Starting a Company? You’ll Want to Watch ‘Stylish with Jenna Lyons’

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A scene from 'Stylish with Jenna Lyons', streaming on HBO Max.

When launching a business, there are many places to turn to for advice. An unlikely place may be a reality-show-meets-documentary-meets-competition, but once you start watching Stylish with Jenna Lyons, you’ll totally understand why its a great show to watch when you want to study how to be a great boss.

Pitched by HBO as a ‘a masterclass in taste, design and fashion’, the show may not have launched with ‘business advice’ as one of its key takeaways, but anyone looking for inspiration as they launch a business and hire their first employee will enjoy tuning in to the eight episodes of Stylish with Jenna Lyons, streaming on HBO Max.

A common theme running through the show is how nervous Jenna is to be presenting herself back in the public’s eye. She’s been away from it for a couple of years, since leaving her place as President of J.Crew, where she earned the title ‘the woman who dresses America’, and is now, understandably, nervous about being judged for what she is going to do next.

But, as the viewer learns, and as Jenna realizes throughout the show, she has no need to be worried about that.

Every business owner stresses about their ideas, are they good enough? will people buy my things? will I get good press?

It’s refreshing to see those same worries from someone like Jenna -someone who has seen so much success- still have the same worries that anyone who owns a business has. She does acknowledge that her past success at J.Crew was with a team of people, and now she is out on her own. Stylish with Jenna Lyons follows her endeavor to build that ‘what’s next’ and find a new hire for her team.

She is joined on the Lyons L.A.D. adventure by Kyle DeFord as her ‘Chief of Everything’ and Sarah Clary as her Creative Partner. And of course, all of the camera people who follow them all around, filming everything.

We get to see Kyle and Jenna interview potential new hires to join the competition, and surprisingly several do not bring resumes. We also get a look at two people who are starting a company and needing to figure everything out on their own.

Not many small business owners have the time or resources to essentially run an extended interview for quite a few candidates for one position. It’s a refreshing way to frame the competition show genre, providing more of an inside look into a business’ process.

It’s an enjoyable way to watch these candidates compete for a spot on Jenna’s team. Yes, there is still some of the drama you’d expect from a high pressure/high stakes competition environment, but it doesn’t create villains.

Jenna handles emotional outbursts from candidates and escalating disagreements the way you’d want a kind, compassionate leader to. She delivers feedback in the moment, even if it is tough feedback, and shares it from a place of understanding. These teachable moments focus on how the person chooses to accept the feedback and learn from it moving forward. She demonstrates over and over how to be a true leader, even in a highly emotional moment, and shares that it’s a learned skill that has come to her with years of practice.

There are candidates that will probably watch this show now that it has aired and cringe – like Fred, when he volunteers to be the first one photographed instead of making sure tasks are done and everything is ready to go for a photoshoot, and Kinley, who disappears in the middle of the team working with a client and then returns but spends time on her phone instead of working.

But most are genuinely present and once they see the kind of work Jenna aspires for her company -transforming peoples’ lives through their approach to fashion, design, and beauty- many are excited about the potential to become part of such a meaningful mission.

As Justin shares in Episode 5, Fashion Bus, after the team gives two women fashion advice and makeovers, “If this is what it’s like working with Jenna; to inspire people and touch people through something that we love, which is fashion, then I really want it. I want this a lot.”

The challenges the candidates do throughout the show all give Jenna, Kyle, and Sarah a look at how each candidate will work with others, help launch the brand, learn and grow, and still stay true to themselves.

Jenna has the fortunate situation that she can have a beautiful open office for her company (a space that the candidates helped design in one of the challenges), but that she also lives a floor above it so she can have the private space to deliver tough conversations and provide one-on-one feedback.

The final episode shows the remaining four candidates and their final projects that had to be reworked due to Covid. It’s amazing to see what these four people were able to accomplish. And of course, Jenna would love to hire them all.

“I think the hard part is, you become connected to people and their hopes,” she emotionally shares to the camera. “I mean, I care. A lot.”

Not everyone can be hired, and when it comes down to making the final decision, it’s nice to watch the leadership team discuss each candidate’s attributes, growth, and potential fit. It shows you how to think about how someone can fit your team now, but how you also need to think about how that person can grow if your business is a startup that is just getting its footing.

“There’s no way to describe how incredible it is to be able to do work that you feel proud of but have fun, and love the people that are surrounding you,” shares Jenna. “It’s the biggest gift in the world.”

Even the people who don’t make it express how much of a fantastic experience it was for them, much in the way each contestant on The Great British Baking Show does when it’s their time to leave.

“Not getting hired isn’t the end of the world, it’s the beginning of something new.”

Stylish with Jenna Lyons is an easy watch with great fashion, amazing makeovers, lots of laughs and F-bombs, with beautiful New York and Los Angeles backdrops; but it’s the real story that emerges about a much admired person launching her business and showing the world what it means to be a great boss that’s really captivating.

Stream Stylish with Jenna Lyons on HBO Max.