Founder Coaching

Why coaching: The short answer

• Building something new and leading your team is deeply rewarding. But it’s also intense: burnout is rife, boundaries are porous and overwork is the norm. How you show up for your team makes a huge difference. I’ve been there and I’ve supported many founders on the journey.

Why coaching: The longer answer

• Performing at a high-level calls on all of you. Coaching can amplify your strengths and fortify your areas of struggle so that when the next crisis arrives, you’re ready and waiting.
• You’re under pressure to deliver impact and to show up for your team. Your energy is a critical resource for your company. In the rush of it all, it’s easy to lose contact with yourself and what drives you.
• Being a founder is 120mph each day. Bad habits and sloppy thinking can quickly set in amidst the chaos. We have so little time to personally reflect, even as we dedicate so much time to reflecting on what we’re building. Coaching is a space to check if your current approaches are working for you. If not, why not try something different?
• It’s lonely at the top. Yes, your calendar is back-to-back. But it can often feel like you’re struggling in silence. Being able to speak candidly to someone outside of your bubble frees up your energy and creates renewed focus.
• Many founders arrive where they are with zero training. This is a testament to their skill and execution, but it can also leave them feeling unprepared when others begin to look to them.

How coaching helps

• Levelled-up leadership. How you show up has a massive impact on the rest of your team. Coaching can help you grow as a leader, deepen your sense of meaning and purpose in work and inspire those around you.
• Accountability amplifier. Founders are often driven by accountability, and coaching can provide a potent support for setting and achieving goals.
• Deep clarity. The coaching relationship bestows a foundation of clarity that will help you find the signal in the noise; to hone in on the deep work that makes a difference and resist the temptation to be doing it all.
• Find your anchors. Leading a company rarely has neat boundaries. In the frenzy, we lose touch with the rest of our lives and what fuels us from the bottom up. You can’t show up for everyone if you lose contact with yourself. Coaching is a way of re-establishing your personal anchors.
• Leading with courage and compassion. Strong, modern leaders unite courage and compassion so that we know when to listen and when to surge forward. Show up as a better leader for your team, whether through confident decision-making, improved emotional intelligence or just leading by example.
• Honest feedback. Because of how people treat The Boss, leaders often struggle to get candid feedback. Having a coach as a neutral sounding-board can challenge perspectives, identify patterns and uproot assumptions.
• Vertical development. Leaders are often skilled at filling their cup, but struggle to expand the cup itself. Coaching can help cultivate what Nick Petrie calls “vertical development”; a level of growth beyond the acquisition of skills and knowledge.

Why me?

• I spent the last 10 years building teams and companies and I’ve been writing code and building software for nearly 20 years. In 2019, I cofounded Almanac and together we raised $45m to change the way we do remote work. Prior to that, I was also the founder of an online meditation community which was acquired in 2017. Before taking on leadership roles, I worked as a Ruby engineer. I’ve also worked in larger tech companies like the Fintech unicorn, GoCardless. You can view my LinkedIn profile here.
• I am familiar with the intensity and excitement of founder life, not to mention how all-consuming it can become. After going through burnout and divorce simultaneously in 2019, I decided to share my story. It was the most difficult piece I’ve ever written, but it was deeply rewarding and set me on to a new path in life.
• Coaching for founders by a founder means you can talk to someone who understands MVPs, GTMs, and OKRs. If you’re moving fast and iterating weekly, you need someone who knows that environment, not a run-of-the-mill corporate or business coach.

How I’m different

• I am honest about the highs and lows of leading and love supporting leaders to succeed without losing touch with the rest of their lives. I learned the hard way and forged a set of tools in the furnace of those environments.
• Alongside my skills as a founder and technical thinker, I’ve supported myself with an eclectic range of other practices, like meditation, bodywork and daily writing. This experience—alongside my training as a transformative coach—means I’m comfortable supporting people in both the inner and outer work required to succeed.
• My coaching is always personalised. There is no 3-step programme or 4-point protocol. While they sometimes sound appealing, they are often a disservice to the breadth of what we’re bringing into the world. Likewise, I draw on what feels salient and useful for each client rather than locking into one coaching modality.

Who do you work with?

• I often work with founders in early-stage startups (pre-seed to Series A) because that’s where most of my experience lies. But I also enjoy supporting non-executive leaders in larger companies. If people are looking to you, there’s likely some powerful work we can do together.

You might be…

• Grappling with a change in what’s expected of you or unsure how to incorporate difficult feedback.
• Struggling with cofounder friction or difficult people on your team.
• Struggling with anxiety and indecision; unable to balance work and the rest of life.
• Feeling more tuned out, burned out & resentful—slipping into patterns of people-pleasing or feeling like what you do is never enough.
• Craving more fulfilment and contentment amidst your daily work.

What it looks like

• I work on a monthly retainer, with a minimum 3 months engagement. That’s two 1-hour sessions each month. This can be adapted if you need more frequent support or longer sessions.
• I also offer email support during our engagement for things that come up between sessions.

Psssst! If what you’re looking for is primarily advisory, I also work with teams and found as a consultant & advisor. Having built many products from scratch, sold side projects, and founded and grown teams of engineers, I can provide a wealth of experience that will help your product succeed.