One way we categorize startups is by whether they have crossed the chasm. I don’t mean that in the Geoffrey Moore sense (although I think it’s still one of the best books on scaling a tech business, and recommend that you read it), but whether you have made it to the other side of your cash flow bridge. Will you need to raise another round of outside funding in order to survive? If yes, fundraising should always be a front & center topic for you as a founder.
If you are not there yet, as a founder, you need to constantly think about your shareholders, and how supportive they are likely to be in the next round. We see examples where the lure of a deep pocketed new investor is very high, and founders are exclusively focused on attracting a new shareholder, sometimes at the expense of keeping the existing investors educated on the progress of the company and motivated to keep up their support.
Those already around the table are a lot more likely to support you (if they can), as long as their confidence in the business remains strong. They have a vested interest in not just seeing you succeed, but also seeing you survive. This is a different type of motivation. Any potential new investor is not motivated in the same way. Therefore, when you categorize your investors, existing and potential, on the top of that list should be your existing shareholders with the capacity (capital-wise) to continue to support you. Their participation in or leading of your next round is your biggest weapon as you market your startup to the capital markets.
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