So I do have kind of an extensive questionnaire, so we just touch on a few things, but one thing I think first and foremost is, what are your values? And I think it's really essential to do some sort of values clarification exercise. You can find a ton of them online. You can find a list of values and just pull out your core values and just compare them with each other because when you are aligned, it's great. Or when you're adjacent, it's also great. I might care a lot about excellence, Lenny, you might care a lot about learning. Fantastic. Those are great values that we can kind of, go together. I might care about excellence and you might care about work-life balance. Wow, let's talk about that because I think it's going to be really important as we go through our startup journey that we understand both of us, what does work-life balance mean and what does excellence mean?

One of the founders I worked with, he would text or Slack his co-founder on weekends and the co-founder wouldn't respond. And that was extremely frustrating to the person, to the co-founder I was talking to. And it turned out, after they finally addressed it, it really was about wanting to have some downtime and some, quote unquote, "Balance."

I'm so great at bringing things up." But the person who's close to you might say, "You seethe until you're ready to bring something up and it's really uncomfortable in the seething period." So it just gives you a little more self-awareness about how you actually handle conflict.

The other person might be a person who totally wants to talk about the conflict but wants to let it settle first and wants to also go through their own thinking process about what's important to them and might actually feel like they've resolved it themselves without having to have a conversation with you.

And if you're the person who's like, "Let's talk about it, let's talk about it, let's talk about it." And they're like, "I'm working through it myself." Now you have conflict over the conflict and it just turns into dynamic that's not necessary.

There are four signs your idea has legs:People pay you money: Several people start to pay for your product, ideally people you don’t have a direct connection toContinued usage: People continue to use your prototype product, even if it’s hackyStrong emotion: You’re hearing hatred for the incumbents (i.e. pain) or a deep and strong emotional reaction to your idea (i.e. pull)Cold inbound interest: You’re seeing cold inbound interest in your product

Every prosumer collaboration product, including Figma, Notion, Coda, Airtable, Miro, and Slack, spent three to four years wandering in the dark until they stumbled on something that clicked.

When I first started meeting founders, I wanted to help with anything and everything. Unfortunately, that's neither realistic or possible. For example, I have many responsibilities at my day job that must come first. Over time, I have honed in my pitch to be explicit about how I can and can't help. See the notes above about ways to be helpful, and find your own unique combination of value to bring to the table.

My contract typically looks like this: We agree to meet ~X hours per quarter/half/year Multiply by Y contracting rate Y ⨉ X = some dollar amount Z Divide Z by the startup's latest price per share to arrive at a number of advisor shares to grant

Be founder-friendly! It's a big deal and a lot of paperwork to get a smaller check or advisor on the cap table (unless they already have a lot of operational infrastructure in place) – this usually means being relaxed about the commitment paperwork or helping out pro-bono for the first few hours while they work through the logistics.

Finding founders you work well with can be a numbers game; you won't be sure what you like doing until you've met a handful of founders, done several advisory meetings, and poked at different types of problems. It's okay to dip your toe and warm up to the process before committing a lot of time and energy to this. I started slow, and have been steadily sharpening my own intuition about what kinds of products and founders get me excited, and where I can add unique value