Black Friday Cyber Monday (BFCM) is the ultimate sales period of the year. Behind every sold-out product and viral campaign is a founder with a carefully crafted plan—and the willingness to pivot when the moment demands it. This year, we spoke with 13 founders, who collectively generate hundreds of millions in annual revenue, to uncover how they approach the biggest shopping time of the year. 

   

What emerged from these conversations wasn’t a one-size-fits-all blueprint. Instead, we discovered that the most successful BFCM strategies share common threads: early preparation, clear communication, smart inventory management, and a deep respect for the customer experience.

How to win Black Friday/Cyber Monday this year 

1. Start your sale earlier than feels comfortable

Sean Frank, CEO of Ridge—a brand that’s scaled to more than $100 million in annual revenue—has seen firsthand that the traditional four-day BCFM event is over. “People start shopping earlier and earlier every year,” he says. “We’re gonna start our holiday sale on November 15, and we’re gonna extend that all the way to December 15.”

This extended timeline isn’t just about capturing early shoppers—it’s also about acknowledging a fundamental shift in consumer behavior. Rachel Hochhauser, cofounder of Piecework Puzzles, has watched this transformation accelerate in recent years. “Black Friday Cyber Monday used to be this four-day event,” she says. “It’s now turned into two-plus weeks. Each year it seems like they start far before Thanksgiving, and each year that passes, they creep even earlier on the calendar.”

For founders hesitant to offer discounts too soon, Sean offers reassurance. After 10 years in business, he says, “it does get easier every single year. The platforms have gotten more mature and more sophisticated.” Giving customers a full 30 days to complete holiday shopping helps mitigate anxiety around missing a better deal.

Lindsey Carter, CEO of Set Active, takes this principle even further by owning her timeline. “We made our own Black Friday in December and we call it Set Miss, and it almost performs [the same] if not better than our Black Friday,” she says. This separate promotional window helps Set Active stand when advertising costs have normalized.

2. Simplify your promotional strategy (ruthlessly) 

The temptation during BFCM is to get creative with 12 days of different offers, flash sales that change hourly, and tiered discounts based on spending thresholds. Sean warns against this: “Nobody shops your website that much. Nobody looks at your website more than you. Nobody really cares that much. They just want to go to your website and know they can shop and not feel like they’re gonna get a worse deal than somebody else.”

Keep discounts simple and messaging clear. Dr. Julie Chung of T3, the luxury hair tool brand, takes this approach through product curation. “We have some of our hero SKUs going on sale, which usually don’t,” she says. T3 focuses on the bestselling products and pairs them with gift-with-purchase items that consistently sell out. 

As Lindsey puts it, “Understanding what your bestsellers are and doubling down on innovating reiterations of what you know sells best already is really important.”

3. Master inventory planning before October arrives

Peter Dering, CEO and founder of Peak Design, puts it bluntly: “If you haven’t pre-bought inventory, you can really get caught with your pants down and miss a ton of sales.” For a brand known for premium camera gear and accessories, the stakes of running out of stock during the critical holiday window are particularly high.

The challenge intensifies for omnichannel brands. “Sales are a massive tactical undertaking,” Peter explains. “You’ve got to get all these different partners aligned. Prices have to go down uniformly at the exact same time. You don’t wanna offend your retail partners.” This coordination requires inventory decisions to be locked in months before Thanksgiving.

Lanny Smith, founder of Actively Black, has developed a focused approach to inventory management that prioritizes depth over breadth. “What are the five to 10 collections that we just have to focus on for this season to make sure they’re in stock?” he says. This question drives their entire BFCM preparation. For a brand whose athletic wear consistently sells out, the opportunity cost of carrying too much variety is carrying too little of what customers actually want.

At protein sweet snacks company Elavi, cofounder Michelle Razavi set ambitious targets that reflect confidence in inventory planning. The brand aims to double the previous year’s sales—possible only if the product is available when customers are ready to buy. The protein dessert category moves quickly during the health-conscious New Year’s resolution season that follows BFCM, making stock-outs particularly costly.

The inventory equation becomes even more complex when you’re dealing with products that require assembly and customization. Gloria Hwang, founder and CEO of Thousand bike helmets, has built personalization into the brand’s children’s product line. “Kids can open them up and then decorate them and then go out for a ride,” she says. This means customization kits and accessories need to be available alongside the core product.

4. Reach beyond your existing customer base

Gloria Hwang is approaching this BFCM season with a specific demographic in mind. “This holiday for us is all about building messaging and a marketing campaign around the family,” she says. For Thousand, that means positioning bike helmets not just as safety equipment but as gifts that create experiences.

Gloria understands that while adults make the purchasing decision, kids need to be excited about receiving the product. During BFCM, new shoppers are in discovery mode. They’re actively searching for gifts and willing to try new brands if the value proposition is clear. Messaging should speak to them, not just your core customers who already know your brand story.

For Canyon Coffee, founded by Casey Wojtalewicz and Ally Walsh, BFCM represents one of its rare annual sales. The scarcity itself becomes part of the appeal. 

Canyon’s BFCM sale gives people who have considered trying its coffee throughout the year a final nudge, while existing customers stock up—knowing the next opportunity won’t come for another 12 months.

5. Consider opting out—but make it meaningful

Not every founder believes in the Black Friday playbook. Matthew Burrows, founder of Plant Material, skips discounts entirely. “We haven’t ever really done sales,” he says. “I think our offering is differentiated enough to the point where I don’t want to devalue the product, especially in season.”

The typical BFCM chaos conflicts with Matthew’s business model and values around staff well-being. “I don’t need to have lines around the block or a rush of customers all at once, only to have the bubble burst and it go to nothing,” he says. “I never want to train people to only wait for this moment in time.”

Instead, Matthew uses Thanksgiving weekend to give back, partnering with a local school and growing partners to give away trees in Altadena. “This is a great time to start planting trees,” he says, pointing out that November is the ideal planting season in Southern California.

The tree giveaway serves multiple purposes: it generates goodwill in the local community, educates people about native plants during the optimal planting season, and creates a positive association with the brand (without discounting). 

Joe Myers and Jeff Eyser, cofounders of Revenge Of—a Los Angeles–based comic book store and pinball room—celebrate “Anti-Black Friday.” 

“We make all the pinball machines free for the whole day, and that’s all we do,” Jeff says. We don’t have sales, but what that does is it brings a ton of people to the store. We end up having crazy high sales for the day. We lose out on the money from the pinball machines, but every pinball machine is packed the entire day.”

6. Make it your only sale and go all in

Nima Jalali, founder and CEO of Salt & Stone bodycare, only has one sale a year. This exclusivity creates anticipation among customers who know they have one chance annually to purchase at a discount.

The single-sale strategy requires absolute confidence in execution, as there’s no opportunity to test, learn, and iterate throughout the year. Everything needs to work the first time. 

For Salt & Stone, each year’s structure is the same—a site-wide discount, free shipping thresholds, and gift-with-purchase incentives. “We’re doing some slightly different things, but for the most part, it’ll be very similar to what we did last year, because it worked so well,” Nima says. Measured confidence beats reinvention.

7. Add physical touchpoints to your digital strategy

Rachel of Piecework Puzzles is doing something many DTC brands talk about but few execute well—combining digital BFCM sales with an in-person pop-up. “We’re doing an in-person pop-up in New York City over that weekend and a couple weeks after, which will be really fun because we don’t have a lot of opportunities for customer interaction and brick-and-mortar experiences.”

For puzzle companies specifically, the holiday season is the Super Bowl. “That’s when we do most of our business,” Rachel says. The pop-up is an in-person moment that aims to build lasting brand connection. 

8. Gamify the experience

Lindsey is experimenting with bringing play into Set Active’s sale. “This year we’re gamifying a lot of what we’re doing,” she says. “When you’re on the page before a drop, you get to color in your own Set, and it can be submitted for something down the line if we want to make that.”

Gamification increases time on site, creates more opportunities for conversion, and generates engagement data that can inform future product development. “We’re trying little creative things here and there that get people wanting to come back to us rather than go to a different deal or sale that goes on during that time,” Lindsey says. Set Active also continues to launch new products on sale during BFCM, setting them apart from competitors.

9. Communicate more than feels comfortable

Sean of Ridge says, “Black Friday is the one time where you have unlimited firepower, and you could just send as many emails as you want.” The data backs this up—unsubscribe rates during BFCM remain comparable to other periods despite dramatically increased send frequency, because customers are actively in shopping mode.

The most effective email in Ridge’s arsenal is a plain-text message sent early, welcoming customers to shop the sale before it officially begins. The plain-text format is crucial, yet deceptively simple. It bypasses the promotional tab in Gmail and feels personal. 

Sean also emphasizes the importance of team availability. “Buy your team lunch. Be online 24/7.” The lunch isn’t just about sustenance—it’s about morale and acknowledging that you’re asking people to work through what would normally be family time.

The founders featured here have generated hundreds of millions in collective revenue by approaching Black Friday Cyber Monday with seriousness and sophistication. Their strategies differ based on product category, business model, and growth stage, but certain principles recur consistently. 

This holiday season will bring record-breaking sales for some brands, and it won’t be a result of luck. BCFM success requires preparation, execution, and the willingness to adapt. The best strategy reflects your unique business realities while incorporating the hard-won wisdom of founders who’ve mastered the moment. 

Watch the full compilation episode on Shopify Masters YouTube channel to hear all 13 founders share their BFCM insights.