"When raising outside investment, many founders focus mostly or even entirely on the valuation of the round. But finding investors who are aligned with your vision of the company and believe in you as the leader to make it a reality is actually, in my experience, the most critical thing.
My advice to founders is to always get to know the people who are investing in your company. Interview them the way that you would a new executive team member: ask them hard questions; push them on why they want to invest in your company; make sure they are going to be staying at the firm that’s making the investment. Next, make sure you get to know them beyond work, the same way that you would a potential friend or even a spouse: go out for drinks; go on a hike; find out what they do in their free time. And finally, trust your gut. Your judgment here doesn’t need to be objective — ask yourself if you have chemistry with the person. In my experience, if the answer is yes, that sets the stage for building a real relationship with your investor, one where you will be able to engage with them on both the business needs and your own needs through the inevitable ups and downs. If the answer is anything less than an emphatic yes, it’s a red flag.
If you want to protect your interests with investors, the most important thing is to pick ones you can trust and build a real relationship with."