Great leaders take risks. That’s why I coach CEOs, founders, and startup executives to unlock their full potential by embracing risk instead of avoiding it. How do I help?

  1. I reveal the leadership risks you’re avoiding that hold you back from greatness.
  2. I challenge you to experiment with how you lead and prove which risks are worth taking.
  3. I teach you the skills to embrace those risks without burning out from stress.

What risks are we talking about? Great leaders make the hard calls that matter: 

  1. Asking for what they want instead of settling for less
  2. Having the hard conversation instead of avoiding it
  3. Changing course when things aren’t working
  4. Protecting their time for their highest priorities
  5. Managing their stress instead of ignoring it
  6. Staying true to their values even under pressure
  7. Building a distinct, opinionated, intentional culture

Reveal What’s Holding You Back

I take the time to understand you deeply, so I can offer you personal insights instead of generic best practices. I ask about your ambitions and what’s holding you back from pursuing them. I listen to what you say and what you don’t say. I read your face for feelings you haven’t quite named. I observe how your actions match your ambitions. Then I share what I see. 

It’s surprisingly hard to see ourselves clearly! Few of our friends, family, and coworkers share their honest assessments of us, and each of them have their own agendas. My only agenda is helping you fulfill your true potential. I’ll be more than a mirror, more than a confidant: I’ll show you what you’re missing to unlock the next stage of your growth. Over time my clients acquire a deep self-knowledge that’s priceless.

Optimize How You Lead with Daily Experiments

I structure each coaching engagement around weekly or biweekly sessions covering whichever topic is top of mind for you that day. With each topic, we seek to understand what change you’re looking to create, what’s holding you back, and how you might change how you lead to make it happen. Instead of waiting to be sure, we test those changes empirically: I ask you to commit to regular leadership experiments to prove what works in the real world.

Most leaders wait to be sure before they act, and lose out on the learning that comes with rapid experimentation. It’s easy to set grand intentions in our heads, but It’s hard to follow through with them. I provide clear structure and accountability to keep you moving towards your boldest ambitions without feeling overwhelmed by risk.

Learn the Skills to Beat Burnout

Embracing risk is stressful! So I teach you the skills to manage stress and prevent burnout. I care about your feelings and your ambitions equally. You can’t achieve those ambitions if you feel stressed all the time! To face life’s risks with courage, you must master your emotions. Not by burying them inside, but by expressing them skillfully.

In many corners of the startup world, constant stress is considered virtuous. Founders talk proudly about cultivating a “culture of urgency” where everything is treated like an emergency. Don’t fall for it! My wife works at San Francisco General Hospital—at her job, everything actually is an emergency. Guess what? They still focus on making calm, thoughtful decisions.

If they can find calm in the emergency room, you can find calm in the chaos of a startup.

How does it work?

Logistics

Typically I meet with each client 2-4 times a month for an hour. We can connect via Zoom, phone, or in person in San Francisco. I charge a flat monthly rate that includes:

  • Unlimited 1:1 coaching sessions (at least 2x monthly)
  • Limited small group coaching sessions
  • Written reflections on each session via email
  • AI summaries if desired
  • Unlimited correspondence via email and text
  • Weekly accountability check-ins via email
  • Typically paid by the company
What topics do you coach?

Over nearly a decade of coaching startup leaders, I’ve covered pretty much any topic you could imagine:

  • Operational: product, design, engineering, data, marketing, sales, manufacturing, legal, etc.
  • Organizational: hiring, org design, delegation, communication, feedback, etc.
  • Personal: imposter’s syndrome, stress, time management, anger, anxiety, etc.
  • Interpersonal: poor relationships with management, peers, reports, board, investors, family, etc.
  • Strategic: fundraising, acquisitions, layoffs, culture change, exit strategy, etc.

Any topic is 100% welcome! I don’t claim to have all the right answers, but I will ask you all the right questions. I take the time to understand you deeply, so I can offer you personal insights instead of generic best practices. I’ll show you what you’re missing to unlock the next stage of your growth.

What’s a typical coaching engagement like?
  • Often the first few months focus on resolving any urgent recurring issues such as interpersonal conflict or stress/burnout. Usually there’s a clear pattern of risks each client has been avoiding. By finding the courage to face those risks, we break the pattern and begin to create new opportunities for growth.
  • Once the most urgent issues have been addressed, we can focus on long term growth. That means clearly articulating both their boldest ambitions as well the risks they’re avoiding that are holding them back. With regular experiments we gradually increase their comfort with risk and confidence handling common challenges.
  • With enough practice, what once was stressful becomes the new normal. My long term clients take on ever bigger risks in pursuit of their ambitions but without the stress that once accompanied them. Instead of avoiding risk, they relish the fun and challenge of gracefully embracing new risks as they arise. 
What results do your clients see?
  • After each session, clients often mention feeling calmer and clear about their plan to move forward. 
  • After a few months, clients usually have a clear understanding of the patterns of risk they’ve been avoiding and how they stand in the way of their ambitions.
  • After six months or a year, clients usually report feeling less stressed overall, and more able to lead in ways they’re proud of even under difficult circumstances. 
  • After a couple years, clients typically are achieving their bold ambitions, know very well how to handle most challenges, and are having fun optimizing how they lead to best express their highest intentions.
How do I choose the right coach for me?
  • Trust your gut! I recommend focusing on finding a good fit in both budget and interpersonal chemistry. 
  • In terms of budget, ask your company to pay for your coaching! Investors see exactly how many companies fail due to failures of leadership, so they’re typically very supportive of coaching at the executive level. Great coaching is expensive but worthwhile, especially for high leverage leadership roles. 
  • Chemistry is harder to predict, you really have to try out coaching together to see how it feels. If you feel inspired by the idea of fulfilling your potential through embracing risk then I’ll bet we’ll get along just fine.
  • Fortunately I offer a free one hour sample session to CEOs, founders, and executives at startups, so please get in touch and we can discuss. After a sample session it’s almost always clear whether we should continue working together.

Curious to learn more? Let’s get started.

Contact me