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Coaching

"Steve has made a meaningful impact on my ability to lead in a very short period of time. He is an excellent listener and constantly asks difficult questions to make me a more self-aware leader. I would recommend Steve to anyone who is looking for a coach to help them improve as a professional."
-Austin Reif, Morning Brew

Becoming A Coach

In the fall of 2011, my wife founded The Sill in our Lower East Side apartment. This provided an unfiltered view into the life and mind of an entrepreneur. I saw her wins, losses, and everything in between. As a VC at the time, this situation helped me gain a deeper appreciation for entrepreneurs and the daily battles they endure and sacrifices they make to realize their visions.

Here’s what I realized: startups are complex human systems led by innovators who are essentially learning on the job with limited support.

By supporting my wife and dozens of founders, I discovered that I could have a much larger impact by investing in their professional and personal development instead of their companies. I also realized that I crave and value authentic relationships and conversations geared towards helping others evolve and succeed. Coaching was my calling.

After several years of soul searching and formal training, I left the world of venture capital to become a coach and to dedicate myself to a new mission: helping the leaders of tomorrow raise their consciousness and realize their full potential as humans.

Who I Coach

I coach senior leaders who want to cultivate inner wisdom, increase resiliency, and lead more effectively. Most of my "partners," as I call my clients, are early-stage technology CEOs, but I also work with VCs and leaders ready for a career change. I look to partner with leaders who are on a mission, are self-aware and curious and are committed to the partnership.

While there are always exceptions, here's an overview of who I coach and how I determine fit.

Who I Coach
Here’s an overview of who I typically coach and how I determine fit. If this describes you and you’re looking to develop, feel free to contact me. WhoEntrepreneurs who want to evolve into high performing leaders (< 100 FTEs)VCs who desire to increase their influence and improve their decision

My Approach

I don’t adhere to a one-size-fits-all approach to coaching—I honor the individual and believe your context matters far more than your content. I leverage proven frameworks and principles depending on your goals, needs and values so you can develop and consistently show up as your best self.

I don't view you as a "client." Instead, I see you as a partner. Our work together is a co-creation. I seek to build and cultivate a symbiotic relationship where we grow, learn, and thrive together. Our partnership is built on a foundation of trust, mutual respect, collaboration, and growth. Like in any relationship, we're going to bump up against our edges and hopefully go beyond them. I am committed to evolving collectively.

I bring my full self to the coaching relationship. Yes, I'm a trained and ICF-certified coach but I'm also an advisor, teacher, meditator, father, recovering VC, AA sponsor, and more. You're getting 40 years of lived experience, 10 years as an operator, 10 years an investor, and 5 years as a coach. Most of the time, I show up wearing my coaching hat. Occasionally, I'll put on my advisor or investor hat if that's what you want or need. I've helped dozens of CEOs and founders both personally and professionally on a range of topics—you get to drive the agenda and topics. Everything we discuss is always confidential.

Holistic Leadership Development

To perform and lead at the highest level, I fundamentally believe you need to bring your full self to work and nurture your body, mind and spirit. This includes tapping into your three centers of intelligence—your head, heart and gut—and integrating all of your “parts” that drive your thoughts and actions. It also includes implementing practices such as meditation, yoga, sleep, breathwork, exercise and mindful eating.

During onboarding, we will dive into who you are as a leader and identify your goals, both as an individual and in the context of your organization. Each time we meet, we will focus on your desired outcomes, explore your context, surface what’s most important, uncover any roadblocks, and establish actionable next steps. Everything we discuss is always confidential. My goal is to help you develop self awareness, resilience, and confidence, so you can rise to any occasion and bring your vision to life.

I've personally helped dozens of CEOs and investors across a range of topics that span the inner and outer game of leadership.

The Inner Game

  • Cultivating courage and making tough decisions
  • Prioritizing self-care and renewal
  • Identifying and befriending your inner parts
  • Cultivating self-awareness and wisdom
  • Understanding patterns and tendencies
  • Learning how to leverage your strengths
  • Identifying and mitigating your blind spots
  • Discovering and developing new strengths
  • Coping with stress and anxiety
  • Managing imposter syndrome
  • Facing and overcoming fears of failure
  • Dealing with isolation and loneliness
  • Developing confidence
  • Cultivating deep work and focus

The Outer Game

  • Fundraising and investor communication
  • Managing and motivating employees
  • Establishing and setting OKRs
  • Delivering feedback
  • Driving more effective 1:1s and meetings
  • Resolving interpersonal conflict
  • Building a conscious culture
  • Crafting and articulating your vision and story
  • Creating alignment across your team
  • Increasing trust and accountability
  • Communicating with more clarity and confidence
  • And more!

Personal Relationships

Our coaching begins at the one-one-one level. We will typically meet twice a month for an hour over Zoom or on the phone. However, like any true partnership, I’m available whenever you need me over call, text, email, and Slack. I become an extension of your inner circle and an integral part of your support team.

Dynamic Services

In addition to one-on-one coaching, I also provide a range of services to help you gather feedback from key stakeholders, work more effectively with your team, create a development plan, and be prepared for future change. These include:

  • 360 reviews
  • Team offsites
  • Mission, vision and values workshops
  • Post-mortems
  • Energy and calendar audit
  • Zone of Genius assessment
  • Co-founder alignment process
  • "Think Week" in The Catskills

Flexible Commitment

There are no long-term contracts, obligations, or large upfront payments. All I ask for is a mental and energetic commitment of at least three months. While most partners start to feel the positive effect of our sessions after just a few weeks, this gives us sufficient time to get to know one another. My hope is this initial commitment blossoms into a successful long-term relationship.

Frequently Asked Questions

I'm asked by prospective clients all the time what it's like to work together. I invite you to read my FAQ here.

Frequently Asked Questions
Who is your ideal client?My ideal partner is an early stage entrepreneur who wants to evolve into high performing CEO. I usually prefer them to have at least 4 FTEs though that isn’t a requirement. I also work with “Leaders In Transition” and GPs at VC firms. If you

Contact Me

To learn more about working together, feel free to contact me here. I'd love to learn more about you, your company, your goals, and your dreams.