Reconnect with why your work matters


I reignite your love for the work by reorienting what you do around a meaningful purpose.

Most founders start their company energized by what they might learn, build, and change. That sense of purpose is what gives great leaders the longevity to master their craft.

Then they hit the parts that aren’t fun. Startups are hard, and not everyone has someone helping them see their own patterns. So many startup leaders end up working in fear, trying desperately not to fail instead of trying to succeed. That’s not work anyone falls in love with.

Burnout doesn’t come from hard work. It comes from hard work that’s stopped meaning anything. When you know what you’re building and why, three things change. The hard parts become worth it. The parts that aren’t worth it become obvious. And the parts you love become central, not peripheral.

Through the years of your startup journey you’ll face thousands of hard calls. Knowing why you’re making them is what lets you keep making them. I can help you find that spark again. Keeping it lit is on you.

Stop making choices that keep you stressed


I show you the choices behind your bad days, and help you find the courage to make different ones.

Most of the pressure in your week comes from decisions you made once and stopped revisiting. You’re not enduring the job. You’re enduring a handful of specific choices you’ve stopped seeing as choices.

We find them by noticing how they feel. The frustration of a truth you’ve decided not to say out loud. The exhaustion of a conversation you keep forcing or avoiding. The anxiety of not knowing which call is right while the runway shortens.

And then we run into the belief underneath: that there was never a choice at all. Naming the unspoken thing would only make it worse. Avoiding the hard conversation is what keeps the peace. Of course you have to be sure before you make a hard call.

I’ve watched leaders at 70+ startups hold those same beliefs. From the outside they’re easy to spot, and it would be my pleasure to show you. Let’s prove those beliefs wrong together—so you can enjoy your days and sleep well at night.

Master your craft through intentional practice


I challenge you to hone your leadership skills through continuous experimentation.

Say you’ve found the courage to make better choices, and you love your work enough to keep making them. That’s real progress. But courage alone won’t build a great business or a great life. Courage will open up new choices for you, but not necessarily the wisdom to know which to choose.

That wisdom comes from practice. Not one good call, but many, over months. Noticing which ones produce results and which fizzle. Which build trust and which quietly erode it. Which feel right regardless of outcome, and which feel wrong even when they look like a win.

Great businesses are largely the ones that survive long enough to figure things out. Same for great founders. That’s why loving your work and life matters so much: not just because it feels better, but because it gives you the patience to master your craft.

So we pick what you’re working on, you try it in real situations, and we reflect on what happened. Every week, for as long as it takes. Over time, you’ll develop your own uniquely effective leadership style through clear-eyed reflection on those courageous choices.

How does it work?

Outcomes

  1. Reconnect with why your work matters, so you love what you do.
  2. Stop making choices that keep you stressed, so you enjoy your days.
  3. Master your craft through intentional practice, so you can do the best work of your life.

Skills

  • Master hard conversations: tough feedback, conflict, crisis management
  • Build a high performance team: hiring, delegating, creating accountability, developing people
  • Make decisions under uncertainty: act without waiting to be sure
  • Protect your time for what matters: reserve your energy for what only you can do
  • Manage stress and prevent burnout: even under the most difficult circumstances
  • Build a distinct, opinionated, intentional culture: not one that happened by accident

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 even offer walking sessions in your local park or along the Embarcadero. 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
  • Unlimited correspondence via email and text
  • Weekly accountability check-ins via email
  • Typically paid by the company
What topics do you coach?

Over 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’m happy to share best practices, but you can get those from your favorite AI chatbot. What’s hard is understanding what’s holding you back from adopting those best practices—and that’s where I can really help. I take the time to understand you deeply, so I can offer you personal insights instead of generic best practices.

What’s a typical coaching engagement like?
  • Often the first few months focus on resolving any urgent recurring issues such as stress or conflict. Usually there’s a clear pattern of choices which perpetuate those issues. By finding the courage to make better decisions, we break the pattern and empower you to focus on work you love.
  • Once those urgent issues are addressed, we take the opportunity to reconnect with your sense of purpose and reignite your love for the work. With regular experiments we gradually reshape your day around work you love and prove empirically how you can deliver results with it.
  • With enough practice, courageous choices that once seemed impossible become the new normal. Having long since found work they love, my long term clients focus on mastering their core skills and building new ones as their business scales. Instead of merely enduring their days, they relish the fun and challenge of embracing each new challenge 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 choices behind their bad days and are actively practicing making better choices.
  • After six months or a year, clients usually report feeling less stressed and more fulfilled overall, and more able to lead in ways they’re proud of even under difficult circumstances. 
  • After a couple years, clients typically are actively scaling their business, feel equipped to handle most any challenge, and are having fun learning the new skills needed to operate at their current scale.
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, the company should pay for your coaching. Investors see exactly how many companies fail due to ineffective 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 doing the best work of your life at a sustainable pace 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