Rainmakers

Latest Episodes:

#24 Robert Holmes a Court: Australia's First Billionaire Oct 04, 2025

Show notes

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/rainmakers
Collateral Partners: https://collateral.com/

Sources:

https://docs.google.com/document/d/12D9sI-cfOWmQZvImZBOunWtym3LH0TuV0o2nhi4CZr8/edit?usp=sharing

Paul McCartney Video: https://www.youtube.com/watch?v=91YLM5l614o

#23 Henry Hillman: The Original LP Sep 26, 2025

Show notes

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/rainmakers
Collateral Partners: https://collateral.com/

Sources:

https://docs.google.com/document/d/1XMnJwZuGOnKnfJZO5u_cExOYkxrI_DRcghgI3KYUehs/edit?usp=sharing

#22 Ross Perot: Texarkana to Tech Titan Sep 18, 2025

Show notes

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/rainmakers
Collateral Partners: https://collateral.com/

Sources:

https://docs.google.com/document/d/11mQ7etaWwkYLpu7eHzn27hFu__fs1h4aAWQYjMS2B20/edit?usp=sharing

#21 Clint Murchison: Wheeler Dealer Sep 11, 2025

Show notes

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/rainmakers
Collateral Partners: https://collateral.com/

Sources:

https://docs.google.com/document/d/1p0FxkHSQ6bn4XGV0tcVMuzcDJWVt6UnUOPjXMFa023U/edit?usp=sharing

#20 Thomas Tull: Global Mogul Sep 04, 2025

Show notes

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/rainmakers
Collateral Partners: https://collateral.com/

Sources:

https://docs.google.com/document/d/1muQnrC-TbXxPN4wrxbQu8InR36SsUQkwWPL94A_6WyA/edit?usp=sharing

#19 Chris Sacca: Venture Cowboy Aug 28, 2025

Show notes

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/rainmakers
Collateral Partners: https://collateral.com/

Sources:

https://docs.google.com/document/d/1aOr9nvi_FuDUux7nW6g0vIxEaYl4gknAD5IDTLmzIbs/edit?usp=sharing

#18 Joe Liemandt: Startup Founder turned Buyout Billionaire Aug 21, 2025

Show notes

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/rainmakers

Collateral Partners: https://collateral.com/

Sources:

https://docs.google.com/document/d/1efBxGrFHrBb8sl1QerGbDHM2OYCtw0ZaX2f1546WR-Y/edit?usp=sharing

#17 Carlos Slim: El Conquistador Aug 14, 2025

Show notes

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/rainmakers

Collateral Partners: https://collateral.com/

Sources:

https://docs.google.com/document/d/1C8F5hnmHCouSoiHK2n8WzSYCj-JPAyqODeO2Dvs-zTk/edit?usp=sharing

#16 Chandler Brothers: A Global Investing Story Aug 07, 2025

Show notes

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/rainmakers
Collateral Partners: https://collateral.com/

Sources:

https://docs.google.com/document/d/1eUZt2XC7bExp5E5LjmEhBxEVh_uX0ZUPKlcK_Jvj1N8/edit?tab=t.0

#15 Jay Pritzker: Creating a Family Dynasty Jul 10, 2025

Show notes

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/rainmakers

Links:

Rockwood Notes Nicholas Pritzker Article: https://www.rockwoodnotes.com/p/nicholas-j-pritzker

Rockwood Notes: https://x.com/RockwoodNotes

Turtlebay_IO: https://x.com/turtlebay_io

Matt's Tweet: https://x.com/ReustleMatt/status/1891638963133108629

Sources: https://docs.google.com/document/d/1ylhoOHb-WU3-nx2DcqwJsfwVW0vF-o1AXMMBIcBkmKI/edit?usp=sharing

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