What this is
No new concepts. This is the whole course, applied to one complete, realistic deal you're being asked to actually decide on, the same kind of decision every lesson from Lesson 1 onward has been building toward.
The deal: Harborlight
- Seed round, $1.2m raised on a SAFE, $9m cap, no discount, MFN clause included
- Founder: second-time founder, prior company acquired for a modest amount, deep domain background in commercial insurance
- Product: underwriting automation software for small commercial insurers; 6 paying pilot customers, $18k in monthly recurring revenue, growing ~12% month over month
- Market: SOM estimated at roughly $180m within reach given the go-to-market plan, TAM slide claims $30bn
- Competition: two direct competitors, both raised larger rounds; founder gives a specific, tested theory on a data-based moat, not yet proven at scale
- Cap table: founders at 71% combined, one prior $150k friends-and-family SAFE at a $4m cap, already converting alongside this round, 12% option pool being created at this round
- Burn: $70k/month, this round gives ~17 months of runway post-close, no pro rata rights offered by default
- Your check under consideration: $30,000, joining as one of nine angels in this round
MRR
$18,000
MoM growth
~12%
Runway post-close
~17 months
Founder ownership
71%
Pro rata offered?
Not by default
Your task
- Run the first-look screen (Lesson 11): does this founder and market combination earn deeper diligence?
- Identify what deep diligence (Lesson 13) you'd realistically prioritize with a few available hours, and what you'd skip.
- Evaluate the moat claim (Lesson 16) against the two funded competitors, is "not yet proven at scale" disqualifying, or a normal early-stage state?
- Check the cap table (Lesson 7) and the SAFE terms (Lessons 6, 8) for anything worth pushing back on, or accepting as standard.
- Decide whether to ask for pro rata rights (Lesson 9), and how you'd frame that ask given your realistic leverage as one of nine angels (Lesson 18).
- Size the check (Lesson 20) against your own hypothetical portfolio plan, does $30,000 fit a disciplined position size, or is it too large for one of many positions?
- Decide: invest, invest at a different size, or pass, and state the single factor that would most change your answer.
There's no single right answer, and that's deliberate, a strong response might argue the 12% MoM growth and specific moat theory outweigh the unproven-at-scale risk and thin 17-month runway, especially if pro rata can be secured to compound into a winning position later. An equally defensible response might treat the missing pro rata rights and modest runway as reasons to invest a smaller amount, or to pass entirely in favor of a deal offering better terms for similar risk.
| Path | What has to go right | What it protects against |
|---|---|---|
| Invest $30,000 as proposed | Growth continues, next raise closes before runway ends | Missing a genuinely strong outlier candidate |
| Invest $15,000, ask to reduce check | Same growth needed, smaller position if it works | Overexposure to one thin-runway position |
| Pass | N/A | A down round or shutdown if the next raise slips |
Where to go from here
You've now walked one deal through the entire arc this course opened with in Lesson 1: sourcing and screening a founder and market, running diligence within realistic time constraints, reading a cap table and a SAFE's terms, negotiating from a small-check angel's actual leverage, and sizing the decision against a portfolio, not just the single deal in front of you. Real deals will rarely line up this neatly, some information will be missing, some founders less forthcoming, but the underlying discipline is the same regardless of how messy any individual deal looks.
If you want to go further from here: the power law from Lesson 25 rewards patience and consistency more than any single sharp insight, the habit worth keeping from this course is treating every deal, however exciting, through the same first-look screen and diligence discipline you'd apply to a deal you felt nothing about, and reserving real judgment for the evidence, not the pitch.
Congratulations on completing the course.