Family Dinner Recap: Sean Jacobsohn

On Tuesday, October 15th, The Garage welcomed Sean Jacobsohn, partner at Norwest Venture Partners, founder at the Failure Museum, and former enterprise cloud executive, as the featured guest for this week’s Family Dinner. With a rich background in technology, sales, and business development, Sean provided Residents and Tinkerers with valuable insights into the realities of entrepreneurship, venture capital, and navigating startup challenges.

Sean began by sharing highlights from his career, focusing on his experience with enterprise software investments and his time serving on multiple boards, including FloQast, Oro, and Enable. His impressive track record in helping companies scale their operations laid the foundation for a series of lessons that deeply resonated with the audience.

One of Sean’s key messages was about the inevitability of failure in the startup world. “Everyone fails,” he said, emphasizing that fear of failure should not deter entrepreneurs from taking risks. He recounted stories of companies like Cornerstone, detailing how strategic pivots either led to success or prevented disaster. "Some of the most successful companies have to pivot," he explained, urging founders to be cautious with capital and track early warning signs in their metrics.

Sean also introduced his Six Forces of Failure™ model, a framework designed to help founders identify potential risks and avoid common pitfalls:

• Product-Market Fit: The most common reason for startup failure. Ensure your product resonates with your target customers and that it is a repeatable solution to their problems.
• Financial Health: A strong financial plan is critical. Avoid relying heavily on debt and ensure you have the capital to sustain growth.
• Customer Success: Focus on maintaining customer satisfaction and meeting their needs. A high churn rate is an early warning sign that something is off.
• Competition: Keep an eye on competitors and understand how their strategies could impact your position in the market.
• Timing: External forces, such as technological advancements or political shifts, can affect your startup’s trajectory, so be prepared to adapt.
• Team: Building the right team is essential. The success of a startup often hinges on having people who can execute the vision, handle challenges, and work cohesively.

He reminded the group that one of the most common reasons startups fail is due to a lack of product-market fit, stressing the importance of listening to customers and adapting quickly. “It’s not about hearing a ‘yes,’” Sean said. “It’s about solving the customer’s biggest problems.”

During the Q&A, Sean shared more about what investors look for in early-stage startups, including how closely customers engage with a product and the importance of building solid partnerships for distribution. He underscored the value of staying close to the customer and how a strong product roadmap can lead to long-term success. "Sales is the most important skill in business," he added, reflecting on the crucial role of CEOs in setting the vision and driving growth.

The evening wrapped up with students asking for Sean’s advice on early investments and the importance of teamwork in entrepreneurship. His encouragement to "fail together, not alone" resonated deeply, reminding everyone of the importance of building a supportive team.

Sean’s visit left both Residents and Tinkerers feeling inspired, offering them a deeper understanding of the challenges and rewards that come with entrepreneurship. The evening was not only informative but also helped strengthen the sense of community, as students engaged in meaningful conversations about their own startup experiences and aspirations.