The Hard Truth about B2B Podcast - B2B Investments with Jack Freeman from PeakSpan

Jack has worked with growth-stage technology businesses his whole career and has partnered with over 25 portfolio companies at PeakSpan. He currently leads PeakSpan’s FinTech and Supply Chain investment themes. Jack was named to GrowthCap’s Top 40 Under 40 Growth Investors List in 2025. Prior to joining PeakSpan, Jack worked at Stackpop, an early-stage startup, where he helped build a SaaS spend management platform that enabled CTOs and IT teams to buy and manage internet infrastructure. After Stackpop was disrupted by AWS, Jack joined Macquarie Capital, where he spent three years executing software M&A and capital markets transactions for technology businesses.

Jack holds a B.A. in Economics from Middlebury College. Prior to Middlebury, he played Division I soccer at Seton Hall University and for the New York Red Bulls U-23 team. Jack lives in Larchmont, NY, with his wife and two dogs, Willow and Leeuwen. Once a year, Jack captains a team in a charity bike ride to the Hamptons to support his brother’s autism program, Quest, where he has raised over $100K. Since retiring from collegiate soccer, Jack has become an avid endurance athlete, completing five of the “Big Six” World Marathon Majors (London remaining), an Ironman, and a 50-mile ultramarathon. He is currently focused on improving his marathon time from 2:32:30 to sub-2:30.