Ep. 066 | How to Know If Your Contrarian Idea Is Real | Lance Cottrell

Lance Cottrell founded Anonymizer in 1995, the world's first consumer internet privacy service, after leaving an astrophysics doctorate five years in. He had been working with the Hubble Space Telescope and was online early enough to see what the data collection would mean. He grew Anonymizer to a million active users and 100,000 paying subscribers, survived the dot-com collapse, then pivoted the company after 9/11 into platforms for online undercover operations for the intelligence community, which is where he says it finally found product-market fit. He sold it to Ntrepid and stayed on as chief scientist. He now runs the free founder education channel Feel the Boot, is president of the North Bay Angels, and coaches a small number of founders directly. In this conversation with Caleb Pedosiuk, Lance explains how a founder can tell a genuine insight from a comfortable one. The test is that you believe it passionately, you keep arguing about it, and almost nobody agrees with you yet. "One of the things to look for is when you discover that something that you passionately believe in is contrarian." Then comes the part most founders skip: "validate the heck out of that." He is blunt about where the current market's money is going, inverting the Gretzky line to say investors are skating to where the puck just was, and he argues the real opportunities sit one or two steps past the models everyone is funding. He walks through why founders who come to him for help raising money almost never have a fundraising problem, explains the returns math that makes angel investing look greedy until you do it, and gives the most honest answer the show has had to its closing question: he knows he has picked a terrible market, and he picked it on purpose. Lance is exactly the kind of founder, innovator, and problem solver this series exists to put a light on. He built a category that did not exist, waited years for a market that was not ready, and now spends his time making other founders' thinking sharper rather than louder. That is what earned authority sounds like: building things worth talking about and keeping an honest account of the work, which is what makes a brand understood, trusted, and findable by the systems people now ask for answers. Learn more about Feel the Boot: https://www.feeltheboot.com Lance Cottrell on LinkedIn:   / lancecottrell   One-to-one founder coaching: https://founderquest.com Feel the Boot on YouTube: free content on startups and fundraising What We Need to Grow is Caleb Pedosiuk's founder conversation series from 79 Development, on growth, judgment, and the thinking behind building great companies. It exists to shine a light on the founders, innovators, problem solvers, and pioneers building things that matter. Listen on Spotify: https://open.spotify.com/show/5O6IiwV... Podcast sponsored by 79 Development Inc | 79dev.com #startups #fundraising #angelinvesting #venturecapital #founders #podcast #productmarketfit #startupadvice