The Side Hustle Exposure Play
Ask your employer if you can do the other thing — most will say yes, and it changes your trajectory.
- Difficulty
- Easy
- Time to result
- ~months to results
- Steps
- 4
- Confidence
- 86%
For the 40-year-old with commitments who can't do the Sal Khan one-year walkaway, Gurley offers a lower-risk move he credits to Ben Gilbert of the Acquired podcast. While at a job, your employer will probably let you do something else if you're willing to do it in off-hours — especially if it has nothing to do with the job. The value is not the side income; it's the exposure to a completely different set of connections and experiences than the role your employer defined for you. Gilbert did this deliberately at three stops: at Microsoft he started Microsoft Garage, a community of entrepreneurs, which generated an entirely different network; at Madrona he simply asked if he could do a podcast from a VC firm and they said sure. The question to ask yourself at 40 and feeling trapped is: would my current career and company let me go do this other thing?
Origin
Gurley credits the framing to Ben Gilbert of the Acquired podcast, who described three deliberate side hustles across his career. Hala corroborates from her own path — her podcast started as a side hustle while she was working at Disney.
Core principles
- 01Employers will often permit an unrelated side project if you do it in your own hours — most people never ask.
- 02The value isn't the income; it's exposure to networks and experiences the job would never provide.
- 03Deliberate, repeated side experiments compound into a differentiated career.
- 04It works precisely because the side thing has nothing to do with the day job.
How to run it
- 1
Name the other thing
Identify what you'd do if you weren't trapped by commitments. It should be genuinely unrelated to the day job — that's where the new exposure comes from.
- 2
Ask the question out loud
Ask yourself: would the career I'm in, the company I'm at, let me go do this other thing? Then ask them. Ben Gilbert asked Madrona if he could run a podcast from a VC firm and they said yes.
Pro tip Frame it as off-hours and unrelated. That's usually all it takes.
- 3
Run it for exposure, not revenue
Judge the experiment by the connections, networks, and experiences it creates — not by what it earns in year one.
- 4
Repeat at each stop
Gilbert did this intentionally at three different points in his career. Treat it as a standing practice, not a one-off.
In the wild
While at Microsoft, Ben Gilbert started Microsoft Garage — a community of entrepreneurs using Microsoft projects — as a deliberate side hustle outside the role Microsoft had defined for him.
→ Led to an entirely different set of connections and networking than the day job would ever have produced.
At the VC firm Madrona, Gilbert simply asked whether he could do a podcast from the firm. They said yes, sure.
→ He became one of the most successful podcasters on the planet and loves what he's doing.
Hala Taha started Young and Profiting as a side hustle while working at Disney, running it outside the job her employer had defined.
→ The side hustle became a $7M/year company competing for an iHeart podcast award.
Common mistakes
Assuming the answer is no without asking
Gurley's whole point is that they'll probably let you do it if it's off-hours and unrelated. People self-reject on an employer's behalf and never test the assumption.
Picking a side project too close to the day job
The exposure value comes from the side thing having nothing to do with the job. An adjacent project reintroduces you to the same network you already have.
Is it for you?
Best for
Mid-career people with financial obligations who can't make a clean break but need exposure to a different field.
Not ideal for
Employees under strict non-compete or moonlighting restrictions, or anyone whose side interest directly competes with their employer.
From the transcript
“While you're at a job, they'll probably let you do something else if you're willing to do it in your off hours or whatever. And…”
“That led him to a whole different set of connections and networking than if he had just sat there in the job they had defined…”
“That's another thing you could do if you're 40 and feeling trapped. You know, ask yourself, could I would the career I'm in, the company…”
From the episode
Bill Gurley: Break Free From Career Regret and Design Work You Love
Bill Gurley