May 25, 2016 · 27m · 20vc
20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
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In this episode of The 20 Minute VC, host Harry Stebbings interviews former Facebook VP and Slow Ventures partner Sam Lessin about co-founding Fin, the concept of Artificial Artificial Intelligence (AAI), and why traditional ad-supported internet business models are failing.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 30.4% of the talking time here. How this is scored →
Harry as informed peer 2.8 Guest teaching 4.6 Guest disagreement 3.1 Harry pushing back 2.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 12:54 Dismissing Harry's Affiliate Business Model Proposal
Sam bluntly rejects Harry's idea of affiliate monetization for bots, calling it a worse form of advertising and directly challenging Harry to name a successful affiliate company.
Hardest push from Harry ▶ 12:54 Harry Proposing Affiliate Model Counter-ArgumentHarry actively intervenes in Sam's argument that bot business models do not exist by presenting an affiliate revenue suggestion for ordering fast food through Slack.
Biggest teaching moment ▶ 12:55 Dismantling the Viability of Affiliate ModelsSam educates Harry on why affiliate fees represent a weak foundation for tech businesses, pointing out that commerce is notoriously tough and collecting small fee margins fails long term.
Harry holds his own ▶ 16:09 Citing Retention Theory and Virtuous LoopsHarry demonstrates deep venture expertise by referencing Sarah Tavel's retention essay on virtuous loops, pressing Sam on how Fin builds engagement cycles into its product.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Sam Lessin's Background and Dual Role as Founder and VC | 2 | 2 | 1 | 1 | Harry opens with conversational questions about Sam's background as both a VC at Slow and founder at Fin. Sam explains how founder experience improves investor empathy and shares his perspective on managing startup emotional rollercoasters. The tone is collaborative and welcoming throughout. | |
| The Origin of Fin and Artificial Artificial Intelligence (AAI) | 2 | 5 | 3 | 2 | Sam dismisses pure AI as overhyped and fictitious, introducing his term Artificial Artificial Intelligence (AAI) which combines human and machine capabilities. Harry asks clarifying questions while Sam reframes the conversation around practical phone utility rather than AI buzzwords. | |
| Exciting Bot Use Cases and Memory Augmentation | 3 | 5 | 2 | 1 | Sam discusses his favorite bot use cases like memory augmentation and contextual restaurant recommendation. He contextualizes the current bot trend by recalling previous bot hype cycles like ActiveBuddy and SmarterChild on AIM. | |
| Business Models and Monetization for Bots and Conversational UI | 3 | 7 | 6 | 4 | Harry challenges Sam's claim about lack of bot business models by proposing an affiliate model. Sam aggressively shoots down the suggestion as a worse form of advertising and challenges Harry to name any durable affiliate business. Harry humorously concedes defeat. | |
| Engagement Metrics and the Internet's Failure as an Information Platform | 4 | 6 | 5 | 3 | Sam makes the bold claim that the internet has failed as an information platform and expresses disappointment in Wikipedia. Harry brings up Sarah Tavel's framework on virtuous retention loops, which Sam admits to only skimming before dodging the direct operational question about Fin's growth loops. | |
| Autonomous Vehicles, Resource Sharing, and Capitalism | 3 | 6 | 3 | 2 | Sam outlines macro predictions regarding autonomous vehicles, arguing private ownership will vanish and leading into an analysis of how extreme resource efficiency challenges traditional capitalism. Harry prompts with forward-looking questions on UBI and truck drivers. | |
| Quickfire Round: Books, Mentors, Echo, and Zuckerberg | 2 | 2 | 1 | 1 | During a fast-paced quickfire segment, Sam names his wife Jessica Lessin as his primary career mentor and expresses enthusiasm for the Amazon Echo as a glimpse into the future. The tone is light and highly cooperative. | |
| Quickfire Round: Universal Basic Income, AI Hype, and Investments | 3 | 4 | 4 | 2 | Harry asks about UBI and Draper's proposal, followed by asking what Sam wants from the AI community. Sam critiques the current AI media hype cycle for being ahead of its skis before sharing details on his investment in co-living startup Common. |
Statements from this episode (16)
Lessin was the first investor in Birchbox and Venmo
“And so I was, you know, one of the first investors in MakerBot and the first investor in Birchbox and, you know, the first investor in Venmo and a bunch of awesome companies.”
Lessin: AI is extremely overhyped and largely fictitious
“We think AI is extremely overhyped. And also kind of fictitious.”
Lessin: Augmenting memory is the most compelling bot use case
“I'll tell you the thing that I love the most is augmenting my memory. I don't have the world's greatest memory. I like to take lists. I try to keep lists together and things like that, but I find it really, really hard to keep track of all The ideas and people…”
Lessin: Conversational bots are not new and recur in cycles
“The bots thing is, you know, look, it's not new. It's the Asian bot ecosystem has been around for a while. There's a bunch of reasons why people are now excited about it, but these things come in cycles. Like, you know, I remember very distinctly the days of a…”
Lessin: Display advertising will become irrelevant in a bot world
“You know, I think obviously in a bot world, a lot of the display driven, engagement driven advertising that, you know, we're all used to seeing as the way services monetize and exist becomes a heck of a lot less relevant.”
Lessin: Fin charges users directly because human-augmented AI is costly
“Our business model for Fin is extremely simple, which is we charge people for it. And, you know, we charge people for it both because of the service we offer is expensive to run. It's, I mean, AAI is not an inexpensive thing to do well because it's not just bi…”
Lessin: Very few companies build sustainable businesses on affiliate fees
“Affiliate models, just, I don't know, like there are very few companies that have made them sustainably good businesses, right? You know, I would challenge you to come up with a company that's deeply driven by affiliate fees that works in the longterm.”
Lessin: The long tail of mobile apps has failed
“The long tail of apps has mostly failed, right? The real estate and time and attention has been taken up by a few head application publishers.”
Lessin: The internet has failed as an information platform
“I personally believe the internet has mostly failed in its mission to become an information platform. It's a great content platform. It's super engaging, but it doesn't inform the way I expect it to. I'm super disappointed in Wikipedia.”
Lessin: Auto industry won't survive as required car volume collapses
“I think it's going to be pretty hard for the auto industry to survive at all. Right. Because just the number of cars we're going to need is going to go dramatically down.”
Lessin: Private car ownership will end in favor of shared vehicles
“I cannot come up with a possible world where we don't end up sharing cars. It just, I literally, it does not, maybe in a world of infinite free energy and, you know, zero pollution and no resource constraints, everyone owns cars, but x that, there's no possibl…”
Lessin: Society will rent everything; only poor people will own items
“I think we're going to live in a world where the only people who don't rent everything are the people who can't afford to. So ironically, it will be only poor people, right? Who won't be completely rental based.”
Lessin: Capitalism cannot survive an ultra-efficient, deflationary world
“So if we get much more efficient and you live in a fundamentally deflationary world, like I don't know how capitalism survives that, you know, which is going to be, I think, really exciting.”
Lessin: Amazon Echo is the best glimpse of the tech future
“It's the future. I mean, it's a total taste of the future. I cannot tell you how excited I am about Echo. I have five in my house, literally. I've built applications for it myself. Finn has an incredible integration with it. It isn't there yet, but it's the be…”
Lessin: Universal Basic Income is inevitable
“I don't actually know what Tim Draper's view is on it, but I think there's no possible way that it won't happen.”
Lessin: Co-living communities will inevitably standardize urban living
“I just like fun, again, like there's, this goes on my list of course, this is the way the world will work. I can't imagine a world in which, you know, everyone's living in these kind of low, these apartments where they don't know their neighbors and there's no…”