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• The challenges of managing finances and dealing with debt after receiving a large sum of money |
• The idea for Letter, a platform for managing finances and getting personalized advice, was born out of Drew's desire to help others who were in a similar situation |
• The timeline of Drew's idea for Letter, with it being conceived around 6 months after he became an employee at GoDaddy |
• The inspiration for Letter came from Drew's frustration with the current state of financial services, including the need for a more personalized and efficient way to manage finances |
• Drew's optimistic attitude and willingness to take risks, as seen in his decision to start Letter and his initial lack of funds to buy a house |
• The founder, Drew Wilson, discusses his startup, Letter, and its initial concept as a banking as a service platform |
• Letter pivoted to become a branded bank, targeting high net worth individuals |
• Drew Wilson recounts his four attempts to get into Y Combinator (YC) and the pitch he made to secure funding |
• The company's market approach and lack of cash were cited as reasons for its failure to succeed long-term |
• Drew Wilson mentions a failed investment deal with a billionaire investor who wanted to create a Western-themed bank |
• The company ultimately ran out of money and failed to secure additional funding to correct its market approach |
• Drew Wilson's startup bank failed to secure funding due to the brand's uncertainty and the 2023 market downturn |
• Wilson's previous startup, Plasso, was sold for an all-cash deal, providing a windfall |
• Wilson then invested in Letter, a business that ultimately resulted in a significant financial loss, estimated to be in the millions of dollars |
• Wilson reflects on the importance of cash flow versus a single windfall and the need to learn from experiences to achieve long-term success |
• Wilson expresses frustration with the repetitive tasks and challenges of entrepreneurship, particularly at his current age |
• Wilson's goal is to create another cash-generating business to secure his financial future. |
• Drew Wilson's frustration with modern tech and his own limitations as an inventor |
• His desire to create something big and impactful, but struggling to do so due to lack of connections and network |
• His involvement with Cortical Labs, a company building biological computers with human brains |
• The technology developed by Cortical Labs, including the CL1, a computer with a human brain as the CPU, and its potential applications and implications |
• Drew Wilson's role at Cortical Labs as a designer and his excitement about the project |
• Adam Stacoviak's reaction to the conversation being derailed by Drew Wilson's enthusiasm for Cortical Labs |
• Drew Wilson's early introduction to Cortical and his fascination with their biological computer technology |
• Drew's experience working on Cortical's design, including the website and CL1 design |
• Drew's dual roles as Head of Design at Clerk and Head of Commerce and Billing, as well as his side work on Cortical |
• Potential uses and benefits of Cortical's technology, including personalized medicine and drug testing |
• Drew's investment strategy and financial situation, including his investment in Letter and its impact on his wealth |
• Discussion of Drew's past struggles with his startup Letter and how he had to get a job |
• Drew's experience with investors in Letter and how they have more respect for him after the failed transaction |
• Drew's current projects, including Cortical and its CL1, and the return of ValioCon conference |
• ValioCon conference details, including its focus on giving non-traditional speakers a platform |
• Update on Clerk's new product, billing, and its features and benefits |
• Clerk's approach to authentication and user table management, and how it differs from competitors like Stripe |
• Clerk's UI allows for easy entitlement management for users and organizations |
• Clerk's has function automatically checks user roles and permissions |
• Clerk aims to take on administrative tasks for developers, starting with user records |
• Clerk plans to expand into other business verticals, including payments and commerce |
• Clerk's billing products are expected to become a major revenue source |
• Drew Wilson is working on a new project called Opacity, a tool for building and maintaining UI components |
• Opacity combines the features of Figma and GitHub, with a focus on version control and exportable code |
• Opacity allows designers and engineers to create components that can be easily extended and customized in code. |
• Opacity is a design tool for building UI components and design systems |
• It's similar to Figma, but focused on building and sharing design systems |
• Opacity allows for visual creation and editing of components, with features like Storybook-like functionality |
• The goal is to help designers and developers move away from Figma and onto Opacity for UI work |
• The company is bootstrapped and not looking for investment, with a focus on building a sustainable cash flow business |
**Adam Stacoviak:** Well, Drew Wilson is back in the house... It's been a while since you've been here. |
**Drew Wilson:** It has. |
**Adam Stacoviak:** I want to say -- gosh, I didn't even do my math here. Let me go search quickly, Drew Wilson... |
**Drew Wilson:** I think maybe 15 years, 12 years... I don't know, something like that. |
**Adam Stacoviak:** Okay, so we had you on Founders Talk a couple of times. Founders Talk was a show that I did solo, where I talked to founders, makers, builders, things like that... And it was Valio. Remember this name, Valio? |
**Drew Wilson:** Yeah. ValioCon, man. |
**Adam Stacoviak:** And part one and part two, for whatever reason. That was the name of the show. It was Drew Wilson / Valio - Part 1 and Valio - Part two. |
**Drew Wilson:** Oh, wow. Maybe we're talking pre-ValioCon, and we're talking back when I was making stuff under the name Valio, which would have been like 2009 or something. |
**Adam Stacoviak:** You know, I don't know. ValioCon was mentioned... You were at \[unintelligible 00:06:15.07\] |
**Drew Wilson:** Oh, dang. So that's probably like 2011. |
**Adam Stacoviak:** That's 2011, man. Yeah, that's right. Exactly. 2011. Pegged it. September 2011. |
**Drew Wilson:** Wow. |
**Adam Stacoviak:** Okay, so that was that show. That was Founders Talk. I think we had you on this show too at some point, but I don't know when. |
**Drew Wilson:** Yeah, I've been on here before, and I think -- it was a while ago. It was a couple years after that one, for sure. So maybe 2014 or 2013, something like that. |
**Adam Stacoviak:** Well, listen, I should have did my better research on when Drew was last on this podcast. It was ages ago. It was basically the beginning, it was basically the earliest of days... And it's been a lifetime. I think I literally haven't talked to you in a decade. |
**Drew Wilson:** It has been a while, man. |
**Adam Stacoviak:** At least a decade. I would say at least a decade. |
**Drew Wilson:** I think maybe one or two tweets, or something like that... |
**Adam Stacoviak:** Yeah, here and there. Nothing special. You got busy, though. |
**Drew Wilson:** Yeah, I got busy. |
**Adam Stacoviak:** You've always been the busiest person I know of, but you got really busy. |
**Drew Wilson:** Yeah, yeah. |
**Adam Stacoviak:** Like, you built a company and sold it busy. |
**Drew Wilson:** Yeah, yeah. That was fun. |
**Adam Stacoviak:** How does that feel? |
**Drew Wilson:** It was -- dude, it was incredible. It's like one of those -- I mean, it's not to the scale of "You're a billionaire now. You never have to work again." But it was one of those, like, you come up with an idea, you build it yourself, you're able to build a little company around it, you raise some money, ... |
**Adam Stacoviak:** Noteworthy scale size... Well, I think you may say that because you've always been a big dreamer. And it's easy, to some degree, when you're in that position to downplay your accomplishments. Would you agree with that? |
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