#19 Chris Sacca: Venture Cowboy

Robert Holmes à Court started as a lawyer in Perth and became Australia’s first billionaire. He built his fortune by spotting value in distressed companies, charming rivals into partnerships, and then cutting ruthlessly to create returns. This episode breaks down Holmes à Court’s rise and fall, and the lessons his playbook still offers for investors today.Thanks to our sponsors!Ayrin Digital: https://go.ayrin.ai/rainmakersCollateral Partners: https://collateral.com/Sources:https://docs.google.com/document/d/12D9sI-cfOWmQZvImZBOunWtym3LH0TuV0o2nhi4CZr8/edit?usp=sharingPaul McCartney Video: https://www.youtube.com/watch?v=91YLM5l614o

Henry Hillman inherited a Pittsburgh empire built on coal and steel and then dismantled it. Instead of holding on, he recycled those assets into bigger bets, backing unproven talent and writing early checks to firms like KKR and Kleiner Perkins. This episode breaks down how Hillman turned a family fortune into billions and what his playbook can teach today’s investors.Thanks to our sponsors!Ayrin Digital: https://go.ayrin.ai/rainmakersCollateral Partners: https://collateral.com/Sources:https://docs.google.com/document/d/1XMnJwZuGOnKnfJZO5u_cExOYkxrI_DRcghgI3KYUehs/edit?usp=sharing

From selling Christmas cards in Texarkana to building EDS into a billion-dollar giant, Ross Perot turned frustration at IBM into a whole new industry.In this episode, we break down exactly how he did it.Thanks to our sponsors!Ayrin Digital: https://go.ayrin.ai/rainmakersCollateral Partners: https://collateral.com/Sources:https://docs.google.com/document/d/11mQ7etaWwkYLpu7eHzn27hFu__fs1h4aAWQYjMS2B20/edit?usp=sharing

From cattle bluffs in Texas to controlling over 100 companies, Clint Murchison built his empire on creativity, information, and relentless deal making.In this episode, we break down exactly how he pulled it off.Thanks to our sponsors!Ayrin Digital: https://go.ayrin.ai/rainmakersCollateral Partners: https://collateral.com/Sources:https://docs.google.com/document/d/1p0FxkHSQ6bn4XGV0tcVMuzcDJWVt6UnUOPjXMFa023U/edit?usp=sharing

From tax prep shops in Cleveland to producing The Dark Knight, Thomas Tull’s rise is one of the wildest stories in business. In this episode, we dig into exactly how it happened.Thanks to our sponsors!Ayrin Digital: https://go.ayrin.ai/rainmakersCollateral Partners: https://collateral.com/Sources:https://docs.google.com/document/d/1muQnrC-TbXxPN4wrxbQu8InR36SsUQkwWPL94A_6WyA/edit?usp=sharing

Chris Sacca went from getting fired as a lawyer to becoming one of the most successful venture capitalists ever.In this episode, we break down exactly how he pulled it off.Thanks to our sponsors!Ayrin Digital: https://go.ayrin.ai/rainmakersCollateral Partners: https://collateral.com/Sources:https://docs.google.com/document/d/1aOr9nvi_FuDUux7nW6g0vIxEaYl4gknAD5IDTLmzIbs/edit?usp=sharing

Joe Liemandt turned the chaos of the dot-com era into a $6.2B fortune. He pioneered software private equity and built an empire from distressed assets. In this episode, we break down exactly how he pulled it off.Thanks to our sponsors!Ayrin Digital: https://go.ayrin.ai/rainmakersCollateral Partners: https://collateral.com/Sources:https://docs.google.com/document/d/1efBxGrFHrBb8sl1QerGbDHM2OYCtw0ZaX2f1546WR-Y/edit?usp=sharing

How did Carlos Slim become one of the wealthiest people in the world? Buckle up to learn one of the best case studies on deal making by one of the best who ever did it.Thanks to our sponsors!Ayrin Digital: https://go.ayrin.ai/rainmakersCollateral Partners: https://collateral.com/Sources: https://docs.google.com/document/d/1C8F5hnmHCouSoiHK2n8WzSYCj-JPAyqODeO2Dvs-zTk/edit?usp=sharing

Learn about two of the best investors of our generation and how they turned $10M into $5B in 20 years by investing all across the world in emerging markets. It will not disappoint.Thanks to our sponsors!Ayrin Digital: https://go.ayrin.ai/rainmakersCollateral Partners: https://collateral.com/Sources:https://docs.google.com/document/d/1eUZt2XC7bExp5E5LjmEhBxEVh_uX0ZUPKlcK_Jvj1N8/edit?tab=t.0

Join us on a journey to learn from one of the best deal makers of all time, Jay Pritzker. Big thanks to our sponsor Ayrin. If you've got a product in your head and want to build it the right way contact the team at Ayrin.https://go.ayrin.ai/rainmakersLinks:Rockwood Notes Nicholas Pritzker Article: https://www.rockwoodnotes.com/p/nicholas-j-pritzkerRockwood Notes: https://x.com/RockwoodNotesTurtlebay_IO: https://x.com/turtlebay_ioMatt's Tweet: https://x.com/ReustleMatt/status/1891638963133108629Sources: https://docs.google.com/document/d/1ylhoOHb-WU3-nx2DcqwJsfwVW0vF-o1AXMMBIcBkmKI/edit?usp=sharing