focus on what you can control.
You can't time the market — which holds for raising money. Instead, companies can focus on being the best at things under their control to set the stage for sustained success.
The best time to raise money is before you need it, and the best market to raise money in is an "up" market. These don't always line up in a company's favor - but that doesn't necessarily mean they are worse off.
These characteristics lower the bar for a good outcome - they don't set the stage for continued, repeatable success. Consider home run-record holder Babe Ruth and a minor league player - they can crush home runs against a little league pitcher, but only one can produce similar results in a major league game while it's pouring rain. The expert-level focus on developing the elements within your control sets the stage for repeatable success regardless of the environment.
The best time to raise money is before you need it. When you need money is when you are cash-strapped, the clock is ticking, you are looking for any solution over the best. You haven't given yourself the time or tools to make well-thought-out decisions.
The best market to raise money in is a "receptive" market. Part of successfully raising money is knowing where to go and being able to read the room. Would you order BBQ from a vegan restaurant? Would you ask for a raise after your department was downsized?
The Uncommon Borrower focuses on what they can control - they 1) identify the size and timing of cash needs by projecting their cash runway, 2) understand the range of outcomes by continuously pressure-testing upside / downside situations to minimize surprises, and 3) are aware of the set of actionable paths to raise money at any given time.