Karen Robinson on raising $100M, embracing failure, and building resilient businesses

On this episode of The Roadmap, host Lee Heisman sits down with Karen Robinson, founder and managing partner of Mara6, to discuss her three-decade-long entrepreneurial journey. From raising over $100 million to mentoring the next generation of business leaders, Robinson shares hard-won insights on funding, leadership, and the importance of integrity in business.

Robinson began her career as an executive with a national data corporation before taking on her first CEO role at age 30. In an early venture, she raised $40 million in just a few months using a concise, four-sentence pitch— which demonstrated her ability to secure funding quickly and effectively. Over the years, her fundraising efforts exceeded $100 million, a huge milestone.

While many focus on securing large investments, Robinson emphasizes that true success comes not from the amount raised but from the value delivered to customers and investors. She mentors entrepreneurs by teaching them to evaluate potential investors carefully, viewing the relationship as a long-term commitment similar to marriage.

Robinson also highlights the importance of resilience and embracing failure. Long before it became a popular topic, she openly discussed learning from mistakes, noting that failure often indicates that an entrepreneur is pushing boundaries. She encourages business owners to analyze setbacks, take responsibility for their role, and use those lessons to move forward.

As a strong advocate for women in business, Robinson advises parents of young daughters to encourage participation in sports, as athletics teach essential skills like teamwork, perseverance, and handling both victories and losses—critical traits for entrepreneurs.

Through her leadership and mentorship, Robinson continues to inspire the next generation of entrepreneurs, demonstrating that success is more than just raising money—delivering value, building strong teams, and maintaining integrity.

"If you're not making mistakes, you're not pushing the envelope." – Karen Robinson