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Fundraising operations and alternatives · Copyable template

Bootstrapping vs. raising worksheet

Work through whether venture capital is the right instrument for this company, and write down the answer.

This is a choice about strategy, ownership, pace, risk, and future obligations — not a verdict on ambition. A bootstrapped company can be ambitious, and a venture-backed one can be badly matched to its capital.

The test is not whether the market is interesting. It is whether the financing path improves the economics and the execution of this business, over the next two or three years of work.

Write the answers down. It makes the decision less emotional, and it usually reveals that the answer is not binary — a smaller pre-seed, customer revenue, grants, or a carefully chosen strategic investment may bridge the company to better evidence.

Copyable template

What is in it

  1. The next two or three years
  2. What the business model suggests
  3. The six tradeoffs
  4. What venture capital would change
  5. What bootstrapping would change
  6. The counterfactual
  7. If the next round does not happen
  8. The paths that are not either of these
  9. The decision, and the reason

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The template is ready. Add your email to open it, and you will also get The Raise Memo — a note for founders raising capital.

How to use it

Notes

Do not raise because a competitor raised, because fundraising feels like progress, or because you want permission to avoid a hard customer question. And do not accept venture terms before deciding whether the company wants the growth path those terms imply — waiting, revenue, grants, or a smaller round may preserve better options.

Where this comes from

The thinking behind it

Take it with you

Investor update template

The monthly update that keeps investors paying attention long before the next round starts.

Copyable template

Board meeting pre-read

The one-pager that goes out before the meeting so the time together goes to decisions, not recap.

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From the publication

Read The Raise Memo

A note for founders raising capital—what investors notice, how conviction gets built, and what to do next.

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