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(4 minute read)

You’ve spent a lot of time and money finding that perfect candidate. But in today’s economy—where side hustles are the norm—hiring isn’t as simple as it once was. According to a MarketWatch Guides survey, 54% of working Americans have taken on extra income opportunities in the past year. That means it’s likely more than half of your potential hires (and co-workers) have a side hustle.

The internet is full of unanswered questions and conflicting advice:

1. Is it illegal to ask about side hustles in an interview?

2. Can you prohibit them in an employment agreement?

3. Should candidates reveal or hide their side hustles?

4. Can employers control what employees do in their free time?

The issue is complex, and endless online rabbit holes only add confusion. Let’s cut through the noise and focus on practical solutions—with no magic, just common sense.

Not All Side Hustles are Bad—Start a Conversation

You have a legitimate business interest in knowing if a candidate’s side hustle could interfere with their job. But the key is how you ask. A direct question might feel confrontational, so frame it as an open discussion.

Suggested script: “It’s important for us to know if you have any other jobs or side hustles that could affect your ability to perform in this role.” Then, be quiet and let the candidate talk.

This approach makes it a dialogue, not an interrogation. If you don’t know about a side hustle, you can’t assess its impact. You might find that it’s completely harmless—like delivering meals for the elderly, something they just forgot to list on their application.

A Word of Caution: Avoid discrimination risks. For example, if a candidate discloses a side hustle as a part-time administrator at a place of worship, be careful. States like California, Colorado, Connecticut, Illinois, Louisiana, Minnesota, Montana, Nevada, New York, and North Dakota have laws protecting legal off-duty conduct, which could include side hustles.

Also, if someone’s side hustle is flipping vintage sneakers, maybe don’t make a big deal about it—unless your business is also flipping vintage sneakers.

Check Internet Sources for Clues

Take the time to look at a candidate’s LinkedIn or other social media profile which can reveal helpful insights. Compare their listed experience with their résumé. Check their posts for side hustle clues. Look at the end dates of past jobs—are they still working somewhere they didn’t disclose?

A candidate’s home-state “division of corporations” website is another good place to search. Most provide a name search for individuals that are officers or registered agents of companies. Florida offers such a search, try it here.

Researching public information isn’t about prying. It’s about ensuring transparency and avoiding surprises after the hire.

Address Side Hustles in Offer Letters

If your business uses offer letters or employment contracts, consider adding a disclosure clause rather than an outright ban. You want employees to tell you about side hustles, not hide them.

Possible language: “During the interview process and on your resume and application, you informed us that you are not currently employed elsewhere or involved in any side hustles. To avoid potential conflicts, you agree to immediately notify us if you take on additional work (whether part time, full time, or as an independent contractor) or start a side hustle during your employment with us.”

This language doesn’t prohibit side hustles—it gives an employer the chance to evaluate potential conflicts before they become problems. It also gives the candidate a final opportunity to disclose just prior to taking the job. “Oh, I completely forgot to mention…”

(If you would like a professionally-drafted Employee Offer Letter template with side hustle language and access to all other templates for future articles, subscribe to The Co. Letter™ Premium).

Competitive Pay Reduces Side Hustles

The best way to prevent employees from seeking extra income? Pay them well. According to the MarketWatch Guides survey, 30% of side hustlers say the high cost of living is their biggest financial obstacle, while 22% cite insufficient income.

If you’re bootstrapping and can’t offer top pay, think creatively. Offer stock options, flexible work arrangements, or professional development opportunities. Build perk loyalty so employees are less tempted to seek extra income elsewhere.

And sometimes, you might have to accept side hustles as part of the deal—at least until your business grows and you can offer pay that makes them unnecessary.

Think about it: Employees having side hustles isn’t always bad. But surprises are. Stay informed, set clear expectations, get the candidate to sign an appropriate offer letter, and focus on what matters most—finding talented and loyal team members.

Try This Instead: Internal Communications

(2 min read)

“Our meetings drag. Status updates get recycled and are long-winded.”

You sit through discussions about projects that don’t need discussion. Sound familiar?

Fix: Before an individual update, require the task or project be labeled Red, Yellow, or Green:

• Green = No issues. Move on.

• Yellow = Potential risk. “What’s the issue, and how do we fix it?”

• Red = Problem. “Is it dead or how can we get it back to yellow or green?”

Example:
Task: Get a signed contract back from a major customer.

• “All green, already turned it into accounting.” ✅ Move on.

• “Green, but stuck in their legal department.” 🚦 Hold on—that sounds yellow. What are their concerns and how do we unstick it?

• “Red, they lost their funding.” 🔴 Serious—how do we salvage the deal?

This is a sliver of a system that worked for Alan Mulally when he turned around Boeing and Ford. Try it. Let it help you and your team cut the fluff and focus meetings on solving problems.

Want more on Mulally’s leadership? Check out American Icon: Alan Mulally and the Fight to Save Ford Motor Company by Bryce G. Hoffman—also on Audible.com.

Old Business

Corporate Transparency Act Compliance Update

What’s the Latest?
The Corporate Transparency Act (CTA) has been on hold due to ongoing federal litigation. Now, a new 21 March 2025, deadline looms for nearly all limited liability companies (LLCs) and corporations to file their Beneficial Ownership Information (BOI) report with the U.S. government.

What is the CTA?
The CTA is a 2021 federal law requiring all U.S.-formed or registered entities to either confirm they qualify for an exemption or submit a Beneficial Ownership Information Report (BOI) to the U.S. Treasury’s Financial Crimes and Enforcement Network (FinCEN).

What’s the deadline for NEW entities formed on or after 18 February 2025?
The 30-day filing rule still applies. For example, an LLC formed on 20 February 2025, must file its BOI report by 22 March 2025 (30 days from formation).

I already filed—now what?
You’re set. No further action needed.

Can I file voluntarily while the CTA is on hold?
Yes. FinCEN is accepting early filings. You can submit yours here. No penalty for waiting, but beware: FinCEN’s system is new and may get overwhelmed as the deadline nears.

Will the new Trump administration scrap the CTA?
Unlikely. While legal challenges could lead to changes, social media chatter is pressuring lawmakers to delay, limit the scope, or repeal the CTA.

We’ll keep tracking this issue and will update you as it unfolds.

New Business

Upcoming Sunday Edition, 23 February, 2025

This Sunday, we’re unpacking a gut-wrenching short case study: A startup built by multiple co-founders, but dependent on one thing— a single social media account. When the co-founder controlling that account had a falling-out, the company unraveled in a mess that could have been avoided with the right legal and operational safeguards.

You’ll walk away with key information and action items, including how simple operating agreement provisions could have prevented the chaos and how social media platforms handle (or generally ignore) business account disputes.

It’s a great read with practical risk management takeaways—because no business, big or small, should hinge on a single password.

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