• 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 grow as fast as their companies.


    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 that 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 from clients

    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."

    Janett Liriano

    COO, MadeMan

    Former CEO, Loomia

    “Dale's coaching is always relevant, empathetic, clear and actionable. It’s empowering and encourages honest self-reflection -- which carries over into how I approach business challenges."

    Partner, Village ($100M seed fund)

    Founder, Military.com (acq. Monster)

    "It was a sincere pleasure to work with Dale! He is entrepreneurial, creative, bright, conscientious and personable.

    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."​