EP 10: Interview with Ryan Breslow, The Silicon Valley Mob, Twilio Insider Trading and Why OnlyFans Can’t Find Investors

(00:20) NFT LA and Nikita’s parties (01:50) Onlyfans ideal for SPAC which surprisingly isn’t a sex thing (15:40) Twilio programmers great at programming, terrible at insider trading (25:20) Ryan Breslow exclusive interview (30:57) How Ryan got good at Twitter (33:34) Is the Silicon Mob real?? (38:40) Why one-click checkout is impossible to explain but very cool (44:11) Is blocking competition conspiracy or just good strategy (49:57) Surprising controversy over early exercise options loans Follow the show: https://twitter.com/cartoonavatars https://www.instagram.com/cartoonavatars/ https://www.tiktok.com/@cartoonavatars Follow the hosts: https://twitter.com/zck?s=21 https://twitter.com/nikitabier?s=21 https://twitter.com/loganbartlett?s=21 Mixed and edited: Justin Hrabovsky Produced: Andrew Nadeau and Rashad Assir Executive Producer: Josh Machiz Music: Griff Lawson REFERENCE LINKS: Onlyfans can't find investors: https://www.axios.com/onlyfans-investors-struggle-9cc92523-6607-40ad-9893-4175e7966b52.html Twilio insider trading: https://www.cnbc.com/2022/03/28/sec-charges-twilio-engineers-with-insider-trading-.html Stripe / YC Mob thread: https://twitter.com/theryanking/status/1485784823641755648?s=20&t=IFRaBDRDtA8J2wTXruhPpQ https://twitter.com/theryanking/status/1485784823641755648?s=20&t=IFRaBDRDtA8J2wTXruhPpQ RB - Meditation tweet: https://twitter.com/theryanking/status/1501953781046689801?s=20&t=IFRaBDRDtA8J2wTXruhPpQ https://twitter.com/theryanking/status/1501953781046689801?s=20&t=IFRaBDRDtA8J2wTXruhPpQ NB response tweet: https://twitter.com/nikitabier/status/1501991588246917130?s=20&t=IFRaBDRDtA8J2wTXruhPpQ https://twitter.com/nikitabier/status/1501991588246917130?s=20&t=IFRaBDRDtA8J2wTXruhPpQ RB – Stock options tweet: https://twitter.com/theryanking/status/1493390167461224451?s=20&t=bvE0FGOApel_hUwqVdwU7A https://twitter.com/theryanking/status/1493390167461224451?s=20&t=bvE0FGOApel_hUwqVdwU7A LB – Stock options tweet: https://twitter.com/loganbartlett/status/1503893316710146053?s=20&t=6s6MaxQikG6l76htdBlEKQ https://twitter.com/loganbartlett/status/1503893316710146053?s=20&t=6s6MaxQikG6l76htdBlEKQ Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:03Logan Bartlett?

  Welcome to the 10th episode of Three Cartoon Avatars. I'm your host Logan Bartlett and I am joined today by my esteemed co-host Nikita Beer and Zach Kukoff. How are we doing guys?

• 0:14Speaker 01

  Fantastic. NFT LA is underway. I've been on a bit of a bender the last couple of days.

• 0:22Logan Bartlett?

  Did you pay $4,000 tickets that we talked about last week? Or did you get some VIP?

• 0:26Speaker 01

  Absolutely not. I snuck into every party, got kicked out of multiple.

• 0:32Speaker 01

  But...

• 0:33Logan Bartlett?

  Basically, we're joking and being serious. I'm pretty sure you're kidding, but I don't know. Maybe you actually were thrown out of parties.

• 0:41Speaker 01

  I was thrown out of at least one.

• 0:44Logan Bartlett?

  Are you hosting one?

• 0:44Speaker 01

  But the funny thing is like virtually every mansion in LA has been rented out. And I've learned that most crypto people do not own any real estate. They simply rent houses.

• 0:58Logan Bartlett?

  You mean in real estate in the physical world? In the metaverse, they own like tons of real, you know, they own plots of land and all that. I would think, Nikita, actually, I mean, we'll maybe talk about this in a bit, but NFT LA broke news with the Axie Infinity thing. I think the guy was on stage actually talking about that. Was that, was that a topic of discussion over the course of the couple of days? Like $625 million just disappearing?

• 1:23Speaker 01

  I did not discuss anything related to crypto or Web 3 at NFT LA whatsoever.

• 1:30Speaker 02

  By the way, $625 million disappearing is actually an expected outcome of crypto. That's not unusual situation.

• 1:37Logan Bartlett?

  Yeah, and I think crypto conferences are actually like, their success or failure is determined by how little you talk about crypto, right? It's like some inverse relationship of discussion and networking versus partying.

• 1:50Logan Bartlett?

  This week, Axios reported that OnlyFans has held talks with different SPACs about a merger to take it public. Now, for those that don't know, OnlyFans is a content subscription platform with millions of monthly users who's cumulatively paid out billions of dollars to creators. I say creators in air quotes because this is mostly adult entertainment. So for quick backstory here, but OnlyFans was in the news last year. They tried to raise private capital to partially cash out the founder/CEO, but didn't get traction because of the platform's explicit content. A number of VCs have vice clauses that don't allow them to invest in things

• 2:33Logan Bartlett?

  like that. OnlyFans subsequently announced that they were banning explicit material, hoping that that would secure investors, but they reversed course after outrage from all their creators. After that, OnlyFans replaced their CEO with the CMO, and they've since tried to reposition itself to a broader platform, a content platform than just adult entertainment, including stuff like cooking, comedy, celebrities, UFC fighting. So Nikita, as our power user here, OnlyFans, what's your perspective on this? You had mentioned before we started taping that you had actually gotten pitched on a potential investment here?

• 3:17Speaker 01

  Yeah, so the most of my income these days comes from my OnlyFans page.

• 3:22Logan Bartlett?

  You're beat, right?

• 3:23Speaker 01

  Yeah, it's from all the e-girls that follow me. They pay monthly. Yeah, so actually, I was, the deal was floated to me by one of the, by one of the tier-one VC firms in the valley. And they asked if I wanted to participate. And as far as I know, there was quite a bit of competition to get money in. And I don't, I don't think they were, I think the, at least the story being told about them struggling to raise is not

• 4:00Speaker 01

  Totally accurate. What I do think was maybe the institutional investors had a diligence process. And when it came to light that payment, uh, some of the payment providers were pulling the plug. That may have jeopardized some of the leads being involved. But I think they had enough to enough interest from, you know, uh, for small checks, non-leads.

• 4:23Logan Bartlett?

  For people's benefit here, like Axios also had an internal pitch deck from them when they were raising this round. And it's an amazing financial profile of a company. Uh, the numbers they had were they did $375 million in revenue in 2020. With 42% free cash flow margins, they generated $150 million in free cash flow. They were expecting the revenue to go from 375 to 1.2 billion, uh, last year in 2021. So, I mean, this is a, from a financial profile standpoint, it's an amazing business. Now, from a morality standpoint, I think people have issues with it.

• 5:01Speaker 02

  I do know, Nikita, to your point, there were a number of folks who were more junior at tier one institutionals who were desperate to put money in. This is a like career making, if this weren't any other vertical, it would be a career making investment, right? For whoever put the money into it. In fact, there's one person I know who said he wanted to pitch it internally as a community app for men to connect with each other. Like that, there were a lot of people who wanted to put dollars into this thing. Um, the challenge ultimately with a lot of these businesses is, you know, not only is there immense platform payment risk to the point that you both have made. But like, over time, if you look at OnlyFans, it actually operates in some ways like a multi-level marketing scheme.

• 5:40Speaker 02

  You know, these women get a cut of all of the proceeds for all the women who they recruit onto the platform. So ultimately you end up in this weird perverse incentive where your, your goal, maybe as much as it is to produce content for the Nikitas of the world, is also to actually get more Nikitas to sign up, uh, and create their own content for their legion of e-girls.

• 6:03Logan Bartlett?

  Are you saying, I mean, MLM, should they just rebrand as Web 3 and then it would all be legal? Isn't that like? The whole premise of Web 3 is MLM? Yeah, for now. One of the interesting things here, I mean, Zach, I didn't realize that about their business. But one of the things that I think is interesting is there's clearly, so they're talking about a SPAC. And for people's benefit, I mean, they've been all over the news, but rather than run a traditional IPO process. What a SPAC is, is it allows a shell, it forms a shell company. And it allows businesses to go public without, without the normal disclosures of an IPO process, right?

• 6:45Logan Bartlett?

  And so you're able to circumvent all the traditional filing and paperwork and IPO roadshow and all of that stuff. Now, it's come under fire for all the kind of usury elements associated with it. The, the main one being that there's enormous financial benefit to people that start SPACs. And so that's why you see Shaquille O'Neal and Jay-Z and Martha Stewart and Donald Trump. And everyone kind of forming SPACs because it's insanely financially beneficial to them. And so that's been issue number one. Issue number two is that you're able, they exist under a safe harbor, right? And so they're able to make financial projections in a way that traditional IPO companies or traditional public businesses aren't.

• 7:30Logan Bartlett?

  And so there's no recourse at all associated with the projections that they make. And so you've seen these companies go public and say, hey, we're going to be, you know, we're going to be doing $10 trillion of revenue in 2026, right? And they can say whatever they want and there's no issue with that, right? And so that's been kind of the two things that have been criticized from a SPAC standpoint as well. Now, there's just a general adverse selection that go along with the companies that are choosing to go public with SPAC. That said, right, all those caveats, there is clearly an inefficiency that exists between the private market and what VCs are willing to fund, the traditional IPO process and the public markets, right?

• 8:15Logan Bartlett?

  And so OnlyFans is a perfect example where traditional VCs won't back this. But I guarantee at this company, we're able to get public. There would be tons of retail investors and even some public institutions that will actually back it. And so we've, we've had success with SPACs. DraftKings was one that similarly had some regulatory concerns or issues associated with it, right? And there was an opportunity in the public markets that people realized, hey, public market investors are willing to take this level of risk that maybe a traditional IPO banker wouldn't take on. And so from a product standpoint, I think this makes a ton of sense for a SPAC. Like this actually could be the, at the tail end of the SPAC boom, we might get the perfect SPAC to go public here.

• 9:01Speaker 02

  But it speaks to a bigger point, right? Which is like, it's sort of ridiculous that ventures become the default funding mechanism for all sorts of businesses that for a variety of reasons, right? Not just because of, of LP issues, but also business model risk, all sorts of different reasons, perhaps ought not to be raising from venture to begin with. Like, to me, this is, as much as it is a vindication of the SPAC model at the exact end of the SPAC boom, I think you're right, Logan. It's also a bigger point that it's ridiculous that OnlyFans went to go raise from traditional VCs in the first place. Like, that doesn't even pass first muster as the place where that business, which is like, what is it, owned by like, three people, right? They're just pulling out tons of cash annually.

• 9:44Speaker 02

  Doesn't really make sense for them to go to venture to begin with in some ways. This is, feels like ought to be a private equity deal.

• 9:50Logan Bartlett?

  Nikita, you looked at the business. What was the reason at all for them to raise money? Was it just purely secondary to cash out one of the founders?

• 9:58Speaker 01

  Yeah, so as far as I know, it was, I mean, the company was acquired by a, like, famous kind of pornographer, Leonid Redvinsky. He bought it from this guy in the UK, Guy Stokely. Oh, no, no, he bought it from Tim Stokely. And he, I think he was the majority owner. And the company is, I mean, if you look at the free cash flow numbers, they're printing money. And there was absolutely, I think, no reason for them to need money for fundraising. But they, I think- They also did need some like institutional validation. They were trying to build like a growth and product team.

• 10:41Speaker 01

  Because, I mean, the product is very rudimentary. It's, I mean, I don't know how long you guys spend on OnlyFans. Couple hours a day. Yeah, same. But from the, I heard that they were trying to recruit product managers because it's a web-based product. The content creators apparently aren't happy with it. And so I think getting institutional validation, actually building a product team was kind of their aim.

• 11:09Speaker 01

  OnlyFans in general is like a very interesting product because like many other creator platforms, the vast majority of the money goes to a handful of creators. But all those creators aren't actually interacting with their fans. There's actually call centers effectively where they have like these kind of operators talking to the, it's kind of very dystopian if you think about it.

• 11:33Speaker 02

  That's the saddest job in the world. I can't imagine a sadder job.

• 11:36Speaker 01

  Yeah, you think you're talking to this beautiful woman, but you're really talking to some guy in a call center. A lot of them, I think, happen to be actually in like Nigeria.

• 11:47Speaker 01

  And that's how these top creators manage their scale.

• 11:51Speaker 02

  I can't imagine a sadder job than being like an L1 support engineer in a call center dealing with, I hate to say it, but like aggressively horny guys trying to talk to, befriend women on OnlyFans.

• 12:03Speaker 01

  And trying to get tips out of you.

• 12:06Speaker 02

  By trying to keep you on the hook. I like, I have to be honest with you, I would basically do any job before that. That's like the worst job in the world.

• 12:14Speaker 01

  That was actually my first job in high school was OnlyFans operator for.

• 12:20Speaker 02

  There will be some day, somebody will say that, like the ice cream scooping of years gone by will turn into, yeah, I started my career as an OnlyFans level one support engineer.

• 12:29Speaker 01

  That's how you break it, break into the valley.

• 12:32Logan Bartlett?

  I actually have tears in my eyes from laughing. I, you know, I mean, it is interesting. Like when the Axios had the data, 300 creators on the platform do own, do earn over a million dollars a year, right? And so like, it's interesting where, when the platform itself is pornography, you know, everyone runs away from it, but the number of things in the internet infrastructure that has been enabled by pornography is like, if you remember back in the day, Akamai, which was kind of the original CDN, was, I think some of the stats they had around IPO was like 60% was, was porn traffic on their, on their website, right? And like a bunch of the video streaming technology that's, that exists on the web today was used for

• 13:13Logan Bartlett?

  like nefarious purposes. And so when it's at the infrastructure level, right? For the most part, people are more willing to, to allow it to be. But when it starts to move to the application level, I think people have more of a problem with it. I think it's interesting in general that Silicon Valley gets to serve as the arbiter in a lot of ways of morality, right? And I'm surprised there isn't a bigger fund that's out there saying, hey, we don't care if it's cannabis, we don't care if it's gambling, we don't care if it's pornography, right? I'm surprised that there isn't. I know there's one or two that have popped up, but there's not one that's gone big and mainstream and, you know, raised an SPV to invest in OnlyFans or something.

• 13:58Speaker 02

  Well, we know there are Vice Ventures and others who have started that model, but it is hard. Like a lot of institutional LPs, and I'm speaking not of our LPs, but certainly generally in the space, tend to run more conservative. So it's not a huge shock. I mean, I think it's not a huge shock someone hasn't scaled it.

• 14:16Speaker 01

  I think it's, it's interesting though, how a lot of these decisions to pass on certain types of businesses, it's, it's only the perception that matters of the business. Many consumer companies grew from things that may have been in the gray area of the law. Like YouTube was primarily pirated content at the beginning. And investors kind of looked the other way as they sort of tried to fix that problem. And I don't think they ever did fix that problem until after the acquisition. So it's interesting how, I think investors navigate these kind of gray areas of, of business. But when it's overtly, you know, pornography, I, there's, I can see why they can't do these sort of deals.

• 15:01Speaker 02

  And by the way, Logan, to your point, far from like there being more scrutiny on Silicon Valley as the arbiter of morality, it feels as though, if anything, there's a public clamoring. Like, in a world where you're not getting leadership from traditional political entities, and in a world where there aren't community entities that provide guidance for people, I can't say it's hugely shocking people want to enact their version of morality via payment processors and advertising networks, et cetera, et cetera. It's sad. Like, I don't love that that's the way that things have trended. But I'm not hugely shocked that in the absence of everything else, people look to what are some of the strongest institutions we have in the valley and ask those to provide moral leadership for them.

• 15:43Logan Bartlett?

  This week, the SEC announced that they were charging three Twilio engineers with insider trading from the early days of COVID. So this happened between March and May 2020. Three software engineers accessed financial information from the company's databases. Through a private group chat, they shared this information with others and their family, who then executed trades before Twilio announced first quarter earnings. Twilio's stock skyrocketed with the earnings and way past estimates, and the group was able to generate over $1 million in profit. So it's interesting, the whole story itself, the fact that it's coming out right now. Nikita, you've worked in the heart of Silicon Valley

• 16:28Logan Bartlett?

  at some of these companies. Maybe talk a little bit about the temptation that exists for people to trade on insider information.

• 16:34Speaker 01

  Insider trading is like pretty ubiquitous, like in biotech, because often there's an FDA trial that comes out, or people know about it before what the results are before the public. But I think it's probably more common in tech, because you have such a large number of people with access to performance dashboards, since it's in the ethos of Silicon Valley to have transparency across a company. So

• 17:02Speaker 01

  I think it's probably happening more than we think. And it's also probably pretty blurry, too, because sometimes you have domain expertise. You're mingling with people working at these companies. In the case of this Twilio insider trade, though, it seems like they were pretty culpable of insider trading. I mean, one of the people involved literally sent a message that said millionaire right after the stock jumped. So I think it's a little bit less defensible in this case. But I certainly think there's some unfair advantages being in Silicon Valley and trading tech stocks.

• 17:45Speaker 02

  Isn't it nice for the SEC that people do crimes and then immediately send messages like, "Boy, do I love doing crimes."

• 17:51Logan Bartlett?

  So it's hard to know in Silicon Valley, often with these software companies, actually how businesses are going to trade with their earnings. Just because you beat on bookings, numbers, or revenue number, net income, or whatever it is, it doesn't necessarily mean that the stock's going to trade up because the CEO is maybe going to guide to some lower number, right? So it totally makes sense that in biotech, where things are much more volatile, and an FDA approval could mean, hey, our stock's going to spike immediately. It makes sense that people actually can correlate individual data points with stock trading, right? Versus in the software market, there's much more ambiguity associated with how the stock is actually going to trade.

• 18:37Logan Bartlett?

  And so this was interesting, where it's this unique moment in time in COVID, where no one knew what to expect. And obviously, we know a bunch of companies now benefited from everything that was going on. So it's interesting, these people had this like unique sliver in time that they were able to act on it. But I have to assume that rank-and-file employees that get access to some financial information aren't going to know how that's going to impact the stock price long-term.

• 19:04Speaker 01

  I actually remember the day that the Twilio skyrocketed. I think it went up almost 100%. So the option contracts probably were up thousands of percent. And I actually looked up what their traffic data was using SimilarWeb, which is like a domain traffic intelligence tool. And it's effectively public information. And I was thinking about making a trade there because I do trade options sometimes. But I had the same sort of thought process was is this priced in? Because I think with a lot of high-growth SaaS company or high-growth, any high-growth company,

• 19:47Speaker 01

  the Wall Street does expect blowouts each time. And if they don't go way above expectations, so then the stock won't like have that spike.

• 20:01Speaker 01

  And so I withheld from making that trade. And I'm sure they were probably also kind of on the fence. I'm sure it was probably a small position, which makes me kind of surprised that they would take that risk because apparently like from the SEC report, they made a million dollars in profits. So it was probably a pretty small option trade, like we're talking like $25,000 to $50,000. Because I think those calls probably went up 20x. I'm shocked that they would take that risk, that professional risk. And I mean, they were doing fine as is just with their own employee grants. So why would they?

• 20:45Speaker 01

  The trade off doesn't really make sense to me.

• 20:47Speaker 02

  Yeah, I think that's the best point, Nikita. You know, to me, it's a real head scratcher. If you're going to take that kind of risk, and to be clear, you know, nobody should. But if you were going to take that kind of risk, you should do it for like a life-changing amount of money. You certainly shouldn't do it for like the amount of money you could make as like a mid-level Google engineer in like 18 months to two years, right? Like that's, that's kind of a moment where you're like, really? You're going to throw away your life for two years of comp?

• 21:16Logan Bartlett?

  That's what's interesting. I feel like just the risk reward here is so off. And Charlie Munger has a quote that the cash register did more for human morality than the congregational church. And it's an interesting concept that like the ability to audit things in a meaningful way is makes people more moral because they think they're going to get caught, right? Are the risks worth the trade off when you see something sitting there? And it's just interesting that these people would be say be willing to say, hey, the upside of, let's say they made a million dollars here and at most could have made, what, two, but they're probably making $500,000 as is as a Twilio software engineer. And so it's just, it's fascinating that these people were willing to taste this level of

• 22:00Logan Bartlett?

  career risk for that level of upside.

• 22:03Speaker 01

  I mean, you see it across all industries too. I mean, a lot of government corruption scandals, if they, you know, like there's a mayor or a some official where they, for a few hundred thousand dollars, they'll bet their entire political career. So I think it's interesting because everything is incremental when you, when you're, you know, trying to build your, your net worth. And so I can see the allure of why people get drawn into these sort of situations. But having said that, I mean, the option order book is public. So it's like, it's just as public as like the blockchain.

• 22:46Speaker 01

  So I, I wonder how like they maybe didn't realize that, how, how easy it is to see when a, when a trade, because I've actually paid for that service before. There's a, is a service called Flow algo that can tell you the, the large option trades that are taking place. And it's obvious when something seems like, well, at least it's obvious when something's fishy because you could see a large trade opened right before earnings, like five minutes before for huge amounts of money. So certainly the SEC looks into those things.

• 23:21Logan Bartlett?

  Totally. Yeah, it's interesting. I mean, I have to assume, I don't know what your guys' perspective is on how often this happens, right? If you look at those options, as you mentioned, or like before a big M and A, there's almost always, people don't like to talk about this, but there's always some level of activity spike that happens, right? And you just assume that like, there's no way of chasing all this down and all the specific things. And so in aggregate, it's just not meaningful enough to prosecute. And so I guess what's interesting here is, I wonder how red-handed these people actually got caught, right? Like, what was the audit trail that led them to this? Because clearly it was a family member doing it, right?

• 24:06Logan Bartlett?

  But they must have done something just so egregiously stupid to get caught red-handed here. Hey, just wanted to jump in here for a second. And first, thank everyone that already listens. We really appreciate all the support. It's been fun doing this over the last 10 weeks. And we were thankful that people want to listen to us riff and joke around about the tech news every week. Second, and ask just to like, subscribe, leave a review, all that stuff, share with a friend. It does actually impact the rankings and our ability to continue to rise and that kind of stuff. And so we really appreciate anyone that does that.

• 24:48Logan Bartlett?

  And also, I did want to put in a quick plug. We are doing now video centric stuff. So if you listen on Apple Podcasts or anyone that doesn't have video centric, we're now doing video on Spotify and YouTube. So you should check that out. We also have an Instagram and TikTok in which we're posting highlights every week too. And so if you want to find that stuff, feel free to go to our website. It's threecartoonavatars.com and you can find all that. Thanks, everyone, for doing what you've done. And yeah, look forward to bringing you more episodes. And here's a quick clip from episode seven of Three Cartoon Avatars that sets up the context of the conversation with Ryan Breslow, which you're about to hear.

• 25:30Speaker 02

  I will say, if we keep talking about him, one more week of talking about Ryan, we have to call him the fourth cartoon avatar. We've basically rolled out the red carpet.

• 25:37Logan Bartlett?

  Do you think we can get him to switch his avatar? I mean, I would be, I would welcome him on at some point if we can get him at least to switch his cartoon avatar.

• 25:47Speaker 02

  Ryan, we will make a cartoon for you and get you on the pod, please. First guest has to be. Well, this week, we're excited to have one of our very first guests, a man who needs no introduction. But in case people are not aware, Ryan Breslow is the founder of a one-click checkout company, Bolt, was most recently valued at 14 billion. Ryan has a little bit of notoriety, not only because of his role founding Bolt, but also because of his tweeting, which we'll talk about in a little bit, and his public advocacy for a variety of things, including a four-day work week, Monday through Thursday, Y Combinator not necessarily being worth it, allowing employees to exercise early stock options, his conscious culture nonprofit, and his community dance nonprofit, which spreads dance to students who are underserved.

• 26:32Speaker 02

  And most recently, people who listen to this have probably seen his most recent thread about Stripe and Y Combinator, the mob bosses of Silicon Valley. We'll definitely go into that a little bit more in detail. And Ryan, as a result, was basically, and Ryan, tell me if you agree with this, basically the main character of Silicon Valley for a week with that thread, and a bunch of other responses and threads that came off it again. And since you moved into an executive chairman position at Bolt, and you've launched a new startup called Love.com focused on solving the opioid crisis, that's a hell of a lot to accomplish. I'm sure I must have missed some things. You tell us, did we get it all right?

• 27:12Speaker 03

  You got most of it. That was great. Great to be here.

• 27:15Speaker 02

  We're really excited to have you on, and Logan and Ryan have been going back and forth a little bit, too.

• 27:19Logan Bartlett?

  Let me give a little bit of background on how this actually came to be. So I frequently make jokes on Twitter about things that are going on in the tech world. I do the best I can to avoid being, making jokes at the expense of founders and companies. It's not a great look, in my opinion, when you're a venture capitalist doing that. But I did, I did make a few jokes about the different things, some of the topics that Ryan was tweeting about. So on his original thread about YC and the mob bosses of Silicon Valley, I said, "I seriously wish..." Like in valley was that badass. One tweet when Kate Clark announced that there was love.com, there was.

• 28:05Logan Bartlett?

  Her title of the article was bolts Breslow teams with psychedelics founder on crypto pharma startup. And I said, this seems like tech Twitter bingo. And then the final one that started our back and forth on this was a few weeks ago. Brian's been a big public advocate for loans to startup employees to early exercise options. And with the market downturn, I said. Remember a few weeks ago when people were advocating for loans to employees to early exercise options? Then someone responded, people question mark. And I said, okay, well, one person and. And Ryan, actually, to his credit, sent me a DM and it was very mature in what he said. He said, just wanted to shoot you a note.

• 28:46Logan Bartlett?

  I'm wondering why you continue these tweets against me. I've recommended Redpoint to a lot of founders. There's been some negative sentiment built up and there's real implications. Always open to feedback and thoughts. And so we went back and forth for a little bit on that. And, and I said, hey, why don't we, why don't we talk about some of this stuff on the, on the podcast in general? So Ryan was kind enough to, to join us. So thanks, Ryan, for coming on.

• 29:12Speaker 03

  It's great to be here, Logan and team and excited to chat about all the above.

• 29:17Speaker 01

  So, Ryan, when, when you reached out to Logan, I mean, Logan's a professional ship poster. I, I don't think I take much, many of his tweets seriously. But I mean, during some of these other tweets, like the Stripe mob boss one, there were a couple of people actually genuinely like trying to attack you and dunk on you like Sean McGuire and stuff. Did, did you reach out to a lot of people that tried to kind of take you down?

• 29:40Speaker 03

  Well, actually, a lot of them reached out to me, funny enough. And they're like, you know, it's just Twitter. I hope you don't take that personally. And A genius. No. What? I would like never do that to somebody I cared about, who I considered a friend. And I consider a lot of those people friends. So it's a very interesting dynamic to kind of, you know, I like definitely spoke up about uh, something that I had experienced. So like you could say my tweet was an attack of sorts or at someone's expense. Like, you know, when you're, when someone you consider a friend is, is taking shots at your expense. Um, that's like a very, you know, personal thing.

• 30:23Speaker 03

  So, um, you know, I've tried to like, you know, there are people on the other side of these, of these comments. Right? Like if you're gonna say something, you better mean what you're gonna say. A real implications, you know, for their employees who are watching, for their, for their teammates, for their investors. And, uh, so I just like, I firmly believe that you have to mean what you say. Obviously there's a place for humor and I don't like, I don't take their responses too seriously either. Um, but I definitely like, like what's up, you know? Here, so.

• 30:55Speaker 01

  So maybe we could add some levity to the conversation. So your, your Twitter account has kind of exploded over the last, uh, like six months. I think you, you've got, you're at like, what? A hundred fifty thousand followers now?

• 31:06Logan Bartlett?

  It's almost more than all of us combined. Yeah, yeah. Nikita's carrying the weight, but now we, we have someone, uh, we have a real title belt holder here.

• 31:14Speaker 03

  Nikita, you've been crushing it.

• 31:16Speaker 01

  I've primarily shit posted my way, uh, to a hundred thousand. Um, I, I'm like, so what was your aim when you started tweeting? Cause I, I think you, it was like a kind of a recent thing that you started doing. Um, were you trying to build a brand with founders? Like what was the?

• 31:31Speaker 03

  Yeah, I, I think it's a few reasons, a few things. One is I had things that I really wanted to kind of share to a broader community. Um, and I've been helping so many founders. Like I spend, you know, a good chunk of my day just on calls with founders. And Have become a resource and so I'm like, I gotta get these thoughts down and out. And so that's why I wrote the book on fundraising. Uh, it's why I wrote the book on recruiting. Which I so many founders reach out to me is like become their, you know, their main guide for doing both of those things. And so I was just like, I gotta scale myself a little bit more. I'm repeating the same thing. So first is, I just wanted to get what's in here, out somehow.

• 32:16Speaker 03

  Um, and uh, it was very rewarding to do that. And then, yeah, like there's extraordinary benefit to having an audience for, from a purely business perspective. Like the amount of customers we've gotten at Bolt because founders are like, yo, I love your content. It's helped me so much. Like I just wanna use Bolt. Uh, without us having to pick up a phone or, or touch our sales team is, uh, has been remarkable. So it's like had extraordinary, you know, hard business impact as well.

• 32:49Speaker 01

  So, um, our style of tweeting is totally different.

• 32:53Logan Bartlett?

  It's actually the, the opposite ends of the spectrum. I think you guys are on the, the, we, and we have both ends of the internet Twitter right here.

• 33:01Speaker 01

  Yeah. And so, uh, my favorite, our, my favorite interaction that we had together on Twitter was, uh, you tweeted, uh, wanna grow five times faster, go on a meditation retreat. And then I replied, my wife went on a meditation retreat with her masseuse and never came back.

• 33:16Speaker 03

  I remember that. That was a good one. I got like hundreds of retweets and likes. That was great.

• 33:24Logan Bartlett?

  Hey, so, uh, so one, one question was just on, um, the, uh, the original one, I think that sort of brought so much, uh, notoriety and attention was the, the, uh, Stripe and the mob bosses of Silicon Valley thread. Um, and you know, I, in full disclosure, uh, Zach and I are investors in Stripe. So I guess we're, we're card carrying members of the, uh, of the mob. So I would tread lightly with, uh, with us given, you know, uh, what happens with people that get on the wrong side of the mob in general. But, um, I'd heard, i- is this something you had been sitting on for a while? That like this was something you had thought of, uh, a while back and maybe drafted out and were sort of waiting, uh, to press publish on?

• 34:08Speaker 03

  Yeah, I wrote it like two, three years ago. Um, and I was just like rummaging through my docs and my files. I'm like, wow, like now may be the right time to, to publish this. Um, and so I just, I just decided, hey, like, and I always thought I'm like, I'm gonna, I'm gonna publish this when we're, you know, I've kind of reached escape velocity as a business. Where like, I know we're going to absolutely crush it. And so, you know, a lot of people afterwards are trying to comment on our metrics and our business. And we're building such a phenomenal business. I'm like, not worried about that.

• 34:50Logan Bartlett?

  Totally.

• 34:51Speaker 03

  At all. And so it's just like, I've got, you know, great kind of loyal backers. Our business is absolutely crushing it. And, um, you know, these are things that I still kind of continued to see. And so, uh, decided it was time to post it.

• 35:07Logan Bartlett?

  Was it, was it by the way, uh, that you were like, hey, I, I'm going to be out the door. Cause I assume you knew at that when you press send on it, you knew you were going to step down. Everyone wanted to speculate that like, oh my gosh, the board came to him and, and I was like, there's no way that's how it played out that quickly. So was it that you knew you were gonna, you were gonna, uh, move to the, step up to the executive chairman, as you like to say, and it made the most sense to press send right, uh, right before all that happened?

• 35:38Speaker 03

  Yeah, I think, you know, I think that like the timing was very coincidental. We were just kind of finishing our discussions. Internally, this was my move that I initiated. I'm like, I've got to go just effectively close more deals. We sign, we've signed a lot of business in the last six months. And that's with me still having like eight direct reports. And I'm like, I just got to focus a hundred percent on deals as a leader. And so Maju had gotten more and more direct reports. It's one of the best leaders I've ever worked with in my career. Um, and probably will ever work with. And I'm just like, just the rest of the company should report into you and I should just go focus on growth and, and closing business. So, um,

• 36:26Speaker 03

  And I, you know, when the Stripe thing came out, uh, we were, the modding thing was being planned to take effect. And everyone was like, why don't you just push it out? And I was like, no, like, I, you know, I actually think it like, you know, people will speculate and it'll create a bit of a frenzy and like, you know, I think, uh, it kind of solidifies that you have to go direct to the source for the truth. Right? So I kind of want to train the audience. Like, if you want to know what's happening with Bolt, you know, you come to us and we'll give you the truth and, and we're not going to play into the kind of media speculation. And so I don't, I don't know. It was, it wasn't much more thought out than that.

• 37:11Speaker 02

  What prompted the initial, uh, the initial threat? Like you wrote it years ago. Like, what was the moment where you, where that crystallized for you?

• 37:20Speaker 03

  Um, yeah, it was just, I think, you know, if we had raised a couple successful rounds, it was hanging out back there. And, uh, just decided one day to do it. You know, I, so I firmly believe you have to speak your truth. Right? Um, I speak my truth to my company, to my team. I'm very transparent. And, um, I, in general, also, I don't love how a lot of things happen in Silicon Valley. Like, there's just a lot of ego. And just like all the time, you know, you're battling ego instead of building. With investors and, and, um, you know, it's just, it's unnecessary, gets in the way of building.

• 38:06Speaker 03

  You know, most founders, when they get to this stage, they're spending 90% of the time managing the egos on their board. Right? Versus operating and building.

• 38:15Speaker 02

  Ryan, I, I don't know what you mean. Nobody on this call has a big ego at all. That's, that's, that's a strange thing for you to say.

• 38:20Speaker 03

  That's why I came on. I'm like, these guys are the exception, you know?

• 38:25Speaker 02

  You know, the only low ego VCs in the entire valley. And coincidentally, we're all on this one call right now.

• 38:30Logan Bartlett?

  Yeah, exactly. Just some, just some mob bosses hanging out here. And, uh, yeah, low egos.

• 38:36Speaker 01

  So Ryan, but what, what motivates every one click checkout CEO to have such a polarizing, uh, Twitter personality?

• 38:44Speaker 03

  Good question, you know, part of the job description.

• 38:49Speaker 03

  It's kind of a crazy business, right? To say, we're gonna do one click checkout, you know?

• 38:57Speaker 03

  And, and everyone's like, but you know, what does that mean? You're like, we're just gonna do one click checkout. Very sophisticated to do behind the scenes. So this is a hard, this is a very hard company to explain to people. You know, because we go around San Jose Road and we'd be like, we're doing one click checkout. And people be like, what? You know, you have no clue what you're talking about. And it's a, it's an extraordinary opportunity. I mean, and it takes really hard tech to build. And so it's a confusing business to understand. Because it's very simple at the surface, very complex behind the scenes, very complex market dynamics. Nobody understands where you fit in the, in the ecosystem.

• 39:41Speaker 03

  Um, and so you have to kind of have this polarity of a very serious side, right? And then there's also kind of like, very like, uh, you have to have this marketing side of you that just says, we're doing one click checkout. It's what we do, you know, very simple.

• 40:00Speaker 02

  But why do you think it is that like the two most prominent, right? Two of the most prominent like CEOs on Twitter both were one click checkout? It's kind of like a strange coincidence, isn't it?

• 40:11Speaker 03

  It, it is, you know, I was, I was, I'm not gonna lie. I was a bit inspired by Dom early on. Because he got a lot of following and a lot of attention. Like he was the talk of the town. And I had been working on this business for like six years, leading up to that. And like, nobody knew what we did and no one was talking about us. And so if his business did really well.

• 40:42Speaker 03

  Right? He would be the talk of the town. Um, so he was talking the talk, but not walking the walk, right? And I was walking the walk, but I wasn't talking the talk and no one knew about us. So I had, my team was like, they were telling me like, Ryan, like we have this other company. We have way more customers, way more everything, but they're getting all the attention. Why don't we have any attention? And I'm like, guys, like, we're gonna walk the walk, but when we're ready to talk the talk, like, I'll step it up. And so they're like, you know, they would keep pestering me like, why don't we make more noise? So one day, like five or six months ago, I was like, all right, you want us to make noise? I'm gonna make noise. And I sat down and I'm just like, I'm gonna figure out the Twitter thing.

• 41:27Speaker 03

  And we just, it was just a full set.

• 41:30Speaker 01

  And, uh, so I mean, do you have any comments on, I'm sure you read the information article about how fast is struggling to, uh, raise, uh, their round at a billion valuation, they're having layoffs. Is this a macro thing happening across, uh, all one-click checkout companies?

• 41:47Speaker 03

  Is that a roundabout way of asking how we're doing?

• 41:51Speaker 02

  I, I mean, I

• 41:54Speaker 02

  Wait, did you feel that was routed down client? Cause we could be more direct.

• 41:58Speaker 03

  Yeah. How are you guys doing? We're, we're absolutely crushing it. We're signing more customers every month than like the last several months. I don't know if you saw, but we, we just post Fanatics, who is one of the fastest growing online businesses in the world. Um, has, you know, mid tens of millions of shoppers that are going to be joining our network very soon. Um, we have, you know, basically a dozen mega deals that haven't gone live yet that are all going live. So you wonder why, you know, we're not raising from, from, from dumb money. You know, if you look at investors in our last round, like BlackRock, HIG, Schoenfeld, like these

• 42:42Speaker 03

  very conservative institutions that most people told me would never give us their money. You know, when you actually peel back the onion in our business. We're building an extraordinary business. We have tech that's almost impossible to replicate, right? Like so many companies have tried to do checkout, all have failed effectively, except for us. We can actually scale a checkout flow. We can take over checkout flow, cross almost any tech stack, implement it and do it for some of the largest brands on earth.

• 43:10Speaker 02

  Ryan, if you're, if you're signing all the platforms and you have all the brands, like, I'm just curious. You have the products, you have the customers. Did it frustrate you that you felt like the other competitor, we don't have to say the name, but the other competitor was getting more attention online?

• 43:26Speaker 03

  I mean, it definitely woke me up to like, you know, there is some value, business value to attention, right? Because they were actually getting business. So we had to intercept a lot of deals and say, no, no, we also exist, right? And when you go through a technical RFP, we'd crush it, but we needed to be in the door with, with as many businesses as possible. So that's what I realized is we have to be known. We have to be able to get a conversation with anybody. And that's what I started doing on Twitter and it's worked amazing.

• 44:01Logan Bartlett?

  No, it's really, it's really impressive how quickly you've, you've grown your presence and following and, uh, and all that. Um, the, the, the one that we were talking about earlier, the, the mob, uh, bosses thing. I mean, I love the title and branding around it. I, uh, so in terms of the specific things that you were, that you think about, I, I was mostly intrigued. Clearly it's great PR, right? And branding and all of that, like having a foe and punching up, uh, against the Silicon Valley. Like it's, it's such a galvanizing story and I think that's why you got so many people, uh, so excited about it.

• 44:40Logan Bartlett?

  But one of the, like, as the specific points themselves, um, I guess I'm interested, uh, so you, you said like not getting into YC was the first one, but then ultimately they invited you, uh, they did invite you in, right?

• 44:55Speaker 03

  To reapply, to reapply again.

• 44:57Logan Bartlett?

  You had to reapply?

• 44:58Speaker 03

  To get a business update, yeah.

• 45:00Logan Bartlett?

  But they invited you, right? Or they wanted you to come on?

• 45:03Speaker 03

  Not to join, they just said, you know, we liked your company, come back and give us an update and we'll reconsider you.

• 45:11Logan Bartlett?

  Got it. Okay. And then the Hacker News upvoting thing, like, you know, Hacker News is a, is a, that's a black box. I know there was someone that responded in very specific like timestamps and hey, you're an enterprise company and we don't like enterprise companies on Hacker News. And I know, whatever. Like, I don't even want to get into that. The one that I'm most, I guess, in the backing of Fast, that was, you know, we don't need to talk about them specifically, but supporting a competitor sort of seems like, I don't know, not mob tactics to some extent. Like, it's almost, if, why would they enable a competitor? So I guess I'm interested in that. But the one I'm most interested in is the, the competition

• 45:56Logan Bartlett?

  and blocking out of fundraising, right? Because I think to some extent, like, of all the points you made, that's the one that I think rang the most true in terms of like, I could totally see that. I mean, it happens all the time, right? People say, hey, no, I don't want you to back XYZ thing. And so I actually believe all this probably happened in some way. Do you, do you view that as like, uh, yeah, is that good business and just like a strategic move? Or is there something more malicious behind it in your mind?

• 46:32Speaker 03

  I would say that it is more of a, just a reality that exists than an ethical or unethical thing, or a good or a bad thing. But they made, they're very intentional to get all the kind of tier one Silicon Valley investors in, even for small checks.

• 46:53Logan Bartlett?

  Redpoint, General Catalyst, all the really important ones.

• 46:56Speaker 03

  All the important ones, right?

• 46:58Logan Bartlett?

  Well, there was one tier one listed in that sentence.

• 47:00Speaker 03

  Yeah, everyone's in Stripe somewhere or another. So.

• 47:06Speaker 03

  You know, I like I'm pretty good at fundraising. I have a remarkable business. I wasn't able to raise a single dollar on Sand Hill Road. I've I've still I've been there a hundred times, never raised a dollar on Sand Hill Road. Okay, I'm not complaining like we still absolutely crush it and have raised tons of money. Um, but it just took, you know, I had to go to other ends of the earth to raise the money. Um, and I did, and we were able to succeed. You know, and it made me a much stronger fundraiser, made me much more resilient as a founder.

• 47:40Speaker 01

  Do you think the strategy was conscious? Because when I raised my first round of funding, I think I got about 50% coverage of Sand Hill Road, and that wasn't even conscious. I was just filling up the round. I had Red Point, Greylock, Founder's Fund. Uh, basically everyone. Um, and I, I mean, I think it's just like a natural part of filling up a round as you, you know, you seek out people who will invest.

• 48:03Speaker 03

  Right. I think it's it's both conscious and unconscious. Some of it happens unconsciously. I'll tell you, every founder thinks about, oh, I'm blocking out investors from my competition. So it's very, it's very conscious. Like, I bet you thought about that when you got all these people involved and probably wanted to have as many logos involved. And there's a bit of a like the VCs all kind of go in on who they think the winner is going to be. And by doing that, you know, together, they kind of block out competition and increase their, you know, odds of success. So it's just a dynamic that happens, right? Whether it is conscious, unconscious, ethical, unethical.

• 48:49Logan Bartlett?

  That's interesting. I I don't know if um, if I think it's as conspiratorial as it is. Uh, there's definitely an insiders group, right? Uh, like I, I, there's, there's a cool kids' club and uh, there's definitely a lot of people that are on the inside and have a ton of soft influence, right? And so I don't know if it's uh, how much it is, you know, soft diplomacy versus like it's stick related to it, but there, there's definitely truth to this like cool kids' group, right?

• 49:18Speaker 03

  I mean, that's why it's controversial, right? Things that are have truth are controversial. So if it was completely phony, it wouldn't have gotten all this attention.

• 49:27Speaker 02

  Do you think that's true? Do you think that things, if you think if it was completely phony, people wouldn't have given it attention?

• 49:34Speaker 03

  I think, yeah, I think it rang true to a lot of people. That's why it was so emotional, right? That's why, why do you think I got so much hate response? You know, it was like, really hit people at their core, like it kind of challenged their identity in a way. And so, yeah.

• 49:54Logan Bartlett?

  So, the other thing that got, that got attention was the early exercise point. And that's where we started going back and forth. And I would say, I found a broad passion for people that went through the last downturn, that were like really passionate about the fact that like, hey, this is a bad idea. And I talk to people that they're, they went bankrupt or their coworkers went bankrupt over this. And so, I guess reasonable minds could disagree about this point, as you and I have. Has, has your mind changed at all over the course of, you know, the last, whatever, three months? As the markets turned down, since maybe when you originally published it? Has, has it changed your perspective on this? Or do you feel just as strongly as you did when you posted it?

• 50:38Speaker 03

  No, I, I feel just as strongly, I understand the other perspective on this topic. You know, I think that I, um, a few things. So, one, early exercise is, should be done at every company. There's, there's two distinct things, early exercise and there's a loans, right? So, every company should allow early exercise. Um, to let employee decide if they want to buy in with their cash on hand and receive all the tremendous tax benefits that come with that. It's usually preserved for founders and executives.

• 51:13Logan Bartlett?

  But let's get into the loan component, because that's actually pretty useful.

• 51:16Speaker 03

  Yeah, so, I generally think that, like, I see loans as a...

• 51:25Speaker 03

  As a privileged financial instrument, right? And so if you can get loans to like hardworking, good people who are diligent with their money, who are earning, right, who are high earners, you know, they can make intelligent decisions when they have, you know, special opportunities to invest their money, right? And so like we're talking about tech workers here. Okay. Our workers are very like high paid, they're top talent. They could go work at any company or we have an exceptionally high talent bar. So we're not talking about an uneducated population or population that's under financial hurt.

• 52:09Speaker 03

  So the question that this begs is, do we trust in them enough to make an educated decision on what to do with $50,000 and or $10,000, right? Or whatever the amount is. And, you know, are they willing to take a loan out for for some number, usually in the tens of thousands in order to multiply their upside by a significant amount?

• 52:36Logan Bartlett?

  I saw the $300 stipend for financial advisors and I guess inherently that can they can whoever they're paying, right? Like it's probably not a sophisticated financial advisor that's been through a tech downturn and can speak to broad based tech multiples and all that. And so I guess the the pushback that I've gotten or when people have talked about it is can they actually internalize the risk? They're taking on leverage, right? And can they actually internalize the risk of the last 12 years? Listen, I'm 34 years old, like the last 14 years has been all up into the right and I've never seen these bankruptcies and I spend all day looking at companies, right? And so can the average rank and file person actually internalize that and take on the

• 53:21Logan Bartlett?

  risk when there's personal recourse?

• 53:24Speaker 03

  Yeah, and you know, I believe in empowering the individual to make their own educated decisions. Give them as much information as we possibly can. We wrote all the risks of the business, like we sat down as an executive team and wrote out all the business risks. Even the most extreme edge cases. And said, you get to make a decision. And because I, if I were in your shoes, that's what I'd want. Right? And so this is a golden rule. All right, I, I only, this, this is hard for me to do. Like to get the board to buy into it, to get legally done. This is, this is kind of new, charting new territory. Uh, but I did it because I'm like, if I'm an employee, I, I would want this option.

• 54:08Logan Bartlett?

  Did you get any pushback? You said charting new territory, like, uh, you know, Ted Wain from Cowboy wrote like a blog post about it. And obviously there's people through the bubble. Did you get any pushback from people that had seen this in the la, or was, was most of the pushback from, you know, paperwork related stuff?

• 54:25Speaker 03

  Yeah, most of the pushback was paperwork related. It was a lot of work to do. Right? And you have to, you have to run a tender offer. We, we did it through like a third party firm that ran a proper tender offer. So we did this as by the book as you can. It's a hard thing for us to pull off. We put a lot of work into it. Another thing that people don't realize is you're only taking a loan on the 409A price. And our 409A to preferred, uh, value has had a huge gap. And that gap narrows later, but up until you're like series E, you're going to have a big gap. Right? And so you're not taking a loan on the full value. You're taking a loan on your 409A.

• 55:09Speaker 03

  So you have, most companies, you have a, you have 5X coverage.

• 55:14Speaker 01

  But do you think, do you think the environment has changed? Cause like, uh, I mean, maybe even three months ago, a typical fintech company was trading at 40X revenue. But as of this last down, like going through this downturn, like many are, you know, way below that. And potentially the, the, uh, the real value of the preferred shares today of many fintech companies are, might be below the FMVs. So you, do you think that fintech companies should maybe, uh, encourage, uh, their employees to, uh, exercise caution with exercising right now?

• 55:49Speaker 03

  Of course. I mean, you need to go into these transactions eyes wide open. But the company should revalue their stock, right? Right size it, right size their 409A, and then allow employees to do the transaction.

• 56:06Logan Bartlett?

  Have you guys thought about that, by the way? Redoing like Instacart did, redoing 409A?

• 56:11Speaker 03

  We're always redoing our 409A. We've typically done it with funding rounds because we've had them so frequently that we're just doing it with each world, but yeah.

• 56:21Logan Bartlett?

  Just as a disclaimer, by the way, for people, so 409A is, is, is based off of, for the most part, uh, the last preferred round, and it's typically to Ryan's point, there is coverage ratio somewhere between, you know, 5X to 3X, 2X. It gets closer to one as you get closer to the IPO. And so that delta is kind of a spread that exists that should serve as a buffer from the, the risk ultimately. And so when they're raising as frequently as Bolt has, you have marked the markets that are happening over time. When the market downturns, uh, because one investor said this in December or January, right?

• 57:02Logan Bartlett?

  It doesn't necessarily mean that's what it would be in the public markets, which is what Nikita was alluding to.

• 57:07Speaker 03

  And all, all are totally fair points. So I think this is a nuanced issue, right? I don't, I was, I didn't think this was going to be a controversial tweet. I thought people would be like, oh, this is interesting, you know? But man, I thought the other ones were going to be, you know, I knew the other ones would be controversial. But this one, I had, I didn't expect it. It was just a casual tweet, you know, because we had done this like many months ago, like almost a year ago. It was like, oh, I need to write about it. You know, let others learn from it or, or use it if they find it interesting. So I just banged it out. I'm like, let's get this out to the world. And, uh, it was like, ended up being the most controversial.

• 57:46Logan Bartlett?

  I know you said you scheduled your tweets in advance, right? So you don't have to spend time on it. Do, do, do you like, did that go out? You like scheduled at the beginning of the month and that went out? And you like, look at your phone and it's just like, the world is set on fire and you have, you know, all these notifications and you're like, wait, which tweet was that? Uh, like why?

• 58:04Speaker 03

  Exactly. What are people so upset about now?

• 58:07Logan Bartlett?

  Yeah, like what? Wait, did I do a follow up mob post? No, wait. Uh, this is, it's the early exercise.

• 58:13Speaker 03

  What went out? What was that?

• 58:14Logan Bartlett?

  Yeah. Literally, reaction?

• 58:17Speaker 03

  100%.

• 58:19Speaker 03

  Like, I was out to dinner or something. I'm like, my phone's blowing up. I'm like, what's going on over here? Cause I knew, I knew the other ones were gonna be controversial. I was ready and I was, you know, on standby, but this one I was completely unprepared for.

• 58:32Logan Bartlett?

  That's funny. Um, well, good. You've been generous with your time.

• 58:35Speaker 02

  Ryan, obviously, we're all super appreciative for you joining us today.

• 58:38Logan Bartlett?

  Yeah, thank you for doing this. Anything that we didn't touch on, I know we didn't get to love.com and we didn't get to, uh, yeah, a bunch of other, uh, stuff that we would, Miami and your, the dance nonprofit, um, and, but anything else before we, before you hop that you wanted to, wanted to say, thanks for doing this.

• 58:56Speaker 03

  Of course. So thank you guys for having me. I thought this was a great conversation. It's what I'm looking to have more of. Um, and I think we just gotta help each other out more, you know? Like,

• 59:07Logan Bartlett?

  Totally.

• 59:07Speaker 03

  It means a lot to be the first guest appearance. Yeah, we made history here. Thanks, Ryan.

• 59:18Logan Bartlett?

  Thank you, everyone, for joining the 10th episode of Three Cartoon Avatars.

• 59:22Speaker 02

  Uh, yeah, we were in danger of getting the Four Cartoon Avatars territory, uh, and so we really toed the line on this one.

• 59:29Speaker 01

  I'm, I'm really genuinely shocked we've made it to 10 episodes. Uh, this, uh, show's been a complete net negative on all of our careers, so, uh, congratulations, guys. Uh, we've, we've made it very far.

• 59:42Speaker 03

  We did it. Mission accomplished.

• 59:44Logan Bartlett?

  We did it. Alright.