A wide-ranging conversation on trading psychology, investment research, risk management, and the tension between building businesses and investing. Mable and Ogle unpack how they form a thesis, test it against opposing views, size positions, handle being wrong, and avoid letting ego drive decisions.
I restarted HODLong as a traders' talk and hosted Ogle as the first guest on the show.
Show Notes
00:00 How Ogle first got into trading as a kid
05:17 Growing up poor and developing a complicated relationship with money
10:52 Stepping back from public life, building companies, and returning to trading
14:09 Why deep research comes before making meaningful investments
18:23 The core thesis: revenue, real users, and value flowing back to token holders
24:53 How to research founders, incentives, and whether a business can sustain its model
27:00 Early bets vs. later entries: balancing risk, upside, and conviction
29:41 Position sizing and the idea of a “sleeping size”
32:19 A real-time example of resizing a position when part of a thesis breaks
36:29 The “wrong train” mental model for cutting a losing position
38:05 Why opportunity cost matters more than comparing investments directly
41:19 What makes a business defensible: moats, partnerships, and distribution
46:16 Self-worth, luck, and proving you can still perform
50:37 Why strong founders can still lose: timing, capital, and staying close to users
57:23 How better user experience helped reshape perpetual trading
60:04 Why investing is easier to pivot than building a company
61:44 Actively looking for evidence that disproves your thesis
65:40 Turning trading lessons into durable mental models
68:23 Ego, detachment, and why traders are often competing against themselves
70:34 Managing liquidity risk and preserving optionality in large positions
72:49 Social trading, signaling, and the danger of performing for an audience
78:25 Closing thoughts: social media, visibility, and the Panopticon