In this episode, John Mulligan sits down with Brad Kugler, CEO and Co-Founder DirectMail2.0 & Who’s Mailing What! Brad shares his entrepreneurial journey from the packaged media industry of VHS, CDs, and DVDs to building a modern marketing technology company focused on combining direct mail with digital advertising and AI-powered insights.
Brad discusses how industry disruption shaped his mindset, why he embraced innovation instead of resisting change, and how DirectMail2.0 helps businesses improve marketing performance through automation, data, and smarter targeting.
He also dives into the launch of DM20.ai, an AI-powered platform trained on the results of over 80,000 direct mail campaigns and billions of mail pieces. The conversation explores entrepreneurship later in life, leadership, scaling a company sustainably, adapting to AI, building strong teams, and the realities of growing a modern business in a changing market.
If you’re interested in AI marketing, direct mail strategy, entrepreneurship, SaaS businesses, business growth, leadership, or marketing automation, this episode is packed with practical insights and real-world experience.
