Samantha Rose joined me this week on Founders and Empanadas to talk about the role failure has played in shaping her businesses including GIR, Mvnifest, and Endless Commerce.

Whether it was product recalls (faulty tongs), software pivots, or figuring out how to build a remote team in Colombia, her career has been defined by learning from missteps, and finding ways to laugh even when things are tough.

In this episode, we chat about some of her most memorable failures, how she manages team morale when things go sideways, and why staying close to your customers is key to getting things right.

Hear about all of this and more in the full episode here:

Below are some of Samantha’s stories and strategies on turning failure into progress:

I'd love to hear a little more about your origin story and walk me through maybe the first failure that you experienced in your career and the learnings that you took away from that.

Samantha Rose: My entrepreneurial journey started in 2012 when I founded a consumer brand called GIR, which eventually was acquired in 2021. It stood for ‘Get it Right’, we had this philosophy that everything we did had to be special in some way. This mission guided us through both our successes and failures, and we had plenty of both.

One of the early failures was with a pair of tongs we designed. They had a unique locking mechanism that I thought was brilliant—one hand to lock, one hand to unlock. In theory, it worked. In practice, not so much. Once friction and manufacturing tolerances came into play, the mechanism would suddenly spring apart. We even tried making a little sock to hold the tongs together, but it just wasn't working.

Sometimes, you really should take "no" for an answer. My industrial designer told me to just let the tongs be normal, but I was stuck on making them special. In the end, we had to replace all the faulty tongs, which cost us hundreds of thousands of dollars. It was a hard but valuable lesson in knowing when to stop pushing an idea that just isn't going to work.

At what point of testing did you realize that the product wasn’t working?

Samantha Rose: Our industrial designer, knew pretty early on that the tongs weren’t going to work. But we didn’t take "no" for an answer. We went to market anyway, which was a mistake. As a younger entrepreneur, I didn’t understand that if signs point to failure, you can still stop. Whatever the opportunity cost or actual losses are at that point, they’ll always be less than after the product is in the hands of the customer.

I think this mentality is part of what defines entrepreneurship—you don’t take "no" for an answer. That can make you successful, but it’s also why entrepreneurs sometimes fail spectacularly. You’re so close to the finish line that you keep pushing, even when you probably shouldn’t.

How do you cultivate team culture and deal with team morale in the face of, for example, that failure?

Samantha Rose: For me, keeping a positive attitude in stressful situations is a bit of a superpower. Being okay through a failure allows me to stay ambitious. I always try to be honest with the team, and I think that helps a lot. Everyone understands that failure is part of the journey, but when you’re transparent about it, the sting isn’t as bad.

When it comes to team morale, you have to show them that the bigger wins are just around the corner. There have been moments when we were all in the trenches, working late, trying to hit a shipping deadline. In those moments, keeping your chin up is critical. If the team sees that you’re okay, they’ll think, “If she’s okay, I’m probably okay, too.” That kind of leadership is really meaningful.

How did you and Brian first land on sourcing talent out of Colombia, and what type of roles are you working with out of that country?

Samantha Rose: For our SaaS product, Endless Commerce, we wanted to create a proof of concept that punched above its weight. Initially, we had a few people in Guadalajara, Mexico, and a small office in Colombia. It allowed us to build stealthily but with a highly dedicated team.

Our product is like the pipes for commerce—inventory management, demand planning, purchase order management, and more. It’s critical that it doesn’t fail because if it does, we’re breaking revenue streams for our clients. We needed people who could help us build this "commerce OS" and take it from a startup to something scalable. We found incredible talent in Colombia for engineering, product management, UI/UX, and business operations.

Any good learnings you can share from software failures?

Samantha Rose: Oh, definitely. For Endless Commerce, we were super ambitious. We wanted to compete with the big players like NetSuite. Our engineers, hearing that, started building an enormous, complicated application. We were building something massive before we even had any customers.

Eventually, one of our engineers took it upon himself to build a lightweight version in his free time, just to show us that it could be done differently. And he was right. We ended up scrapping most of the backend and starting over, keeping just the front-end. That was a hard, expensive lesson in learning that you don’t need to build a power plant when all you need is a flashlight.

What were the conversations like with your husband and business partner, Brian, about making that significant pivot from the power plant to scrapping it for the flashlight?

Samantha Rose: We should have failed much faster, but we didn’t. We kept thinking, “We’re so close.” The team was also really invested in the project and believed we could get there. It wasn’t until our engineer built the lighter MVP that we realized we were way off.

It’s a difficult balance—learning to trust your instincts as a leader while also relying on the expertise of those around you. I was new to building enterprise software, so I had to listen to a lot of opinions. But ultimately, knowing when to pivot and how to manage that pivot as a team is something we’re all still learning.

How do you handle the messaging to your customers, and how did you strike that balance between being positive but not overly optimistic when things needed to be fixed?

Samantha Rose: I’m a big fan of candor and, sometimes, humor. One time, when we had to recall a batch of faulty glasses, we sent out an email with the subject line, “We are so, so sorry.” We even used one of the broken glasses as a cactus planter and took a photo for the email captioned, “Grabbing this would literally be less painful.”

Sometimes humor works, sometimes it doesn’t. You have to gauge the room. But being honest and straightforward has always been my go-to. I think people appreciate it when you own your mistakes, and it helps maintain trust, even in difficult times.

What unconventional metrics do you use to measure 'productive failure' in your operations?

Samantha Rose: It’s probably not all that unconventional, but staying really close to the customer is the best metric for success—or failure. In the early days, I was literally the customer service person for all of our businesses. I handled every email. Now, even though we’ve grown, I still read every customer email and every Slack message in the business. It’s a lot, but it keeps me in touch with what’s working, what’s not, and where we can improve.

How would you wrap it up for our early founder listeners today—how do you know when you’ve failed and should shut it down, or when to keep pushing forward?

Samantha Rose: That’s the million-dollar question. I don’t have a perfect rubric for it. Entrepreneurs are wired to not take "no" for an answer, and sometimes that leads to success, but sometimes it leads to failure. You need to be honest with yourself about failures and extract the information from them as quickly as possible. The longer you hide from it, the worse it gets.

I’m still learning this lesson myself. There’s a balance between pushing through and knowing when to pivot, and every failure teaches me a little more about that balance.

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