Cofounder Coaching
The relationship between cofounders is one of the most critical - and fragile - assets in a company. When aligned, it generates trust, resilience, and clarity that ripples throughout the entire organization. When strained, it drains energy, creates confusion, and can quietly undermine even the most promising ventures.
Cofounder coaching provides a structured, intentional process to examine and strengthen this relationship. It offers both a proactive investment for healthy partnerships and a restorative path for those experiencing friction or breakdown.
When the partnership is strong
Strong cofounder relationships thrive not only because of shared vision and high trust, but also because of consistent attention and alignment given to their working relationship. Coaching creates the space to:
Cultivate habits of communication that endure under stress and scale
Build a deeper understanding and appreciation of each other’s values, perspectives, and blind spots
Establish frameworks for navigating difficult conversations with clarity and respect that lead to greater trust
Ensure alignment between personal ambitions and the company’s long-term mission
This proactive work turns a solid relationship into an enduring one - capable of weathering the inevitable pressures of leadership and growth.
When the partnership feels strained
Even the most visionary and well intended partnerships encounter turbulence and distress. Left unaddressed, tensions can harden into entrenched patterns of distrust, miscommunication, and reactive decision-making. Coaching provides a disciplined process to:
Surface and interrupt relational patterns that quietly erode trust and create greater misalignment
Name unspoken frustrations and translate them into constructive dialogue
Restore confidence in each other’s intentions and commitment
Develop a more intentional approach and framework for resolving old problems in new ways
This restorative work helps cofounders move from reactivity and skepticism to productive engagement and high trust, creating a renewed foundation for both the partnership and the company it supports.
"My cofounder and I approached Jay after having trouble with alignment and communication, which was beginning to have negative effects on us operationally. Jay acted as an unbiased mediator to reconcile our differing viewpoints and establish clearer communication protocols. After the initial crisis was resolved, Jay turned to executive coaching, which helped us get to an eventual exit. Jay has a very dynamic skillset for founders and business leaders, which helped us dramatically."
- Cofounder & CEO
"Jay helped me, my cofounder, and my company tremendously during our time together. From navigating distractions in my personal life, to helping me see the kind of leader I could be, to mending what I thought was an irredeemably damaged cofounder relationship, Jay could handle it all. I wouldn't have been able to survive the turbulence of venture-backed startup life without him."
- Cofounder & CTO
Explore Cofounder Coaching
Cofounder Coaching is an investment in your partnership - strengthening alignment, clarity, and your working relationship. Each engagement is designed around your unique goals as cofounders and the cadence that best supports your collaboration.
A standard engagement includes two individual sessions per month for each cofounder and two joint sessions per month for a total monthly investment of $3,900. For cofounders who want to accelerate their progress and deepen alignment, more frequent coaching options are available.
If you’re curious about what’s possible for your partnership and ready to take the next step, reach out - we’d love to explore how coaching can support both of you.