Chicago: A Finance Town With Crypto Blind Spots #
Chicago has always been a finance town. Futures trading, Options markets, Commodities. The city understands derivatives and speculation better than most.
The metro has 3.6 million households with a median income of $84,000. About 13% earn over $200k, which translates to roughly 468,000 households. That’s the third-largest concentration of high earners in the country after New York and LA.
Around 215,000 of those households don’t have a financial advisor.
Chicago’s Complicated Relationship with Crypto #
Chicago’s finance community gets trading. CME launched Bitcoin futures in 2017. The institutional infrastructure for crypto ran through Chicago before most cities were paying attention.
But retail crypto adoption here is more moderate. The culture is traditional finance. People trust institutions. They’re skeptical of things that feel speculative or unregulated.
That said, crypto ownership among Chicago’s high earners probably runs at or slightly above the national 28-30% rate. Self-directed investors, tech workers, and younger professionals have been accumulating. They just don’t talk about it the same way people in Miami or SF do.
The problem is that many of these holders are managing their crypto the same way they’d manage a stock Portfolio. And crypto doesn’t work like stocks.
What Traditional Investors Miss About Digital Asset Management #
Traditional finance experience can actually be a disadvantage with crypto.
You’re used to cost basis being handled by your brokerage. With crypto, you’re responsible for tracking it yourself across every Exchange and Wallet you’ve used. If you’ve swapped tokens on a DEX, moved assets between chains, or received Staking rewards, you’ve got a tracking challenge.
You’re used to wash sale rules that apply to stocks. Crypto has been in a gray area. Some advisors treat it one way, some another. The IRS hasn’t given clear guidance.
You’re used to assets being held by custodians who handle security and pass holdings to your heirs without friction. Crypto in self-Custody works differently. If you haven’t planned for what happens to your holdings, your family might not be able to access them.
Chicago’s finance sophistication doesn’t automatically translate to crypto sophistication. They’re different games.
Finding the Right Crypto Custody and Wealth Advisor #
Chicago has plenty of financial advisors. Walk through the Loop and you’ll pass a dozen offices. But how many of them actually understand crypto at a technical level?
Not many. And the ones who specialize in digital assets often work remotely, serving clients nationally rather than limiting themselves to one city.
Remote advisory makes sense for crypto because:
- The Asset Class is digital and borderless
- The best specialists built practices that match how crypto works
- Secure communication tools handle sensitive conversations well
- You don’t need to schedule around office visits
What you want is someone who can speak to the specifics of your situation. How do they approach cost basis for DeFi transactions? What’s their framework for tax-loss harvesting with volatile assets? How do they think about Custody versus convenience?
Getting Started #
Digital Wealth Partners focuses on crypto and works with clients remotely. If you’re in Chicago with substantial Digital Asset holdings alongside your traditional Portfolio, they’re set up for exactly that. Visit digitalwealthpartners.net.
The 215,000 high-income households in Chicago without advisors include plenty of sophisticated investors who’ve underestimated crypto’s complexity. Traditional finance skills help, but they’re not enough.
