Fundraising is tough. It can get exhausting, overwhelming, but it’s also the single most important job of a startup CEO. I’ve raised six rounds of funding over the course of my career — twice at my first company before it was acquired by eBay in 2001, and now, after raising $92 million in Series D funding last week, four times at Turo, the world’s leading peer-to-peer car sharing marketplace.
With fundraising fresh on my mind, I thought I’d share some insights I’ve gleaned to help other startup CEOs as they chart their courses to profitability.
1. Always be raising.
You’re never not raising. Echoing Alec Baldwin’s character’s advice to “always be closing” in Glengarry Glen Ross, all CEOs of cash flow negative companies should always be raising.
A wise person once told me that CEO actually stands for “Cash Extraction Officer” when your company is not yet profitable. Tongue-in-cheek as that may be, cash-burning startups are existentially reliant on venture capital to execute on their mission, vision, and growth plan, so you always need to be thinking about your next milestone, and how to get there…