This Week in Startups – Episode E2031 Summary

Date: October 23, 2024
Host: Jason Calacanis
Co-host: Alex Wilhelm
Episode Theme:
Exploring breakthroughs and big news in tech and startups, with a focus on agentic AI, the luxury headphone market, anti-drone technology, and a deep dive into “data licensing” startups.

1. Overview

Jason Calacanis and Alex Wilhelm cover a range of notable tech stories and conduct founder interviews, featuring in-depth discussion on the rise of “agentic” AI (specifically Anthropic’s Claude 3.5 Sonnet), the story behind premium domain startup Headphones.com with its founder Andrew Lissimore, a student duo tackling drone defense with sound waves, and insights on TollBit’s sizable Series A for AI-powered data licensing marketplaces.

2. Key Discussion Points & Insights

A. Advances of Agentic AI & Automation

Timestamps: 02:08 – 20:05

• Anthropic Claude 3.5 Sonnet & Computer Use API
  New functionality enables AI to “use” the browser as a human would — ordering pizza, scraping product prices, and automating web workflows.

  “If you look at the new iOS 18, every single app has a checkbox to allow superintelligence, essentially, Siri, to review your behavior in that app ... they want Siri to ... have watched you use Uber to call a car, United to book a flight.” — Jason (04:18)

• Demo Example – Live AI Automation
  Featured a founder video: AI agent gathers and enters headphone data from the web into a spreadsheet.

  “It literally kind of walks you through the steps that it's doing and the actions it's taking … I love seeing the steps here, so very encouraging.” — Alex (05:49)

• Implications for White Collar Work
  Jason’s prediction: AI will cause a "cataclysmic employment landscape" for white collar jobs, especially for creatives and junior developers.

  "I think we're going to see half of white collar jobs go away … bottom third of developers, if they don’t level up, are going to be ... replaced by AI agents." — Jason (12:25, 12:52)

  "We're going to lose 10% of jobs a year for three or four years, compounding.” — Jason (16:41)

B. Interview: Headphones.com & the Hi-Fi Audio Hobby

Guest: Andrew Lissimore, founder and CEO, Headphones.com
Timestamps: 22:53 – 49:54

• Origin Story:
  Andrew’s audio gear obsession led him to found Headphones.com with his brother, fueled by a passion project and the accidental acquisition of a million-dollar domain name via persistence, creative negotiations, and a friendly seller.

  “If you told me eight years ago I’d be here with this company, I would have said not a chance … things kind of just took their own course.” — Andrew (23:31)

• Business Model & Market Strategy:
  Focused on high-end audiophile gear (“$1,000+ average order") — successfully carved a niche unserved by Amazon and Best Buy. Emphasized honest reviews & building a media-like presence to drive sales.

  “We’re like a media and reviews company that monetizes through E-commerce ... building awareness through content and building trust.” — Andrew (38:03)

• Audio as Luxury, Hobby, and Emotional Changing Tool
  Discussion covered the genuine experiential difference in high-end audio, aesthetic vs functional elements, and the passionate, obsessive elements of the hobby – including the wild “Steve Jobless” headphone designs of friend Phil Kaplan (Pud).

  “I actually buy that I’m hearing something completely different than I experienced for the first 50 years of my life.” — Jason (34:49)

  “Audio is one of the few ways that you can change your mental state really reliably… for a certain subset of people, it’s totally worth it if you can afford this stuff.” — Andrew (49:20)

• Navigating Google, Algorithms, and YouTube
  Organic search is fading in relative importance (“SERP now is a big money-making engine for Google... wiped organic below the fold” — Andrew, 47:33), so they are focusing on educational YouTube content for customer acquisition.

C. Interview: Anti-Drone Startup by University of Toronto Students

Guests: Founding team of Prandtl Dynamics
Timestamps: 50:32 – 66:55

• Context: The New Face of Drone Warfare
  Cheap, hobbyist or hand-built drones are dramatically reshaping battlefields in Ukraine, Gaza, and beyond. Defensive counter-measures need to be just as affordable.

  “Soldiers are not just fighting other soldiers, they're fighting robots… a drone for 50 bucks in your house and strap munitions to it…” — Asad (51:34)

• Innovation: Using Sound Waves for Drone Defense
  Developed a prototype to disrupt drone electronics using targeted ultrasonic sound waves, effective across a range of drone types (from cheap kits to pro models).

  "We disrupt the electronics ... using our ultrasonic sound waves ... we were able to find the effect they had on the actual electronics inside these drones ... [and] hamper how a drone flies." — Anna (57:29)

• Business Model & Recognition
  Team of four 4th-year engineering students, recently awarded a $270,000 non-dilutive grand prize from Canada’s Dept. of Defense.

  “Quarter milli check. Non dilutive funding. You guys are my heroes. That’s amazing. The cap table stays pure.” — Jason (64:07)

• Future Direction:
  Exploring commercialization/investors; aiming for real-world deployment (potentially Ukraine).

D. TollBit’s $24M Series A: Licensing Data for AI Models

Timestamps: 68:43 – 74:17

• What Is TollBit?
  A startup facilitating a legal, marketplace-driven approach for publishers to license data to AI companies.

  “TollBit ... wants to sit in between ... create a marketplace so that if you own data, you can license it, and if you need data, you can pay for it.” — Alex (70:53)

• Industry Context:
  Part of a wave of new startups (including Human Native and Created by Humans) attempting to solve the “data licensing” and “cold start marketplace” problem for generative AI.

• Analysis of Funding Size:
  Unusually large Series A ($24M) given business model; speculation that much of funding will bootstrap the marketplace by offering guarantees to early data suppliers.

  “It’s perplexing that you would raise that much money ... but if you want to bootstrap the publisher side ... and crush the competition..." — Jason (72:49, 73:30)

3. Notable Quotes & Memorable Moments

On AI Disrupting Work:

• “I think we are going to see a cataclysmic … employment landscape for white collar in the coming years.” — Jason (12:25)
• “Increasing economic power of the best and decreasing economic viability of the lower half ... I just don't know if we're ready as a species to deal with that kind of economic change.” — Alex (19:14)

On Audio Fandom:

• “Luxury begins where necessity ends.” — Jason (41:36)
• “I want to just ruin...this term audiophile ... I think an audiophile is just someone who loves sound.” — Andrew (46:11)

On Scrappy Student Innovation:

• “We realized the deadline was about 24 hours away and we still had to come up with a name ... I think like using a renowned scientist as the name of a company is a good way to go. I mean, look at Tesla.” — Michael (66:13)

On Early-Stage Startup Joy:

• “...somebody just paying attention to what you’re doing and showing interest ... is so valuable because they might have feedback ... might motivate the team.” — Jason (68:17)

4. Timestamps for Important Segments

| Timestamp | Segment | |------------|-------------------------------------------------------------------------------------------------| | 02:08 | Deep Dive: Anthropic’s Claude 3.5 Sonnet, “computer use” API, live agentic AI autonomy | | 12:25 | Jason’s “cataclysmic” white collar workforce prediction | | 22:53 | Interview: Andrew Lissimore, Headphones.com – founder story | | 34:43 | Luxury audio, audiophile obsession, and what makes high-fidelity gear interesting/tangible | | 50:32 | Interview: Prandtl Dynamics anti-drone student team | | 57:29 | Technical dive: how ultrasonic sound disables drones | | 64:07 | Team awarded $270,000 Canadian defense grant (“Quarter milli non-dilutive funding!”) | | 68:43 | Segment: TollBit & funding analysis of AI “data licensing” startups | | 73:30 | Jason’s analysis of large Series A and competitive pressure in data licensing |

5. Tone and Style

The episode is informal, energetic, and conversational in Jason’s classic “startup-insider” style. There’s a strong emphasis on practical implications, founder psychology, and the blending of technical deep dives with relatable startup stories.

6. Useful for Listeners

• Provides insight into the rapid automation threatening white collar work, illustrated with clear, relatable examples.
• Shares a founder saga that’s equal parts startup grind and passionate consumer obsession.
• Spotlights student ingenuity and how grant funding can spark real-world, high-impact ventures.
• Analyzes venture capital trends and nuances in a hyped AI market.
• Offers ample resources and role-model moments for founders, investors, and tech enthusiasts.

7. For Further Exploration

• Claude 3.5 Sonnet and the rise of “agentic AI”
• Headphones.com reviews/media as E-commerce hybrid
• Prandtl Dynamics: Student hardware deep tech
• Marketplaces for data licensing—TollBit, Created by Humans, Human Native

Podcast guests and topics cover a broad swath of the startup and tech world, anchored by hands-on founder narratives, real examples, and an honest look at what’s next in tech disruption.