Duolingo is adopting an “AI-first” approach to its business, and the language learning platform will reduce its reliance on human contract workers as it assigns AI their responsibilities.

In a memo to employees on Monday, Duolingo CEO Luis von Ahn detailed the company’s official “AI-first” stance.

“AI is already changing how work gets done,” Ahn wrote in an email publicly shared through Duolingo’s LinkedIn account. “When there’s a shift this big, the worst thing you can do is wait.”

As part of its AI-first strategy, Duolingo will shift workloads from contractors to AI and “gradually stop using contractors to do work that AI can handle,” per the email. The company will also reward AI use in hiring new employees and in performance reviews of existing employees. Teams will additionally only be permitted to hire new members if the group cannot automate the work.

Related: ‘Make Chess as Accessible as Possible’: Duolingo’s Next Move Is Teaching Users How to Play Chess

Duolingo has eliminated contract workers in favor of AI before. Last year, the company cut 10% of its contractors after reportedly deciding to use AI for translations.

However, Ahn reassured staff in the email that “Duolingo will remain a company that cares deeply about its employees,” and that being AI-first wasn’t about “replacing” workers with AI but about allowing existing employees to focus on creative work and problem-solving over repetitive tasks. The company said that it would support staff with full-time staff training, mentorship, and AI tools.

^{Duolingo CEO Luis von Ahn. Photo by Kevin Dietsch/Getty Images}

Ahn also explained why Duolingo was choosing to go all-in on AI now. He stated in the email that Duolingo bet big on mobile in 2012, focusing on creating a mobile-first app at a time when mobile apps were primarily companions for full-fledged websites. The move worked out well: Duolingo’s app won the 2013 iPhone App of the Year with 10 million downloads and grew organically after that. Now, Duolingo has over 500 million registered users.

“This time the platform shift is AI,” he wrote in the email.

Related: ‘Get 100X the Work Done’: Shopify CEO Tells Employees to Try AI to Get Work Done Before Asking for More Human Workers

Duolingo is focusing on AI by using it to create content and power features like Video Call, which Duolingo introduced in September. Video Call allows learners to practice speaking in their target language through a video chat with an AI character named Lily.

Duolingo isn’t the first company to recently announce an AI-first strategy. Earlier this month, Shopify CEO Tobias Lutke told all employees in a memo that “using AI effectively is now a fundamental expectation of everyone at Shopify.” Lutke told Shopify staff that they should maximize what they could do with AI before asking for more resources or additional human employees.

He also said that Shopify would add AI use questions to its performance and peer reviews.

Duolingo had a market capitalization of over $17 billion at the time of writing.

In an industry built on big moments, Sebastien Centner bets on the small stuff.

“In our industry, there are things people just expect,” he says. “If it’s hot food, it should be hot. The food should be good. That’s the foundation. But that last five percent? That’s what makes us stand out.”

Centner is the founder of Eatertainment, a Toronto-based catering and events company that now runs more than 1,000 events a year. His journey started with confidence and a hard lesson.

Related: This ‘Chopped’ Champ Beat Cancer 6 Times, Lost Nearly 200 Pounds and Found Power in Presence

At the time, Centner wasn’t in the catering business. He was running a bar and restaurant when a loyal customer asked if he could help cater his daughter’s engagement party. It would be his first attempt at doing an event like that.

He figured he had everything covered: chefs, servers, drinks and food. It can’t be that hard, the hospitality entrepreneur thought.

“It was a disaster,” he tells Shawn Walchef, host of Restaurant Influencers. “If we delivered 50 percent of what the client expected, I’d be surprised.”

But instead of walking away, he got obsessed. “In the first year, we did 20 events,” he says. “I learned from event to event to event. I did a less and less sh*tty job each time.”

Over time, he developed a system based on preparation and precision. Every detail of an event was mapped out in advance so his team could handle curveballs and still deliver something special.

“I always say we can only deliver the five percent if we’ve already planned out the first 95,” he says. “If you’re scrambling to fix something basic the day of the event, you don’t have time to go above and beyond.”

Related: How a ‘Finance Guy’ and ‘Restaurant Guy’ Joined Forces to Invest in Over 55 Companies

The philosophy stuck. So did the pressure.

“You’re tasting wine together, you’re flying to South Africa to scout venues, you’re basically on vacation with your clients,” he says. “But if something goes wrong, we’re the help. They’re not our friends.”

Centner loves the energy of the catering world — the pace, problem-solving and creativity. But he’s clear on one thing: This is a business, and it only works if you consistently deliver.

And that’s not something he does alone. His wife, Sheila, has been with him since the very beginning, helping to drive both the business and the brand forward. “She balances me,” Centner says.

The couple’s connection wasn’t just instant in business. It was instant in life. “When I did meet her, we met, [and] she moved in within a week,” he says. “We were engaged within a month, and we were married within the year.”

Related: How a Jersey Kid Grew His Restaurant Business Into a West Coast Powerhouse

They’ve worked side by side for decades. While Centner focuses on logistics and scaling, Sheila leads the creative side — developing content, directing strategy and constantly pushing the company to evolve.

“She’s the one who’ll say, ‘If I see one more matcha green tea mini burger, I’m going to scream,'” he laughs. “And she’s right. We’ve been doing it for six months. We gotta get rid of it.”

With Sheila leading the creative direction and content strategy, Eatertainment’s in-house team now captures every event, edits video reels and sends clients curated highlight recaps. It’s a layer of polish that didn’t exist in catering just a few years ago. That personal touch has become part of their five percent.

What keeps Centner going after two decades isn’t just growth or scale. It’s the people. “My favorite part is seeing people’s faces when they walk into a room,” he says. “They smile. They pull out their phones. That’s the reaction we want.”

For Centner, that moment is everything. The lights, the food, the music — it all builds to that spark of joy. That connection. It’s the extra five percent that Eatertainment was built to deliver.

Related: Most Creators Are Doing Brand Deals Wrong — And This Sponsorship Expert Has Some Advice for Them

About Restaurant Influencers

Restaurant Influencers is brought to you by Toast, the powerful restaurant point-of-sale and management system that helps restaurants improve operations, increase sales and create a better guest experience.

Toast — Powering Successful Restaurants. Learn more about Toast.

In an era shaped by uncertainty, rapid innovation and blurred lines between physical and digital leadership, executive presence has become one of the most critical — and yet most underestimated — skills for high-impact leadership.

It’s not just about how you look in a boardroom or sound on a Zoom call. It’s about the intangible authority you project, the trust you build and the decisions you influence. Executive presence is the signal that tells your team, your board and your investors: “This is someone worth following.”

But here’s the catch: Most executives are never taught how to build it.

In 2025, as leaders navigate hybrid organizations, global uncertainty and evolving stakeholder expectations, executive presence has shifted from a “nice-to-have” to a core leadership competency.

Related: 5 Core Strategies for Cultivating Executive Presence

What is executive presence really?

Executive presence is often mistaken for confidence or charisma. While both are ingredients, presence is much more layered. It’s the sum of how you show up, communicate, listen, decide and lead — especially under pressure.

It’s the quiet authority in a crisis. The clarity of vision in a crowded room.
The ability to hold space, earn trust and command respect — without saying much at all.

In practical terms, executive presence can be broken into three key dimensions:

1. Gravitas: How you carry yourself, especially in high-stakes moments.

2. Communication: Clarity, tone, body language and the ability to engage with purpose.

3. Appearance: Not vanity, but intentionality — how you present yourself and align with your message.

These elements matter not just in the boardroom, but in every room: investor calls, media appearances, team meetings and digital platforms. In a hybrid world, executive presence has to translate across both physical and virtual spaces.

Why it’s underrated — until it’s not

Companies spend billions on digital transformation, strategy and systems. But leadership presence — how decisions are conveyed, how vision is embodied, and how trust is projected — is rarely prioritized.

Until there’s a crisis.

Until a founder can’t inspire confidence during a funding round.

Until a CEO loses the room during a high-stakes negotiation.

Until a board realizes their executive lacks the influence to rally talent, partners or the market.

In today’s landscape, presence can be the difference between buy-in and breakdown.

How executive presence has changed in 2025

Post-pandemic, presence is no longer about simply walking into a room and owning it. Today, leaders must know how to:

• Lead confidently on camera

• Build connection through virtual platforms

• Manage asynchronous communication without losing clarity

• Influence across diverse, cross-functional teams

• Earn trust in a remote-first or hybrid workplace

It’s not about volume — it’s about value. The modern executive doesn’t have to be the loudest voice — they must be the clearest, the calmest and the most aligned with purpose.

Related: How to Create an Executive Presence That Actually Persuades and Inspires Others

The mindset behind presence

You can’t fake true executive presence. It must be built on mindset and self-awareness.

Leaders with strong presence carry an internal belief that they belong where they are, and they’re responsible for elevating those around them.

Here’s what that looks like:

• They don’t just communicate — they connect.

• They don’t just show up — they show purpose.

• They don’t just speak — they spark action.

In short, they lead from the inside out. And that starts with intentional development.

How to build executive presence — practically

No one is born with executive presence. It’s developed like any strategic muscle — through deliberate practice, feedback and alignment.

Here are six actionable steps to strengthen your presence in 2025 and beyond:

1. Develop clear, purpose-driven communication

Speak less, say more. Remove filler. Pause for impact. Practice articulating your ideas with clarity and confidence, whether in person or online.

Tip: In virtual settings, make eye contact through the camera. Don’t look at yourself — connect with your audience.

2. Master your body language

Your posture, gestures and facial expressions speak louder than words. Be still when making a key point. Use open gestures. Maintain calm energy.

Presence is physical before it’s verbal.

3. Manage emotions under pressure

Executive presence isn’t tested when things are smooth — it’s revealed in the fire. Learn to breathe, reset and regulate your energy. Others take their emotional cues from you.

4. Dress with purpose, not just style

Appearance isn’t about flash. It’s about intention and consistency. Whether you’re on stage, on Zoom or on LinkedIn — show up as a unified brand.

Ask: Does how I show up match what I stand for?

5. Create room for others

True executive presence includes how you make others feel. Elevate voices. Listen deeply. A leader who creates space for others will always own the room.

6. Get feedback and record yourself

Video yourself during presentations. Watch without sound. Watch with sound. What message are you sending?

Then ask your team: “How do I show up when stakes are high?”

Feedback sharpens presence faster than theory ever will.

A final word to executives and emerging leaders

As someone who works with boards, executives and founders every day, I can tell you: Presence isn’t just an individual skill — it’s an organizational asset.

A company is often judged by its leadership’s ability to communicate, inspire and project vision with confidence. When an executive walks into the room or logs onto the screen, their presence sets the tone.

And in 2025, tone drives trust.

Trust drives talent.

And talent builds everything else.

Related: How to Develop an Executive Presence and Earn Respect

So ask yourself:

• Do I project clarity in every setting I lead?

• Can I inspire confidence — even in moments of uncertainty?

• Does my presence align with the future I want to build?

If the answer is “not yet,” then now is the time to invest in this skill.

Because strategy may open doors, but presence is what keeps them open.

A mid-level Google employee made $331,894 in 2024, a 5% increase from the median salary of $315,531 in 2023, per a new filing submitted by Google’s parent company, Alphabet, to the U.S. Securities and Exchange Commission.

The figure aligns with compensation at other tech giants in recent years. At Meta, for example, the median pay for employees in 2023 was $379,000 a year.

The filing further showed that Alphabet and Google CEO Sundar Pichai received total annual compensation of $10,725,043 last year, about 32 times more than the median employee. Pichai received a nearly $2 million raise from the $8,802,824 he made in 2023.

^{Google CEO Sundar Pichai. Photo by Klaudia Radecka/NurPhoto via Getty Images}

The bulk of Pichai’s compensation came from the “All Other Compensation” category, besides his $2,015,385 base salary and $405,630 in stock awards.

The remaining $8,304,028 included Pichai’s personal security costs, which climbed 22% from the $6,775,631 Google paid in 2023 to $8,267,123 in 2024. The category also included his retirement plan and use of company aircraft or cars.

Related: Google CEO Sundar Pichai Says ‘You’ll Be Surprised’ By How Google Search Changes in 2025

“Due to Sundar’s significant public profile, Alphabet provides him with security protection,” Alphabet’s 2025 proxy statement reads. “In 2024, Sundar’s security arrangements included residential security and consultation fees, security monitoring services, car and driver services, and personal security during all travel.”

Alphabet called Pichai’s personal security expenses “reasonable, appropriate, necessary and in the best interests of Alphabet and its stockholders.”

Other tech CEOs also have seven or eight-figure security costs. For example, Meta CEO Mark Zuckerberg’s $27.2 million total compensation in 2024 included a $14 million pre-tax security allowance. Meanwhile, Nvidia spent nearly $2.5 million in 2024 on CEO Jensen Huang’s security costs.

Related: Here’s How Much 8 CEOs Made in 2024, From JPMorgan’s Jamie Dimon to Disney’s Bob Iger

“Non-gearheads” now have the chance to design their own cars.

Last month, an image appeared on Reddit of an unidentifiable small truck in a parking lot in Los Angeles. The sighting was first noted by Carscoops just after TechCrunch reported that Jeff Bezos was making an “affordable” vehicle through a “secretive EV startup” called Slate Auto.

Related: I Tried Buying a Car on Amazon. Here Are the Pros and Cons.

Internet sleuths quickly put together (and TechCrunch confirmed) that the truck in the Reddit image was the actual Slate Auto concept car.

Now, the company is ready for reservations, and personalization is key. Everything is customizable, from the exterior look to the color to the interior knobs.

“We think everyone should be able to personalize their car,” the website says. “But vehicles aren’t built to be customized by non-gearheads (we love you, gearheads). So, we changed that.”

^{Provided by Slate Auto}

In a video announcing the new “radically simple, radically affordable Slate truck” on X, CEO Chris Barman said the price starts in the “mid 20s,” though it will be closer to $20,000 (after federal EV tax credits). The single-cab electric truck is set to be delivered to customers in late 2026. The company is based in Troy, Michigan.

The people spoke. We built. Meet the radically simple, radically affordable Slate. Reserve yours at https://t.co/Y5RkOIFCRo pic.twitter.com/uvSZVpdkWv

— Slate Auto (@slateauto) April 25, 2025

“There’s a massive population of people out there when it comes to safe, reliable, affordable transportation; there just really aren’t many alternatives for them,” CEO Chris Barman told Business Insider ahead of the official unveiling.

Related: The ‘Secretive’ Electric Vehicle Affordable Truck Was Just Spotted in Los Angeles

One way the company is keeping it affordable is through its customization options. For example, the trucks are wrapped, not painted, and can be changed at a customer’s whim.

“With other cars, you pick your color when you buy it, and that’s it,” the website says. “With a Slate, you can pick your color whenever—and change it whenever. It’s the first vehicle of its kind designed to be easily wrapped.”

Wrap kits will start around $500, according to the company. (Though keeping it the simple gray—as per the Reddit reveal—will still stand out.)

What is this car?
byu/discostranger09 inwhatisthiscar

Amazon founder Bezos, Mark Walter (Los Angeles Dodgers majority owner and CEO of Guggenheim Partners), and investor Thomas Tull have helped the new car company raise at least $111 million, per TechCrunch.

NBC reports that, according to a document filed with the Securities and Exchange Commission, Melinda Lewison, the head of Bezos’ family office, is the new Slate Auto director.

Thirty-two percent of business owners say that the biggest challenge to running a business is lack of capital or cash, according to Guidant Financial. So, expensive software subscriptions may be out of reach. Fortunately, you can save big on a lifetime license of Microsoft Office 2024 for your business. Licenses for Macs and PCs are available for $159.97 (reg. $249) — 36% off.

This Office license offers the five most valuable Office programs for both home and business users: Excel, Word, PowerPoint, OneNote, and Outlook. This 2024 edition of Office has many improvements over the 2021 version.

The entire suite has increased performance, most obviously in Excel. It has no lag when managing multiple workbooks and large datasets so that you can make data-based business decisions in a more timely manner. PowerPoint offers new advanced content creation tools, including integrating video and voice narration, even live camera feeds. Word has a new Focus Mode that hides non-essential options and toolbars to minimize distractions.

Accessibility features have been upgraded, such as Outlook’s accessibility checker, which will flag poor formatting and unclear language issues to ensure emails meet standards for effective communications. The user interface has been modernized, as well, for more intuitive navigation that new users will appreciate. Even better, the interface is consistent throughout all of the applications.

Touch and pen support has also been updated, making them more responsive and providing a better experience on tablets and hybrid devices. Easily customizable pre-designed templates help users create spreadsheets, presentations, and professional-looking documents. Small businesses will find these useful for presenting a polished image without graphic design experience.

Collaboration tools have been improved with a deeper integration of Microsoft Teams, chat and commenting features, and more. Exciting new AI-powered features are now available, as well. Best of all, this license is a one-time purchase, so there’s no need to worry about expensive subscriptions anymore.

Why this deal is worth it

This deal gets you a lifetime license to Microsoft Office 2024 Home and Business for just $159.97—no subscriptions or recurring fees necessary. You’ll get the latest versions of Word, Excel, PowerPoint, Outlook, and OneNote with upgraded features, faster performance, and AI-powered tools to boost productivity. It’s a smart, one-time investment for entrepreneurs, freelancers, and small-business owners looking to cut costs without sacrificing quality.

Get a Microsoft Office 2024 Home & Business lifetime license for your Mac or PC for $159.97 (reg. $249) while downloads are still available. Act before they sell out, or before this price drop disappears for good.

Microsoft Office 2024 Home & Business for Mac or PC Lifetime License – $159.97

See Deal

StackSocial prices subject to change.

It’s not unusual for entrepreneurs to run high on energy, and I’m no exception. I’ve been pulling 60- to 70-hour weeks for decades, and I’d like to think I’m no worse for wear. But, like many business leaders, I’ve also seen my energy levels plummet following intensive projects. After going full-tilt for weeks in preparation for our IPO, for example, I was genuinely surprised by how worn out I felt — and how much downtime I needed to recover.

That moment changed the way I think about productivity. Entrepreneurs love to talk about time management — optimizing schedules to squeeze more hours out of the day — but what I learned is that time isn’t the real constraint. Energy is. You can meticulously plan your calendar, but if you don’t have the energy to execute, none of it matters.

Arianna Huffington learned this the hard way when she famously collapsed from exhaustion, breaking her cheekbone in the process. Countless founders have run themselves into the ground, thinking that working harder was the answer — until they hit a wall. And with workplace burnout skyrocketing, we’re in what some have called a human energy crisis.

The good news? Energy management is a learned skill, and when you master it, you don’t just avoid burnout — you unlock higher levels of productivity, creativity and resilience.

Here are four approaches I recommend to keep your energy levels high, and your business thriving.

Related: How to Let Go of Unnecessary Tasks and Focus on What Matters

1. Pinpoint your energy vampires (and boosters)

It’s no secret that low energy can put a serious damper on productivity. Fatigue costs employers an estimated $136 billion annually. But leaders who understand how to manage their own — and harness their teams’ — energy can significantly increase their capacity to get things done.

Energy management often goes hand in hand with time management, but it’s not the same thing. Keeping your energy high also requires understanding exactly what drains it and what replenishes it. If you’re not sure, a great place to start is by tracking your daily activities.

For me, the biggest drain isn’t busyness or overscheduling, it’s conflict in work relationships. The stress it causes literally keeps me up at night, particularly how one bad relationship can balloon into a mass energy vampire. On the flipside, good relationships can be huge energy boosters, and studies have shown that leaders who prioritize relationship building have teams that are more productive, enthusiastic and loyal.

2. Reclaim energy from draining tasks and people

You may not be able to avoid everything that drains you, but you can find ways to manage problem areas. For me, that means investing in improving the situation. I’ve seen many entrepreneurs cut and run when things get tough, but I believe it’s worth the effort to make something right.

Here’s an example: when a relationship with a team member is going great, I am quick to assume the best intentions. But if it’s not going well, I’ll often assume the worst. Changing this requires that I step back and re-process their communication by imagining how I’d react if it came from someone else. It’s an easy hack to shift my perspective into a more positive frame, and it helps me clear up my biases and repair the relationship.

Frankly, we all need to own our part rather than applying labels like ‘energy vampire’ that put the blame on the other person. If showing up as your best doesn’t work, then it may be time to end the relationship.

Whatever you do, don’t wait for a catastrophic moment to take action. Consider offsetting energy drains with things that replenish you. For me, it’s carving out time for the basics — lifestyle habits like sleep, nutrition, exercise and family time — and creating a work environment optimized for a flow state. I’ve realized that minimizing interruptions and taking breaks is essential for sustaining my energy levels through deep work — and I think a lot of people could benefit from this, too.

Related: Don’t Let These 8 Common Business Expenses Drain Your Profits

3. If you can’t optimize an energy drain, find a workaround (it might just be acceptance)

We all have to do things we don’t enjoy at work, and sometimes there’s no way around it. You might be tempted to cut out the fatiguing task altogether, but consider this: if you could optimize the situation, could it become an energy booster?

I figured out, for example, that I can make conference networking more enjoyable (and less of a drain for an introvert) if I focus on creating quality connections with two or three people, rather than striving to shake as many hands as possible.

Small optimizations can go a long way toward turning a negative into a positive, but I find it also helps to accept the fact that not every task will be an energy booster — and that’s okay.

Related:

4. Lead with energy: set expectations and keep momentum high

In your role as a team leader, you can model healthy energy management, but you can also set clear goals and expectations that eliminate energy-wasting arguments. That means being clear on who’s making a decision and when, keeping the time for debate to a reasonable minimum, documenting the decision, and ensuring that after it’s made, it doesn’t devolve into relitigation. Failing on any of these points can be a massive energy drain for your team.

Being crystal clear on the big picture helps keep spirits high when the days are long. Plus, identifying an end point and celebration markers can have a big impact on keeping motivation and morale high (and can actually lead to more success). I witness it every year during our Black Friday sales campaign, when every department comes together to root for success and watch our dashboard hit its targets.

If you take away one thing, let it be this: managing your energy isn’t a luxury — it’s a necessity. The most productive entrepreneurs aren’t just masters of their calendars, they’re masters of their stamina and their teams’. Before you pack another hour into your already full day, ask yourself: Am I managing my time, or am I managing my energy?

This Side Hustle Spotlight Q&A features Colorado-based entrepreneurs Boone Whiteside, 29, and Ben Medalie, 28. Whiteside and Medalie are the co-founders of Highland, a haircare brand that started as a DIY passion project in a Denver apartment and has grown into an eight-figure business in three years. Responses have been edited for length and clarity.

^{Image Credit: Courtesy of Highland. Boone Whiteside, left, and Ben Medalie, right.}
When did you start your side hustle, and where did you find the inspiration for it?
Whiteside: When Ben and I became best friends during our junior year at CU Boulder, one of the things that brought us close was our shared aspiration of building our own thing — in not walking a 9-5 path working on someone else’s dream. This shared passion wouldn’t manifest until much later, though.

When I first started dreaming of a hair product company that went beyond styling one’s hair with toxic sh*t, I was working at an ecommerce startup in a marketing and operations role. We were a small team, and the company was struggling hard to establish itself. I learned a ton about problem-solving through the early stages of business, but I had one foot out the door, pulling me toward my calling of being my own entrepreneur.

Related: This 17-Year-Old High School Student Has a $20,000-a-Month Side Hustle — and It All Started With a Skill He Learned in Class

Ben was working at a payroll tech company in an analyst role, but the actual role changed so much during his tenure because he hated doing the same thing every day. Juggling sales, learning to code, handling risk analysis, dabbling in marketing and growth… his managers were constantly breathing down his neck to “JUST FOCUS” on “his main role.” Neither of us were happy with those career trajectories.

Sick of the archaic legacy brands that dominated the hair styling space with cheap, chemical-based formulations and wasteful packaging, and unsuccessful in my search for a brand that was disrupting the industry, I stumbled into an idea that would solve my own consumer need. I had a hunch this problem would resonate with people like me.

What were some of the first steps you took to get the side hustle off the ground?
Whiteside: The first steps were hitting the Google machine (BAI, or before AI) to uncover naturally occurring, plant-based ingredients that could replace plastic, endocrine-disrupting formulas. Without a lick of chemistry or cooking experience to my name, I began ordering waxes, clays, oils and other botanical ingredients and started mixing them on my stovetop.

Fortunately I’ve always been a weirdo, so I was weird enough to start putting these failed concoctions into my hair, weird enough to make all of my friends do the same and give me feedback and weird enough to be unbothered by my roommate, Ben telling me how weird I am… soon to become a hair weirdo himself.

^{Image Credit: Courtesy of Highland}

Are there any free or paid resources that have been especially helpful for you in starting and running this business?
Medalie: Some tech standouts include: Klaviyo for email marketing, Shopify (and all its awesome plugins) to power our site, Triple Whale for attribution metrics, Amped (now Mailchimp) for lead capture, Adobe Premiere for content creation and finally Figma for making the non-designer look and feel like Rembrandt.

Whiteside: Ben covered most of the paid ones. For free, the best resource we tapped into was our polite persistence in demanding help from other business builders. People generally want to help, but you can’t be afraid to ask. We recently grabbed coffee with Justin Gold, founder of Justin’s, the peanut butter brand, and he summed it up nicely: “Be unreasonable.” This mentality has been instrumental in building an unbelievably helpful network of people who have helped us build the Highland strategy from the ground up and in avoiding mistakes other founders have made. So go be unreasonable — just be polite about it.

Related: This Couple Started a Side Hustle to Improve a ‘Terribly Made’ Bathroom Essential. Now the Business Earns More Than $3 Million a Year.

If you could go back in your business journey and change one process or approach, what would it be, and how do you wish you’d done it differently?
Whiteside: I think Highland gets high marks for doing this early, but I wish we’d done it even earlier. Get very serious about your unit economics from day one. Learn what your gross margins are. Make a plan for how you will bring down COGs over time, and know that every penny counts. Get serious about your finances, and figure out how and when you can make your business profitable. For now, the days of raising capital and figuring out how to become profitable later are gone, as are most of the businesses that took this route.

One of the most magical days of Highland was when the June 2023 books closed, and we had $113 in profit. We’d figured out how to make the business self-sustaining, and that meant our runway was unlimited. Become profitable, don’t die, then figure out how to effectively scale.

But also, no regrets. The journey was the journey, and it shaped us. Let yours shape you.

When it comes to this specific business, what is something you’ve found particularly challenging and/or surprising that people who get into this type of work should be prepared for, but likely aren’t?
Medalie: Formulations (of any kind, but especially in beauty) that are truly natural are incredibly hard to get right. We learned fast why all of those who came before us cut the corners they did, and we were offered the same formulation shortcuts that ensure consistency and so-called “performance.”

In being adamant that our products would be different, we ran into issues left and right. Our ingredients are volatile and misbehaving; early batches would vary greatly, and they had a much shorter shelf life than the products we were going up against. Multiple times, we lost thousands of units to failed batches, went out of stock as a result and questioned if it was all worth it. In the end, we broke through on the other side of this challenge, now redefining what innovation is possible within “better for you, better for the planet” formulation.

^{Image Credit: Courtesy of Highland}

Can you recall a specific instance when something went very wrong? How did you fix it?
Whiteside: We’ve never raised a multi-million-dollar round — at least, not yet — but that hasn’t spared us from facing serious cash flow challenges. Right after our friends and family round, we hit a rough patch. We were burning about $10,000 a month as we worked toward reducing our losses and slowly ramped up our marketing spend. Still, we weren’t too worried. We had three months of runway and what felt like the perfect investor lined up — someone ready to write the full check and bring industry expertise and mentorship that Ben and I had only ever hoped for. We were set. Until, suddenly, we weren’t.

The process dragged on for months. Our bank account drained. The deal ultimately fell through. We had to stop paying ourselves, cut expenses to the bone, delay growth plans and strain relationships with our manufacturing partners. It was the first time we really confronted the possibility of losing the company, and it was a gut check.

Medalie: So, we scrambled. We raised less capital than we had planned, but we made it work. We kept a confident front for our investors, got lean and stayed scrappy. Looking back, it was one of the best things that could’ve happened. It forced us to prove our path to becoming cash-flow positive and helped us retain more ownership. But it was a hard-earned lesson: Fundraising isn’t real until the money hits the bank. And no matter how promising a deal looks, you can’t build a business on potential alone.

Related: After Losing $5 Million Overnight at Age 25, He Started a Business on Track for $50 Million. Here’s the ‘Lightbulb Moment’ That Made It Happen.

How long did it take you to see consistent monthly revenue? How much did the side hustle earn? What does growth and revenue look like now?
Whitside and Medalie: We didn’t start earning consistent monthly revenue ($10,000-$20,000 per month) until mid-2023. The side hustle kicked off all the way back in 2021, when Ben and I were making the batches of our Glacial Clay Pomade in our KitchenAid mixer, packing the units by hand and selling them on our Shopify storefront and to a couple of salons and barbershops. The side hustle probably generated an average of $1,000-$3,000 a month between 2021 and 2023.

Now in 2025, after launching our third-ever SKU, we hit our first million-dollar month and have been profitable for nearly two years straight. It’s not a race. Become an overnight success in five to 10 years.

What do you enjoy most about running this business?
Medalie: Honestly, hot take… getting to do this whole thing with the people we love and cherish most in life. People always warn against getting into business with best friends or family, but this part has been the most fun. Every single day is different, and getting to see yourself and friends grow, thrive and even fail in front of each other is incredibly powerful and motivating.

Whiteside: What I enjoy most is waking up each day with a purpose, solving challenging problems with my best friend and co-founder and choosing our own adventure in every facet of what we do. Being your own boss is NOT an overrated part of being an entrepreneur. It’s incredibly hard, but it’s also the best.

^{Image Credit: Courtesy of Highland}

What is your best piece of specific, actionable business advice?
Whiteside: Getting started is often the hardest part, but if someone has, I’d offer a piece of advice from my dear friend and Shopbop founder, Bob Lamey: “Beware the incoming call.” It means to be laser-focused on what you think the roadmap is for your business and striving toward those goals with intention. Many emails, phone calls, pitches and day-to-day tasks become a distraction from what you know you need to be working on.

This doesn’t mean to ignore opportunities as they arise — it is a call to define your vision and hold yourself accountable in working to bring it to life. You know what you need to be doing; don’t let the noise distract you.

The majority of Windows users still haven’t upgraded to Windows 11, according to TechSpot. With the clock ticking on support for Windows 10, if you keep waiting to upgrade, you may be stuck without security fixes, technical assistance, or free software updates if you don’t upgrade to Windows 11 Pro ahead of the discontinuation.

To ease the blow, we’ve been selling Windows 11 Pro license keys at an all-time low price of $14.97, but today, April 27, is the last day to get this price (reg. $199).

Up your workday productivity

The changes to Windows 11 Pro include a seamless interface to help you tackle your to-do list more conveniently. Support for biometric login, encrypted authentication, and advanced antivirus defenses are just a few of the features that boost your online security. And improved voice typing and a better search experience aim to save you time and increase your productivity.

With Windows 11 Pro, Microsoft Teams and Widgets capabilities are all built-in. There’s also the addition of Copilot, Windows 11’s AI-powered assistant that answers your questions and serves as your own (unpaid!) personal assistant.

Since you’re always working so hard, you need to make sure you’re playing hard, too. Windows 11 Pro offers unprecedented gaming advantages, with DirectX 12 Ultimate providing incredible graphics so you can play your favorite games in all their splendor.

Before purchasing, make sure this license is the right fit for your computer. This particular Microsoft Windows 11 Pro license requires your device to be running Windows 10 or higher, with a processor of 1GHz or faster, 4GB of RAM and 64GB of storage or larger.

Why this deal is worth it

Upgrading to Windows 11 Pro isn’t just about staying current, it’s about working smarter. With new productivity tools like Snap Layouts for better multitasking, deeper Teams integration for faster communication, and support for multiple virtual desktops, this upgrade can genuinely streamline your day. If your PC is still running Windows 10, you’re not just behind on security, you’re missing out on built-in features designed to help you move faster, focus better, and get more done.

Get Microsoft Windows 11 Pro for just $14.97 through April 27 at 11:59 p.m. PT with no coupon needed.

Microsoft Windows 11 Pro – $14.97

See Deal

StackSocial prices subject to change.

AI tools are rapidly changing how businesses across industries operate. Whether you’re a business owner juggling a dozen responsibilities, a marketer trying to stay relevant, or a team lead looking for an edge, mastering tools like ChatGPT and automation is an essential skill.

The ChatGPT & Automation E-Degree Bundle can seriously help you amp up that skillset, and it’s only $29.99 (reg. $790).

Automate repetitive tasks with AI

This online learning bundle includes 12 courses and 25+ hours of content that break down everything from the basics of ChatGPT to real-world applications of over 20 top AI tools. You’ll learn how to customize and use AI to streamline business tasks, automate repetitive processes, improve team communication, and boost your productivity without needing to be a developer.

Courses cover a range of in-demand topics like data visualization, AI-enhanced creativity, automated marketing, chatbot design, and business process optimization. Instead of general concepts, the content focuses on how to apply AI in everyday work scenarios. Think: writing better proposals, creating engaging content faster, or building smart workflows that free up your time.

And if you’ve ever been overwhelmed by the number of new tools out there, this bundle is a curated introduction to what’s actually useful and how to use it without drowning in tutorials or tech jargon. It’s beginner-friendly, available 24/7, and optimized for desktop or mobile.

You’ll also walk away with a Certificate of Completion, which is great for your resume, portfolio, or just letting clients know you’re not winging it.

Why this deal is worth it

At just $29.99, you’re getting lifetime access to a course bundle originally priced at $790. That’s a serious return on investment for professionals who want to future-proof their skills and stay ahead of the curve. With practical lessons, expert instruction, and no subscriptions or surprise fees, this deal delivers real value for anyone ready to embrace the AI-powered workplace. It’s not just about learning how to use AI; it’s about using it to work smarter.

It’s only $29.99 to get the ChatGPT and Automation E-Degree.

ChatGPT & Automation E-Degree – $29.99

See Deal

StackSocial prices subject to change.