Entrepreneur and CEO Coaching

Need a coach?

When I started my first company…

I’d never been a CEO.
I’d never hired a team.
I’d never fired an employee.
I’d never written a business contract.
I’d never managed an investor syndicate.
I’d never had a million dollars in the bank.

I felt overwhelmed even as I tried to hide it. One moment I felt like a god; the next, like a fraud. More than once, I rode the startup rollercoaster.

Along the way, I was lucky enough to have seasoned mentors like Marc Randolph (founder/CEO of Netflix), Seth Sternberg (founder/CEO of Honor & Meebo) and Joe Kennedy (CEO of Pandora) to coach me through the company-building process. They didn’t have all the answers––each of us have to create our own––but they helped sustain me through the confusion and the hard times, of which there were plenty.

I coach entrepreneurs because I love helping people and I want to pay it forward. I feel immense gratitude to the people who helped me, and think that everyone should be so lucky.

If  you think you need help managing your team, your investors, your business or just your own psychology, then share your details and fill out the form below.  Your answers will go straight to my inbox and only I will read them.

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  • Why do you think you need a coach? What problems are you dealing with? Be honest. I won't share this with anyone.

Matt’s Coaching FAQ

Q: What’s the difference between an advisor and a coach?
A: An advisors is reactive; a coach is proactive.

When you ask an advisor for help, a good advisor will meet with you over coffee or on the phone, giving you his/her undivided attention and candid opinion. When the meeting is over, most advisors will stop thinking about your problem(s) unless or until you ask for their help again.

I’ve had advisors before. What I do goes beyond advising.

As a coach, first and foremost I work with you to understand what your key problems are, whether they are with your business, your team or your psychology. Together, we identify the problems to be solved and come up with goals & success metrics for our time together. Typically, I meet with you in person once a week, plus make myself available as needed via phone or FaceTime. The key is that I really try to understand your business, its’ challenges and your personal goals––then proactively work with you to help you win.

Your lawyer, your board, your investors are focused on your business.

I focus on you.

I’ll suggest books to read, experts to talk to, strategies to pursue and classes to take. But in the end, it’s your company and your life. I don’t have all the answers and I don’t know more than you.

Q: Do you charge for your coaching services? 

A: Yes, I work on retainer. $5,000/month plus equity. The cash keeps you honest about whether you’re really getting value from me; the equity keeps me honest about whether I really believe in you.

Q: I’m intrigued, but I’m not sure whether I want to commit. Can we meet for coffee?

A: Sure! I typically meet with prospective clients 2 to 3 times before we officially start working together. You should be picky about who you work with. I know I am! So these meetings are as much about me getting to know you as they are about you getting to know me.


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