Hi, I’m David Bosscher.

I work with people in real leadership roles where decisions affect money, teams, families, and outcomes beyond just themselves.


My clients include leaders in finance, insurance, tech, homebuilding, and founder-led service businesses. These are people whose choices matter.


At this level, better tactics are not enough. You need support that fits the role and helps you think clearly, stay grounded, and stay connected to what actually matters. That is the work I do with my clients.

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My Approach

My approach is grounded in the reality of leadership. I work with people whose decisions affect money, teams, and outcomes beyond just themselves.

The work blends practical business context with the internal side of leadership. We focus on how pressure shapes decision making, how clarity gets lost when responsibility stacks up, and how to stay grounded while leading in uncertain environments.

This is not about templates or surface level mindset work. It is about creating the conditions for clear thinking, steady leadership, and decisions you can stand behind.

At its core, this work offers real support for the mental, emotional, and inner heaviness that comes with responsibility.

  • David is simultaneously the one person I would want on my team and the person who’s team I would want to be on. He will make your cause his cause, your mission- his. Capable of a storm of ideas and focused action and implementation, David will get it done and in a more wonderful way than you ever imagined. Intelligence, talent, drive, heart and wit make David the rarest and most precious of people as well as a fantastic friend.

    —Corinne Kleinberger

  • "Over a decade! That’s how long the span of this man’s coaching has affected my professional and personal capacity I have coached with many a great leader, CEOs, and life coaches. Nothing can prepare you for the look in the mirror that David can offer. You know it hits when you’re pissed, but better for it the next day He has such a captivating way of capturing true leadership and thoughtful attention to detail within how you do everything specifically you’re coaching game If you have an opportunity to coach with him as an actual coach, I promise you’ll never be the same."

    —Candice Motley / MöT

Coaching Services

All coaching is tailored to the specific business and the people involved. There is no fixed package or one-size approach. Services can be combined and customized based on your role, your team, and the stage of your work.

  • Two private coaching calls per month (45 minutes each) plus unlimited text support between sessions.

    This is ongoing, high-touch support for leaders who want a consistent place to think clearly, work through real decisions, and stay grounded while carrying responsibility.

    Sessions are used for:

    • Clarifying priorities and next steps

    • Working through complex decisions and leadership challenges

    • Navigating team dynamics, boundaries, and communication

    • Processing pressure, uncertainty, and internal friction

    • Aligning strategy with values so your business supports your life, not the other way around

    Text support is for in-the-moment questions, decision checks, and support between calls so you are not carrying everything alone.

    This is not templated advice or surface-level accountability. It is a steady, private space to think, recalibrate, and lead with clarity.

  • Team coaching is designed for leaders who manage teams and want support that extends beyond 1:1 work.

    These sessions create shared clarity across leadership and staff, align decision making, and surface the dynamics that impact performance, communication, and culture. The work focuses on how the team operates in real time, not just on individual development.

    Sessions can take place monthly or quarterly, depending on your needs and the stage of your organization, and can be held in person or over Zoom. This offering can be paired with 1:1 coaching to create continuity between personal leadership work and how that leadership shows up inside your team.

    Team coaching enhances the overall coaching experience when your goal is alignment, shared language, and a team that is actually working from the same page.

  • Partnership Coaching

    Partnership coaching is for business partners, and sometimes romantic partners, who want support both together and individually. This offering is designed for two partners or small partner teams.

    Each partner receives one private 45-minute phone session per month to work through personal leadership challenges, decision making, and the internal side of being in partnership.

    In addition, partners meet together for one shared 45-minute session each month. These sessions are used to work through issues, align on direction, surface unspoken tension, and strengthen how you make decisions together.

    This structure creates space for both the individual and the partnership. It allows each person to be supported in their own process while also building clearer communication, stronger alignment, and healthier collaboration across the partnership.

Book a consultation

Schedule a complimentary consultation

In the consultation we will cover your goals, constraints, and the strategy to move you forward.

Book a consultation