Funding a company

Should I bootstrap or raise outside capital?

Short answer

Start by mapping what the business can fund today and what it needs to reach its next meaningful milestone. Bootstrap when available resources can support that plan and you can accept a more measured pace. Consider outside capital when the plan requires resources you cannot provide and you can identify investors whose interests fit the business. Raising capital also takes sustained work from the leadership team, including investor conversations, clear materials, follow-up, and diligence. Compare that work with the time you would spend growing the business from current cash flow. Make the choice against a specific plan, team capacity, and investor audience.

Checklist

  • Write down the next milestone the business needs to reach, such as launching a product, entering a market, or expanding capacity.
  • Estimate the money, time, and people required to reach it, and state the assumptions behind each estimate.
  • List what the company can fund from current revenue, savings, or other available resources.
  • Identify the gap between available resources and the cost of the plan.
  • Separate essential spending from work that can wait or be tested on a smaller scale.
  • Decide what outside capital would change, including the milestone, timing, and execution risks.
  • Identify one investor group likely to understand the company, its industry, and its stage.
  • Compare the team's experience and credibility with what that group will want to assess.
  • Set aside leadership time for investor outreach, follow-up, materials, and due diligence.
  • Revisit the choice as customer demand, cash flow, costs, and investor feedback change.

From my talks

"Performance does not market itself; pedigree does not swing all doors wide open."

Capital Raising Book

Common scenario

A founder has enough cash to test demand with a small launch, but not enough to build a full sales team and expand immediately. The founder writes two plans: a lean plan funded by current resources and a larger plan that depends on outside capital. Each plan names its cost, next milestone, and the evidence that would show whether it is working. The founder can then discuss the larger plan with investors who understand the market while continuing the smaller test.

What to do next

  1. Build a one-page budget and milestone plan using current resources, then identify the exact funding gap for the larger plan.
  2. Write a short description of the business, why capital is needed, and what progress it will fund.
  3. List a focused group of likely investors and schedule time each week for conversations, follow-up, and preparing accurate materials.

Work through it with the how much to raise calculator. See all funding a company questions.

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Richard C. Wilson

About Richard C. Wilson

Richard C. Wilson has run the Family Office Club since 2007. It is the largest investor club in the world by media reach. The 15-person team hosts 30 events a year, including 16 in person, and has hosted more than 340 events since 2007. Richard shares what he has learned on the Centimillionaire Strategies YouTube channel.

Text or WhatsApp Richard at (808) 600-9260 or email Richard@FamilyOffices.com with a question about your raise. More about Richard.

General education only. Not legal, tax or investment advice.