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The Startup CEO Show

David Cancel: Lessons from HubSpot, Drift, and Beyond

Jan 27, 2025
In this engaging discussion, David Cancel, a five-time founder known for Drift and his role at HubSpot, shares invaluable lessons from his entrepreneurial journey. He reveals how selling Performable to HubSpot transformed both companies and discusses rebuilding HubSpot's engineering team during rapid growth. David delves into Drift's rise in conversational marketing and the importance of customer interaction for growth. He also reflects on the challenges of work-life balance and the transformative power of personal adversity.
51:32

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Quick takeaways

  • David Cancel's pivotal decision to sell Performable to HubSpot was driven by shared values and the vision for Boston's tech scene.
  • Transforming HubSpot from a sales-driven to a product-driven organization involved rebuilding the team and overhauling software infrastructure.

Deep dives

The Decision to Sell Performable

The decision to sell Performable to HubSpot was a significant turning point for David Cancel, who had initially not envisioned selling his successful marketing attribution startup. Despite having raised substantial Series A funding and achieving operational success, Cancel was influenced by the alignment of values with HubSpot’s founders, leading to a pivotal moment as he acknowledged the potential life-changing opportunity the sale would provide for his co-founder and team. The offer’s appeal also stemmed from a vision of creating a leading company in Boston’s technology scene, which greatly motivated him to pursue the deal, even amidst external pressures from investors who were against the sale. Ultimately, the decision proved beneficial, as it strategically positioned him and his team within HubSpot, contributing to its rapid growth and subsequent public listing.

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