We just raised our Series E in the middle of Covid. Raising this round was so different from other rounds! Biggest differences/lessons we learned:
1. Own the awkwardness. Pitching over video is just awkward. Just own it. After many attempts, I just decided to begin our pitches with: "I haven't mastered the art of pitching over Zoom and it'll be boring if I talk for the whole time -- so please interrupt, ask questions etc!".
2. Don't pitch. Don't do a traditional pitch. Talking over 30 slides via Zoom is the definition of boredom. You can't read the room. People easily get distracted. Make it a discussion. Let the conversation guide the flow.
3. Perfect the transitions. I pitch with our VP of Finance. We've done it together for years, but this time it was so much harder, because we couldn't read each other's cues about when to make hand offs. What finally worked: doing multiple dry runs and practicing hand offs.
4. Don't overplay the pandemic. Everyone knows at some point it will end. Investors want to know how your business is doing during this time, but they care much more about the fundamentals. We usually gave a quick 2 min update on it up front.
5. Always, always, always have your camera on.
6. 2x Back Channels. I always rely on investor back channels. It's even more important now because it's harder to read someone. I spoke to 5+ people (that weren't given to us as references) per investor. Other CEOs and investors who are on boards with them are the most helpful.
7. Use shared connections. If someone is going to write a check without meeting you -- every signal is worth more. Use your shared connections to vouch for you.
8. Over communicate with your team. Your team always care about a fundraise, but they care even more now. Over communicate status with them. We tried doing a quick update every week at all hands.
9. What else am I missing? What have you learned?
8.1 (adding 1 more). More than ever, get help from your existing investors. Not only do they help on decks, intros, terms, references etc -- they give great guidance and advice about the market. Big big thanks: @rickyang @eliaw @alex_gurevich @JedKatz @imthemusic @AmitMukherjee
