The best advisor I ever had asked for the Chairman position and 5% of the company. I literally laughed at him over the phone. Four months later we made him CEO and gave him a third of the company. Here's what happened.
About a year into building MyBlogLog with my best friend Todd, some random guy named Rafer emailed me out of the blue. Said he saw what we were working on. Had a VC friend with an interesting problem. Thought he might be useful to us.
We had a few calls with him and dude was (is) sharp. So after three or four conversations, Todd and I just asked him directly: "So what do you want to get out of this?"
Rafer says: "I want 5% of the company. And I want to be chairman."
I honest-to-god laughed at him. "Are you kidding? We barely know you, dude."
And here's the part I've been talking about for for 20 years.
Scott didn't flinch. Didn't negotiate. Didn't get defensive. He just said, "Don't worry about it. Let me just be helpful and we'll figure something out."
That's it. That was the entire thing.
Four months later we made him our CEO and gave him a third of the company. He's the one who suggested MyBlogLog could be more than a stats tool and "should be a social network across the entire internet." Without Scott, that pivot never happens. Yahoo! never acquires us. None of it.
I am not telling you to give your skills away for free forever. That's a losing game and I'll fight anyone who preaches it.
But Scott understood something most people who slide into your DMs don't: if the opportunity is actually real, and you're actually good, you don't need to lock in the terms upfront. You need reps. You need to prove it. The equity conversation gets a lot easier when the founders are the ones bringing it up because they're terrified of losing you.
My clients get pitched by "advisors" every week who want 1-2% before they've done a single thing. Every week. And every week I think of Scott saying "let me just be helpful and we'll figure something out."
I discount my coaching fees in exchange for equity that vests over a year. And I give everyone a 90-day cliff and explicitly say "you don't know me well enough to put me on your cap table yet; but you will in three months."
That's the founder move. That's someone who believes in themselves and believes in the opportunity enough to bet on both.
Don't be a thirsty bitch. Go be useful. The equity will find you.