Questions:

• (1:54) How to transition into business after being an athlete?
• (7:58) How to start a community for high-net-worth individuals?
• (9:12)  Opportunities in the legal field?
• (14:09) Should first-time investors get into venture?
• (16:43) How to learn how to run a holding company?
• (26:17) How do you create your tweets?
• (35:15) How to acquire home services companies?
• (37:20) Who did you cold email when you first started?
• (45:22) How to deal with criticism?
• (54:52) How to work for Farnam?
• (1:00:22) Shopify vs Amazon ecosystem?
• (1:03:32) What have you guys learned during the pandemic?
• (1:15:57) Should you send gifts when you network?

Questions:

(1:02) How can I become a Tiny Foundation Fellow?

(2:39) How do I turn my music production website into my full-time job?

(6:05) Should I focus more on my agency or go all-in on my SaaS business?

(11:20) Does the founder staying or leaving a company affect it? Best predictor of an operator’s success?

(15:25) How do you go about finding executives?

(20:21) Why does Castro omit conservative podcasts from the list of podcasts users can subscribe to?

(21:11) Opinions on my startup and pitch?

(24:53) How would you have created a positive outcome for Flow?

(28:57) How do I find a CEO to run my businesses independently?

(32:27) To both of you: What is actually your favorite hobby outside of anything work related? Is it typically (w/o covid) a group activity or something on your own? Thanks!

(34:23) Should I start my own company or look for a job?

(38:20 Why did you build Capital Daily as an investigative journalism newsletter?

(41:18) How and why did you decide to do Tiny as a holding company?

(44:40) How do I best incentivize my COO?

(48:00) What’s the best way to learn how to be a good operator?

(51:35) How would you recommend balancing early free customers vs. paid for a B2B SaaS company?

(53:13) Can you please explain the scout system in detail. Thank you!

We answer questions from donors for our first ever charity Ask Us Anything session.

We raised over $50,000 (with Chris and I matching dollar for dollar) and will be donating it to 1Up Victoria Single Parents Resource Center. Thank you to all the generous donors!

Stuff We Recommended:

• The Dhando Investor by Mohnish Pabrai
• The E Myth by Michael Gerber
• How To Get Rich by Felix Dennis
• The Tao of Charlie Munger by David Clark
• Howard Marks Memos
• Charlie Munger Lecture on The Psychology of Human Misjudgement (our animated version / full audio version)