Hey friend,
In 2019, a man in a nice suit stood in front of the most expensive painting at my first art show (Dimitra’s painting). He told me it reminded him of his late wife.
I talked him right out of buying it.
If you’ve ever watched someone fall in love with your painting and then walk away, you know the drive home. You replay it. Was it the price? Should I have said something different?
For me, the problem was my mouth.
A lot of artists lose in-person sales the exact same way. Someone hands you the reason they love your painting, and you hand them yours right back. It feels generous. It’s also the fastest way I know to lose the sale.
Let me back up.
Back then I’d just started working at Milan Art. It was a very different Milan Art, we only had a few team members. And my one real skill besides copywriting was throwing parties (I’d just finished being the social chair for my fraternity), so they asked me to help put on an art show. And what is an art show if not a good party that is trying to sell art?
So I threw one. We partnered with a charity, and they brought in more than 50 serious collectors. We got a house in Scottsdale worth over $3 million (in 2019 prices), hired live musicians, and I brought in a friend who could sell anything.
Right at the start of the night, it hit me that none of it counted until art sold. These collectors were way out of my league, and the only thing I’d ever sold was skincare at trade shows. So I pulled my friend into a back room, kind of panicking. “Dude, how do I sell these people?”
He said, “It’s not about how many people you sell. It’s about how many times you ask.”
That line changed how I think about selling forever. We sold over $43,000 of art that night. (He outsold me, obviously.)
But I also blew a $15,000 sale.
I asked a LOT of people that night. I just didn’t listen to them enough.
Later on, I saw a man staring at Promise Land, a massive painting of Dimitra’s. I sized him up by his nice suit and thought, “Yes.”
I walked over, and almost right away he told me about his wife.
I didn’t know what to do with that. It felt too heavy. So I asked him what about the painting reminded him of her, and then I started talking about what Dimitra meant when she painted it.
Then I made it worse. I brought Dimitra over without telling her a thing about his wife. With no context, she did what any artist would do. She explained her painting, beautifully.
When I asked if he wanted to take it home with him, he said he’d think about it.
He left without it.
To this day, Promise Land hasn’t sold, even though Dimitra has sold tons of her art since. I believe that painting was meant for him. I failed him, I failed Dimitra, and I failed myself.
Here’s what I should’ve said: “Tell me more about your wife.”
Then let him talk.
He’d already told me why he wanted it. My whole job was to get him talking about her, so he could picture that painting on his wall, a piece of her with him every single day. Instead I gave him my reasons, then Dimitra’s. None of them were his.
Now I think of every painting as a mirror. People see their own story in it, and the sale happens when they hear themselves say that story out loud.
Only share what you meant if they ask. Then keep it short and hand the mirror back: “That’s what it means to me. What do you see when you look at it?”
(If you’re in the Mastery Program, I filmed the full lesson for Part 3: nine ways to lose a sale, and how to avoid each one.)
Here’s what to do this week if you sell in person:
- Write three questions on a note card, in your own handwriting: “Tell me more about that.” “What do you see when you look at it?” “Is it the piece, the price, or the timing?” Bring it to your next show, open studio or collector call. When the nerves hit, you’ll have something to say that isn’t about you.
- Message the last person who said they’d “think about it” and ask if you can help them think it through. Worst case, you learn what stopped them. Best case, you sell a painting.
Rooting for you,
Jake
P.S. please take a moment to rate this week’s newsletter here.
P.P.S. As promised, here’s the link to the first song from the course I’m taking. Please note, this is not the style that I plan on releasing in. Nor did I choose the vocals. But that being said, it was a ton of fun to learn this very bold style.