• Hi, I'm Dale.

    I help entrepreneurs learn to thrive under pressure, prioritize what truly matters, and overcome ego when making business decisions. Being the best CEO possible is the most important factor in creating a great company and a successful outcome for your employees and investors.

     

    Bottom line: I help founders and executives thrive.

     

    I know the journey because I've lived it myself: I was one of the first Thiel Fellows and ran UnCollege for six years. Along the way, I wrote a book Penguin published, became an angel investor, and experienced the highs and lows of life in Silicon Valley.

     

    I've trained with David Peterson (Head of Coaching at Google) at 7 Paths Forward and Marcy Swenson (Helped to create over $40B in market value as coach to the founders of Lyft, Twilio, Pivotal, and Reddit).

    Why choose me as your coach?

    For nearly a decade, I’ve faced many of the struggles that you are likely to face: raising money, pivoting, managing teams, building products, selling, marketing, recruiting and more.

     

    Through coaching, I’ll help you:

    • Develop into the best leader you can be

    • Become more self-aware

    • Understand your core beliefs (and how they hold you back)

    • Address your most challenging issues

    • See around corners

    • Set and track more effective OKRs/KPIs

    • Manage and hire a team more experienced than yourself

    • Leverage what I’ve learned - and hopefully avoid some of the pain

    I use powerful coaching frameworks to ask the right questions, deepen your thinking, and encourage self-reflection. I’m curious and nonjudgmental, but I won't let you get away with magical thinking.

     

    My clients know me as passionate and committed to self-development. You can expect:

    • Weekly sessions focused on your most important issues

    • 24/7 phone support when you need it most

    • Accountability to enable you to achieve your goals

  • What investors say about coaching:

    (Seriously, performance is important)

  • Recommendations

    The word around town

    Growth Advisor, Ticketmaster & Masterclass

    “Dale never shies away from the root cause while remaining pragmatic. His genuine, caring nature and experiences as an operator have made his advice indispensable in my career."​

    Saku Panditharatne

    CEO, Asteroid AR

    Breakout list CEO, former A16Z investor

    “To people looking to learn soft skills, I definitely recommend Dale - he's taught me so much about how to network and talk to people - and that was before he became a coach!"

    Founder, Degreed.

    Raised $80M from Jump, Techstars & GSV

    "As an advisor, Dale was always proactive in offering support. His experience spans movement building, communications, operations, and perhaps most distinguishing is his ability to attract and connect interesting people."

     

    Amy Chantasirivisal

     

    Director of Engineering, Wildbit

    Former Head of Engineering, Double Dutch

    "I approached Dale for coaching when I was having trouble articulating what I valued as a leader, and applying those values in my day to day work. Our conversations were as structured or unstructured as I needed them to be for any given session, and Dale took great care to listen closely and sympathize with my struggles. He helped me frame my challenges from different angles so that I could make progress on the problem-solving. He ultimately helped me clarify my thoughts, and I was able to find a path forward for myself. In that way, he was a true coach: he didn't give me any answers (despite me asking for them), but gave me the structure to arrive at them on my own"