I coach CEOs, founders, and startup executives to pursue their boldest ambitions by embracing risk instead of avoiding it. Why might you want to work with me? 

Speak Freely without Being Judged

Leadership is lonely when you don’t have a confidant. It helps to have someone besides ChatGPT to talk through your challenges: you can’t improve how you lead if you can’t admit what’s not working. 

But it can feel risky to admit failure when everyone around you is so invested in your success! Your board, your investors, your manager, your team, even your partner all have their own agendas that may or may not align with your own. 

Let me be at least one person in your life who’s not judging you by your performance. I will help you learn from your failures by normalizing them, not judging you for them. 

Pursue Your Boldest Ambitions

Often leaders get stuck on the way to their boldest ambitions. Maybe you keep waiting for a moment that never comes. Maybe you keep repeating strategies that aren’t working for you. Maybe you aren’t clear on what exactly your ambitions are in the first place. 

It feels risky to explore change, so many leaders remain stuck—often believing there’s nothing they can do anyway. But there’s always a way forward if you embrace risk. 

I will help you find that way forward. By experimenting with new behaviors and perspectives every week, you’ll build comfort with risk-taking—and prove empirically which strategies work for you.

Learn to Manage Your Stress

It’s easy to say you’ll embrace risk. It’s harder when the moment arrives and stress sends your whole body into danger mode. When we’re stressed, we tend to abandon our best intentions and react with fight, flight, freeze, or fawn. Stress signals danger to our bodies and naturally makes us risk-averse.

That’s why it’s so critical to learn to manage your stress. Not just to make your day-to-day more pleasant—but because you can’t assess risk accurately when you’re stressed! It’s impossible to make good decisions when your whole body is in danger mode.

I will help you embrace risk by managing your stress. No doubt your job is hard, but it’s not dangerous! Worst case you have to get a new job—most of us change jobs every few years anyway. You can work through that feeling of danger without believing the threat is real.

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

Judgement-Free Discussion

This is your space for real talk, so anything goes! Our sessions are confidential: I don’t share anything we discuss with your manager, HR, board, or investors. My loyalty is to each individual client, not their company. I hold you accountable to your commitments, but without judgement. Failure is a normal and necessary part of growth.

Pursue Your Boldest Ambitions

We discuss whatever feels most urgent to you in each session. We explore what’s happening at a deeper level: goals, risks, stressors, etc. Once the goal is clear, we discuss potential solutions, and you commit to taking action within the next few days. Whether you succeed or fail, there’s always something to be learned from each experiment. Over time, you’ll prove empirically what style of leadership produces the best results for you.

Learn to Manage Your Stress

When you feel stressed, we don’t ignore it, we learn from it! We investigate what feels dangerous about the situation and check the facts: is there any real threat here? Usually we find the risk of danger is remote—you can handle any potential outcome just fine. With the threat resolved, we can focus on letting the feelings pass.

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 answers, but I do have the context to understand where you’re coming from and help you find the right way forward.

What’s a typical coaching engagement like?

Broadly speaking, often the first few months focus on resolving any urgent recurring issues such as interpersonal conflict or stress/burnout. Usually clear patterns emerge that explain why these challenges keep reappearing and how the client’s actions are contributing to them. 

It can be extremely satisfying to suddenly understand the big challenges in your life and know how you can permanently resolve them! Easier said than done, unfortunately. Changing how you lead can feel risky, so it often takes time to get comfortable with experimentation.

The latter stage of coaching is slower, but it builds to big results. With enough experience, what once was stressful becomes the new normal. You can take on ever bigger risks in pursuit of your ambitions. That’s how you learn to pursue ever more ambitious visions—without unsustainable levels of stress. 

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 that stand in the way of their ambitions: the key risks that trigger their stress response and lead to bad outcomes. 

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 true selves.

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 subpar 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. 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