In this episode of World Class with Chris Vasquez, we dive into the mind of one of Silicon Valley’s most influential entrepreneurs and investors, Keith Rabois. Keith, a founding member of PayPal and an early investor in companies like LinkedIn, Square, and Yelp, shares his profound insights on scaling world-class companies, leadership, and what it takes to succeed in the fast-paced world of startups.

Throughout this conversation, Keith opens up about his decision-making frameworks, operating fast-growing startups, and hiring the right executives. He discusses why talented salespeople sometimes flop as VPs, the importance of knowing when to delegate versus doing things yourself, and how to manage time effectively as a leader. Keith also reveals his personal motivation, including how proving people wrong has fueled his incredible drive.

In a deep dive into current events, Keith shares his thoughts on the Kamala vs. Trump dilemma and explains why he believes the upcoming election could result in a massive win for Trump—providing a candid perspective on the political landscape and what’s at stake for the country’s future.

Chapters:

1:25 Founder Mode Explained

4:06 Why Sometimes Talented Salespeople Flop as VPs

4:57 Delegate vs Doing Yourself

9:00 Scaling Fast-Growing Startups

14:42 Key Executive Hires

16:20 Hiring Mistakes

17:25 Time Management Hacks

31:03 The Kamala vs Trump Dilemma

47:54 World Class Life

Key topics in this episode include:

• Founder Mode Explained: Keith’s approach to leadership and thriving in a startup environment

• Why Talented Salespeople Flop as VPs: The mismatch of skills at the executive level

• Delegate vs Doing: When to delegate and when to take charge yourself

• Scaling Fast-Growing Startups: Strategies for rapid growth in the tech industry

• Decision Frameworks & SOPs: Keith’s structured approach to running a business

• Investment Decision-Making Model: Keith’s method for evaluating high-potential investments • Key Executive Hires & Hiring Mistakes: How to build an effective executive team and common pitfalls to avoid

• Motivation & Success: Keith’s insights on what drives him, and using negativity as fuel for growth

• Time Management Hacks: How to manage your time as a startup leader

• The Kamala vs Trump Dilemma: Keith’s perspective on the 2024 election and why he thinks Trump will come out on top

• The World Class Life: Insights into what it takes to live at the highest level of success

• Growth Philosophy: Keith’s personal approach to growing businesses and people

In this insightful episode of “World Class with Chris Vasquez,” Chris is joined by Ed Sim, the #1 seed investor in the world, to share his invaluable lessons from 28+ years of venture capital investing.

We cover the best startup funding lessons from 28+ years of investing and the exciting world of AI & VC trends in the next 12 months.

Ed breaks down his approach to “inception investing,” diving into his unique 5 Ps model for evaluating startups and why starting small with your investments can lead to big payoffs. He shares his philosophy on the importance of having three founders, a concept honed over decades of successful investments. You’ll also hear about “The Weekend Test,” Ed’s method for evaluating founders’ true dedication.

As the venture space continues to evolve, Ed discusses the biggest shifts in the industry and how they’re shaping the future of startups. He takes a deep dive into the current AI investment landscape and shares stories of successful startups, including Parker Conrad and the rise of Snyk.

For founders, this episode is packed with advice on how to market the vision of your startup, when to deploy more capital, and why the first round of funding is so critical. Ed also talks about the ins and outs of launching a VC fund, and the importance of having “skin in the game,” especially as an underdog in the world of venture capital.

Ed’s journey is one of resilience and determination, and he shares his mantra of staying “poor, hungry, and determined,” a mindset that has guided him through decades of success in investing.

If you’re interested in venture capital, the future of AI, or want to know how to navigate the startup world from a master investor’s perspective, this episode is for you. Tune in for a wealth of knowledge from one of the most successful seed investors in the world.

Myles Shear also known as Manager Myles, a pioneer in the music industry who manages some of the world’s biggest electronic artists like Kygo, Thomas Jack, Gryffin and Sam Feldt. Myles is the Co-Founder of Palm Tree Crew, an entertainment and hospitality empire spanning music, live events, consumer brands & investments. Whether you’re an aspiring artist manager, an entrepreneur looking to break into new industries, or simply a fan of Kygo and the Palm Tree Crew, this episode is packed with valuable insights and inspiration. Join us as Myles Shear shares his journey of building a world-class brand and offers a fresh perspective on pursuing your passions while staying true to who you are.

Timestamps:

00:00 - 01:08 - Myles’ Origins

01:08 - 04:37 - How Myles and Kygo connected

06:18 - 10:16 - What Kygo saw in Myles

10:16 - 14:40 - Lowest Low/Highest High Moments

14:40 - 15:15 - Peak Fulfillment

15:15 - 18:22 - Palm Tree Crew Inception

18:22 - 27:24 - Starting Music Festivals

27:24 - 29:00 - Monetizing Music

30:09 - 31:57 - Passion for Service

31:57 - 36:14 - World Class Managers