How Tax-Free Wine Returns Beat the Volatile Stock Market | CEO, WineFi, Callum Woodcock

Everyone in wine investment claimed to have an algorithm. When Callum Woodcock went to hire his head of investment, he found out almost none of them did, and what WineFi built instead let it rise while the market fell.Callum Woodcock is the CEO of WineFi, a data-led wine and spirits investment platform using machine learning to find investment-grade wines likely to beat the market. Before WineFi, Callum spent eight years as a self-confessed “wantrepreneur”: he studied history at Bristol, joined the Fidelity graduate scheme, moved into sales at JP Morgan and then became the first non-technical hire at legal tech startup Nomio. He started WineFi in 2023, at one of the hardest times in years to raise money, and still raised £477K in pre-seed funding. WineFi made seven figures in revenue in its first seven months and went on to raise a £1.5M seed round. During a period when the wine market fell 29%, WineFi’s portfolios were up 11% against the Liv-ex 1000 benchmark.In this episode you’ll hear:- Why Callum spent eight years starting businesses and quitting, and what finally broke the loop- How a father-in-law’s wine cellar turned into a tax-efficient investment platform- The Cold War lesson behind WineFi’s data models, and what happened when it found out competitors were “swimming naked”- Why Gen Z have stopped drinking wine, and what that means for the next 15 years of wine investment- Why WineFi is betting on tequila as the next whiskyChapters00:00 The Wantrepreneur Years02:26 Miserable at JP Morgan09:35 Why Grad Jobs Are Vanishing19:06 When Your Ego Is the Business21:42 The Unicorn He Let Slip23:23 The Chief of Staff Shortcut30:24 A Cellar Full of Profit33:48 The Algorithms That Didn’t Exist39:24 Gen Z Have Quit Wine47:12 The £48K Bottle Nobody Opens49:32 Raising at the Worst Possible Time53:44 Inside the £250K Data Engine1:04:49 Why Tequila Is the Next Whisky1:12:05 Never as Good as LinkedIn1:18:42 What It TakesFollow Callum:https://www.linkedin.com/in/callumwoodcock/Follow Olly: https://www.instagram.com/olly.303/https://www.tiktok.com/@ollyfawcett303?is_from_webapp=1&sender_device=pchttps://www.linkedin.com/in/olly-fawcett-668566177/Get frequent behind the scenes updates from Olly: https://whatittakes.kit.com/51cd36dc35Keywords:Callum Woodcock, WineFi, WineFi CEO, wine investment UK, fine wine investing, how to invest in wine, is wine a good investment, wine investment tax free, capital gains tax wine UK, wine syndicate, Liv-ex 1000, tequila investment, tequila barrel investment, alternative investments UK, machine learning investing, leaving JP Morgan to start a business, startup founder story, raising pre-seed funding UK, chief of staff career, What It Takes podcast, Olly Fawcett