There's a few ontologies for describing the phases leaders -- and their startups -- go through, whether it's product-sales-etc. or pioneer to settler. In any case, as companies evolve, so must the leaders -- but can the same person transition across all these phases? When and when not; what are the qualities, criteria, and tradeoffs to be made? In this episode of the a16z Podcast, originally recorded as an internal hallway-style chat (pre pandemic!) a16z general partner Martin Casado, who co-founded but decided to remain CTO of Nicira -- and previously shared his own journey, lessons learned, and advice for founders about bringing in an external CEO and the question of "to CTO or not to CTO" -- and Armon Dadgar, co-founder (with Mitchell Hashimoto) and CTO of HashiCorp, chat with Sonal Chokshi about both managing their past psychology through these common questions and decisions. They also share their strategies on managing the specific tactics behind it all: Everything from the "dating" process of finding an external CEO to figuring out swim lanes; handling debates and decisions; who presents, who sells. And while the conversation is a brief glimpse into their longer personal journeys, there's lessons in it for startups and leaders of all kinds on the art of hiring and sales, managing credit and conflict, and more...

This episode features Q&As with two artists who are exploring crypto-powered auction sites and marketplaces – this is part of our ongoing series on the creator economy. The big picture is that emerging "tokenization" models, especially non-fungible tokens, or NFTs, are creating new ways for collectors and investors to buy, sell, and trade digital art. More broadly, these innovations open the door to the tokenization of any products or collectibles that can be captured and owned digitally.  Marketplaces powered by NFTs open up new revenue streams for creators, because anytime digital work is resold or their tokens traded on these platforms, no matter how many times, the creator gets a percentage of those secondary sales. It's all transparent and governed by code on the blockchain, and it’s a big shift in creator economies. Our first guest is one of the biggest names in crypto art, and one of the most mysterious. Murat Pak is the artist and industrial designer who created the AI-powered image sharing site Archillect. Pak has made it a policy to separate their personal identity from their online work, and prefers to keep their quote-unquote real identity hidden, so we conducted this interview by email and converted Pak’s answers to audio using text-to-speech software. As Pak has expressed in other interviews, it's really the work that matters. And we do know a lot about the work, Pak has sold more than 60 pieces of digital art this year on the auction site SuperRare, for more than $350,000. And that’s just one of the several platforms on which Pak’s work is sold.  In this Q&A, Pak talks with a16z's Zoran Basich about NFTs. These "non-fungible tokens" are unique assets that are not interchangeable. Dollar bills are fungible — each dollar bill is worth exactly the same as every other one. But works of art, for example, or any collectible, can be non-fungible — their value varies based on the market for that particular asset. With crypto, these assets carry digital ownership rights that can be easily exchanged. We start by discussing the whole concept of digital art, and why anyone would pay for something that (seemingly) can be easily copied. Our second interview is with Signe Pierce, a visual, digital, and performance artist whose work has appeared in major galleries in Paris, Los Angeles, and New York. She’s currently featuring her artwork on the creator marketplace Foundation. On that site, in addition to auction-style NFT markets, the price of tokens associated with individual works of art is something like you’d see on a stock market – the pricing is real-time, and dynamic and fluctuates according to demand by buyers, who might be investors, collectors, or fans. Signe discusses why she went from working exclusively with galleries to trying crypto marketplaces, how this move affects her work and her business, and how crypto could change the way she engages with her fans. She also offers advice for creators interested in getting into the world of crypto. She starts off by talking about how social media popularity several years ago opened her eyes to the idea of new monetization models for creators.