Nick Kennedy

Audacious coaching for courageous leaders.

Don’t build a successful business at the expense of a life you love.

You carry the decisions and the pressure. If every win only raises the bar, you can spend your life chasing more while the people you love get what’s left.

I help leaders decide what matters and build a life they’re proud of.

Book a conversation

Most clients come through referrals, and every client is referenceable. If you found me another way, you’re welcome here too.

“Nick has changed my life. I know that sounds crazy, but I think of my life in terms of ‘before Nick and after Nick.’ The clarity, the courage, the accountability, it’s all different now.”

Lauren A. · Founder and CSO

Sound familiar?

When more becomes the goal, nothing feels like enough.

You hit the number and the relief lasts about a weekend. The next problem follows you home, and you’re at dinner with your head still at the office. The business keeps growing while the life it was supposed to pay for gets pushed to next year.

Do that long enough and you’ve spent a decade succeeding at something you never decided you wanted.

  • You’re working harder and enjoying it less.
  • Every hard call lands on your desk. Alone.
  • Your team tells you what you want to hear.
  • Home is getting the leftovers.

The choice

You get a say in what happens next.

Under pressure, most leaders go one of two ways. Some feel trapped by their circumstances. Others grip harder and expect everyone to keep up.

There’s another option. You can face what’s true and take responsibility for what comes next, even though you don’t control all of it. You can chase big goals and become someone you respect along the way.

Your company and your life are the same project.

The decision you keep avoiding at work comes home with you, and whatever’s unresolved at home shows up in how you lead. So we work on both.

Nick Kennedy
Nick Kennedy · Founder, coach, author

Your guide

I’ve sat in the chair you’re sitting in.

I co-founded an airline, grew it and sold it. I raised capital, built leadership teams from scratch and made the hard firing calls.

I also came close to losing what mattered most. My marriage was on the rocks, my kids didn’t know who I was, and without my title I didn’t know who I was either.

Now I bring that experience and more than 10,000 hours of coaching to candid conversations about your business and your life. You bring the hard questions. I’ll help you see them clearly and hold you to what you decide.

More about Nick →
10,000
hours of one-to-one coaching
$6B+
in transactions
EY Entrepreneur of the Year
and Hall of Fame inductee
Co-founder of RISE
acquired by Surf Air
“I wondered if the cost was worth it, but I can tell you that the ROI is easily 50:1. I had no idea how many blind spots I had, and Nick was the perfect partner to wake me up.”George H. · Founder and CEO

How it works

Define your win. Then build toward it.

Book a conversation

Start with an honest conversation

Tell me what’s working, what it’s costing you and what you want to change. We’ll both decide if it’s a fit.

Get clear on what matters

We define success for your company and your life, and name the decisions and patterns standing in the way. It starts with a short Discovery Questionnaire.

Put it into practice

We meet regularly. Every session ends with specific next steps, and my notes hit your inbox so you follow through.

What coaching with me looks like →

What’s possible for you

It’s still going to be hard. Choose your hard.

Building something worth building is hard no matter what. Coaching won’t change that. It gives you clarity about which hard things are worth it, so the effort goes where you actually want it to go.

You can’t have it all. But you can have what is important.

  • The hard calls still come. You make them with a clear head, and you know why you’re making them.
  • Your team knows what you expect, and you have the honest conversations instead of putting them off.
  • You still have something left for the people you love, even in the brutal weeks.
  • You go after the next goal because you picked it. The last win was enough.

Most clients get clearer within a month or two. Plenty feel it in the first session.

Your next step

What do you want your success to make possible?

You don’t need the answer yet. Let’s discuss what you’re working on.

Book a conversation