Member Insights

The Challenge:

The situation at hand was brought by a CEO of a bootstrapped company that needed investors. He was looking for insight on handling his short-term cash needs while remaining focused on the company’s long-term vision.

If you were in this situation, what would you do?

First off, it’s good that you’re thinking about balancing your short-term needs and long-term goals. Fundraising is always harder and more time-consuming than you’ll think it will be—that’s just the foundational rule. You have to knock on a lot of doors, and the stakes are super high. If I were you, I would make the process as simple as possible by ‘gamifying’ it. Before I start making meetings, I’ll make sure I have all my research, due diligence data and desired terms of the investment out of the way. Then I’ll load my pipeline with a certain number of meetings to make within a certain number of days, and set incremental goals to measure my progress. When making meetings, I’ll be very clear about what I need. I’ll also approach each call like it’s the first and be excited to talk with each person, so I’ll get more value out of every conversation.

Fundraising is a lot like running a marathon with only one goal – to win. However, you have to start out by running one mile at a time. I’ve seen people become super set on reaching their fundraising goal by a certain time period. But by doing so, they become more prone to making mistakes and getting burnt out. You need to have successes along the way even if that success is just practicing and learning. By gamifying fundraising, I’ll have incremental successes that I can measure, which will keep me excited on a daily basis. As I go along, I’ll also become more relaxed and more controlled in what I’m saying, which will build my confidence. This makes it much easier to maintain resilience and deal with high volume rejection/disappointments along the way, and ultimately get what I really need.

Remember, it only takes one conversation to turn everything around. Gamify it, and the chances of success can go up dramatically. Best of luck to you!