In this book, Charlie O’Donnell shares his insights on how to navigate the fundraising process, drawing on his experience as a 20-year veteran of the venture capital industry, with stints at Union Square Ventures, First Round, and running his own fund, plus being a failed founder himself.
The book is filled with tactical tips:
- how to build relationships and networks that will support you when you start a company
- how to write a cold email that will get the attention of an investor
- the elements of an effective pitch: venture-scale market, the right team to capture that market, and traction
- what the people you encounter actually mean when they say “We’re interested” (aka “no”)
- what you can learn from each meeting even if you get rejected
I liked his framing of the founder’s journey as learning how to address a problem, one rejection at a time: “The founders that last the longest … are curious, not delusional. They experiment, get feedback, accept when they have to change course, and improve without the panic of having to be perfect right now.”
Lastly, I appreciated his acknowledgment of the bias present in venture capital. Even beyond the implicit bias, the founders who have greater financial security and have friends and mentors who provide advice on what to do next (which typically correlate with more privileged backgrounds) are going to have an advantage when VCs quickly pattern match to evaluate a potential investment.
This book is a helpful tool to close that information gap by giving any reader the knowledge of how the game actually works so that they can navigate it more effectively.
On a personal note, I’ve been friends with Charlie for 20 years after meeting him at New York tech meetups and starting to follow each other’s blogs. I’ve been a fan of his work as a blogger and investor and community organizer, and was excited to read his new book when it was released this week, and it lived up to my hopes.
