How to pick an investor in good or bad times

Trust your instincts — you’re hiring your next boss

In 20 years of working for startups, I’ve never seen as many plot twists and turns as I have in the last several months. Times are tough.

But, from the perspective of raising capital, 2020 has not been an awful time to be a startup founder. The world has changed, but the fundamentals of raising capital are the same. In the first half of the year, VCs invested $129 billion, and Q3 is up 9% year-over-year, reports Crunchbase^.

After the screeching halt to business in April subsided, founders and investors, people who are generally comfortable with uncertainty, got back to work raising and investing.

Choosing the right VC is one of the most important decisions startup founders will make. In good times, the choice can make or break a startup. When times are bad, it’s even more likely that the wrong VC partner could be the catalyst that starts a downward spiral. With many funds still looking to make investments before the end of the year and startups jockeying for cash, founders need to know how to find the right investor.

It’s not about simply choosing an investor — you are hiring your next boss. The investor should be someone you feel comfortable working with and working for.

You don’t want an investor who is checked out, but too much focus isn’t good, either. And, you don’t want an investor who is completely agreeable since your best outcome will be driven by a constructively demanding advisor.

My company, Quiq, had several term sheets when the dust settled on our Series B pitch meetings. Since the financial terms were similar, selecting an investor was made on a more subjective basis and boiled down to two fundamental questions: