Imagine this. You open your phone to an alert. It says, “you spent $236,000,000 more this month than you did last month.”

If you were the top bidder at Sotheby’s fall auctions, it could be reality.

Sounds crazy, right? But when the ultra-wealthy spend staggering amounts on blue-chip art, it’s not just for decoration.

The scarcity of these treasured artworks has helped drive their prices, in exceptional cases, to thin-air heights, without moving in lockstep with other asset classes.

The contemporary and post war segments have even outpaced the S&P 500 overall since 1995.*

Now, over 70,000 people have invested $1.2 billion+ across 500 iconic artworks featuring Banksy, Basquiat, Picasso, and more.

How? You don’t need Medici money to invest in multimillion dollar artworks with Masterworks.

Thousands of members have gotten annualized net returns like 14.6%, 17.6%, and 17.8% from 26 sales to date.

Explore offerings

_{*Based on Masterworks data. Past performance is not indicative of future returns. Important Reg A disclosures: masterworks.com/cd}

My team and I have worked with hundreds of companies over the past few years.

Almost all of them had one common problem: the founder was the bottleneck of the business.

They were the geniuses with a thousand hands, making everything happen. Without them, there wouldn't be a business.

In other words, they had a high-paying job. Not a business.

This becomes even worse during the holiday season. Your team is on vacation. Things are busy. You're prepping for the new year. And guess who all the work falls to? You.

We call this key man risk.

Here's what most founders miss: being indispensable doesn't make you valuable. It makes you trapped.

Every decision that only you can make is a decision that can't scale. Every process that lives in your head is a process that breaks when you're gone. Every client relationship built around your personal involvement is a relationship that won't survive your exit.

You think you're building equity. You're actually building dependency.

1. Document one repeatable decision this week.
Pick something you do constantly: approving content, handling refunds, prioritizing features. Write down the exact logic you use. Turn it into a checklist someone else can run.

2. Identify one thing only you do that someone else could own.
Not delegate. Own. The difference matters. Delegation keeps you in the loop. Ownership removes you entirely. Find one thing and transfer it completely.

3. Stop answering questions you've already answered.
If someone asks you the same question twice, the problem isn't them. It's your system. Build a decision framework, record a Loom, write it down. Make the answer accessible without you.

You're not supposed to be the answer to every problem. You're supposed to build a system that generates answers without you.

The companies that scale aren't led by founders who do everything. They're led by founders who made themselves optional.

This week: Pick one thing only you can do and make it so someone else can do it without asking.

So if you're stuck working in the business this holiday season, I'd love to help you make sure it doesn't happen again.

Book in a call here to see if it’s a fit

 Let's level up in 2026.