This Week in Startups

Today’s show: Jason, Alex, and Lon break down today’s top tech and startup stories — from Slate Auto’s customizable $25K EV truck to Discord’s major leadership shakeup ahead of a potential IPO. They also cover Uber’s self-driving push with Volkswagen, Perplexity AI’s aggressive growth moves, and why value-driven products are winning in a tough economy. Plus, Alex sits down with Tailscale CEO Avery Pennarun to unpack how they grew from 5K to 10K customers — and why fixing internet networking could spark the next huge wave of innovation.*Timestamps:(0:00) Jason, Lon and Alex kick off the show!(3:26) Introduction and features of Bezos-backed EV truck company, Slate(7:55) Market impact and value proposition of Slate's EV trucks(9:48) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups(14:04) EV features and market potential discussion(17:42) Discord CEO steps down and IPO prospects(20:19) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(24:00) Uber and Volkswagen's self-driving car partnership(28:39) Superpower - The best founders know: better health = better business. Visit http://superpower.com/twist to skip the waitlist.(30:00) Pace of self-driving car adoption and regulation(37:20) Butterfly Effect secures Benchmark investment(38:37) Perplexity and Motorola Razr partnership(43:12) Jason's experience with Light Phone(45:39) New York Times and Ziff Davis lawsuits against OpenAI(50:09) Nonprofit structures and OpenAI's mission issues(54:01) Founder Friday: Pitchfire and TACTUN's two-year plans(1:02:28) Introduction to Tailscale and Avery Pennarun(1:10:17) Tailscale's enterprise adoption(1:21:13) Current Internet networking issues*Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcp*Links from episode:Check out Tailscale: https://tailscale.com/ Check out Slate vehicles: https://www.slate.auto/enCheck out Not For Private Gain:https://notforprivategain.org/Check out the Light Phone: https://www.thelightphone.com/Check out Oregon lawmakers article: ****https://www.oregonlive.com/politics/2025/04/oregon-lawmakers-to-decide-whether-big-tech-should-pay-to-support-local-journalism.htmlCheck out Manus: https://manus.im/*Follow Lon:X: https://x.com/lons*Follow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis*Thank you to our partners:(9:48) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups(20:19) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(28:39) Superpower - The best founders know: better health = better business. Visit http://superpower.com/twist to skip the waitlist.*Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland*Check out Jason’s suite of newsletters: https://substack.com/@calacanis*Follow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.com*Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

The FTC's lawsuit against Uber raises questions about consumer protection amid subscription management. Cursor's astonishing growth as an AI startup showcases the potential of innovative solutions. Dark patterns in UX design are scrutinized, highlighting the need for transparency. Insights from GoShare's CEO emphasize focus and customer obsession for navigating market turbulence. The discussion also touches on compliance challenges in the gig economy and strategies for startups to adapt and thrive.

Join Jason Reminick, Co-founder and CEO of Thalamus, as he dives into a compelling discussion about his platform that expertly matches medical residents with hospitals, boasting an impressive 85% market share. Discover how Thalamus is addressing the U.S. doctor shortage while navigating the complexities of becoming a Public Benefit Corp. The conversation also touches on the challenges of OpenAI's new models, the impact of fintech innovations like TapCheck, and intriguing technology such as robot lifeguards and humanoid races. This is a must-listen for tech and healthcare enthusiasts alike!

In this engaging discussion, Scott Bair, Director of Strategy for Lunor, shares his expertise in branding and design for startups. He offers actionable tips on logo creation, emphasizing color theory's emotional impact. The conversation also dives into the rise of LMArena, a competitive AI leaderboard, and the changing monetization strategies in tech, highlighting the significance of user engagement for startups. Additionally, the dynamic landscape of AI acquisitions and emerging application-layer AI startups are examined, making for a thought-provoking listen.

Jill Chase, a Partner at CapitalG, dives into how AI is transforming the startup ecosystem. With insights from successful companies like Motif and Abridge, she highlights the importance of durability in product offerings, emphasizing that speed alone isn't enough. Jill discusses practical AI applications in business operations, the evolution from copilots to autonomous agents, and the need for unique user experiences in a competitive market. For founders and investors in AI, her insights present a roadmap to navigate the challenges ahead.

Steven Borrelli, CEO of Cuts Clothing and e-commerce expert, discusses the unsettling impact of tariffs on his business and the larger retail landscape. He shares insights on how these policies affect supply chains and pricing, urging a focus on American craftsmanship. The conversation shifts to the recent buzz around Figma's IPO and the competitive dynamics shaping the tech market. Borrelli also touches on the challenges e-commerce faces amidst a changing economic environment, highlighting the necessity for startups to adapt strategically.

David Moscatelli, founder of Abacus, specializes in bringing generative AI to the finance sector, focusing on data control and accuracy for banks. Victor Riparbelli, CEO of Synthesia, leads an AI platform transforming corporate documents into engaging videos. They discuss the unique challenges of implementing AI in regulated industries and how on-prem LLMs enhance data management. Additionally, they explore the rise of customizable AI avatars that streamline communication for enterprises and the critical balance of ethics in AI development.

The latest discussion ignites excitement over Blue Origin's all-female crew mission and what it means for space tourism. Hugging Face's surprising acquisition of Pollen Robotics sparks debates about AI's role in real-world applications. Jack Dorsey's controversial views on intellectual property laws fuel heated discussions. Meanwhile, the staggering $39 billion valuation of Figure AI raises eyebrows, highlighting the unpredictable landscape of startup investments and the importance of navigating their inherent risks.

In this discussion, Brian Watson, the founder of InviteJet and a graduate of the LA 33 accelerator, shares insights on innovative calendar marketing tools. They delve into Palantir’s new fellowship program, which challenges traditional education paths for tech talent. The conversation also touches on DoorDash's partnership with Coco robots for food delivery in urban settings. Plus, practical strategies for startups on acquiring their first customers and a wild cautionary tale involving an AI deepfake investor. A wealth of actionable advice awaits!

Sergie Poe, CEO of Orchestra, a communication software company, shares insights on navigating today's startup landscape. He discusses the rise of 70mph drone deliveries in Dallas and their potential impact on logistics. The conversation then dives into the implications of Trump's 125% tariff on China, warning founders about possible layoffs and bankruptcies. Sergie also highlights the risks posed by small startup exits, where founders walk away with significant sums, influencing their future funding needs.