Failure as Fuel: A Conversation with Serial Entrepreneur Samantha Rose

If you’ve ever felt like your entrepreneurial journey is more of a zigzag than a straight path, you’re not alone. In a recent episode of the Founders and Empanadas podcast, Samantha Rose—founder of Endless Commerce—shared her refreshingly real story of building, failing, and rebuilding with host Joshua Eidelman, founder of NeoWork.

Over empanadas and honest conversation, Sam opened up about the tough lessons that came from product flops, team missteps, and the chaos of scaling too fast. But instead of hiding those moments, she leaned into them—turning each failure into a stepping stone.

“The entrepreneurial path isn’t linear—it’s more like a series of fascinating detours that eventually connect,” she said.

And those detours? They led to Endless Commerce, the platform she built to help growing brands manage operations with more clarity and less chaos.

If you’ve ever doubted your progress or questioned if those missteps were worth it, Sam’s story is a reminder that failure isn’t the opposite of success—it’s often the fuel that drives it.

Stopped Trying to “Get It Right” and Started Learning from Failure

Sam’s journey as a founder started back in 2012 with GIR (short for Get It Right)—a consumer brand built around the idea that every product should have a clever innovation. It sounded great in theory. But as Sam quickly found out, some ideas are better left on the drawing board.

“We created these tongs with a unique one-handed locking mechanism,” she said. “Perfect in theory—you could handle food with one hand and lock the tongs with the other. But in reality? They kept springing open unexpectedly.”

Even after her industrial designer raised concerns, Sam stuck to the brand’s “Get It Right” mission. The result? A full-scale product recall that cost the company hundreds of thousands of dollars.

Looking back, she sees it clearly.

“That was an expensive lesson in knowing when to walk away,” she admitted. “Whatever losses you’ve made in development are nothing compared to what it costs when a flawed product hits the market.”

It’s a tough but familiar moment for many founders—especially when you’re scaling fast and trying to stay true to a vision. NeoWork sees this often in the businesses they support, where learning when to pivot can save both time and trust.

The "Power Plant vs. Flashlight" Dilemma

When Sam set out to build Endless Commerce, she didn’t start small. In fact, she and her team went all in—trying to compete with giants like NetSuite right from day one.

“We told our developers we wanted to take on companies with a 30-year head start,” she said with a laugh. “So, of course, they built us this massive system—50+ repositories, complex Lambda architecture—the whole thing.”

It was impressive. But it was also completely overwhelming for a young startup.

That’s when Sam came up with what host Joshua Eidelman called “the best product development analogy I’ve heard”:

“We wanted to deliver light to users. But instead of building a simple flashlight that gets the job done, we built an entire power plant. Sure, a power plant gives you light too—but now you need a whole team of engineers just to keep it running. We should’ve just made the flashlight.”

Eventually, they ditched the heavy backend and started fresh—this time with a lean, focused MVP that solved the core problem without overengineering it.

That moment of clarity is something every founder should hear: solve one real problem first—then grow from there.

Building in Colombia: Global Team Insights

One of the most unexpected (and inspiring) parts of Sam’s journey with Endless Commerce was how she built her team—not in Silicon Valley, but in Colombia.

“We set up a full Colombian business entity—a SAS—so we could offer real benefits to our team,” Sam shared. “It involved a surprising amount of biometric scanning and legal paperwork,” she joked, “but it was absolutely worth it.”

By investing in local infrastructure, Sam was able to build a strong, full-time team that included engineers, product managers, designers, and business leads—some with experience at top Latin American companies like Mercado Libre.

This kind of international team-building really struck a chord with host Joshua Eidelman, founder of NeoWork, whose company helps brands scale by building remote teams.

“There’s incredible talent around the world that American companies often overlook,” Eidelman said. “When you tap into that, you’re not just saving costs—you’re creating real, two-way opportunity.”

Sam’s experience is a great reminder that the right team might not be where you're used to looking—and that building globally can create huge advantages when you're bootstrapping and scaling at the same time.

Management Strategies: When Things Fall Apart

Every founder hits rough patches—but how you respond as a leader can make all the difference. For Sam, maintaining team morale during tough times has become one of her core strengths—and it’s something she believes every entrepreneur needs to master.

“Your team looks to you during crises,” she said. “If they see you keeping your chin up, they think, ‘If she’s okay, I’m probably going to be okay too.’ That psychological impact is huge.”

So how does she actually lead through those moments? Here’s the approach she shared:

• Be Radically Honest About Failures. “Complete transparency helps the team process what’s happening. It reminds them that setbacks are normal—not something to hide.”
  
  
• Share Good and Bad News Equally Fast. Inspired by Ben Horowitz, Sam believes that bad news should travel just as quickly as good news. “When people sense that failures get buried or punished, they stop speaking up.”
  
  
• Use the Right Tone With Customers—Honest, Human, and Sometimes Even a Little Funny. During a recall of glass cups, her team sent out an email with the subject line “We are so, so sorry” and included a picture of a broken cup repurposed as a cactus planter. The caption? “Grabbing this would literally be less painful.”
  
  

“Humor can be powerful, but only when it’s appropriate,” she said. “The key is being human first.”

This kind of clear, authentic communication lines up perfectly with NeoWork’s philosophy around customer experience—where honesty and empathy aren’t just buzzwords, they’re business strategies.

Staying Close to Customers: The Ultimate Failure Detector

Want to catch problems early and build a better product? According to Sam, there’s one simple (but often overlooked) strategy: stay obsessively close to your customers.

“I read every single customer email that comes through any company I have majority ownership in,” she shared. “I read every Slack message in every channel. It sounds excessive, but I’d lose my edge without that direct connection.”

For Sam, this isn’t micromanagement—it’s how she learns. Day in and day out, customer feedback tells her what the product should be, where it’s falling short, and what’s working better than expected.

Sure, it might seem unsustainable as a company grows. But Sam’s view is that the further you get from your customers, the more filtered your feedback becomes—and the easier it is to miss the warning signs.

That kind of hands-on customer focus has helped her spot issues long before they turn into full-blown failures—and it’s a principle that aligns closely with NeoWork’s belief in building feedback loops that actually reach decision-makers.

The Entrepreneur's Eternal Question: When to Pivot vs. When to Quit

If you’ve ever found yourself stuck between pushing forward or pulling the plug—you’re not alone. It’s one of the hardest calls a founder has to make, and even Sam admits there’s no perfect formula.

“Not taking no for an answer is both essential to entrepreneurial success and a potential cause of failure,” she said. “If you give up too easily, you leave opportunities on the table. Push too hard, and you risk pouring resources into something that will never work.”

So, how does she approach it now?

“Be honest about failures. Extract information quickly. Don’t avoid hard conversations. I’m still biased toward pushing things to the nth degree—but I’ve gotten better at recognizing when it’s time to pivot or stop.”

That balance between grit and self-awareness—between fighting for your vision and knowing when to walk away—is something NeoWork explores often when guiding startups through high-stakes decisions.

And if you’re facing that same tension right now, Sam’s story is proof that you don’t need to have all the answers—just the courage to ask the hard questions.

Mice on Ice: Creativity in Unexpected Places

Toward the end of the podcast, things took a fun turn when Sam shared a mock business idea from a founder retreat: Mice on Ice—a subscription service delivering frozen rodents in tiny coffin-shaped packages for reptile owners.

“It’s a circular economy,” she laughed. “We catch mice behind restaurants—who pay us to remove them—we flash-freeze them in cute little coffins, and ship them to your doorstep for your scaly little friend.”

Clearly not a real startup (yet?), but the joke landed—and also revealed something deeper about Sam’s approach: she doesn’t take herself too seriously, even when talking about serious business.

This moment of levity underscored what makes her such a resilient founder: a mix of sharp creativity, real-world grit, and a sense of humor that helps her stay grounded through the chaos of entrepreneurship.

From Failures to Future Success

Sam’s path—from costly recalls at GIR to rebuilding Endless Commerce with focus and clarity—is a reminder that setbacks don’t have to stop you. They can shape you.

“Each failure has made the moments between failures a little bit longer,” she shared. “I’ve gotten better at spotting the warning signs, extracting lessons faster, and building systems that prevent similar issues. But I haven’t stopped taking risks—that’s where the magic happens.”

If you’re building something right now—or thinking about it—remember this: failure isn’t the opposite of success. It’s part of the process. And when you face it head-on, with honesty, humor, and curiosity, it can become your greatest teacher.

Want the full story? Listen to the Founders and Empanadas podcast episode featuring Samantha Rose and host Joshua Eidelman. They dig deep into the messy, rewarding reality of entrepreneurship, from global hiring to product pivots.

Joshua Eidelman is the founder of NeoWork, a company that helps fast-growing businesses build and manage global teams with agility and heart.

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