The Side Hustle Culture Meets the C-Suite

Side hustles are no longer just for Uber drivers or freelance designers. Increasingly, CEOs — the top leaders of business — are getting in on the action. Whether it’s investing in startups, launching a podcast, writing books, or even running e-commerce brands, today’s executives are blurring the lines between corporate leadership and entrepreneurial experimentation.

But this trend raises a pressing question: Should a CEO have a side hustle at all?

Is it a distraction? A conflict of interest? Or is it simply a smart way to stay innovative and connected to emerging trends?

In an era where burnout is high, top talent is mobile, and reputation is everything, the answer is more nuanced than a simple yes or no.

Why Some CEOs Are Turning to Side Hustles

Creativity Needs an Outlet

CEOs often thrive on building things — not just managing them. Once a company matures and daily operations stabilize, creative leaders may look for new stimulation. Side hustles offer a sandbox to explore ideas without risking the core business.

Staying Connected to the Ground

By running a smaller venture, a CEO can stay sharp, relevant, and attuned to the startup ecosystem. Think of it as innovation scouting — a way to stay close to what’s new, especially in fast-moving industries like tech, media, and fintech.

Diversifying Personal Brand and Income

The average tenure of a CEO is getting shorter — 6.9 years in the U.S., according to a 2023 PwC study. A side hustle can act as a reputation hedge, a fallback, or a platform to amplify thought leadership through books, speaking engagements, or digital products.

Mental Health and Fulfillment

Surprisingly, some CEOs report that side hustles actually help them decompress. Running a passion project outside of corporate KPIs can provide a sense of autonomy and enjoyment — two things not always guaranteed in board meetings.

Famous Examples of Side-Hustling CEOs

• Jack Dorsey ran Twitter and Square (now Block) simultaneously — though not without criticism.

• Elon Musk is perhaps the most high-profile multitasker, juggling Tesla, SpaceX, xAI, and more.

• Whitney Wolfe Herd, founder of Bumble, invested in multiple women-led startups and launched side initiatives through her foundation.

• Brian Chesky (Airbnb CEO) regularly publishes thought leadership and design essays that serve as side projects extending his public persona.

While these leaders blur the lines between their companies and other ventures, they also raise questions about bandwidth, optics, and priorities.

Pros of a CEO Having a Side Hustle

Personal Growth

Leading something small can bring a sense of groundedness and humility. It reminds CEOs what it’s like to hustle — without a large team or budget.

Talent Attraction

Employees often admire leaders who are multi-faceted. A CEO who writes, speaks, or invests is seen as more dynamic and relatable, potentially helping with recruitment and retention.

Networking and Synergies

Side hustles — especially those involving media, investing, or advisory roles — can lead to business development opportunities for the CEO’s main company.

Legacy Building

Some CEOs use side projects to pursue causes they care about, from sustainability to education. These projects can enhance their legacy beyond the company balance sheet.

The Risks and Ethical Dilemmas

Of course, it’s not all upside. The CEO role demands focus, and side hustles can invite legitimate concerns.

Perception of Divided Attention

Stakeholders may question whether the CEO is “all in.” Optics matter. A single media article about a CEO’s side business could spark rumors of burnout, disengagement, or future resignation.

Conflict of Interest

If the side hustle overlaps with the core business (e.g., launching a product in a similar space), there could be legal and ethical red flags. Intellectual property misuse, insider knowledge, or poaching talent are serious concerns.

Board Pushback

Not all boards are progressive. Many still view outside ventures as a red flag. Some will even include clauses in contracts prohibiting “extracurricular business activity” without prior approval.

Time Management Strain

Leading a company is already a 70+ hour-a-week commitment. Add a side hustle, and burnout can sneak in. Worse, poor time management could lead to underperformance in both arenas.

When It Works: Guardrails and Governance

If a CEO decides to pursue a side hustle, clear boundaries and governance are essential. Here’s what that should look like:

1. Transparency With the Board

Before launching anything, CEOs should disclose side ventures and document any potential conflicts. Boards appreciate proactive transparency far more than reactive explanations.

2. Time Commitment Clarity

If the side hustle consumes more than 5–10 hours a week, that’s worth revisiting. A CEO’s first duty is to their shareholders and employees — side projects must fit around that, not compete with it.

3. Legal Review

Contracts should be reviewed to ensure no intellectual property leakage and compliance with non-compete agreements.

4. Alignment With Brand Values

If the CEO of a sustainability company launches a fast fashion side hustle, it could spark backlash. Projects should align with the values of the CEO’s primary company.

5. Exit Strategy

If a side hustle ever starts to take off, the CEO must ask: Will I step away from the company? Can this be delegated? Plan for success — don’t get blindsided by it.

So, Should a CEO Have a Side Hustle?

The real answer is: It depends.

If the CEO is using their free time to grow, innovate, and amplify their vision — without compromising their leadership — a side hustle can be a powerful asset. But when ego, distraction, or misalignment creeps in, the cost can outweigh the benefit.

More than ever, the modern CEO is not just a steward of business but also a curator of reputation, trust, and transparency.

The side hustle question isn’t just about business — it’s about integrity.

Final Thought

In a world where everyone is expected to be more than one thing — founder, content creator, mentor, investor — CEOs are no exception. But leadership, unlike side hustling, isn’t optional.

The best CEOs don’t just ask, “Can I do this?” — they ask, “Should I?”