Entrepreneur Head to Head

Nigel and Joe

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Entrepreneurship
Weekly

Legendary founders, investors and inventors, their wins, their disasters and their comebacks. From Gutenberg to Buffett, Bill Ackman to Shopify’s Tobi Lütke, Entrepreneur Head to Head tells the stories behind the greatest businesses ever built, sometimes one legend at a time, sometimes two eras head to head, and always with what it means for today.

2d ago

Is It Better to Be First or Second?

Xerox invented the modern computer interface, and Apple made the money. MySpace ruled social media, and sold for a fraction of what it cost. Nokia owned the phone market until the iPhone. Britain started the Industrial Revolution, and Germany and the US overtook it. El Salvador became the first country to make bitcoin legal tender, then walked it back. But in mobile money, M-Pesa went first and kept its lead. In this episode we follow companies and countries to answer one question: is it better to be first, or second? The answer might surprise you.
5d ago

Ink vs Links: Gutenberg vs Wikipedia

In 1455, a moneylender sued Johannes Gutenberg for 2,026 guilders, the money behind the machine that put books in ordinary hands. 550 years later, a former options trader in Chicago launched a side project that made an encyclopedia free for the whole planet. This episode tells both stories, and you'll be surprised how much the second sounds like the first: a failed first venture, a side project that took over, a fight over money and credit, and a world-changing idea that made other people rich. Then we bring it to 2026, as AI companies build on Wikipedia while fewer people visit it. Would you rather change the world, or get paid for it?
Nov 1

The Comeback Kid of Wall Street: Bill Ackman

He turned $27 million into $2.6 billion in under a month, and lost more than $4 billion on a single stock. In this solo episode we follow Bill Ackman from the mentors who shaped him and a first fund that closed, to the six-year bet against MBIA, activist fights at Wendy's, Target, J.C. Penney and Canadian Pacific, and the dark years of Herbalife and Valeant. At his lowest point, with his fund down 30%, rivals circling and his marriage ending, he leaned on one simple rule: make a little progress every day. Then came the COVID hedge and his 2026 bet to build the next Berkshire Hathaway. A story about investing, and about how to keep going when everything falls apart. Resources & references Bill Ackman (Wikipedia): https://www.Wikipedia.org/wiki/Bill_AckmanBill Ackman profile (Motley Fool): https://fool.com/investing/how-to-invest/famous-investors/bill-ackman/How Ackman made his fortune in 3 plays (Motley Fool): https://www.fool.com/investing/2023/06/23/billionaire-bill-ackman-has-made-a-fortune-3-playsAckman lost $7.7 million per day on Valeant (Fortune): https://fortune.com/2017/03/15/valeant-stock-bill-ackmanPershing Square USA's public market debut (CNBC): https://www.cnbc.com/2026/04/29/bill-ackmans-5-billion-pershing-square-ipo-to-start-trading-testing-berkshire-style-vision.htmlPershing Square losing money but asking for more (Institutional Investor): https://www.institutionalinvestor.com/article/bill-ackmans-pershing-square-losing-money-hes-still-asking-investors-morePershing Square's latest holdings (HedgeFundAlpha): https://hedgefundalpha.com/strategies/bill-ackman-portfolio/Lex Fridman Podcast #413 with Bill Ackman (transcript): https://lexfridman.com/bill-ackman-transcript/How a book that inspired Buffett helped Ackman get started (Fortune): https://fortune.com/2026/08/11/how-a-book-that-inspired-warren-buffett-and-a-14000-side-hustle-helped-billionaire-bill-ackman-get-started-as-an-investor/The fight for control of Canadian Pacific (Globe and Mail): https://theglobeandmail.com/globe-investor/the-fight-for-control-of-canadian-pacific-railway/article4197390
Oct 18

Judged in 50 Milliseconds

In business, does the best product win, or the best-looking one? We take sides on everything from the Pepsi Challenge and Liquid Death to M-Pesa’s zero-glamour success, then look at how founders’ looks shape who gets funded. And with AI agents starting to shop for us, do looks stop mattering, or just move into the data?
Oct 12

Tobi Lütke: Shopify, AI, Entrepreneurship

On this episode of Entrepreneur Head to Head, we dive into the story of Tobi Lütke, the co-founder and CEO of Shopify. From a German-born programmer who moved to Canada to pursue his interests in technology to building a platform that powers millions of businesses, Lütke's journey is a masterclass in engineering-led entrepreneurship. Resources & references The Knowledge Project, “Tobi Lütke: AI Agents, Better Decisions, and the Future of Work”: https://fs.blog/knowledge-project-podcast/tobi-lutke-3/The Knowledge Project, Ep. 41, “The Trust Battery”: https://theknowledgeproject.libsyn.com/the-trust-batteryTobi Lütke on David Senra’s show (summary): https://www.founded.com/shopify-co-founder-tobi-lutke-on-commitment-culture-and-building-a-real-company/Tobi’s “Reflexive AI usage” memo (coverage): https://workplacejournal.co.uk/2025/04/shopify-ceo-calls-for-reflexive-ai-use-as-baseline-expectation-no-headcount-growth-until-options-explored/“Context engineering” tweet and Liquid speed-up: https://simonwillison.net/tags/tobias-lutke/Shopify, AI commerce at scale: https://www.shopify.com/news/ai-commerce-at-scaleAgentic commerce for Shopify merchants (2026 guide): https://ecommercefastlane.com/agentic-commerce-for-shopify-2026/OpenAI’s Instant Checkout reversal: https://godberrystudios.com/posts/agentic-commerce-2026-chatgpt-shopify-visa-merchant-playbook/Tobi Lütke biography: https://en.wikipedia.org/wiki/Tobias_L%C3%BCtke
Sep 15

Tim Cook: What a Tenure

For 15 years, Tim Cook ran Apple after Steve Jobs arguably one of the hardest succession jobs in modern business. And now, as Cook steps down as CEO and moves into the executive chairman role, we look back at what he actually built
Aug 15

The Man Who Buys the Wreckage

Is Ken Griffin actually one of the greatest investors alive or is his real genius that he built perhaps the greatest financial organization of his generation?
Jul 5

One Year of Entrepreneur Head to Head

365 days. Dozens of legendary founders. Countless debates. In this special 1-Year Anniversary episode of Entrepreneur Head to Head, we're looking back at the entrepreneurs and quick fire questions about entrepreneurship as a whole

Legendary founders, investors and inventors, their wins, their disasters and their comebacks. From Gutenberg to Buffett, Bill Ackman to Shopify’s Tobi Lütke, Entrepreneur Head to Head tells the stories behind the greatest businesses ever built, sometimes one legend at a time, sometimes two eras head to head, and always with what it means for today.

Creator

Nigel and Joe
Years Active

2025 - 2026
Episodes

27
Rating

Clean
Copyright

© Nigel and Joe
Show Website

Entrepreneur Head to Head