INDIE AUDIO

My friend, Michael Dempsey, Managing Partner at Compound, and I have an ongoing thread about the intersection of indie ideals and his areas of focus in deep tech. Most of these conversations happen over meals or online, so we decided to dive in a bit with the cameras on.Our conversation was as fun as it was wide ranging. I’ve watched for years as Michael has built Compound into a research focused, thesis-driven firm that has moved from the edges to the center of some of the hottest investment areas today. We get into details behind his early conviction around AI juggernauts like RunwayML and Wayve, to new themes they’re exploring in crypto and biology. Some quick takeaways and highlights to look for —There’s a trend of deep tech startups pursuing overly ambitious “narrative rotations” by constantly expanding into new areas, which Michael aptly calls a “Ponzi scheme of ambition.” This is driven by the need to justify raising large amounts of venture capital.His bias towards building one big business in a massive market rather than narrative expansions. For shelling point investments, like SpaceX and Palantir, the focus is on owning and expanding a principle or market over time, rather than narrative rotations.Compound’s approach to investment themes that are considered “too early or too ridiculous” with no real customers yet, and funding those contrarian opportunities.The value of developing specific year-by-year theses on how certain sectors will play out, acknowledging that 80% may be wrong but aiming for the 20% that are very right. You only really need to be right twice per fund.

We invited our friend, Reggie James, to help unpack what's happening in hardware and break down what's behind many of the recent negative viral product review videos currently hitting the internet. Reggie is a longtime friend to indie and prolific advisor to many of this new crop of hardware startups in market and in development. He cuts right to the point with strong opinions and spicy takes that may not be obvious to the casual observer. You'll also hear a view on technology and culture that extends far beyond any single device. In this one, we touch on —The disconnect between the world of venture capital/tech startups and the reality of many creatives/builders who don't view capital as a tool for building. With AI enabling code generation, this group could potentially produce venture-scale outcomes without relying on traditional funding.The tech industry has struggled with effectively communicating and branding themselves, especially after the era of Steve Jobs and Apple's lifestyle branding. This has led to insular narratives and misunderstandings around emerging technologies like crypto and AI.Physical products and hardware still hold importance for branding and communicating a clear lifestyle/use case, unlike software companies that often neglect this aspect. Successful hardware brands like Teenage Engineering have a distinct identity tied to their products.Devices like Humane's are attempting to break people's "addiction" to smartphones by offering an alternative that frees the user's hands and gaze, challenging the narcissistic nature of current mobile devices.Niche hardware products like USB Club's file-sharing network cater to specific communities (DJs, designers, etc.) and could enable new economic models by tying hardware to digital networks and data storage.There is a potential cultural shift happening around the perception of manufacturing/trade jobs, with younger generations being more open to these paths instead of defaulting to universities and white-collar work.

One of the most frequent requests we get is to hear directly from indie founders. Today's conversation is just that. And we did it in style. James Nord, founder of Fohr, has had a front row seat to indie having been one of the very first investments we made. In turn, I've had a front row seat for their growth from hundreds of thousands in revenue to 10s of millions.

I had the opportunity to know Christina Cacioppo early in her time at Union Square Ventures. Always whip-smart and ever curious, we found ourselves drawn to similar founders and edges of emerging markets. When her time at USV ended, we lost touch. She moved from NYC to San Francisco, took a job at Dropbox, and carried on with her post-VC life. Fast forward a few more years, and she’s leading one of the fastest-growing SaaS businesses as the co-founder and CEO of Vanta. A few weeks back, we got to reconnect for a long overdue catch up at Vanta’s office in San Francisco. Initially scheduled for 30 minutes, our conversation expanded into nearly two hours of lessons learned, hilarious anecdotes, and a genuine reconnection between two old friends.Although Vanta is not an indie portfolio company, you’ll quickly notice Christina’s indie-aligned approach to starting and scaling Vanta. From her quick product iteration, to early paying customers that led to early profitability, and intentional decisions around how and when to best capitalize the business. We cover it all. I’ve watched a bunch of Christina’s past interviews and feel like this one gets closest to the intensely whip-smart and soulful person she is.

A few weeks back, we had the unique opportunity to sit down with Tom Preston-Werner, co-founder and former CEO of Github. We met in a church he recently renovated into an incredible event space and rolled the cameras to capture our wide-ranging conversation. Over the better part of an hour, we covered his early years, the founding and scaling of Github prior to its acquisition by Microsoft for $7.5B, and so much more.