“I got my ass handed to me”: North Shore agent Jena Radnay talks staying on top in Chicagoland

@properties agent Jena Radnay was peeved.

During her routine morning deep dive into the news recently, she read that Chicago’s top residential broker by sales volume, Compass’ Jeff Lowe, was bringing on an agent to open a Winnetka shop focused on the high-end suburban North Shore.

It led her to recall her own struggle to break into the local scene.

“I got my ass handed to me up here. No one liked me when I first started,” Radnay said inside her home in Winnetka, while wearing a Tulane University sweatshirt in celebration of her teenage daughter recently being accepted to the school.

 “I love Jeff, but do you think this is easy? … I spent years, headaches, tears, problems, doors closed on me, lockboxes jammed, to get where I am. … It’s [messed] up how people think things work up here.”

In her transition from selling homes in Chicago into exclusively working along the North Shore, Radnay started pragmatically. She dabbled on the North Shore and kept her business in the city for two years until she felt she had a solid foothold with an annual sales volume pipeline of $30 million to $40 million.

For the past eight years, she’s served exclusively the North Shore, and notched the two priciest sales in all of Chicagoland last year — both Winnetka mansions that went for more than $12 million — and three out of the top 10.

So how does Radnay, 49, spend her time to stay at the top of the competitive North Shore housing market?

From parenting her two New Trier High School students, grabbing hot dogs for lunch, to showing homes for business magnate and celebrity clients and skirmishing with Winnetka’s village president over lakefront property regulation (more on that coming soon), here’s Radnay’s typical weekday schedule.

5:50 a.m.

She starts her day by reading six newspapers online.

“I skim first for headlines always. I write creative copy for ads. Think about how a listing should come to life, and I bug [fellow agent] Annie [Kenyon] in emails,” Radnay said.

7:43 a.m.

Off to New Trier High School for dropoff.

After that, she meets up with Kenyon at Radnay’s home, where they plot marketing strategies for various listings and talk business, and plan out the rest of the day.

“My mornings, I think my best, I’m the clearest, I write my best emails. My work sucks past 4 o’clock.”

10:35 a.m.

Preparing to depart for errands, Radnay was interrupted by a phone call.

“When can you come for the servicing? Just let me know. What’s good for you guys? Great, what time today? Twelve to 4 would be great. Also, I need to have two thermostats. I need to have these pieces of shit Nests pulled out of the walls. I’m on some eco-friendly thing, and then in the middle of the night it goes to 60. I don’t want Nests anymore, I just want regular Honeywell thermostats. Can you guys bring two of those?”

Randay then climbed into her Range Rover.

10:45 a.m.

She arrives at a Winnetka home under construction that’s set to be the town’s biggest non-lakefront home — at close to 20,000 square feet of finished space — once completed for the owners, investor couple Aaron and Yeming Rankin. She has to drop off a check for a plumber on the site, but takes a quick tour of the in-progress home.

11:15 a.m.

Back in the Range Rover to cruise by billionaire Justin Ishbia’s lakefront megamansion construction project, composed of three lots that used to hold homes before he demolished them.

The project, set to cost more than $70 million, has sparked debate in the town over a new lakefront preservation ordinance that would prevent property improvements from within 50 feet of Lake Michigan’s high-water mark. There’s a crane on the construction site. Trucks have to move in and out of the property.

“This is what people are all pissed about,” Radnay says, driving by. “What happened is, everyone just blew up at once. Looking back, what should have happened is there should have been a model of what this beautiful house would be. He’s going to have botanical gardens in front. It’s going to be more than a museum, gorgeous.

“Let’s take Ishbia out of it for a second. What if I told you Michael Jordan was building right here? Everyone would say, ‘How can we see it?’”

11:45 a.m.

Radnay stops by a client’s house that’s set to be sold, where the buyer wants to add on a few pieces of the seller’s furniture to the purchase.

Kenyon and Radnay whip out tape measures and quickly rattle off dimensions of the furniture that’s not being sold with the house in order to market and sell it online themselves.

“We have a warehouse full of furniture. We do all our own staging. Annie does it all,” Radnay says. “We could have a whole design staging arm of my business and Annie could run it, but if we do that, then we don’t have lives.”


She pulls up to her favorite hot dog joint, The Little Island, a tiny shack in the middle of a busy intersection in Wilmette.

“This is real America. This is called, ‘fucking luxury 101.’ Annie doesn’t eat this shit, so I’ll just get her a Diet Coke,” Radnay says. She orders a char dog and a Diet Coke. “And then I’m back on my phone.”

12:30 to 1:30 p.m.

Heads back home to get ready for and shows a Winnetka listing to potential buyers.  

3:10 to 4 p.m.

Back to New Trier High for pickup, then Culver’s or Portillo’s with her son for food. Then she finalizes details for her schedule the next morning.

5 p.m. to 7 p.m.

Grazing time.

“It could be dinner out or meeting friends for dinner. Tonight it will be a later one, as I’ll be at Pomeroy in Winnetka for a birthday party I’m hosting until about 10:30 p.m.,” Radnay said.

8 p.m.

She takes a hot shower, puts her hair in a ponytail and then does some architecture reading.

“Now on my nightstand: Patrick Ahearn’s ‘Timeless,’ with incredible Nantucket and Cape Cod homes,” she says.

9 p.m.

Screen time.

“Bravo junk on TV as I am on social media looking at what happened in the world,” she says.

9:20 p.m.

She takes two Olly sleep gummies. “And that’s all they wrote folks.”

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