What happens when a founder becomes a venture capitalist? In this episode, we sit down with Andrew Ackerman, who brings his unique founder's perspective to his role at Dreamit Ventures. We trace the evolution of Dreamit's focused strategy on prop tech and urban tech, and unpack how empathy—forged in the trenches of startup building—creates a powerful advantage in the investor-founder relationship.

Andrew shares incredible stories from the front lines, from navigating the funding landscape post-9/11 to the unexpected revenue pivots that save startups. He provides a masterclass on the nuances of working with corporate venture capital, managing complex board dynamics, and the art of the term sheet.

This is a must-listen for any founder or aspiring VC, packed with tactical advice on everything from Dreamit's famed sprint process to how to properly research and align with the right investors for your journey.

Key Takeaways:

• The Founder's Edge: How Andrew's experience as a founder shapes his empathetic and effective approach to venture capital at Dreamit.
• Inside Urban Tech & PropTech: Why these sectors are ripe for disruption and how Dreamit identifies the most promising startups.
• The Corporate VC Playbook: Strategies for successfully engaging with corporate venture capital funds and navigating investor board dynamics.
• The Dreamit Sprint: A behind-the-scenes look at their intensive process for preparing, matching, and supporting startups long after the sprint ends.
• Tactical Deal Advice: Actionable tips on valuation, term sheets, and how founders can intelligently research and choose their VC partners.