Show Notes
"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.
More from Do Hard Things Podcast
"People don't change because you give them housing. People change because they're given community, accountability, purpose, work, and people around them who actually believe in them." - Moe EganPreston and Moe Egan came to The Other Side Village from opposite ends of the problem.Moe grew up in East Oakland, surrounded by addiction and crime, and became a lifelong addict and criminal himself. He went through six or seven recovery programs and graduated from every one. Each time he relapsed. Then came his seventh arrest, and the officer who cuffed him was his old football coach. The coach told him about Delancey Street, and facing San Quentin, he wrote a letter begging for help.Preston has spent 30 years in nonprofit work and never lived any of that. He's upfront about it. His problem is with the systems around the work, which measure beds filled and boxes checked instead of whether people reach long-term independence.Together they lead The Other Side Village, a permanent community built on peer accountability, where residents run social enterprises like a donut shop. Preston brings the strategy and Moe brings the lived experience, and neither is enough alone.Recently Moe took a group of people who spent decades on the street to New York. For some it was their first flight. On the way home they asked him how to get a passport."People don't fundamentally change when they feel temporary... When people know they have a permanent place in the community, they start thinking about next year instead of next week." - Preston L. Cochrane
"None of us engage perfectly with technology when we're overwhelmed or stressed. You shouldn't build a system that requires perfect engagement in order to be useful." - Ellie Gordon
"If there's something I can do and should do, then I have a responsibility to do it. That is what I signed up for when I became a nurse." - Melinda Yormick
"It didn't matter what I had accomplished before, what I had achieved, what awards I had. None of that mattered. It only mattered what I brought that day." - Mary Crafts
"Don't make an assumption, ask the question. Ask your senior people two things: what's slowing you down, and what would make you consider leaving. That pattern is your real priority list." - Alex Seiler