How do you separate genuine innovation from pure hype? That is perhaps THE question of the moment for investors when it comes to AI, and it is also the question Kara Swisher has thought about for her entire career as the premier tech journalist of our time. She is co-founder of Recode and the host of powerhouse podcasts like Pivot and On with Kara Swisher, and she brings her trademark candor – and the occasional swear word – to the latest episode of The Master Investor Podcast to break down the realities behind tech’s biggest narratives. Kara has interviewed every major tech CEO of the modern era, and reflects on the traits that lead to trillion dollar companies and those that destroy shareholder value. Ultimately she thinks society overestimates the intelligence of many tech innovators, reflecting on the failure of the Metaverse and Cyber Truck, and identifies the character traits to watch out for – losing your passion and focus for the original job; talking too much to the media; and spending money on vanity projects. She reflects fondly on the lessons she has learned from Steve Jobs and Satya Nadella – and the extent to which they simply focused on running a business instead of talking to the press. Wilf and Kara discuss why OpenAI will likely struggle to IPO this year even if Anthropic succeeds, and the ways in which the current AI frenzy mirrors the dot-com bubble. In particular the fact that not all frontier models will stay the course. In fact, the name she backs is Google’s Gemini much more than the much hyped new names like OpenAI, Anthropic and SpaceX. Kara also reflects on social media and AI regulation and how it might impact share prices; the secret to building successful podcasts and her number one piece of career advice – “step out of line”. Recorded Thursday 9th July 2026 Listen to Kara’s podcast Pivot here - https://podfollow.com/1073226719 And On with Kara Swisher here - https://podfollow.com/1643307527 0:00 Intro 3:00 AI alarm bells 4:38 Only one AI winner 6:18 “Absolutely” bubble territory 9:37 Valuing tech companies 14:27 Valuing tech CEOs 16:37 Capital mkts generous to tech 18:22 Operators vs Innovators 22:35 CEO warning signs 27:36 Tech regulation 30:13 Under 16s social media ban 34:28 What makes a great podcast? 42:13 Wealth isn’t happiness 44:03 “Step out of line” For more content like this, subscribe to The Master Investor Podcast Youtube Channel - https://www.youtube.com/@TheMasterInvestorPodcast And follow @WilfredFrost on X - https://x.com/wilfredfrost?lang=en And Linked In - https://www.linkedin.com/in/wilfred-frost-279667374/ Sponsored by BNY Investments, World Gold Council, London Stock Exchange Group (LSEG) and Interactive Brokers - ibkr.com/masterinvestor. The Master Investor Podcast is produced by Paradine Productions and Master Investor Ltd in association with Bird Lime Media. This podcast is for information purposes only. It does not constitute an invitation or inducement to engage in any investment activity. It is not a financial promotion as defined under section 21 of the Financial Services and Markets Act 2000 (FSMA). The views expressed by the presenter of this podcast are those of the presenter and are provided in the course of journalism. This podcast benefits from the exemption under Article 20 of the Financial Services and Markets Act 2000 (Financial Promotion) Order 2005 (FPO), It does not require approval by a person authorised under the FSMA. Generic information, not identifying any specific investment, fund, provider or service, about a class of investments such as shares, bonds, derivatives and cryptoassets, might be provided and/or discussed during this podcast. Such discussion falls within the generic promotions exemption (Article 17 of the FPO). Such discussion is not a financial promotion requiring approval by an authorised person under section 21 of the FSMA. Investing involves risk. You should consult a suitably qualified adviser who can assess your individual circumstances before making any investment decision