Do Hard Things A Podcast With Gabe Lullo Ft. Sam Hollander

"You still have to have some form of human personalization. You still have to pick up the phone. You still have to build relationships." - Sam Hollander That's Sam Hollander's view on AI in sales. Not because he's anti-AI. Quite the opposite. After 18 years building revenue in markets where the traditional playbook doesn't exist, he's seen firsthand where technology helps and where it doesn't. He's led two companies through successful exits, and his first 90 days always look the same: talk to customers, pressure-test the messaging, and build operating structure. Because in startups, ambiguity is the biggest challenge. The only way through it is to create your own anchor. When it comes to outbound, Sam doesn't think the answer is more automation. At a conference last month, he watched a friend open her inbox: 1,000 unread emails from vendors. Just sitting there. That's why he's building LynkUp, a marketplace that connects high-intent buyers and sellers at conferences, turning random badge scans into intentional, confirmed meetings. The biggest deals of his career didn't start in an email sequence. They started in person. His advice for enterprise sales is simple: map stakeholders early, identify champions and blockers, and stay in touch consistently. Momentum matters. AI is great for saving time. Great for research, writing, and prep work. But relationships still close deals.