The Two-Person Problem: Why Startups Thrive with Cofounders

Starting a company is an exhilarating but demanding journey, filled with sleepless nights, tough decisions, and constant uncertainties. My experience as an entrepreneur and venture capitalist reveals one undeniable truth: the right cofounder transforms startups. A startup, much like raising a child, thrives on nurturing, discipline, and vision. Most importantly, it flourishes with strong partnerships.

The cofounder relationship resembles a marriage: it thrives on complementary strengths and shared commitment but can falter under strain. My entrepreneurial journey began with John Gilkey at Artemis Solutions Group while at Michigan State University. Together, we launched Enliven Software (Fidesic), scaling to $1 million in revenue by 2003. John’s caution balanced my boldness, and his pragmatism tempered my optimism. However, when I pushed for rapid scaling during a changing market, we learned tough lessons about balance and scalability.

These insights laid the foundation for Venture Garden Group (VGG), co-founded with Demola Idowu and Kunmi Demuren. Demola and I met in 1999, united by a shared passion for solving inefficiencies with technology. Kunmi joined in 2009, bringing government relations expertise and business acumen, complementing our technical and strategic strengths. This synergy enabled us to build Nigeria’s first tech holding company, incubating 15 subsidiaries and investing in 65 African businesses.

Cofounder dynamics are crucial at every growth stage. Just as Sergey Brin and Larry Page of Google brought in Eric Schmidt for leadership balance, at VGG, we encouraged subsidiary founders of companies like EduTech Global and Advancly to identify partners with complementary skills. Cofounder relationships evolve through stages: storming (clashing ideas), forming (role alignment), and norming (productive harmony). Investing in coaching and fostering these stages ensures resilience and success.

However, challenges are inevitable. Life events, burnout, or misalignment can disrupt partnerships. To address this, VGG enforces vesting schedules and buyout clauses across its subsidiaries. These mechanisms safeguard equity and ensure smooth transitions, protecting the startup’s future.

Startups also alternate between wartime and peacetime leadership, as Ben Horowitz explains in The Hard Thing About Hard Things. Wartime demands aggressive leadership, while peacetime requires stability. Cofounders enable startups to adapt to these shifts, balancing risk and growth as needed.

Building a strong cofounder relationship requires following five key principles:

1. Write the prenup — Set equity splits, roles, and exit plans early.

2. Define the relationship — Align on values, decision-making, and conflict resolution.

3. Invest in the relationship — Understand each other’s strengths, and consider hiring a coach.

4. Prepare for transitions — Use vesting schedules and buyout clauses to navigate change.

5. Share equity fairly — Use frameworks like Slicing the Pie to avoid future resentment.

Startups, like families, thrive on collaboration. At VGG, these principles have enabled us to build a legacy of innovation and resilience. From our early ventures in Michigan to incubating companies like AviTech and VigiPay that have revolutionized aviation and remittance, our journey underscores the transformative power of cofounder relationships. Strong partnerships allow startups to weather storms, seize opportunities, and create lasting impact.