The Best Entrepreneurial Insights and Advice of 2022 –

by: Heather Mack Greymatter

As 2022 draws to a close, we’re reflecting back on some of the most impactful discussions we’ve had with the top leaders in technology and business. We’re fortunate to have spoken with people hailing from a variety of industry sectors who have generously given their time and expertise to provide guidance, insight, and illuminating anecdotes to entrepreneurs.

We’ve compiled excerpts from 22 of our most popular podcasts aired in 2022. These interviews encompass a wide range of topics — from insights on specific sectors like artificial intelligence, cybersecurity, web3, and commerce — to tactical guidance on recruiting, leadership, and fundraising from experts who advise founders every day. Guests include iconic leaders such as OpenAI’s Sam Altman, Cloudflare’s Michelle Zatlyn, and Nike’s John Donahoe; and industry experts like former New York Times Cybersecurity reporter Nicole Perlroth. We also have plenty of operational advice and domain expertise from Greylock’s own investing team including Reid Hoffman and Christine Kim, and guidance from the leaders of our talent and marketing teams.

Cloudflare’s Michelle Zatlyn | Cyber Stewards

The vastness of the internet, as an entity, can be difficult to put into perspective. Cloudflare, however, has a clear sense of its scope, as it handles roughly 20-percent of internet traffic. To frame it with another stat: More than 70 billion cyber attacks are stopped by Cloudflare each day. Cloudflare Co-Founder, President, and COO Michelle Zatlyn joined us to discuss what it’s like to run a company that a massive constituent of users touch – often without them even knowing it. You can listen to her full interview with Greylock’s Holly Rose Faith here.

Michelle Zatlyn

I think that we led our company a slightly different way, and we had some assumptions early on.
We thought it was important to have a face to the company. What I meant by that was: We were groups of people working on this. Because of what we were doing, we felt we sat in a very privileged place online, and that when it works, it provides a ton of value. Again, 80 billion cyber attacks were stopped every day because of the technology we built. It’s amazing, you can make things faster and safer. That’s all the good side.

The shadow side of that is: Are you like a big brother watching everything? That’s kind of sketchy. And so, early on, we thought it was really important to have a face to Cloudflare. So we showed up to things, we had public profiles. The point is: this is a service made by people for people, for companies, and we take responsibility, and we care. These are things that we cared about.

And then there were things that happened where: bad things would happen, sometimes there would be a security breach or whatnot. And you don’t have to talk about these things — in our space, the common approach was not to talk about it. We felt like to build trust, you need to be transparent. We believe it’s important.

And so we started to be really transparent about why we were building something, or, when something went wrong, what happened and what we were doing to fix it. We were very committed to being transparent, both internally with our team — we shared a ton of information, we still do to this day — but also externally.

The world has really changed in the last 11 years. Now so many more companies are more transparent. It was interesting how that was not the case, but we were trying to share why we made a decision, what we were going to do about it. That’s a big responsibility, but it was a choice. No one told us, I don’t even think it was conventional, but it was a choice that we made, and then you got to stick with it.