I've sat in your chair.
I know the weight and the thrill. The hard calls, the sleepless nights, the pressure of payroll. But also the rush of building something great, the drive to win, and the belief that you can pull it off.
I've been in your shoes and built a lot of muscle and earned many scars. I want you to benefit from all of them.
The short version
I've spent 30 years building, scaling, and selling technology companies. I was CEO of Bitly (sold to Spectrum Equity, 2017), CEO of Outside.in (sold to AOL, 2011), and CEO of Castiron (sold 2024).
Before that, I held leadership roles at Seevast and About.com. I've raised venture capital, managed PE transitions, hired and fired, and learned what actually works when everything's on the line.
Now I coach founders and CEOs of high-growth, venture and PE-backed companies. I work with leaders who are scaling beyond their comfort zone — transitioning from doers to strategic leaders without losing what made them great.
My approach is simple: I care deeply, I've done the job, and I'll tell you what I actually think.
Career Highlights
Full Time Coach
Coaching founders and executives full time.
Founder & CEO, Castiron
Built and sold the company.
Sold 2024First Coaching Client
Began executive coaching.
CEO, Bitly
Grew team and business, led sale to Spectrum Equity.
Sold to Spectrum EquityAOL Local
Grew AOL Local to $50M+ revenue.
CEO, Outside.in
Built and sold the company to AOL.
Acquired by AOLSeevast
Grew Seevast to $100M+ revenue.
About.com
Helped grow About.com to public offering, sold to Primedia.
Sold to PrimediaWhy coaching?
Both of my parents were therapists. I grew up watching people help other people think through hard things. It's in my DNA and I've always been drawn to it.
For this chapter, I realized the thing I loved most wasn't just building companies, it was the meaningful conversations and navigating the critical moments along the way. I get joy from helping people be their best selves. I always got energy from killer one-on-ones, team meetings, and all-hands. Seriously.
I started coaching because it's the work I was already doing. Now I do it full time and love every minute of it.
Speaking, Writing & Leadership
Outside of work
I'm married with three sons and live in Sag Harbor, NY. When I'm not coaching, you'll find me listening to Bruce Springsteen, following Boston sports, or on the search for the perfect chocolate chip cookie.
Critical Moments Podcast
Conversations with leaders about one specific moment in their career that changed everything. I talk with founders, CEOs, and leaders about the decisions that defined them; the hard calls, the lessons, the things they wish they knew.
Listen now
Let's talk
If you're scaling and want someone in your corner who's been there, reach out.
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