Colin Powell’s Leadership Rules for Military Entrepreneurs

Jim Delaney
Jun 2, 2025
5
min read

I first met General Colin Powell in 2010, at Marc Benioff’s house during Dreamforce.

Marc—a tech visionary with unmatched entrepreneurial spirit—had gathered a small group of executives and founders for one of those intimate, only-in-Silicon-Valley evenings.

I didn’t expect to be in the same room as a four-star general, let alone find myself locked in a quiet, one-on-one conversation with him.

There we were—just the two of us, standing off to the side.

Of course, he was the former Chairman of the Joint Chiefs and one of the most respected leaders of our time.

I was a former Navy lieutenant who had already made the leap to civilian life—building a career that took me through JPMorgan Chase, earning a Wharton MBA, and into an executive role at Dun & Bradstreet.

But in that moment, none of that mattered. There was no hierarchy. No ceremony. Just two service members talking about leadership, sacrifice, and the quiet weight of responsibility.

Let me be clear: I was a student. And General Powell was the standard.

The embodiment of what I hoped to one day become—a leader grounded in purpose, driven by service, and unmoved by ego.

That night, I didn’t just see General Powell’s stature—I witnessed his substance, steady and strong.

He didn’t speak in abstractions. He spoke in truths—earned on battlefields, in boardrooms, and from a lifelong belief in something bigger than himself.

Marc would later describe Powell as one of the most important mentors in his life:
The moral compass behind Salesforce’s philanthropy. The quiet force reminding every CEO that leadership isn’t about power—it’s about responsibility.

I asked Powell what had shaped his career the most.

He answered without hesitation: “Servant leadership.”

Not as a philosophy.

As a mandate.

For me, as a veteran navigating the ambiguity of entrepreneurship, Powell’s “13 Rules of Leadership” became more than just advice.

They became:

  • A framework when structure falls away.
  • A moral compass when situations fog in.
  • A reminder that even without rank or uniform, I still had a duty: to lead, to serve, and to build something that lifts others.

Colin Powell's 13 Rules for Leadership

1. It ain’t as bad as you think. It will look better in the morning.


Entrepreneurship amplifies emotions. A bad sales call feels like a failure. A missed funding round feels like the end.
But most of those feelings aren’t direct; reflection, not reaction. You need endurance more than intensity.

2. Get mad then get over it.


You’ll get betrayed. Lied to. Ignored.
You’re allowed a human reaction—but can’t build a business from that emotional state.
Vent to your inner circle, then return to the mission. Anger without recovery erodes judgment.

3. Avoid having your ego so close to your position that when your position falls, your ego goes with it.


Your startup idea is not your identity.
Your product, market, idea—doesn’t make it failure, nor its formation.
The faster you separate who you are from what you’re testing, the stronger your leadership becomes.

4. It can be done.


This is the mindset that built our military muscle—and it still applies.
Constraints are real, but so is resourcefulness.
The solution isn’t if it can be done.
And if you don’t believe it can be done, your team won’t either.

5. Be careful what you choose. You may get it.


Every yes closes a thousand future commitments.
Choose co-founders, customers, and capital with precision—not desperation.
If you win the market you’re selling to, it will feel like losing.
Vision without discipline creates chaos.

6. Don’t let adverse facts stand in the way of a good decision.


Sometimes the data says no—but the gut says go.
Great leaders align both.
Don’t ignore facts, but don’t be paralyzed by them either.
Especially when you’re the only one with a 360-degree view of the battlefield.

7. You can’t make someone else’s choices. You shouldn’t let someone else make yours.


Advisors can guide you, investors can influence you.
But at the end of the day, you’ll live in the arc of the outcomes.
Have courage to hear hard truths.
Own the steps you do not delegate well.

8. Check small things.


The best founders still read their own emails and check their own data.
A shaky CRM or an unclear pipeline flow? A broken customer journey? It signals weaknesses up and down the line.
Excellence shows up at the edges.

9. Share credit.


Leadership isn’t about hoarding spotlight.
Your mission scales when your team feels empowered.
Make recognition part of the culture.
The most powerful phrase in a founder’s vocabulary is: “Look what they did.”

10. Remain calm. Be kind.


In the military, chaos clears under composure. In startups, it’s no different.
Your energy sets the tone in every meeting, every crisis, every customer call.
Kindness isn’t weakness—it’s confidence without insecurity.
And when decisions must divide—remain intentional.

11. Have a vision. Be demanding.


People don’t follow companies—they follow convictions.
Paint a clear picture of what you’re building. Then demand the best from those who choose to follow.
High standards feel like love when it molds a mission.

12. Don’t take counsel of your fears or naysayers.


Fear is natural. But don’t elevate the lies. Unstrap the scarcity.
And the naysayers? Most of them are just rehearsing their own limits.
Respect risk, but don’t worship it.

13. Perpetual optimism is a force multiplier.


No battle repeats.
Strategy optimists—the builder that can re-iterate, win, move forward.
Your team will feed from your belief.
And in this day’s edge, belief is the only fuel you can afford.

🚀 At Traction AI, we help veteran entrepreneurs turn leadership into leverage. Because principles don’t just survive transition—they scale with it.

You don’t have to go it alone.

Let us build systems that match the standard you lead.

Go Navy!

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Jim Delaney
Jun 2, 2025
5
min read