Bill Gurley’s Thoughts on Alternatives When Raising Isn’t Optimal

Over the last few weeks, several founders have shared their 2023 plans with me. A few of them intend to fundraise—otherwise, they’ll run out of cash. With those founders, I chatted about cash balance, burn, and runway. And I always asked them what plan B is if the fundraising environment further deteriorates. Most of them have no plan B. Raising is the only option they’re considering, which bothers me.

When I hear a founder say they must raise, it makes me think of this blog post from Bill Gurley. Though it’s a few years old, it’s relevant to today’s environment. Bill was ahead of his time in his thinking. I like how he laid out the following alternatives when founders can’t raise a clean round of financing at a flat or up valuation:

  • Dirty term sheets – These are terms sheets that give founders the valuation they want but come with many surprises down the road. Bill does a great job of explaining this and who “shark” investors are.
  • A clean round at lower valuation – Valuations don’t only go up. Many high-profile companies raised down rounds and went on to have massive success. A down round is better than a dirty round (i.e., a dirty or structured term sheet).
  • Positive cash flow – I focused on this when I bootstrapped my company. The best way to gain leverage and control your destiny is to not need to raise capital from others. Easier said than done for sure, and not an option for all founders, but a good exercise for founders to go through. I personally think we’ll move to a focus on a path to profitability over growth for start-ups because valuations will likely start being pegged to profits rather than revenue.
  • Go public (i.e., IPO) – This is more of a longer-term goal. Bill makes the point that founders’ and employees’ common stock is treated as equal to investor stock after an IPO because investor preferred stock converts to common. This eliminates liquidation preferences and other rights that preferred stock has over common stock.

Bill’s post is thoughtful and contains a lot more great material relevant to the current environment. It’s worth a read for founders and anyone else in, or considering entering, the start-up world.