Discussions about financing companies, choosing investors, and understanding venture capital. Read founders’ and investors’ perspectives in context, with links to the original announcements and room for follow-up questions.
A line from Matt Cynamon’s conversation with Fred Wilson and Nikhil reminds me of a useful standard for advising founders: writing a check doesn’t automatically qualify you to tell someone how to run their company.
When Fred was 29, a founder challenged him to spend a week doing every job in the company before offering advice. Fred flew to Buffalo and did it. He quickly learned that advice lands differently when it comes from someone who has taken the time to understand the work and the people doing it.
The conversation also touches on the other side of the job: building conviction when your partners disagree, while staying open to evidence that challenges your strongest beliefs. That balance seems hard to maintain. Confidence without curiosity turns into stubbornness; curiosity without conviction makes it difficult to act.
I’m curious how founders and investors here think about this:
What earns someone the right to give you advice? And what makes advice useful even when the person giving it hasn’t done your job?
Read discussion →I am an advisor, board member, investor, who writes a lot. I started off as a computer science / chemistry double major back when almost no one used a computer in chemistry and the computer science department was more like a math department. I did undergraduate research in the very earliest IDEs (called “syntax directed editors”) which made me want to be a professor. So I went to graduate school and promptly dropped out when I realized that programming was more fun that writing about programming. I interviewed at a “software company in the Pacific Northwest” when no one in my family had ever been to Seattle or had any idea what a software company might do. Everyone I interviewed with seemed to know everything about everything so I took the job and then spent almost 24 years there from 1989-2013. I worked on the first C++ compiler and tools—that research. I did a weird job as “Technical Assistant to the Chairman” and became something of an internet-is-a-big-deal clarion call. I then spent over 10 years working on Office from the last 16-bit version to the biggest redesign of the products, introducing Clippy, email, web versions of the tools, and web-server collaboration along the way. I then moved to Windows where we shipped Windows 7 and Windows 8. I’ve managed teams from single digits to five digits in size, managed teams in a dozen countries, and hired more people than I can count from college to join Microsoft. Along the way I lived in China to combat piracy. I taught MBA students in Boston to gain a different perspective. And wrote more blog posts than I can count.
I have a lot of stories. I love to compare and contrast old and new. I love thinking about the stories of product development and how they were told and retold over years. You can read many on "Hardcore Software" hardcoresoftware.substack.com—a tale of my time at Microsoft serialized on Substack and a my long form posts on current events in tech.
I’ve advised, invested, or served on the board of quite a few companies and worked closely with a16z on several companies where I served as a board partner representing the firm’s investment.
This is an AMA about these topics. Thank you!
Read discussion →
Zach Davidson
Steven Sinofsky