Yehuda Gittelson Picks Guests the Way He Picks Routes on the Water

Yehuda Gittelson sea kayaks in Casco Bay most summer weekends. He launches from near his East Bayside neighborhood, paddles out past the breakwater, and picks a route based on the tide, the wind, and what he feels like looking at that day. Sometimes he heads for Peaks Island because the crossing is short and the coffee shop on the other side is open. Sometimes he aims for the outer islands, Jewell or Cliff, because he wants to be alone with the water for a few hours and doesn’t mind the paddle back.

He plans podcast episodes with a similar instinct. Loose structure, clear destination, willingness to adjust based on conditions.

On The Roof, his renewable energy podcast, is built primarily around long-form interviews. Gittelson books one guest at a time, records a conversation, edits it himself, and publishes every two weeks. The people he’s had on so far work at the ground level of the clean energy industry. Not executives or spokespeople. Field technicians, crew supervisors, auditors, and tradespeople who spend their days solving problems with tools in their hands rather than talking about policy from behind a desk.

“I’m not interested in talking to the person who writes the press release,” he said. “I want the person the press release is about.”

How He Finds Them

Gittelson doesn’t have a booking producer or a submissions form on a website. Most guests come through his own professional orbit. Working as a NABCEP-certified solar installer for Solaris Energy Solutions puts him in regular contact with other tradespeople across southern Maine. He meets electricians on job sites. He crosses paths with energy auditors during weatherization projects. He talks to inspectors and contractors throughout a normal working week. When one of those conversations turns interesting, he files the name away.

Referrals account for another chunk. A guest will mention someone during a recording, usually while telling a story or pushing back on something Gittelson said, and he’ll follow up afterward. A weatherization crew supervisor mentioned an energy auditor who had an unusual take on how Maine’s older housing stock should be prioritized for retrofits. Gittelson reached out. The auditor said yes. Some of his strongest episodes have started that way, as a name dropped offhand that turned into a two-hour phone call and then a recording session.

Occasionally, he sends cold messages to people whose writing or project work caught his attention through industry channels. The hit rate is lower than referrals, but better than he expected.

“Most people in this industry aren’t getting asked to be on podcasts,” he said. “When you ask, they’re surprised. And then they say yes.”

What He Does Before Recording

Yehuda Gittelson prepares for interviews more thoroughly than the show’s casual tone might suggest. Before each recording, he reads whatever he can find by or about the guest. Published articles. Company bios. Conference presentations, if they exist. LinkedIn profiles, which he admits are often the most useful source for understanding someone’s career arc in compressed form.

From that research, he builds a question outline. Not a script. He never reads questions verbatim during a recording. The outline identifies the three or four things he actually wants to understand by the end of the conversation and maps out a rough sequence to get there. The questions he writes down are starting points. The real questions come from listening.

That groundwork is audible in the finished product. Gittelson doesn’t jump between unrelated subjects or lose the thread when a guest goes off on an unexpected tangent. He knows enough about the person sitting across from him to recognize when a tangent is worth chasing and when it’s time to pull the conversation back. Getting that balance right is part of the interviewing process, he says, and he’s still figuring it out.

The Kayaking Parallel

Gittelson briefly drew a comparison between guest booking and kayak route planning during “From Wind to Wire,” his solo second episode. He didn’t elaborate much, which is probably why it stuck. The parallel isn’t neat. Kayaking and interviewing don’t map onto each other in any tidy way. But the underlying habit is the same.

A Casco Bay paddle starts with checking the tide chart and the weather. You have a direction in mind. Once you’re on the water, though, the fog comes in faster than you expected, or the wind shifts, and the crossing you planned gets rougher than it looked from shore. You adjust. The plan doesn’t survive contact with the actual bay, and that’s fine because the point was never to execute it perfectly. The point was to get out there and respond to what you found.

Yehuda Gittelson walks into a recording knowing what he wants to ask. He usually asks about half of it. The rest of the conversation happened because a guest said something he didn’t see coming, and the follow-up question was better than anything in his outline.

He’s building a list of future guests that outpaces the release schedule. Installers from other states. Technicians who work on battery storage. A lobsterman who put solar on his processing facility. The names accumulate faster than the open slots, which is a problem he seems happy to have.

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