Fundraising & Investors

How do I decide the right time to start raising, if at all?

A starting point

Raise when you have a specific, fundable milestone the money unlocks, not when the runway gets scary. The strongest position is raising from a place of strength, when you don't strictly need it and the metrics are climbing. If you're only raising because you're about to run out of cash, you've already lost the negotiation.

Go deeper

Read

📄 Article
Free Beginner

A Guide to Seed Fundraising

From Y Combinator Startup Library by Geoff Ralston 20 min read

Why we picked it

The canonical, no-nonsense overview of how seed fundraising works, written by a former YC president who has seen thousands of rounds. It's the single best starting point before you talk to a single investor.

  • Only raise if the capital genuinely accelerates you toward a big outcome; fundraising has a real cost in time and control
  • Decide how much you need to hit a real milestone, and understand the instruments (SAFEs, notes) before negotiating
  • Run fundraising as a focused, time-boxed process rather than a background activity
Open ycombinator.com →
📄 Article
Free Intermediate

Default Alive or Default Dead?

From paulgraham.com by Paul Graham 10 min read

Why we picked it

The single most useful mental model for whether you actually need to raise. Graham's 'default alive vs default dead' framing forces the financial clarity most founders avoid until it's too late.

  • At constant expenses and current growth, will you reach profitability before the money runs out? Answer that first
  • Founders systematically ask this question too late, often after over-hiring
  • Being default alive gives you leverage; being default dead means you're fundraising from weakness
Open paulgraham.com →
📖 Book
Paid Advanced

Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist

From Wiley by Brad Feld & Jason Mendelson book (~300 pages)

Why we picked it

The definitive book on how VC deals really work, written by two Foundry Group VCs. It demystifies the term sheet term-by-term so you negotiate from knowledge, not fear.

  • Term sheets divide into economics and control; the dangerous clauses often live in control, not the headline valuation
  • Understand liquidation preferences, option pools, and protective provisions before you sign anything
  • Know the VC's incentives and fund structure so you can predict how they'll behave
Open venturedeals.com →

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