would think. And it wasn't you who were saying it. [23:30] No. So that's unclear in the tweet. It's a little unclear in the tweet, but now I do [23:37] get that you were on the receiving end of it and that makes it just as funny doesn't lose it okay [23:41] What's something that you hate but also makes you cry? [23:43] For me, it's flash mobs. [23:45] they make you cry that's so weird dina it's like it's like i honestly even just thinking about him starts to make you cry it's like a a biological trigger is it just like you just like seeing people like working on a shared goal it's not even i like it i don't okay i don't like it i hate it but there's something about yeah [24:07] It does something for you. It does something in me that I like can't control and it makes me cry. That's so funny. But I hate them so much, like for the record. So much. Couldn't hate it more. This will only be funny for people who are watching industry, but there was an incredible episode last night. You must watch it. But there's this character who is married to this like finance guy and she seems to have some sort of media business, a little cute media business. And

[24:37] with the subtitles on, I was like, screenshot it, post it. One of them being her being like, "I've made some money in my media at work." [24:46] perfect put it on main so there's some work to get it together i gotta like take a picture of the right moment but yeah it's a great episode just gotta get back there very anxiety inducing episode episode four of season three [24:59] The director said this episode should be read and directed as if a new bar has been set for borderline unwatchable tension. No, for real. It was uncut gems level tension. Yeah. And the episode ended and it made me genuinely anxious about my life, like my literal real life. I was like in a spiral. I was like, whoa, this had a powerful effect. There's art right there. Also, the premise of it is someone who has gambling addiction. And I was just like, man, get this man on Polymarket. Would never recover. [25:29] *laughs* [25:31] *laughs*