AVAILABLE ON
Episode 48

How a Pilot turned into a CEO: Ben Klein, CEO at Aero

AVAILABLE ON
Episode 48

How a Pilot turned into a CEO: Ben Klein, CEO at Aero

Key Insights

1. Scale Breaks Ad Hoc Legal Decision-Making

Ben explains that what works for a small company fails quickly at scale.
Individual judgment calls don’t translate when volume increases.
GCs must build frameworks and processes so decisions remain consistent even as complexity grows.

2. The GC’s Value Is in Making Risk Understandable

Executives don’t need exhaustive legal analysis — they need clarity.
Ben stresses translating risk into concrete business implications: timing, cost, and exposure.
When leaders understand risk clearly, they can move faster with confidence.

3. Systems Beat Heroics

Early-stage legal teams often rely on individual effort and responsiveness.
At scale, this model collapses.
Ben advocates for building systems that reduce dependency on any one person, including the GC.

4. Legal Should Enable Speed, Not Just Safety

Ben challenges the idea that legal’s primary job is risk avoidance.
In growing companies, speed is often a competitive advantage.
The GC’s role is to enable responsible speed, not default caution.

5. Consistency Builds Executive Trust

Executives need predictable guidance to make fast decisions.
Ben notes that inconsistent legal advice slows teams and creates uncertainty.
Clear principles allow leaders to anticipate legal input without waiting for it.

6. Founders Want Partnership, Not Permission

Ben highlights that founders rarely want legal approval — they want collaboration.
GCs who position themselves as partners, rather than gatekeepers, gain influence.
This mindset shift is critical as companies mature.

7. Closing Insight

Ben Klein’s lesson is clear: the GC’s job at scale is not to answer every question, but to design how questions get answered.
For modern GCs, systems are the real force multiplier.

In this podcast, we cover

0:00  Introduction
6:17 Transitioning from corporate law to aviation law
10:07 Founding an aviation-focused law firm
12:20 Learning to manage an executive team as a first-time GC at Skyryse
14:58 Counseling an airline through the coronavirus pandemic
16:58 Taking on a GC and First Officer role at Aero
24:56 Leveraging your experience in the cockpit to lead as CEO
26:45 Instilling confidence in investors as you transition from GC to CEO
32:08 Inspiring teamwork in c-suite reports and hiring for your replacement GC
36:57 Book Recommendations
40:33 What you wish you’d known as a young lawyer

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