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Opinion Editorials

Becoming a better broker – six lessons from J. Crew CEO Mickey Drexler

Being a better leader often takes learning lessons from other industries and other leaders. This inspirational look at J. Crew’s CEO will leave you inspired to lead your own charge!



Above: the interior of the men's J. Crew in Tribeca, New York.

The eternal pursuit of improvement

In my mind, what separates true leaders from the pack is the eternal pursuit of improvement. In an era where Twitter has made some appear to be leaders and conferences have propped up egos, it is the elite few who are focused on this pursuit of improvement that are true leaders. They may not be on a stage near you, they may not be profiled in the NY Times, but they are leaders in their companies.

I have long been a fan of J. Crew CEO Mickey Drexler and have read endlessly about his career, not because he collects real estate like art but because his personality inspires actionable goals. While much of the world looks at Steve Jobs as the quintessential CEO, I look to Drexler. Both are of the school of thought that there is an eternal quest for improvement.

Last year, the Wall Street Journal wrote a lengthy piece on Drexel that has had me inspired for quite some time. I encourage you to take a few minutes to read it in full.

How to become a better broker, Lesson One:

Drexler was an executive at Gap prior to J. Crew and he cashed out. Big time. Drexler doesn’t have to work, he’s a millionaire, yet he obsesses over his work as if the day is never over. How many executives can say they never have to work a day in their life again, yet they suit up every morning? Few.

The lesson: Brokers, do you have to work every day, or is it an act of passion? There are brokers running small teams that became highly profitable years ago. Some made investments that even in today’s climate would allow them to retire. But they suit up every morning and fire up their business.

Lesson two

Drexler is a very fast paced person, he relies on his instincts and teaches his staff to do the same. He has a sophisticated intercom system so he can speak to any of his 695 employees at any given time and impulsively checks his phone and computer for messages. He is extremely connected and personally handles endless communication, he welcomes direct feedback and responds to customers himself.

The lesson: Many brokers prefer not to speak to anyone but their assistant or the client in front of them. It is a prestige thing in this industry to be so big you don’t have to do that. Take a page from Drexler and handle your own communication. Will it mean extra hours at work each day? Sure. Does it mean his staff, production team, designers, sales people and ultimately consumers appreciate the access and feel tended to since they didn’t have to deal with a gatekeeper? Of course. And his team and customers are fiercely loyal to him for it.

Lesson three

What impresses me the most about Drexler is his “drop ins.” He visits physical stores four to five times each week. He rearranges shelves, he asks staff what is going on, and most importantly, in his unassuming J. Crew style outfits, he walks up to customers and without announcing who he is, asks what they think of the product. He asks what they’re seeing on the street and what they plan on wearing next season. But what is most inspiring about Drexler’s visits is that he makes changes in real time as he gathers intel first hand, not translated by a marketing group.

The lesson: Brokers need to be more hands on. You don’t see yourselves as retailers, but you are. Visit your properties every day, get angry when they’re not presentable, when your sign is crooked or dirty, when the flyer box is empty. Don’t let the homeowner be the one to tell your assistant to tell you something is wrong- know before they do. Be a retailer and obsess over the details. It’s not just about your damn Twitter profile picture, it’s about the box in that person’s yard- is it up to your standards and are you personally insuring that it is?

Lesson four

Drexler not only touches every step of the product from conception to the store windows, he is willing to experiment. Last year, Drexler was getting considerable feedback that brides were buying simple dresses in multiple colors for bridesmaids and his lightbulb went off and they’ve since opened a stand alone bridal store in NYC. Drexler doesn’t believe in “can’t” and is willing to experiment so long as it avoids distractions.

The lesson: Be willing to experiment. In order to expand your business, is there a niche that is underserved that you know you could provide high quality services to? Is there a demographic that is growing and not being tended to? Are you able to switch up your focus based on live data, or as real estate tradition goes, does it take you a decade to shift gears?

Lesson five

Drexler still gets angry when he walks by a Gap. To this day. He was fired from his executive role and his best revenge, I believe, is that he has moved on and succeeded. Wildly. Drexler thrives at a smaller company and is extremely modest about his achievements. He doesn’t have time for the spotlight and takes his role at J. Crew very seriously.

The lesson: Brokers are getting distracted by shiny things and chasing after ghosts. Be okay with running a nimble company, it is no less prestigious, and don’t let the blue hairs convince you otherwise. Wherever your strengths lie, that’s where you belong and you should not covet what others have. If you don’t franchise, don’t get distracted just because there is buzz around someone else franchising, put your nose to the grind and shore up your existing services. Bigger is not always better and humility and success running a boutique may not go far at the Realtor luncheon, but it will wildly please consumers.

Lesson six

Drexler decided when he came to J. Crew that for a higher price point, consumers deserved to receive a higher quality product. His strategy revolves around “consumers aren’t stupid.” He chastises the CEO of Saks for lowering price points because they also lowered quality. Drexler believes that consumers see through that and has set out to provide higher quality products for that price point you’re used to at J. Crew.

The lesson: Many brokerages focus on growing team sizes and adding more agents most of all. Growth, growth, growth. It makes sense if you’re on the desk fee model, but if you’re on the quest for eternal improvement and your focus is service, you should think like Dexler- consumers aren’t stupid. If you offer them a rebate and sneakily reduce your services, they’ll sense the disservice. If you show them that you’ve added services to your offering yet kept your commission the same, they’ll appreciate that. And furthermore, when you add real benefits (I’m not talking the “we’re offering classes” or free koozies or “10% off at X store” gimmicks) for your agents yet keep their split the same, you’re tending to what is right and they’ll sense that.

The takeaway

Brokers, always push for better and forget what the blue hairs say about you at broker opens. If you stay focused and always seek ways to improve your business based on your gut instinct rather than what the social media guru told you on stage last month, you’ll win. Obsess over the details, act like a retailer, manage your own communication lines and always focus on the consumer. Do that and it won’t matter the accolades or industry perception because you’ll be so well off that like Drexler, you’ll suit up every morning because you want to, not because you have to.

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  1. elizabeth cooper-golden

    March 25, 2011 at 7:11 pm

    Lani, Bravo! My favorite line that you wrote is: “Bigger is not always better and humility and success running a boutique may not go far at the Realtor luncheon, but it will wildly please consumers.” Yes!

    I was very disgruntled with the company I worked with after relocating to Huntsville from Nashville…They didn’t get it then, and don’t get it now. Bigger is NOT always better and the consumers are catching on. I let 3 agents go my first year. All 3 were great people, just not great agents. No one could believe I would do that, including me quite frankly. My vision is mine and I don’t have to bend to those that don’t believe in the model that I am forming. Some local competitors have made “light” of my “where the consumer comes first, always” branding. Poke jabs all you want. My agents are producing, a sure sign that the consumer likes us. The consumer deserves better and they realize there is a choice.

    My company is still a baby and I’m learning daily. I’ve had a few bumps and bruises along the way and will always be searching for ways to improve and make it a wonderful experience not only for the consumer, but also for my agents. My intent is never to be the biggest, but to be the best. Ya know…that 20% that does 80% of the business!

    I’m excited because I am now expanding so I can grow my culture…more on that later 😉

    • Lani Rosales

      March 27, 2011 at 11:46 am

      Elizabeth, I’ve very much enjoyed watching your brokerage grown from afar and your consumer focus is evident in all that you do- keep up the great work! 🙂

  2. Jay great falls Virginia

    March 25, 2011 at 9:11 pm

    Wonderful piece…

  3. Lisa Heindel

    March 27, 2011 at 9:55 am

    I’m not a broker, but certainly you could substitute the word agent and get the same great lessons you’ve laid out here, Lani. It took me my first 5 years in business in the halls of a very traditional, old school local brokerage to figure out that this is my business, my company and I’m the CEO of it. So, I moved to a more progressive broker, formed a team and have focused on consumer education and internet lead generation as a model.

    I truly wish that all of my colleagues were on the same page, worried about the consumer instead of the next awards banquet or Realtor night out.

    • Lani Rosales

      March 27, 2011 at 11:51 am

      Lisa, you’re right that the words can be interchanged. In most cases, it takes running “in the halls of a very traditional, old school local brokerage” (or running Gap in Drexler’s case) to realize what the ideal path is. You and Drexler are right- if you worry about your trophies and not the consumer, you’re in the majority and consumers know they’re getting the short end of the stick.

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Opinion Editorials

Can we combat grind culture and injustice with a nap?

(OPINION EDITORIALS) A global pandemic and a climate of racial injustice may require fresh thinking and a new approach from what grind culture has taught us.



Sleeping cat with plant, fighting grind culture.

Information is delivered to us at warp speed with access to television, radio, and the internet (and more specifically, social media). We are inundated with messages. Oftentimes they’re personalized by something that a friend or family shared. Other times we manage them for work, school, or just keeping up with news. Many entrepreneurs already wear many hats and burn the midnight oil.

During this global pandemic, COVID-19, we have also seen a rise in awareness and attention to social injustice and systemic racism. This is not a new concept, as we all know. But it did feel like the attention was advanced exponentially by the murder of George Floyd on Memorial Day 2020. Many people and entrepreneurs felt called to action (or at least experienced self-reflection). And yet they were working at all hours to evolve their businesses to survive. All of this happening simultaneously may have felt like a struggle while they tried to figure out exactly they can do.

There are some incredible thought leaders – and with limited time, it can be as simple as checking them out on Instagram. These public figures give ideas around what to be aware of and how to make sure you are leveling up your awareness.

Dr. Ibram X. Kendi, Director of the Center for Antiracist Research – he has been studying anti-racism and has several books and interviews that help give language to what has been happening in our country for centuries. His content also delves into why and how white people have believed they are more than people of color. Here is a great interview he did with Brené Brown on her Unlocking Us podcast.

Tamika Mallory – American activist and one of the leading organizers of the 2017 Women’s March. She has been fighting for justice to be brought upon the officers that killed Breonna Taylor on March 13. These are among other efforts around the country to push back on gun control, feminist issues, and the Black Lives Matter movement.

Brené Brown – research professor at the University of Houston and has spent the last two decades studying courage, vulnerability, shame, and empathy. She has been listening and engaging on how racism and our shame intersect. She also speaks about how people can reflect on themselves and where they can take action to better our society. She has some antiracism resources on her website.

With all of this information and the change in our daily routines and work habits (or business adjustments), what is a fresh approach or possibly a new angle that you haven’t been able to consider?

There is one social channel against grind culture that may not be as well-known. At an initial glance, you may even perceive this place as a spoof Twitter and Instagram that is just telling you to take a nap. But hold on, it’s actually much smarter than that. The description says “We examine the liberating power of naps. We believe rest is a form of resistance and reparations. We install Nap Experiences. Founding in 2016.”

It might be a great time for you to check out The Nap Ministry, inspired by Tricia Hersey. White people are called to action, and people of color are expressly told to give time to taking care of themselves. Ultimately, it goes both ways – everyone needs the time to recharge and recuperate. But people of color especially are being told to value their rest more than the grind culture. Yes, you’re being told you need to manage your mental health and include self-care in your schedule.

Through The Nap Ministry, Tricia “examines rest as a form of resistance by curating safe spaces for the community to rest via Collective Napping Experiences, immersive workshops, and performance art installations.”

“In this incredibly rich offering, we speak with Tricia on the myths of grind culture, rest as resistance, and reclaiming our imaginative power through sleep. Capitalism and white supremacy have tricked us into believing that our self-worth is tied to our productivity. Tricia shares with us the revolutionary power of rest.” They have even explored embracing sleep as a political act.

Let this allow you to take a deep breath and sigh – it is a must that you take care of yourself to take care of your business as well as your customers and your community. And yes, keep your drive and desire to “get to work”. But not at your expense for the old grind culture narrative.

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Opinion Editorials

The actual reasons people choose to work at startups

(EDITORIAL) Startups have a lot going for them, environment, communication, visible growth. But why else would you work for one?



Startups meeting led by Black woman.

Startups are perpetually viewed as the quintessential millennial paradise with all of the accompanying perks: Flexible hours, in-house table tennis, and long holidays. With this reputation so massively ingrained in the popular perception of startups, is it foolish to think that their employees actually care about the work that startup companies accomplish?

Well, yes and no.

The average startup has a few benefits that traditional business models can’t touch. These benefits often include things like open communication, a relaxed social hierarchy, and proximity to the startup’s mission. That last one is especially important: While larger businesses keep several degrees of separation between their employees and their end goals, startups put the stakes out in the open, allowing employees to find personal motivation to succeed.

When employees find themselves personally fulfilled by their work, that work reaps many of the benefits in the employee’s dedication, which in turn helps the startup propagate. Many aspiring startup employees know this and are eager to “find themselves” through their work.

Nevertheless, the allure of your average startup doesn’t always come from the opportunity to work on “something that matters.”

Tiffany Philippou touches on this concept by pointing out that “People come to work for you because they need money to live… [s]tartups actually offer pretty decent salaries these days.”

It’s true that many employees in their early to late twenties will likely take any available job, so assuming that your startup’s 25-and-under employee base is as committed to finding new uses for plastic as you are may be a bit naïve—indeed, this is a notion that holds true for any business, regardless of size or persuasion.

However, startup experience can color a young employee’s perception of their own self-worth. This allows them to pursue more personally tailored employment opportunities down the road—and that’s not a bad legacy to have.

Additionally, startups often offer—and even encourage—a level of personal connection and interactivity that employees simply won’t find in larger, more established workplaces. That isn’t symptomatic of startups being too laid-back or operating under loosely defined parameters. Instead, it’s a clue that work environments that facilitate personalities rather than rote productivity may stand to get more out of their employees.

Finally, your average startup has a limited number of spots, each of which has a clearly defined role and a possibility for massive growth. An employee of a startup doesn’t typically have to question their purpose in the company—it’s laid out for them; who are we to question their dedication to fulfilling it?

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Opinion Editorials

How Peloton has developed a cult-following

(OPINION EDITORIALS) How has Peloton gotten so popular? Turns out there are some clear takeaways from the bike company’s wildly successful model.



Man riding Peloton bike with instructor pointing encouragingly during workout.

Peloton is certainly not the first company to gain a cult-like following–in the past we’ve talked about other brands with similar levels of devotion, like Crossfit and Yeti. Now, full disclosure: I’m not an exercise buff, so while I’d vaguely heard of Peloton–a company that sells stationary bikes–I had no idea it was such a big deal.

I mean, it’s not really surprising that an at-home bike that offers the option for cycling classes has grown so much during the pandemic era (a sales growth of 172% to be exact). But Peloton has been highly popular within its fanbase for years now. So, what gives? A few factors, actually.

Vertical Integration

If your company really wants to guarantee the vision and quality you’re aiming for, one of the best ways to enact it is through vertical integration, where a company owns or controls more than one part of its supply chain. Take Netflix, for example, which not only distributes media, but creates original media. Vertical integration lets companies bypass areas that are otherwise left to chance with third-party suppliers.

Peloton uses vertical integration–everything from the bike to its Wi-Fi connected tablet to the classes taught are created by Peloton. Although this may have made the bike more expensive than other at-home exercise bikes, it has also allowed Peloton to create higher quality products. And it’s worked. Many people who start on a Peloton bike comment on how the machine itself is well-built.

Takeaway: Are there any parts of your business process that you can improve in-house, rather than outsourcing?

Going Live

But with people also shelling out $40 a month for access to the training regimen Peloton provides, there’s more going on than simply high-quality craftsmanship.

Hey, plenty of cults have charismatic leaders, and Peloton is no exception. Okay, joking about the cult leader part, but really, people love their trainers. Just listen to this blogger chat about some of her favorites; people are connecting with this very human element of training. So much so that many people face blowback when suggesting they might like training without the trainers!

The trainers are only part of this puzzle though–attending live classes is a large draw. Well, as live as something can be when streamed into your house. Still, with classmate usernames and stats available while you ride, and teachers able to respond in real time to your “class,” this can simulate an in-person class without the struggle of a commute.

Takeaway: People want to see the human side of a business! Are there any ways your company could go live and provide that connection?

Getting Competitive

Pandemic aside, you can get a decent bike and workout class at an actual gym. But the folks at Peloton have one other major trick up their sleeve: Competition. Whether you’re attending a live session or catching up on a pre-recorded ride, you’re constantly competing against each other and your own records.

These leaderboards provide a constant stream of goals while you’re working out. Small accomplishments like these can help boost your dopamine, which can be the burst of good feeling you need while your legs are burning mid-workout. With this in mind, it’s no wonder why Peloton fans might be into it.

Takeaway: Is there a way to cater to your audience’s competitive side?


At the end of the day, of course, Peloton also has the advantage of taking a unique idea (live-streamed cycle classes built into your at-home bike) and doing it first. Plus, they just happened to be poised to succeed during a quarantine. But that doesn’t mean you can’t learn from what Peloton is doing right to build your own community of fanatics. There are plenty of people out there just waiting to get excited about a brand like yours!

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