Today’s guest asked to remain anonymous due to the nature of our conversation. He gets raw and real about what it’s like to be a partner at a Venture Capital firm and answers questions like - Should you pursue a career in Venture Capital? How to tell who your real friends are. How to live an intentional, authentic life. What to do when your values come in conflict. And How to effectively make decisions.

#venturecapital #entrepreneurship #decisionmaking

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TOPICS WE DISCUSS

(00:00:00) Intro

(00:02:11) Prioritizing Privacy Over Social Media Presence

(00:03:58) Should You Seek Fame And Recognition?

(00:04:41) How Social Media Affects Your Relationships and Mental State

(00:07:20) Boiling Life Down to Its Essentials. Essentialism By Greg McKeown

(00:08:20) Beer Friends, Wine Friends, and Whiskey Friends

(00:11:21) Living an Intentional, Authentic Life

(00:12:03) Why Sean Doesn't Drink Alcohol

(00:13:04) The Negative Effects of Alcohol, Andrew Huberman

(00:14:37) Are Your Friends Really Your Friends? Putting Your Friendships to the Test

(00:19:55) The Perils of Venture Capital. What to Think About Before Working in VC

(00:22:57) When to Work in Venture Capital

(00:23:27) What to Think About When Picking a Career

(00:24:30) Does Venture Capital Pay Well?

(00:25:42) Defining the Life You Want and the Self Authoring Program

(00:28:33) Conflicting Goals and Making Compromises

(00:30:20) How the Compounding Effect and a Clear Vision Lead to Success

(00:32:50) Stop Judging Yourself for What You Want

(00:35:13) How to Handle Risk and Thinking in Bets

(00:36:54) Sean’s Approach to Investing, Nassim Taleb, and the Barbell Approach Towards Risk

(00:39:09) The Financially Optimal Investment Portfolio, The Psychology of Money, and Morgan Housel

(00:41:16) Staying on Top of Trends and Keeping Your Finger on The Pulse

(00:44:17) Being an Independent Thinker, Questioning Common knowledge, and Interpreting Advice

(00:47:39) Building Synergy Into Your Life

(00:49:22) Sean’s Faults, Failures, and What Makes Him Human

(00:51:06) There’s a Cost and Benefit to Everything

(00:52:24) Life Reflections and Priority Shifts as Sean Gets Older

(00:55:01) Reaching Success at a Young Age: The Work, Benefits, and Drawbacks

(00:58:44) Awareness and Getting Clear on Your Future

(01:00:59) Living Your Authentic Life

(01:01:52) Advice For People in Their 20s

(01:05:00) Why Sean Doesn’t Watch TV

(01:05:35) Your Actions Show Your Real Priorities

(01:08:02) Relationships, Having Kids, and Handling Conflict

(01:11:36) Lessons Learned Traveling the World and Being a Digital Nomad

(01:14:33) The Importance of Alone Time

(01:15:17) What Success Means to Sean

(01:16:53) Outro