Startups Are Hard. Here’s What Two Leaders Wish They Knew

What It Really Takes to Launch (and Grow) a Breakout New Product/Category

Before Flip Video became an iconic hit in 2007, and long before its $590 million acquisition by Cisco, it was just an ambitious idea fighting to survive. From the outside, it looked like a runaway success. But behind the scenes, the journey included a string of close calls and deeply formative lessons about leadership, resilience, and startup growth.

Simon Fleming-Wood was the founding head of marketing for Pure Digital Technologies, the company that created Flip Video. He later recruited Scott Kabat as his partner to lead brand, product, and acquisition marketing. Together with a lean team of engineers and product thinkers, they helped build Flip into one of the most beloved consumer electronics brands of the late 2000s, selling 10 million cameras and becoming the world leading video brand in 3 short years.

Flip’s simplicity and ease of use were revolutionary for the time. But the real story lies in what it took to get there and the lessons Simon and Scott still carry with them today.

Flip Video rose to #1 market share in under 3 years.

Startups Often Don't Feel Like a Success Until the Very End

In the beginning, Flip’s future was anything but certain. Simon noted that it often felt more like a cautionary tale than a case study.

“I tell people all the time that for 80% of that timeline, it felt like we were going to fail. The challenges often felt insurmountable. It was only at the very end when we got some escape velocity that it felt like, oh, we’re onto something. The flywheel has begun.”

That sense of precariousness wasn’t unusual, it was the norm. Even with strong leadership and a compelling idea, the team was constantly adjusting, iterating, and questioning whether the path they were on would ever yield a real business.

Starting from Zero is Its Own Reward

Some of the most rewarding moments at Flip came long before the headlines or the acquisition. It was the early days – naming the product, crafting the pitch, figuring out how to introduce an entirely new concept to the world – that left a lasting impression.

Scott reflects that there was something deeply satisfying about shaping every part of the story from scratch. “Those first few months, it was everything: What’s the value proposition? What story are we going to tell? What do we name it? Our amazing team shared so much satisfaction in seeing it all take shape, from the first unit sold to reaching number one in the market.”

Simon added: “The funding pitch laid out the strategy and story of how Flip was going to take over the video category long before it happened. But that pitch, which I still have, ended up happening almost exactly as we had sold it.”

Success is Rarely a Straight Line

It’s easy to look back on a successful outcome and see it as the result of a single bold vision or a master plan flawlessly executed. But more often, success is made up of dozens of smaller choices, some deliberate, some serendipitous, that accumulate over time.

As Simon put it, “a lot of smart and lucky small decisions” played a role. It’s a reminder that behind every win is a series of tiny pivots and unexpected turns that add up to something big.

There were moments when the team felt like they were on the edge of a breakthrough, and others when it seemed like everything might fall apart. “It taught me a lot about the entrepreneurial roller coaster,” Simon said. “You can’t get too attached to the highs or the lows.”

Scott added, “It’s easy to look back and see a clear path, but the truth is, it was a long, winding road with plenty of moments that felt like staring over the edge of something terrifying.”

The Most Important Factor: The Team You Build

One of the most defining themes of Scott and Simon’s Flip journey was the affection they hold for the team itself. More than product design or marketing genius, it was the quality of the people and the trust they built that helped them weather the chaos.

Scott said, “That was an incredibly special team. We didn’t have that many people, but we were intentional about every hire – not just for skills, but for how each person fit into the organism of the team. There was creative tension in the right places, and a sense that we were all going to battle together. After so many moments on the brink, succeeding as a team was incredibly satisfying.”

Don't Take Yourself Too Seriously

Startups are intense. There’s pressure and urgency. But amid all that chaos, one of the most underrated survival skills is simply knowing when to have fun.

As Scott put it, “Take the time to just laugh and not take yourself too seriously. It's important. We want to do right by it, but we made a point to have fun along the way. I think it was part of how we managed the stress we were feeling, especially on a business that was so dependent on an impactful holiday season… and part of perpetuating an enjoyable workplace culture.”

That mindset wasn’t just about morale, it was about resilience. When you can crack a joke to cut the tension, or bring a little levity to a product launch, it reminds the team: we’re in this together. A touch of humor can be the pressure valve that keeps the whole thing running.

Simon added: “I have never worked so hard or laughed so hard as I did with that team. We bonded very deeply and we are all very close to this day.”

From Grit to Acquisition

What began as a long shot, with no distribution, no name recognition, and no defined category, eventually ended in a $590 million acquisition by Cisco. But for Scott and Simon, that wasn’t the biggest takeaway. It was the grind, the guts, and the team that made it happen.

As Simon reflected, “The day after the acquisition, we just came back to work. There was a humility in the culture, a sense that this was something worth building, and we were still in it together. Success didn’t change that.”

That mindset, of showing up, staying grounded, and continuing to build, is what truly defined the Flip journey.

Enjoyed this article? Don’t miss out on the first part in the series to see how Simon and Scott launched their careers and the early risks they took that shaped everything that came next.