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Timestamps:
00:00 - Intro
00:01:45 - How can you afford this?
00:03:28 - First job
00:05:01 - On financial security
00:06:42 - Going from $0 to $10 million
00:07:35 - Buying investment properties
00:08:59 - Sponsor - Netsuite
00:10:13 - Why not invest in stocks?
00:10:48 - Balancing financial risk
00:14:25 - Going broke
00:16:25 - Biggest positive net worth swing
00:17:47 - First time gambling
00:18:59 - Why are you drawn to gambling?
00:23:42 - Can you improve at gambling?
00:27:26 - Sponsor - Zocdoc
00:29:00 - Meeting his son EJ
00:31:20 - Turning gambling into a business
00:38:12 - Slot machines: which to play?
00:38:47 - Knowing when to walk away
00:44:23 - Are you addicted to gambling?
00:50:03 - Gambling glamorization concerns
00:56:21 - Why can’t you write off losses?
01:03:22 - Why are you more successful than others doing similar content?
01:07:14 - Sponsor - Ramp
01:08:19 - Open your own casino?
01:11:36 - How calculated is your content?
01:14:09 - Most $ you saw someone lose
01:32:28 - Most $ you saw someone win
01:35:43 - When do you walk away winning?
01:39:25 - Craziest gambling story
01:46:35 - Your biggest single bet
01:47:45 - Thoughts on online casinos
01:57:20 - Biggest insecurity
02:01:35 - On marriage and family
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