20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon

20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon

Author: Harry Stebbings September 19, 2025 Duration: 59:19

Jesse Zhang is the Co-Founder and CEO @ Decagon, the conversational AI platform for customer experience. As one of the fastest growing companies in the valley, they have raised over $230M at a last round price of $1.5BN. Prior to Decagon, Jesse founded Lowkey (acquired by Niantic), studied CS at Harvard, and worked at places like Google, HRT, Citadel, and Intel.

AGENDA:

00:00 Introduction and Sponsor Messages

03:43 Olympiad Mathematician to Startup Founder

05:34 Selling to Niantic and What I Did Differently the Second Time

07:16 Why 90% of Founders Build Companies the Wrong Way

12:19 Scaling to $50M ARR in 15 Months

31:31 Is the AI Talent War Out of Hand: How To Compete with Meta Pay Packets

32:38 Why Remote Work is Total BS

34:06 Competitors in AI Customer Experience: Sierra, Intercom and more

37:34 AI Market Predictions

44:56 Embracing Stress and Winning Culture

50:13 Quick Fire Questions: Most Underrated AI Founder, Biggest Changed Opinion

 

 

 


Hosted by Harry Stebbings, The Twenty Minute VC (20VC) pulls back the curtain on the high-stakes worlds of venture capital and startup building. Each episode is a compact, twenty-minute dive into the minds shaping the future of technology. You’ll hear candid conversations with legendary investors, the very individuals who fund and guide the next generation of companies, featuring voices like Sequoia's Doug Leone and Benchmark's Bill Gurley. Beyond the capital, this podcast dedicates time to the founders themselves. Weekly, Stebbings sits down with transformative entrepreneurs such as Spotify's Daniel Ek, LinkedIn's Reid Hoffman, and Snowflake's Frank Slootman, unpacking the real journeys behind their iconic companies. The format is direct and focused, cutting straight to the core insights on funding strategies, pitch dynamics, and the personal philosophies that drive success. Tuning into this podcast means gaining an unfiltered perspective from both sides of the table, all delivered in a concise and accessible style that fits into your day.
Author: Language: English Episodes: 100

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Podcast Episodes
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Duration: 56:00
Gérald Marolf is the Chief Product Officer at On Running. Gérald oversees the full range of On's shoes, apparel and accessories to make sure each delivers performance, comfort and style. Before On, Gérald spent over a de…
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Duration: 1:31:48
AGENDA: 03:46 SpaceX's $800 Billion Valuation: A Deep Dive 09:18 IPO Market Predictions for 2026 18:18 Netflix's Bold Move: Acquiring Warner Brothers 27:43 Tiger's New Fund Strategy 33:02 Databricks' Head of AI $500 Mill…
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Duration: 1:05:28
Bending Spoons is the acquisition machine of the tech world. They have acquired the likes of Evernote, Vimeo, Eventbrite, Streamyard and more. However, they never open their gates to the secrets behind Evernote's product…
20VC: Scale, Surge, Turing, Mercor: Who Wins & Who Loses in Data Labelling | Is Revenue in Data Labelling Real or GMV? | Why 99% of Knowledge Work Will Go and What Happens Then? | Why SaaS is Dead in a World of AI with Jonathan Siddharth @ Turing [not-audio_url] [/not-audio_url]

Duration: 1:08:16
Jonathan Siddharth is Founder and CEO of Turing, one of the fastest-growing AI companies advancing frontier models. Jonathan has led the company to an astonishing $300M ARR with just $225M raised and a profitable company…