Two companies, one $25,000 check each
Before the capstone, it's worth seeing the whole course applied side by side to two deals that looked similarly promising at the time of investment, one that became an outlier, one that returned nothing. Neither outcome was obvious at the time you'd have had to decide, which is precisely the point: good process doesn't guarantee a good outcome on any single deal (Lesson 25), it improves the odds across a portfolio.
| Winning deal: Fieldnote | Failing deal: Parcelwise | |
|---|---|---|
| First-look screen (Lesson 11) | Founder ex-operator in the exact niche, growing market | Founder domain fit weaker; market described as "massive TAM," no clear SOM |
| Deep diligence (Lesson 13) | Reference calls strongly positive; real usage data shown live | Only one informal reference call happened; usage data shown as screenshots only |
| Moat theory (Lesson 16) | Specific, credible network-effects theory, tested against a real competitor | "We're just moving faster," no deeper answer under follow-up |
| Terms (Lessons 6, 9) | $7m cap, pro rata rights granted | $14m cap (high for the stage), no pro rata offered, didn't push for it |
| Follow-on (Lesson 21) | Exercised pro rata twice as metrics kept improving | Never came up; growth stalled after 18 months |
| Outcome | Acquired at a 40x return, four years in | Shut down after 3 years, full loss |
What actually separated them, in hindsight
The gap wasn't luck alone, though luck plays a real role in any single outcome. Fieldnote's founder gave clearer, more falsifiable answers from the very first conversation (Lesson 15), and every diligence step confirmed that first impression rather than contradicting it. Parcelwise's warning signs were present at first look, a weak SOM answer and a vague moat, but were talked past rather than treated as reasons to invest less, or not at all.
What good process looked like here, regardless of outcome
Notice that the diligence and terms discipline applied to Fieldnote wasn't run with the benefit of hindsight, it was run the same way any first-look-passing deal should be. Parcelwise's diligence was thinner and its terms worse specifically because the process wasn't applied with equal rigor, not because the outcome was unknowable in advance. That gap in process rigor, more than any single missed red flag, is the pattern worth carrying into every future deal.
Checkpoint
- Comparing a winning and a failing deal side by side shows the same course concepts, applied consistently, separating the two more than luck alone.
- Warning signs present at first look in the failing deal were talked past rather than treated as reasons to slow down or pass.
- Consistent process rigor across every deal, not hindsight, is what a good angel process actually looks like in real time.
If anything here still feels unclear, ask before moving to Lesson 35.