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How top CMOs are making risk central to their marketing playbooks

BI at cannes lions at sport beach
Top CMOs spoke at Business Insider’s annual CMO breakfast at Cannes Lions.

Want to be a successful marketer today? Think more about risk-taking, less about AI.

Top marketing executives argue that ditching the traditional “brand safety” approach in favor of authenticity, moving fast, and taking creative risks are the only ways to survive in a fragmented digital world.

American Express' Elizabeth Rutledge
American Express’ Elizabeth Rutledge said having an in-house agency provided key perspective.

Execs from Duolingo, Gap, and American Express spoke Tuesday on a panel at Business Insider’s annual CMO Insider Breakfast at Cannes, which had support from founding sponsor BCG, supporting sponsor PayPal, and contributing sponsor LinkedIn.

Taking big swings

Duolingo’s Manu Orssaud talked about pushing the envelope with the brand’s five-second farting Super Bowl ad that was a bold move, even for the boundary-pushing brand.

“It was very weird, but I think we proved that our content-first strategy over the years on social media really has paid off,” he said.

Duolingo's Manu Orssaud
Duolingo’s Manu Orssaud is evolving the brand’s unhinged marketing.

AmEx’s Elizabeth Rutledge discussed persuading internal stakeholders to create an in-house agency to complement the company’s outside partners.

“Those perspectives, both internal and external, are really important to have great work,” she said.

Fabiola Torres discussed Gap’s 2025 “Better in Denim” campaign that featured the global pop girl group Katseye dancing to “Milkshake” by Kelis. The campaign went viral, and Gap said it was the brand’s best-performing.

“I told my team, I feel like this is going to be the best one yet because it felt so different, but it was a risk — the outfits, the genre, the talent, the point of view itself,” Torres said.

It’s not all about AI

For all the talk these days about AI in marketing, AI-related skills aren’t the first thing some CMOs are looking for in their next hire.

For Torres, love for the brand is paramount.

“If you don’t have an affinity to the brand that you’re going to be working with, why are you actually applying?” Torres said.

Rutledge said she’s looking for a mix of generalist and specialist creative skills in new hires as AI expertise becomes democratized.

“We’re all going to have access to the same capabilities at the end of the day,” Rutledge said.

Man celebrates
At the event, Business Insider unveiled the most innovative CMOs list.

Cutting through the clutter

Marketers are constantly trying to find new ways to break through, as people’s attention becomes more fragmented.

Some CMOs shared tips for getting noticed.

Torres said Gap tailors content to each platform, like TikTok or YouTube, from the outset — rather than shooting a project and adapting it later.

“We actually produce and edit the content according to the platform. So far, it has been performing better when you think platform-first, and you shoot it accordingly to that,” she said.

Rutledge focuses on how AmEx can improve customers’ experience when they’re going to a restaurant, traveling, or seeking entertainment at home or outside. She emphasized the need for deep expertise in the platforms where people spend their time.

“The average US consumer is on 11 video services” across linear, streaming, and social platforms, she said. “What I am really proud of in terms of our team is that they see that media fragmentation not as a negative, but as an opportunity to kind of meet customers where they are.”

Gap's Fabiola Torres
Gap’s Fabiola Torres warned about focusing too much on brand safety.

Duolingo is constantly reacting to culture and coming up with ways to grab people. Still, Orssaud said it’s important to know when it’s time to move on from tried-and-true strategies, like being sassy with its social media accounts. He said the brand is dialing back its unhinged playbook because it’s become expected. It’s also moving from short-form to long-form content that allows for more character development.

“There is also the risk of trying to always go and chase the next big viral moment by increasing the shock factor,” he said.

Brand safety views change

Marketers used to pound their chests a lot about protecting their brands from appearing near unsavory content, but in recent years, they’ve gotten quieter about it. Marketers discussed how authenticity is taking priority these days.

Rutledge said automation has made it easier for brands to protect themselves online. She focuses on “premium” environments that align with customers’ dining and travel, music, and entertainment interests.

Business Insider installation at Cannes 2026

Torres cautioned against focusing too much on brand safety at the expense of staying true to one’s identity.

“If you use the terminology on brand safety, you just may close yourself to opportunities,” she said. “This is the era where Gen Z is asking you for more. Millennials are asking you for something new and different, and Gen X are saying: ‘Take me back to the things that I love.’ So it’s important to really make sure that you don’t get distracted by brand safety versus following your DNA.”

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Chip and Joanna Gaines are selling the 135-year-old castle they renovated for nearly $2.7 million. Take a look inside.

A side-by-side of a castle and Chip and Joanna Gaines.
Chip and Joanna Gaines are selling their castle.
  • Chip and Joanna Gaines are selling the castle they renovated in Waco, Texas, for almost $2.7 million.
  • Called the Cottonland Castle, the historic home has four bedrooms and three and a half bathrooms.
  • They previously put the castle up for auction in 2023.

Chip and Joanna Gaines are selling off a fairytale space.

The “Fixer Upper” couple owns several properties in their home city of Waco, Texas, including a 135-year-old castle they bought in 2019.

They renovated the space for their show, “Fixer Upper: The Castle,” and they previously tried to auction off the castle in 2023.

Three years later, it’s back on the market for nearly $2.7 million. Check out the historic property.

Chip and Joanna Gaines bought a castle in 2019.
A castle sits on a lawn.

As Joanna shared in a blog post, Chip had wanted to buy the Waco, Texas, property called Cottonland Castle for over 20 years before they finally purchased it in 2019.

They spent the next several years restoring and renovating it, as they documented for their Magnolia series, “Fixer Upper: The Castle.” 

They completed the renovation in 2022, and they allowed groups to tour the property for $50 per ticket before the show aired later that year.

They put the home up for auction in July 2023.
Chip and Joanna Gaines sit in the window of a castle.

After offering tours of the property in 2022, Chip and Joanna decided to auction it in July 2023.

Chip and Joanna’s company, Magnolia Realty, partnered with Concierge Auctions to auction off the castle from July 20 to July 27, 2023.

They said in a statement at the time that they hoped the person who bought the property would turn the castle into “a well-loved home once again,” The Wall Street Journal reported.

However, the auction sale never went through, and they reopened the home for tours six months later, according to Country Living Magazine.

“Magnolia is pleased to share that the Historic Waco Castle is staying in the Magnolia family,” Magnolia told the outlet in a statement at the time. “A prospective buyer and Magnolia mutually agreed not to close, and the unique property will not be sold at this time. This decision is made with much enthusiasm and anticipation as the beloved Castle’s story continues with Magnolia.”

Three years after they first attempted to auction the home, Chip and Joanna put the castle up for sale.
A photo of a castle with trees and grass around it.

On June 18, the Gaineses listed three of their properties in Waco for sale through their company, Magnolia Realty, including the castle. Representatives for the couple did not immediately respond to a request for comment on the listings.

In addition to the castle, Chip and Joanna listed the Hillcrest Estate, a rental property, for $1.7 million, and the Gristmill, a landmark the couple restored, for $935,000.

The castle is the most expensive listing of the bunch, with the couple hoping to sell it for $2.699 million.

“As Magnolia looks ahead to new opportunities in the hospitality space, the timing feels right for these three properties to begin their next chapter,” Magnolia Realty said in an Instagram caption about the listings.

The castle was first purchased in 1890.
A living room with large windows and a fireplace.

According to Waco History, the original buyer abandoned the castle after beginning work on it in 1890, and it was abandoned again by a second owner in 1908. 

Alfred Abeel then bought the property in 1913 and worked with architect Roy E. Lane to finish construction of the home, keeping German castles in mind in its design.

Different people owned the property throughout the 20th century, and it fell into disrepair after becoming a historical site in 1977. By the time Chip and Joanna bought the property, it needed a lot of work. 

The 6,176-square-foot house sits on less than an acre of land.
A dining room with mahogany walls and a white fireplace.

The castle has four bedrooms and three and a half bathrooms. 

As befits a castle, it also features a tower.

The dining room features restored paneling and historic wallpaper, along with dramatic details such as a large chandelier and an ornate fireplace.

Chip and Joanna wanted to maintain some of the house’s original features while making it work for a modern dweller.
A kitchen with white countertops and a big white refrigerator.

For instance, Joanna explained in “Fixer Upper: The Castle” that the kitchen was originally in the basement, which she didn’t think would work for a modern dweller.

The kitchen now sits on the main floor, so it’s more functional. However, they maintained the original mahogany paneling on the walls, blending old and new.

The area also features a butler’s pantry with additional appliances.

The couple transformed every room in the house.
A dining room with a tile fireplace and modern, round table.

The basement was also completely refinished, and it now includes an entertainment room, guest room, laundry room, and game room (photographed above). 

The castle also has a conservatory and a library, as well as seven fireplaces.

The primary bedroom includes the castle’s original flooring.
A bedroom with a white fireplace, big chandelier, and large windows.

The upstairs houses a built-in library and three of the home’s four bedrooms, each decorated by Joanna.

Some of the home’s vintage charm is most obvious upstairs, like the diamond-paned windows and antique tile in the bathrooms, as detailed in the home’s listing.

The castle is listed for almost $2.7 million.
A bathroom with green walls and a large bathtub.

The listing states that the home will come furnished, so the future owners can buy a space designed and decorated by Chip and Joanna.

“All furnishings, accessories, and decor have been thoughtfully curated to complement the home’s design and are included with the purchase, creating a truly turnkey opportunity,” it said.

You can learn more about the castle here.

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Uber is set for a payday from Lime’s IPO — and is interested in doubling down on the scooter bet

A person rides a Lime electric scooter, with only their black boots and blue pants visible in the photo.
Uber is the largest shareholder in Lime heading into its IPO.
  • Uber is the largest shareholder in scooter rental service Lime.
  • Lime filed a prospectus on Monday detailing plans for an IPO, targeting a price of $24 to $26 per share.
  • Uber also has an option to double down on its investment, according to the filing.

Uber has a lot riding on scooters.

The ride-hailing company, which was an early investor in scooter rental business Lime, is the company’s largest shareholder, according to a prospectus detailing plans for an initial public offering that Lime filed on Monday. Uber owns about 14 million shares, or a 24% stake ahead of the IPO, according to the S-1 securities filing.

Uber’s stake would be worth about $350 million if Lime prices its IPO at $25 a share, the midpoint of the $24 to $26 target range the company shared in its filing.

Lime said Uber has shown interest in buying up to $20 million in additional Lime common stock as part of the IPO, according to the prospectus.

Uber did not respond to a request for comment.

Precisely how much Uber stands to make on its Lime investment remains to be seen. The companies have not publicly shared how much Uber has invested in Lime over the years. Lime could revise its planned price per share before it goes public. Uber also faces restrictions on how many shares of Lime stock it can sell over the next two years — and thus how much it can cash out — as part of the IPO terms.

Lime and Uber go way back. Wayne Ting, Lime’s CEO, previously served as chief of staff to Uber CEO Dara Khosrowshahi. Uber also invested in some of Lime’s fundraising rounds, including leading a $170 million round announced in May 2020.

Many Lime users find a scooter or bike to ride through Uber’s app. Such trips accounted for about 14% of Lime’s revenue in 2025, according to the prospectus.

That relationship has helped Lime acquire new customers. “By leveraging Uber’s existing infrastructure and rider network, we tap into an existing rider base that can drive awareness without upfront marketing costs,” Lime wrote in the filing.

The relationship between Lime and Uber might serve as a model. Uber has struck partnerships with around a dozen self-driving car providers over the past few years, from Waymo in the US to Baidu in Asia and the Middle East.

Uber, which already has millions of riders signed up to use its app, can match those robotaxi services with riders, Khosrowshahi has said.

“I do think the aggregator model certainly would be helpful for all of those companies to succeed,” he told the “Stratechery” podcast last year.

Do you have a story to share about Lime or Uber? Contact this reporter at abitter@businessinsider.com or via encrypted messaging app Signal at 808-854-4501. Use a personal email address, a nonwork WiFi network, and a nonwork device; here’s our guide to sharing information securely.

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I ordered the same meal from Olive Garden and Carrabba’s, and the winner blew me away with its generous portions

A composite image of tiramisu at Olive Garden and tiramisu at Carrabba's.
I tried to order the same dishes at Olive Garden and Carrabba’s to see which chain I preferred.
  • I dined at Olive Garden and Carrabba’s to see which Italian-food-serving chain had better dishes.
  • Olive Garden’s take on fettuccine Alfredo, chicken Parmigiana, and lasagna came out on top.
  • I thought Carrabba’s bread was good, but Olive Garden won this taste test for me.

As someone who grew up in the suburbs, restaurant chains like Olive Garden and Carrabba’s always had a special place in my heart.

Some get a bad rep and, sure, they may not always be the most authentic, but sometimes there’s comfort in knowing exactly what to expect. Plus, they can have some pretty great dishes.

Both chains serve tons of Italian-American classics, and I was curious which had the better bites and dining experience. So, I headed to both an Olive Garden and Carrabba’s in the Panama City Beach area of Florida and tried ordering almost the same meal at each.

Here’s how they compared.

First, I stopped by Olive Garden for an early dinner.
The writer stands in front of Olive Garden

I started this taste test with my local Olive Garden since I was more familiar with it.

The Italian-inspired chain has more than 900 locations worldwide (most in the US) and is known for its “Italian generosity,” in part because its meals come with unlimited breadsticks and salad.

Olive Garden felt welcoming when we stepped inside.
Light-brown wooden tables and wine rack at Olive Garden

I thought the Tuscan-themed exterior of Olive Garden was warm and inviting.

The restaurant’s interior seemed pretty basic, with glowing digital-order tablets at each table. Still, an effort seemed to be made to warm things up with artificial plants, brick accents, and yellow curtains.

My husband and I were greeted and seated immediately as an instrumental of “That’s Amore” played overhead.

At Olive Garden, we started with the house salad and breadsticks that came free with an entrée.
House salad with breadsticks in background at Olive Garden

After we ordered our entrée to share, our waitress brought out chilled salad plates, a massive bowl of Olive Garden’s house salad, and three breadsticks.

She offered to grate cheese onto the salad, which we declined, and said she could bring out more breadsticks if we wanted them.

I was surprised by how generous the salad portion was, especially since we just ordered one entrée. We also could’ve asked for more at no extra charge.

The salad came topped with red onions, tomatoes, olives, pepperoncinis, and croutons. I thought it was crispy and refreshing, and the chilled plates were a nice touch, especially in the Florida heat.

The buttery breadsticks were warm, just a touch salty, and perfect for sopping up soups and sauces.

Olive Garden’s Tour of Italy was a combo plate of classics.
A plate of lasagna, pasta, and chicken Parmigiana.

For an entrée, we ordered Olive Garden’s Tour of Italy, which came with fettuccine Alfredo, lasagna classico, and chicken Parmigiana.

The dish felt like a perfect opportunity to try a little bit of everything, and it felt like a solid deal at only $21.

Since my partner and I ordered it to share, our server asked whether we wanted the kitchen to divide the dish into two portions. I appreciated the offer, but we opted to have it served as-is and split it ourselves.

I thought the lasagna classico had a nice mixture of textures and flavors, with classic Italian seasonings and tomato sauce. It featured a meat sauce made with pan-seared beef and Italian sausage, along with Parmesan, mozzarella, and Romano cheeses.

The fettuccine Alfredo was creamy without being greasy and was exactly what I expected from a saucy pasta dish. I thought it was good, but it wasn’t my favorite out of everything on the plate.

For me, the clear winner on the plate was the chicken Parm. The chicken was crispy on the outside and moist on the inside, with just the right amount of cheese and homemade marinara sauce on top.

The tiramisu at Olive Garden was a creamy, dreamy ending to a lovely meal.
Tiramisu.

We followed up our Olive Garden feast with some tiramisu that cost us $9. The dessert has always been a must-order for us when we’ve done takeout, so we already knew we loved it.

The restaurant served it with whipped cream and a fine dusting of cocoa powder. The tiramisu was creamy and sweet, with just the right amount of coffee flavor and bitterness from the espresso-dipped ladyfingers.

When the meal was finished, our server packed up our leftovers from the Tour of Italy, along with two breadsticks, and handed us the check with two chocolate mints.

A few days later, we headed to Carrabba’s for dinner.
Exterior of Carrabba's

Carrabba’s is a smaller Italian-American restaurant chain with around 200 US locations, 66 of which are in Florida. Like Olive Garden, Carrabba’s has a family-centric vibe.

According to the chain’s website, the Sicilian-American founders’ family recipes have been on the restaurant’s menu for years.

Carrabba’s didn’t feel quite as welcoming as Olive Garden.
Mix of light and dark wooden seating and dimly lit dining area at Carrabba's

I appreciated that the Carrabba’s I visited had outdoor patio seating, an open kitchen, a main dining room, and a bar area.

However, I didn’t find the interiors quite as warm as Olive Garden’s, with white tables and bright overhead lights. Perhaps it didn’t feel as cozy because the restaurant was so empty, which I found surprising for a Wednesday night.

Carrabba’s bread, which was included with the entrée, was my favorite part of the meal.
Bread and olive oil at Carrabba's

At Carrabba’s, we were served complimentary bread, along with a small dish of dried spices. Our server poured some olive oil from a cruet already on the table onto the spices.

The loaf of bread was warm and fluffy had a crisp crust on the bottom that I enjoyed. It was nice to dip pieces of it into the seasoned olive oil, which elevated the flavor.

A house salad was also complimentary with my entrée, but it didn’t impress me much.
House salad at Carrabba's

Carrabba’s house salad featured carrots, shredded red cabbage, olives, sliced pepperoncinis, and a side of creamy Parmesan dressing.

It wasn’t bad, but I didn’t find Carrabba’s house salad as flavorful or as texturally or visually appealing as Olive Garden’s.

It was also considerably smaller than the family-style salad we got at Olive Garden.

Carrabba’s Italian Classics trio had some hits and misses.
A plate with lasagna, pasta, and chicken Parmigiana.

Carrabba’s Italian Classics trio, which cost me $25.50, had similar dishes to Olive Garden’s three-part entrée and came with fettuccine Alfredo, lasagna, and chicken Parmesan.

Carrabba’s entrée presentation wasn’t as impressive as Olive Garden’s, either, and overall, the flavor was a bit of a letdown for me.

The lasagna was made with two different sauces (pomodoro and meat) and had Romano, ricotta, and mozzarella. Despite its many ingredients, I thought the dish was flat, lacked distinct layers, and mostly tasted like basic tomato sauce.

The fettuccine was cooked well, and the Alfredo sauce was creamy with a nice flavor from the Romano cheese. I thought it was OK, but nothing too memorable.

Carrabba’s chicken Parm came topped with the same pomodoro sauce used in the lasagna, along with Parmesan, Romano, and mozzarella. The chicken was crispy and had a pleasant smoky flavor, but I thought the cheese on top was over-toasted and a bit goopy.

The tiramisu at Carrabba’s was served with elegant chocolate shavings.
A tiramisu with chocolate shavings on top.

I had high hopes for Carrabba’s tiramisu, which sounded delicious on paper and cost us $9.80.

According to the menu, the ladyfingers had been dipped in liqueur-laced espresso and layered with sweetened mascarpone, Myers’s rum, and chocolate shavings.

When we got the dish, I noticed the chocolate shavings were also sprinkled on top. But for me, the dessert — particularly the cream — had what I’d describe as a somewhat artificial flavor. I honestly enjoyed the chocolate shavings more than the tiramisu.

We scraped the plate clean at Olive Garden despite being pretty full, but at Carrabba’s, we left about half of the tiramisu on the plate.

From the food to the service to the atmosphere, Olive Garden won every category for me.
The writer poses with the Tour of Italy dish at Olive Garden

I came into this taste test as a slightly bigger Olive Garden fan, and my affinity for the chain felt validated by my dining experiences.

I was a big fan of the portions, which seemed larger than Carrabba’s, and appreciated the small added touches like chilled salad plates, extra breadsticks packed with leftovers, mints with the check, and even our server’s offer to split our shared entrée.

At the time of writing, prices were comparable, though I appreciated that Olive Garden’s were lower. Since then, prices of both have shifted: Olive Garden’s Tour of Italy would now cost $23, whereas the Italian Classics Trio would be a whopping $28.50.

Ultimately, I enjoyed the flavors of each dish at Olive Garden and definitely plan on returning to the Italian-American restaurant chain when I get the chance.

This story was originally published on October 13, 2023, and most recently updated on June 22, 2026.

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Lucid’s goal to ‘simplify’ the company includes 18% layoffs — and eliminating the COO role entirely

A Silver Lucid Gravity drives down a two-lane road past a wooded area.
Lucid said it’s cutting a production shift to align “production plans with anticipated demand.” Its COO is out, too — and won’t be replaced.
  • Lucid Motors plans to lay off around 18% of the company to align “production plans with anticipated demand.”
  • The cost-cutting push also reached the C-suite: Lucid has eliminated the COO role entirely.
  • Lucid has experienced a year and a half of exec upheaval since former Tesla engineer Peter Rawlinson stepped down as CEO.

In the era of leaner companies, even the C-suite isn’t insulated from downsizing. Just look at Lucid.

The luxury EV maker filed an 8-K to the SEC on Monday detailing plans to cut about 18% of its US workforce — including full-time employees, contractors, and hourly manufacturing workers at its AMP-1 factory in Arizona.

But the restructuring is also notably impacting its C-Suite, with Lucid announcing “the elimination of the Chief Operating Officer position.” As a result, Marc Winterhoff, Lucid’s COO who had served as interim CEO earlier this year before resuming the chief operating role when a new CEO was announced, has departed. Winterhoff did not respond to a request for additional comment from Business Insider.

Lucid is looking to “simplify the company” and “sharpen execution,” a spokesperson told Business Insider in a statement.

“These are difficult decisions taken to align production with demand, reduce inventory, and adapt to declining market conditions,” a company spokesperson. “They are part of a broader effort to simplify the company, sharpen execution, and position Lucid to become more competitive over time.”

Lucid expects the cuts to generate about $158 million in annualized cost savings. Lucid will eliminate the second shift at the plant to align “production plans with anticipated demand,” the filing said.

The move comes during a year and a half of upheaval at Lucid.

Longtime CEO Peter Rawlinson abruptly resigned in February 2025, prompting Winterhoff to serve as interim CEO.

Several leaders have since left the automaker: SVP of engineering and software Emad Dlala and SVP of strategy Claudia Gast both left earlier this year. Chief engineer Eric Bach was fired in November after 10 years at the company and has since filed a wrongful termination lawsuit against Lucid. The EV maker previously called Bach’s legal claims “absurd” in a statement on the lawsuit.

The company also cut 12% of its US workforce in February.

On June 1, Lucid officially installed Silvio Napoli — the former boss of The Schindler Group, an elevator maker — as the permanent CEO.

Napoli inherits a long to-do list. The Saudi Arabia-backed automaker is hoping to launch the Cosmos, its first sub-$50,000 mass-market SUV, later this year to challenge the Tesla Model Y and Rivian R2. It also has robotaxi ambitions after inking a partnership with Uber and Nuro.

In the first quarter, Lucid faced a supplier issue that delayed delivery times on its Gravity SUV, while some owners have openly complained about software issues. Lucid continues to receive praise for the engineering of its vehicles, including the Lucid Air sedan, which remains among the most efficient EVs on the market.

For Winterhoff, the elimination of the COO role doesn’t mean that he’ll be leaving empty handed. In addition to severance, Lucid said it “agreed to provide certain continued security support and have him keep his company vehicle.”

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I left the Navy SEALs to have more time with my 3 kids. What I learned in the military helped me raise confident kids.

Dad with three kids
Brandon Webb says his time as a Navy SEAL helps him parent his kids.
  • Brandon Webb left the Navy after 13 years to focus on fatherhood.
  • He taught his kids to ignore negative talk, including from adults.
  • He didn’t over-advocate and allowed them to make mistakes, he says.

This as-told-to essay is based on a conversation with Brandon Webb, author of Puddle Jumpers. It has been edited for length and clarity.

My parents were hippies who gave me a lot of freedom.

I was homeschooled, and we traveled frequently. At 10 or 11, I was making friends in dusty Mexican streets. At 16, in Tahiti, my dad kicked me off the boat during a family sailing trip in the South Pacific (that’s another story).

While it wasn’t traditional, the way my parents raised me gave me a lot of confidence.

The Navy was my ticket to something different. I joined when I was 18, and four years later, I met Gretchen. Back then, the Navy paid you more once you were married. We were in love, and with the financial incentive, the decision was easy.

Brandon Webb while deployed
Brandon Webb served in the Navy for over 13 years

I’d already been on deployment to the Middle East with the Navy SEALs, but on September 11, 2001, I knew everything had changed for Gretchen and me. By the time our first child was born in November 2001, I was in Afghanistan.

My ex-wife and I did counseling to become good coparents

Gretchen and I had two more children, and like many military couples, we struggled. I looked around me and realized that the guys who had been in the Navy for 20 or 30 years hardly had any family relationships. Their family was the SEAL team, and I didn’t want that. After 13 years, six months, and six days, I left the Navy.

I’d been investing in real estate while enlisted, so we were OK financially. I was also able to work on lucrative defense contracts. Unfortunately, being out of the military didn’t solve my relationship issues, and Gretchen asked for a divorce.

We were in couples counseling when that happened, and we continued working with a psychologist so that we could be the best coparents. Gretchen and the kids moved to her parents’ ranch, and soon her parents were inviting me to stay at the guest house. Even today, Gretchen and I have a great relationship.

I used visualization in sniper school and Little League

The first time I realized that military principles could apply to parenting, I was coaching Little League. In the SEALs, we use mental management: visualization, mantras, and positive self-talk that can improve performance.

dad with kids at the beach
Brandon Webb used the same skills that he taught at sniper school with his Little League team.

One day on the field, I realized that the same thing that helped my sniper students could now help the 8-year-olds I was coaching. I started implementing it with my kids at home. I helped my oldest visualize a school presentation, over and over again. At the end, he wasn’t as nervous — and I had identified an important parenting tool.

I taught my kids to reframe negative talk, even from adults

Part of mental management is noticing negative self-talk: the little things we tell ourselves, like “I’m a klutz,” or “I’m bad with numbers.” I wanted my kids to identify their own negative self-talk and also recognize when teachers, coaches, or other adults were unintentionally leading them to focus on the negative.

As a sniper trainer, I’d seen that pointing out problems wasn’t helpful. If I told a SEAL not to flinch, flinching was all they’d think about. Instead, I’d tell them to take a deep breath and focus on a smooth trigger pull. That was much more productive. I taught my kids to reframe criticism to focus on what they should be doing — now the habits they should leave behind.

I gave my kids lots of independence and MetroCards

I saw what my own upbringing did for me, so I wanted to give my kids plenty of independence to build their confidence. My oldest son and daughter both got New York City MetroCards when they were 16: my son for an internship, and my daughter for a job.

Both looked like deer in headlights when I handed them the card and sent them out into the city. But I could see immediately the impact it had, especially for my daughter. Because my kids knew I trusted them, they stepped confidently into their adult roles.

I let my kids cope with their consequences

Today, parents often want to do everything for their kids. That’s a way that even very successful people mess up their kids. It’s why I’ve always focused on not over-advocating for my children.

My youngest made the basketball team as a freshman and was thrilled. A few weeks later, he got kicked off for having a bad attitude. A lot of parents might have spoken to the coach on his behalf, but I didn’t.

Instead, I made sure he knew this was an important life lesson: no matter how talented you are, no one wants to work with a jerk. Knowing that will be much more impactful in his life than a missed season of basketball.

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