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Fundraising: Given a successfully bootstrapped business showing strong profitability & success, what advantages & pitfalls do you see in raising a round?
JC
JC
Jason Cohen, Founder at WP Engine answered:

For the business, the advantage is the *potential* to grow bigger, faster, and the disadvantage is you're taking on new risk.

The real challenge is to solve for what you want from the business, and -- cheesy though I know it sounds -- from life. Do you want to stop running this company some day? Do you want to pull a decent amount of money from the company for 10 years or go for a larger sum? Are you still interested in running a business like this or do you yearn for a new challenge?

Even then, there are many more options than just raising money or not, and what kind of money from what kind of investor.

Therefore, the first thing is to decide what you want -- which is a sort of CEO-therapy -- and then you solve for the path which maximizes the chance of that path, and also takes some risk/money off the table depending on the situation.

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