The Too-Hard Pile Filter
Default every opportunity to 'too hard' unless it's an obvious no-brainer that costs you almost no time.
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 4
- Confidence
- 45%
Borrowed conceptually from Charlie Munger's 'too-hard pile,' this decision filter for investing (or any high-volume opportunity flow) works by having a primary occupation that is not opportunity-evaluation itself. Because your main job absorbs your attention, every incoming opportunity defaults into a 'too-hard pile' unless it's so obviously good that it doesn't require extended diligence. David found that after shifting his primary identity from full-time investor to full-time show host/historian, he became a better investor, because arm's-length distance meant only genuine no-brainers claimed his limited time.
Origin
David observed that becoming a full-time podcast historian rather than a full-time VC unexpectedly improved his investing, because most opportunities now had to clear a very high, fast bar to earn his attention.
Core principles
- 01Have a primary focus other than opportunity evaluation to create natural distance
- 02Default classification for new opportunities is 'too hard,' not 'maybe'
- 03Only opportunities requiring minimal diligence time should proceed
- 04Broad domain knowledge (built elsewhere) helps you recognize true no-brainers quickly
How to run it
- 1
Anchor to a primary occupation
Maintain a main focus (research, operations, a core craft) that isn't opportunity sourcing, so you have a legitimate reason to say no by default.
- 2
Default new opportunities to 'too hard'
Treat every incoming opportunity as belonging in the too-hard pile until it proves otherwise.
- 3
Set a fast-decision threshold
Only let opportunities that can be evaluated quickly and confidently graduate out of the pile; anything requiring weeks of deliberation stays out.
Pro tip If you're still debating after a short window, that's itself the answer — pass.
- 4
Use accumulated pattern recognition
Rely on broad research and historical study (built through your primary occupation) to quickly recognize genuine no-brainers when they appear.
In the wild
After making the podcast his primary occupation instead of venture investing, David found that most potential deals fell outside his attention by default, and only the clearest opportunities broke through.
→ He describes this shift as having genuinely made him a better investor, with more selective, higher-conviction decisions.
Common mistakes
Trying to have an opinion on everything
Spreading diligence effort across too many marginal opportunities dilutes judgment on the ones that matter.
Confusing busyness with good decision-making
Spending weeks deciding on a borderline opportunity is itself a sign it should be in the too-hard pile.
Is it for you?
Best for
Part-time angel investors, operators, or side-investors who need a fast filter to protect their primary focus.
Not ideal for
Full-time investors whose entire job is opportunity sourcing and evaluation, where a too-hard default isn't compatible with deal flow requirements.
From the transcript
“It's also very nice because what it does is it puts most things in your too hard pile.”
“The no-brainers that don't take up weeks and weeks of your time to decide if you should do it or not, are the ones that…”
From the episode
Holiday Special 2023