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The Holloway Guide to Raising Venture Capital

2 resources from The Holloway Guide to Raising Venture Capital we point founders to, and the questions each answers.

📄 Article
✓ Link checked Free Intermediate

Why we picked it This is the sharpest framing of why your ask is really a bet on the next valuation step. It introduces 'accretive milestones' and 'clearing the valuation hurdle': ask whether the milestones this round buys will let you raise the next round at roughly double the valuation. That single test forces your use-of-funds slide to map spend to value creation instead of listing cost buckets.

Determining How Much to Raise

From The Holloway Guide to Raising Venture Capital by Holloway (Andy Sparks et al.) 15 min read

  • Every line of your use of funds should be an accretive milestone: if you hit your goals, can you raise the next round at a much higher valuation than today's post-money
  • 'Clearing the valuation hurdle' is the real job of the round, so size the raise to the progress needed to justify the next markup, not to a comfortable runway
  • Investors like Fred Wilson and Mark Suster converge on 18 to 24 months of operating runway, giving you a defensible band to anchor the amount
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📄 Article
✓ Link checked Free Intermediate

Why we picked it This is the founder-side reference that draws the exact line you need: it says outright that not every seed investor takes a board seat, keeps early boards to 1 to 3 people, and it is blunt that an observer seat is not a free consolation prize (observers push investor interests, every future investor then demands one, and confidentiality leaks). Use it to justify offering an observer seat instead of a voting seat to a lead who wants in.

Board Seat

From The Holloway Guide to Raising Venture Capital by Holloway (with Alex MacCaw and startup counsel) 15 min read

  • A board seat is real governance control, not a thank-you; keep the early board tiny (1 to 3) and grant seats deliberately, not per investor
  • Observer seats look harmless but compound: they carry influence without accountability and set a precedent every later round will invoke
  • Information rights (financials plus budget, monthly or quarterly) are the standard thing you give investors, separate from and much cheaper than a board seat
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