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National Gingerbread Latte Day, celebrated every December 15, is a time to honor the cozy flavors and traditions of the holiday season. A perfect blend of bold espresso, creamy milk and warming gingerbread spices, this festive beverage has earned its place as a holiday favorite.

Rooted in centuries-old traditions, the gingerbread latte combines the rich history of spiced gingerbread with the comforting allure of a latte. It’s a drink that bridges past and present, inviting us to celebrate the season with a blend of nostalgia and creativity.

A Blend of History: Gingerbread and the Latte

The History of Gingerbread

Gingerbread has a history as rich as its flavor. Its roots trace back to ancient Greece and China, where ginger was prized for its medicinal qualities. By the 11th century, European bakers began incorporating ginger into bread, and over time, gingerbread became a beloved holiday treat. Its association with festive cheer grew stronger with the introduction of intricately decorated gingerbread houses in 16th-century Germany.

The Rise of the Latte

Meanwhile, Starbucks revolutionized holiday beverages when it debuted its Gingerbread Latte in 2000. Combining espresso, gingerbread syrup, steamed milk, whipped cream and a dash of nutmeg, this dreamy drink quickly became a winter favorite, filling people with coziness and lifting holiday spirits. For over 20 years, it has been a staple of the Starbucks holiday menu in the U.S. 

International Starbucks locations have even introduced a Chocolate Gingerbread Latte, adding a decadent twist to the classic, blending the best of hot chocolate and gingerbread flavors. 

How to Celebrate National Gingerbread Latte Day

Bring the warmth and joy of the season to your multifamily property by turning your communal spaces into cozy havens of holiday cheer. These simple, festive ideas will delight residents and make National Gingerbread Latte Day an unforgettable celebration!

1. DIY Gingerbread Latte Party

Set up a DIY gingerbread latte bar with all the essentials: fresh espresso, a variety of milk options, gingerbread syrup, whipped cream and a selection of festive toppings like cinnamon, nutmeg, crushed cookies and candy sprinkles. Enhance the party vibe with cozy seating, holiday music and warm lighting to create an inviting atmosphere. 

      If your property features a SipWithMe coffee amenity, make it the centerpiece of the event by showcasing its ease of use and versatility. Engage residents with a hands-on demonstration of how they can easily create their own café-quality gingerbread lattes (recipe below), making the experience interactive and fun.

      Add an extra layer of excitement by including gingerbread-themed treats, like cookies or muffins, and consider giving out small holiday favors, such as recipe cards or custom mugs, to make the event even more memorable. This party isn’t just about the coffee—it’s a celebration of the season and a great opportunity for residents to mingle and enjoy the holiday spirit together!

      2. Gingerbread Decorating Challenge

      Unleash creativity and foster community spirit with a gingerbread decorating contest! Provide residents with pre-assembled gingerbread houses or cookie kits, complete with icing, candies and sprinkles. Add a competitive edge by offering prizes for categories like “Most Creative” or “Best Overall Design.” This engaging activity doubles as a fun way to build connections among residents while embracing the holiday spirit.

      3. Gingerbread Latte Photo Booth

      Elevate the fun with a themed photo booth that screams holiday cheer! Include props like oversized coffee cups, gingerbread characters, festive hats and twinkling backdrops. Encourage residents to snap and share their photos on social media, tagging your property for added exposure. This activity not only fosters resident engagement but also highlights the vibrant community lifestyle your property offers.

      4. Interactive Gingerbread Workshops

      Take the celebration up a notch by partnering with a local baker to host an experiential workshop. Residents can learn tips and tricks for baking gingerbread cookies. Hands-on activities like these bring people together, provide new skills and create lasting memories—all while highlighting your property’s commitment to offering unique and enriching experiences.

        DIY Gingerbread Latte Recipe Featuring SipWithMe Espresso

        Whip up a SipWithMe gingerbread latte with this easy recipe from The Big Man’s World:

        Ingredients

        Directions

        1. In a small saucepan, add all your ingredients, except for the whipped cream. On medium heat, bring to a simmer. Once the mixture begins to simmer, reduce to low and stir regularly. Remove from heat after 2 minutes.
        2. Pour into a cup and top with whipped cream.

        Enjoy this cozy beverage as part of your Gingerbread Latte Day celebration or anytime you need a little holiday magic!

        Celebrate National Gingerbread Latte Day with SipWithMe

        National Gingerbread Latte Day invites us all to sip into the spirit of the season. From the comforting blend of gingerbread spices to the warmth of shared traditions, it’s the perfect excuse to embrace the holiday cheer, one cup at a time.

        With SipWithMe, you can bring the magic of premium coffee experiences to your community, making every day feel like a celebration. Whether it’s teaching your residents to craft a perfect gingerbread latte or exploring other seasonal favorites, SipWithMe makes it easy to spread joy.Ready to spice up your coffee amenity? Request a demo or get pricing today and discover how SipWithMe can make every moment memorable.reach out today to see how SipWithMe can transform your coffee amenity.

        As the seasons change, so do your residents’ needs and desires. Providing amenities and planning events that align with these shifting demands can be a game-changer for property managers. In fact, resident events have been shown to boost satisfaction, improve online reviews and impact lease renewal decisions, making them an essential tool for long-term property success.

        According to WithMe Inc.’s 2025 amenity outlook survey, which gathered insights from senior multifamily professionals at the country’s top property management companies, including Bozzuto, Greystar and Willow Bridge, there is a rise in resident demand for multipurpose spaces where they can relax, connect with neighbors and work.

        If there’s one thing I’ve learned in the multifamily industry, it’s this: the best way to ensure your amenities are valued is to ask the people who use them – your residents.

        At WithMe, Inc., we regularly survey thousands of residents, and the results from our latest round of questions reinforced something I’ve always believed: practical, everyday amenities win over flashy, trend-driven features every single time.

        It’s not about chasing fads or selecting features that look good in a photo. It’s about creating spaces that truly fit into residents’ lives. From coffee bars that power up their mornings to full-service fitness centers and smart-home features that add convenience and control, the amenities residents love are the ones that make life a little easier.

        Let’s talk about what really matters to residents and how focusing on practical, impactful options can transform your properties into communities people are proud to call home.

        ‘Tis the season for coffee celebrations, and December 3 is dedicated to one of the most iconic holiday latte flavors: peppermint. National Peppermint Latte Day honors the beloved blend of bold espresso, smooth milk and refreshing peppermint that perfectly captures the spirit of the season. Now a seasonal staple, the peppermint latte began gaining popularity in 2002. However, it wasn’t until 2015 that the internet declared it deserved its own day of celebration.

        The Historical Roots of Flavored Lattes

        Flavored coffee is not a modern innovation. Its origins trace back centuries to the Middle East, when coffee was often brewed with cardamom, cinnamon or dried fruits. These traditions, still reflected in Arabic and Turkish coffees, introduced layers of unique, complex flavors to the beverage.

        The American flavored latte, however, emerged in the 1980s in San Francisco’s North Beach neighborhood. LC "Brandy" Brandenburg, a retired coffee industry veteran, began experimenting with Torani syrups to craft what is considered the first flavored latte. His creation, the Fantasia, blended vanilla and orange flavors, igniting a flavored coffee trend that brought syrups like caramel, chocolate and vanilla to café menus across the country.

        The Evolution of Café Culture and Flavored Lattes

        Flavored lattes rose to prominence alongside broader changes in coffee culture. During the early 1980s, most American coffee shops offered only basic options like straight espresso or cappuccino. Flavored syrups made espresso drinks more approachable, appealing to customers who found traditional coffee too bitter.

        By the 1990s, Starbucks and other chains fully embraced flavored lattes, popularizing holiday classics like the Eggnog Latte (1986), Pumpkin Spice Latte (2003) and Chestnut Praline Latte (2014).

        Beyond flavor, lattes became a form of self-expression. Syrups and customizations allowed customers to craft drinks that reflected their personal tastes.

        The Starbucks Peppermint Mocha: A Holiday Legend

        The peppermint latte owes much of its popularity to Starbucks, whose Peppermint Mocha has become a holiday icon. After the success of the Gingerbread Latte in 2000, Starbucks’ research and development team set out to create another festive drink inspired by the season.

        Inspired by the candy canes and peppermint candies that dominate the season, the team developed a recipe combining espresso, bittersweet mocha sauce, peppermint syrup and steamed milk. The final touch was whipped cream and red sprinkles, later swapped for dark chocolate curls.

        Debuting in 2002, the Peppermint Mocha quickly became a fan favorite, earning a permanent spot on Starbucks’ seasonal menu. Today, it’s available hot, iced and blended, and it can even be found in grocery stores as pre-made drinks and limited-edition ground coffee.

        How to Celebrate National Peppermint Latte Day

        National Peppermint Latte Day is the perfect excuse to create meaningful moments and foster community connections. From interactive workshops to indulgent tasting experiences, there are countless ways to make this day special. Below are fresh, festive ideas to inspire your celebrations:

        Peppermint Latte Recipe

        Grab your favorite SipWithMe espresso or coffee and brew up some holiday happiness with this delicious recipe from Recipe Rebel

        Ingredients:

        Directions:

        1. Combine milk, sugar, and cocoa powder in a small saucepan. Heat over medium heat until small bubbles form and sugar dissolves.
        2. Stir in espresso or coffee, mint extract, and vanilla extract. Remove from heat.
        3. Pour into your favorite mug and top with whipped cream and chocolate shavings if desired.

        Celebrate the Holidays with SipWithMe

        National Peppermint Latte Day is a delightful opportunity to unite your community while savoring the season’s most beloved coffee flavor. From crafting personalized lattes to hosting festive workshops, these engaging activities encourage residents to connect, share joy, and create lasting memories.

        With SipWithMe, you can make premium, café-quality beverages a seamless part of your community’s lifestyle. Whether it’s a festive event or an everyday indulgence, SipWithMe makes it easy to create memorable experiences for your residents. Bring the joy of the season home - reach out today to see how SipWithMe can transform your coffee amenity.

        The multifamily housing market is constantly evolving, and so are the expectations of tenants. Today’s renters are looking for more than just a place to live—they want an apartment that fits their lifestyle and supports their needs. While luxury features like rooftop pools and concierge services may still have appeal, the amenities that truly matter to renters in 2025 are rooted in convenience, technology, and practicality.

        For property managers, understanding and implementing the right mix of amenities can be a game-changer. The competition for tenants is fierce, and staying ahead of emerging trends is essential for maintaining high occupancy rates and tenant satisfaction. This article will explore the apartment amenities tenants are prioritizing, highlight trends shaping the multifamily housing industry, and introduce innovative solutions from WithMe, Inc., a leader in technology-driven apartment amenities.

        November 23 marks National Espresso Day, inviting coffee lovers to raise a cup in honor of one of the world’s most beloved beverages. From its humble beginnings as a time-saving innovation to its current status as a symbol of coffee craftsmanship, espresso continues to inspire and connect coffee enthusiasts worldwide.

        But what makes espresso so special? Beyond its bold flavor and velvety texture, espresso is a unique blend of art, science and cultural significance that has captured hearts across the globe.

        The Origins of Espresso: Born Out of Necessity

        Espresso was first invented in the early 1900s in Italy to meet a very practical need: reducing the time workers spent on coffee breaks. Back then, long breaks were standard in factories and offices, so Italian inventor Luigi Bezzera designed a machine that could brew coffee quickly using high-pressure steam.

        This innovative method cut brewing time dramatically, providing workers with a fast, invigorating pick-me-up. The word espresso itself comes from the Italian esprimere, meaning "to press" or "to force out," referring to the high-pressure process that creates that intense, concentrated shot.

        What began as a productivity solution evolved into a beloved tradition, making espresso a cornerstone of global coffee culture.

        Espresso: More Than Just a Bean or Roast

        Many people mistakenly believe that espresso refers to a type of coffee bean or roast, but it’s actually a brewing method. Unlike drip coffee, which relies on gravity, espresso machines use high pressure (132 pounds per square inch) to force nearly boiling water through finely ground coffee beans.

        This high-pressure process produces a rich, concentrated shot with bold flavors and a velvety texture. Interestingly, espresso is 90% water, compared to the 98.5% water content of drip coffee, yet its high concentration of dissolved solids creates a much fuller body and flavor.

        The Perfect Shot: Crema and the Four M's

        A great espresso is about more than just getting the right ratio of water to coffee. It's an art that relies on precision, timing and the right ingredients. The four M's of espresso — macinazione (grind), miscela (blend), macchina (machine) and mano (barista) — are the keys to a perfect shot.

        A hallmark of a great shot is the crema — a golden, hazelnut-colored foam that adds texture and flavor. Crema indicates a well-extracted shot and adds texture and flavor. A properly pulled shot should be able to hold a sprinkle of sugar on the crema for about 30 seconds before it sinks, a sign of freshness and balance.

        Espresso Around the World

        Espresso’s influence extends far beyond Italy, where it’s deeply ingrained in daily life. Italians often drink espresso standing at a café bar, savoring a quick moment of connection with baristas or fellow patrons. It’s so central to Italian culture that the government has regulated its price in public spaces since 1915 to keep it accessible to all.

        Globally, espresso has inspired countless variations, including cappuccinos, lattes and macchiatos. Despite its global reach, espresso retains its Italian heritage as a symbol of quality, simplicity and community.

        Even in space, espresso remains essential. In 2015, Italian engineers developed the ISSpresso machine, allowing astronauts aboard the International Space Station to enjoy a freshly brewed shot in microgravity.

        From bustling cafés to orbiting space stations, espresso continues to unite and delight.

        The Science of Espresso: The Role of Water and Caffeine

        Espresso's bold flavor reflects a fascinating balance of science and craftsmanship.

        How to Celebrate National Espresso Day

        National Espresso Day is the perfect time to savor the craftsmanship and flavor of this iconic beverage. Here are some ways to celebrate:

        A Sip of History and Craft

        Espresso is more than just a fast way to get your caffeine fix. It’s a drink steeped in history, a product of Italian innovation and an art form perfected by baristas around the world. Whether you’re savoring a single shot or enjoying a latte or cappuccino, every cup of espresso represents a harmonious balance of grind, blend, machine and skill.

        Celebrate National Espresso Day with SipWithMe

        At SipWithMe, we believe great coffee turns ordinary moments into extraordinary experiences. With premium amenities designed to deliver barista-quality espresso shots, indulgent lattes and more at the touch of a button, we make luxury coffee service effortless and accessible.

        Whether it's National Espresso Day, National Cappuccino Day or simply an ordinary morning, SipWithMe helps you create moments worth savoring.

        This National Espresso Day, celebrate the artistry of the perfect espresso shot with a coffee amenity upgrade that delights and simplifies. Contact us today to schedule a demo or request pricing details.

        It’s holiday crunch time, and that one perfect gift is nowhere to be found. But who needs store shelves when you’ve got PrintWithMe in your community? 

        You can turn your apartment printing solution into a personal gift factory with a touch of creativity and a few clicks. From heartfelt keepsakes to personalized greeting cards, these DIY ideas will have you wrapping up holiday magic in no time. 

        1. Personalized Calendars

        A custom calendar is an easy but super useful gift! Gather some favorite photos (holiday memories, pets, vacation snapshots) and arrange them in a simple template (Canva has some great options). Print, stack and staple for a gift that brings joy all year. 

        2. Recipe Books with a Personal Touch

        If you’re the go-to chef or baker in the family, share your favorite recipes in a custom book. Create a collection of your favorite tried-and-true recipes, complete with photos or handwritten notes to add a personal and heartfelt touch. Finish the project by binding the pages with ribbon or a stylish binder clip for a charming and thoughtful presentation.

        3. Holiday Coloring Books for Kids

        Running out of ideas to keep little ones busy? Use your community printer to print a fun holiday-themed coloring book. Search for free holiday coloring pages online, print them out and bind them all together for a simple yet thoughtful gift. 

        4. DIY Wrapping Paper with a Personal Touch

        Bring a personal flair to your gift wrapping by printing custom holiday paper with festive themes or cherished photos. This DIY approach adds a personal, thoughtful touch that makes every gift extra special. Use apartment printing solutions to make each package a work of art, perfect for smaller items or gift bags. Simply print, wrap and watch your loved ones marvel at your creativity!

        5. Last-Minute Holiday Cards

        No gift list is complete without classic holiday cards. Use your community printer to create custom holiday greetings. Personalize with photos, add a message and print—no need to rush to the store. Designing and printing cards at home allows you to make each one special, ensuring your holiday greetings are as thoughtful and unique as the people receiving them.

        PrintWithMe—The Ultimate Gift-Giving Sidekick

        With PrintWithMe, you can skip the shopping stress and create gifts that feel personal and thoughtful. So, if you find yourself in a last-minute bind, let your community printer be the secret ingredient to a smooth holiday season. Happy printing!

        For more information on how PrintWithMe can enhance your property’s amenity offerings, contact us today.

        As resident expectations continue to evolve, the multifamily housing industry must set a new standard for amenities in the new year. With remote work, wellness and technology shaping everyday life, property managers and developers are introducing innovative amenities to create vibrant, adaptable and highly personalized living spaces.

        Village Green’s Executive Vice President Marketing & Brand Loyalty Ashley Sinclair and WithMe Inc.’s CEO & Founder Jonathan Treble know about the latest amenity trends. From tech-enabled conveniences and wellness-focused spaces to creative areas for crafting and leisure, these industry leaders share their insights on how multifamily properties are embracing the future of resident experience in a rapidly changing market.

        EPISODE SUMMARY

        How do you lead a team of 18,000 associates while managing 9,000 communities across North America? For David Diestel, CEO of FirstService Residential, the answer lies in trust, culture and a people-first approach to leadership.

        In this episode of Multifamily Excellence, David joins host Jonathan Treble to share his fascinating career journey—from his beginnings as a chemical engineer and entrepreneur in the apparel industry to becoming the leader of North America’s largest residential property management company. Along the way, David learned invaluable lessons in adaptability, continuous learning and the importance of reputation.

        Here’s what you’ll walk away with:

        This episode is about learning how to lead in a way that feels human, scalable and deeply impactful. David’s insights are both timeless and timely—perfect for anyone navigating the fast-changing landscape of property management or leadership.

        Ready to rethink what leadership looks like in your world?

        This conversation will challenge how you see your team, your culture and yourself. Tune in now and start building something that truly lasts. of people-first leadership and AI innovation. This is one episode you won’t want to miss. Listen now.

        CONNECT WITH DAVID

        SUBSCRIBE TO MULTIFAMILY EXCELLENCE

        Entrepreneurship is often sold as a dream. Inspirational LinkedIn quotes, founder stories ending in IPOs or exits—it all paints a pretty picture. But after ten years of building, breaking and rebuilding, I’ve learned that the reality is much messier.

        Here’s what I know:

        If you want the truth, here it is: You’ll make mistakes. Your plans will blow up. People will let you down — and you’ll do the same to others.

        Entrepreneurship isn’t about having it all figured out from the start; it’s about adapting, pivoting and occasionally face-planting on your way to the next big thing. The key is learning, adapting and building momentum through all the messy moments.

        Here are ten hard-won insights I wish someone had handed me on day one. They’re hard-earned, often expensive and painfully simple. But if you absorb even one of them, it might just save you a year of setbacks — or at the very least, a couple of sleepless nights.

        1. Big ideas matter, but execution pays the bills.

        People love big talk about “moonshots” and “world-changing ideas”—but here’s the reality: ideas are the easy part. If you can’t roll up your sleeves and execute on them, you’re just playing mental gymnastics. The real differentiator? Consistent, relentless action. Week in, week out. Fancy pitches are great, but it’s the follow-ups and unglamorous day-to-day that get results.

        Think big. Ask, “How can we 10x this?” Then break down your goals, tackle them piece by piece and keep moving. At WithMe, we don’t scale on vision alone; we thrive by stacking small, consistent wins, building momentum step-by-step. Fancy pitches won’t pay the bills, but focused, gritty follow-through will.

        My tip: Track your team’s progress on micro-wins. Those add up fast.

        1. Growth doesn’t happen by accident.

        Scaling isn’t something that just “happens” if you’re in the right place at the right time. If you want exponential growth, you have to be intentional and take risks. That often means tearing down something you thought was working and rebuilding it with new insights.

        You have to be intentional. That means asking yourself uncomfortable questions: What’s working? What’s not? What’s the bottleneck? 

        If you want 10% growth, tinker. If you want 10x growth, rethink everything. Big leaps require uncomfortable choices and serious risk-taking. Growth only happens when you let go of ‘good enough.’ If you’re not rethinking the fundamentals regularly, you're just coasting.

        My approach: Regularly challenge the status quo. If something is only “good enough,” it’s time to rethink.

        1. People are your greatest investment.

        Hiring the right people is like collecting rare art. The best talent isn’t always on job boards; they’re out there doing great work. Finding these people requires patience, vision and sometimes years of connection-building. 

        Some of the best people I’ve hired were conversations years in the making. Play the long game with talent acquisition. It always pays off.

        Remember, the best talent isn't on the market — they’re out there waiting to be discovered. When you find them, move fast. Pay upfront in value, and over time, they’ll return more than you imagined. When you spot someone with the right spark, act fast.

        Pro tip: Find smart people, pay them well and get out of their way. When you spot a standout talent, move fast.

        1. Leadership is serving your team.

        The most effective leaders serve their teams by removing obstacles, providing direction and stepping aside. If you think your team works for you, you’ve already lost. Your job is to clear obstacles and make sure they have everything they need to win. Enable people to perform at their highest level—and that starts by empowering them to own their roles.

        Key insight: Leadership isn’t about control—it’s about service. If you’re micromanaging, you’re bottlenecking your business.

        1. Don’t confuse movement with progress.

        Being busy doesn’t mean you’re being productive. There have been weeks where I felt like I was running on a treadmill—doing a lot but moving nowhere. Progress is about completing the right things, not just checking off endless tasks.

        Here’s how I spot wasted effort: If it’s not moving the needle, it’s a distraction.

        My rule: Ruthlessly prioritize what matters, and let the noise go.

        1. Mistakes will happen. Own them.

        No one gets through entrepreneurship without a few bruises. I’ve micromanaged when I should have trusted my team. I’ve raised more capital than I could deploy effectively. But every mistake became a lesson that shaped how I lead today. Create space for yourself (and your team) to learn from missteps.

        You’ll screw up—more than once. It’s part of the game. Admit your mistakes fast, learn from them and move on. No one has time for excuses. The trick is to own those mistakes fast, learn from them and get back on track.

        Pro tip: Create a culture where your team feels safe to fail and learn. If they’re too afraid to make mistakes, they won’t push boundaries—and neither will your company.

        1. Competitors are a distraction.

        It’s easy to get obsessed with what the competition is doing. But unless they’re paying your bills, their moves shouldn’t drive yours. Focus on listening to your customers and solving their problems. Listen to their pain points. Build solutions that genuinely help them—and your growth will follow.

        Markets evolve, and so do your customers' needs. Obsess over meeting those needs better than anyone else.

        My approach: Keep your head in your game and stick to your strategy.  Outflanking competitors is easy — listen to customers louder than they do.

        1. Your best salesperson is a happy customer.

        No ad campaign can compete with a customer saying, “You need this.” The strongest growth comes from people who genuinely love what you do and tell others about it. A product with undeniable value creates advocates naturally.

        Nail your product-market fit, and customers will sing your praises.

        If your product isn’t generating enthusiastic referrals, it’s time to go back to the drawing board.

        Takeaway: Build something that people love so much, they can’t help but tell others. Happy customers are the lifeblood of sustainable growth.

        1. Not every fire needs your attention.

        In a growing business, there are always fires to put out. But knowing which fires matter—and which ones to let burn—is a game-changer. Early on, I tried to handle everything myself. Now, I triage: if it doesn’t impact the long-term vision, it can wait.

        You’ve got limited time—spend it on the fires that actually matter. The art of prioritization is everything.

        Lesson learned: Prioritize only the fires that matter. Not every problem deserves immediate attention.

        1. Sometimes, the best move is no move.

        In moments of stress — a sleepless night, a tough quarter or a rough meeting — pause. Acting rashly rarely helps. Inaction, when applied wisely, can prevent avoidable damage and keep trust intact.

        When you’re overwhelmed, resist the urge to react impulsively. I’ve learned the hard way that acting while exhausted, stressed or frustrated rarely ends well.

        My advice: Sleep on it. Most problems can wait a day. The ones that can’t? They’re rarely solved with rushed decisions.

        Enjoy the journey, or what’s the point?

        If you’re always chasing the next thing, you’ll miss the good stuff. The best moments aren’t just milestones—they’re found in the chaos along the way.

        There’s always another mountain to climb, but if you don’t enjoy the journey, what’s the point? The biggest wins come in unexpected places—sometimes between meetings, other times during failures that seem devastating at first.

        Entrepreneurship isn’t a straight line. It’s messy, unpredictable and exhausting—but it’s also incredibly rewarding if you stick with it. Just remember: It’s okay to stumble as long as you keep moving forward.

        Reality Check: You’ll Wear Every Hat—and You’ll Still Drop a Few

        In the early days, I was the CEO, customer support, IT troubleshooter and supply chain manager. You name it. And yes, things still slipped through the cracks sometimes. That’s just reality. As we grew, I learned the importance of building a strong team—one that could take some of those hats and wear them even better than I could. Eventually, I learned the importance of knowing which hats I could keep and which I needed to pass on to someone better suited for them.

        As WithMe grew, I made a conscious choice to hire people who were stronger than me in specific areas. This wasn’t easy; it meant letting go of control and trusting my team. But it was a game-changer. Each person I brought on brought something unique that took WithMe to the next level. The lesson? You might start out juggling it all, but eventually, you need to step back and let others wear some of those hats. That’s when your team—and your business—will really take off.

        Advice: Hire people who are better than you at specific things and let them shine.

        The Bottom Line

        Ten years in, and here’s what I know for sure: you’ll never have it all figured out—and that’s okay. The journey is about learning, evolving and staying curious. If you can embrace that, you’ll find that every setback is a step forward and every challenge is an opportunity to grow.

        The journey isn’t always glamorous, but it’s worth every stumble. These 10 lessons? They’re battle-tested and scraped together from 10 years of face-plants, late nights and surprising wins. Take them in, and they might just save you a few trips down the “What the heck am I doing?” road.

        And if you’re curious how WithMe is applying these lessons to reimagine multifamily living, check us out. From simplifying daily life to creating standout resident experiences, we’re just getting started.


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