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Reduce Downsides


Reduce downsides from being absent in day-to-day operations while fundraising by planning your company’s roadmap and offloading responsibilities to your cofounders and team.

Just as it makes sense to work in advance to secure advantages during the fundraise, it is also prudent to plan ahead to avoid downsides. That primarily has to do with managing the company in ways which minimize disruptions to the fundraising process as well as day-to-day operations especially in light of the fact that the founder and CEO will be busy talking to investors for a prolonged period of time.

Roadmap Planning

The goal of the company during a fundraise should be business as usual and up and to the right. Since fundraising takes a bit of time, the last thing you want is to enter a meeting number three with an investor and show metrics that look worse than in the beginning of the conversation. That can be very harmful if not outright kill the fundraising effort.

Beware of fundraising around releasing a new feature or product or expanding into a new location or market. Generally speaking, this is very tricky because it introduces uncertainty. Instead of being able to tell a coherent and powerful story, now you have a brand new effort, which may or may not pan out. Investors naturally have a huge incentive to wait as long as possible before making a decision, and such developments provide the perfect excuse - let’s wait and see how it goes!

Thus, I recommend being very conservative with such tactics. Unless something is extremely certain and clearly beneficial, I recommend delaying it for after the fundraise or at the very least not making it part of your fundraising efforts and story. Indeed, it is far better to have a narrative along the lines of “what we are doing is working, we are looking for funding because we see great opportunities to expand in X and Y ways and grow the business 10x.” Simple, straightforward, and powerful - just the way investors like it.

Offload Responsibilities to Others

One of the hardest aspects of fundraising is that it is a full-time job for the CEO of the company. This is a problem because running the company itself is also a full-time job. Until cloning becomes possible, this creates a conundrum - namely, how to split your time as the CEO?

Fundraising is a rare and important event of the “do or do not, there is no try” kind. And if it works, it can help put your company on a whole different trajectory. That is why, if you have committed to fundraising, you need to give it your all - otherwise, it just won’t work.

Therefore, it is vital to have a conversation with your cofounders and team about splitting responsibilities. Ideally, you can offload everything but the most critical parts of your job to others. It really helps to be surrounded by people that you know well and trust and who can pick up the slack.