What would happen if you could spend five days on an island with five of your biggest entrepreneurial role models?

For online mattress retailer Leesa Sleep, there was a whole lot of learning going on.

As one of six startups that won Shopify's 2015 Build a Business competition, Leesa received a five-day getaway to Necker Island with Richard Branson, Tim Ferriss, Marie Forleo, Seth Godin, and Daymond John during the first week of September. Having recently returned from the trip, Leesa's CEO David Wolfe and head of marketing Matt Hayes shared with Inc. their biggest takeaways. 

From Richard Branson: When you're David chasing Goliath, focus on a higher quality product and user experience. 

Leesa is one of many Davids in a mattress industry awash with Goliaths. So Branson's lessons--from his days of competing with powerful British Airways, when Virgin Atlantic was just starting out--truly resonated with Wolfe. 

Of course, focusing on product quality and user experience is easy to say, but harder to do. What Wolfe really took to heart was how Branson did it: By constantly flying on Virgin planes as a passenger, so he could personally pore over details and improve quality. "He lived it, he flew on his own planes--he didn't fly on private jets," explains Wolfe, 53.

On a more macro level, Branson was persuasive about one of his central tenets: That if you provide an enjoyable, end-to-end experience to customers, it will reach them emotionally, stay with them, and create brand loyalty. In other words, "more marketing is not always the answer," says Wolfe. 

From Tim Ferriss: Don't let continual product improvement take a backseat to raising money and building partnerships. 

Ferriss has had a "front row seat to some amazing companies," says Hayes, noting Ferriss's role as an early investor in Evernote, Shyp, and countless others. For this reason, Leesa sought his advice about the pitfalls of life as a fast-growth startup. 

Ferriss told the Leesa team to be leery of spending too much time courting venture capital and building partnerships. Those things, enticing as they are, can take you away from what matters more, especially if you're in e-commerce: continually improving the touchpoints and user design of your website.

Obvious as it sounds, it's not the easiest thing to stay on top of, when sales are rolling in, as they've been for Leesa. (The Virginia Beach, Virginia-based startup is on track for a profitable, $30 million year.)

Ferriss's take? The work of pleasing customers never ends. "If you don't keep improving the customer experience, there comes a point when [what you're doing] goes stale--and the incremental changes your competitors are making will start to surpass you," says the 32-year-old Hayes. 

From Marie Forleo: Face your vulnerabilities. Paint a picture of where you'd like to be. 

As the founder of New York City-based Marie Forleo International, a $12 million business offering entrepreneurship and personal-development programs online, Forleo is a life coach and a master of connecting people. Wolfe showed her a photo of how he looked in 2006, when he weighed 170 pounds. Today he weighs 270 pounds. "I feel like this is the one area of my life where I'm not in control,'" Wolfe says. 

Forleo cited some goal-setting advice from Cameron Herold's book, Double Double: How to Double Your Revenue and Profit in 3 Years or Less. One of the tips in the book is to visualize your success with as much specificity as possible--and to create a document in which you write it all down, every last detail. 

On the subject of his weight, Wolfe also sought the advice of Ferriss, who authored the book The 4-Hour Body. Ferriss told Wolfe to bet on himself by vowing to do something that would be truly embarrassing if he didn't meet his weight-loss goal of 50 pounds in six months. Following the advice, Wolfe, left-leaning in his politics, has pledged to give a six-figure sum to Donald Trump's campaign if he doesn't meet the goal. "It's not gonna happen," he says confidently. 

From Seth Godin: Prepare for a challenging next phase, in which you move from enthusiastic early adopters to the consumer mainstream.  

Godin has helped Leesa see that its fast early growth--on the strength of zealous early adopters--is actually the easy part. The hard part will be becoming a brand customers return to, each time they need a mattress, over the next 20 to 30 years. 

"We're not yet at or close to the point where the mass market will think of Leesa when they're thinking about mattresses," says Wolfe. "Most people have never heard of it."

The difficulty of crossing this chasm--from early adopters to mainstream adoption--is in providing customers a reason to give their long-term loyalty. How can Leesa create an enduring competitive advantage in an increasingly competitive space? That's the challenge Godin outlined for them. 

From Daymond John: Operate your company like you're broke.  

One of Leesa's competitors--Casper--seems to be sprinting away from the pack of online mattress startups, thanks to a creative and widespread marketing campaign. Wolfe says Leesa (which has already raised $9 million at a $45 million valuation) could raise more money--and spend more of it on marketing--if it truly believed doing so were the smartest approach. "But we don't want to pin a huge valuation against ourselves that we have to grow into," he says.

John confirmed for Wolfe that his bootstrapping sensibility is the wise one. "He completely validated our view," says Wolfe. "There's a danger you'll do the wrong things when you have too much money. And you don't want to be beholden to someone else's cash unless you really need it for something."

From the Shopify team and the other winners: Give your younger employees the space to operate. 

While the celebrities were the big draw, they weren't the only successful entrepreneurs on the island. The Leesa team also learned some great lessons from Shopify's leaders, and from the leaders of the five other contest winners. 

One of those takeaways was to make it clearer to the young employees at Leesa that they were empowered to make decisions. In other words, that they did not need to check with Wolfe about every little action. 

As a first step, Leesa is going to be more diligent about keeping up with its regularly scheduled meetings to facilitate more internal communication. The other founders on the trip helped Wolfe realize that these meetings were precisely what he needed not to cancel. 

In addition to daily standing meetings each morning, Leesa will recommit to its weekly "Top 5" meetings, in which team members briefly run down the top five things they're working on. Ideally, the once-a-week fill-ins will replace the constant check-ins with Wolfe. In the intervening six days between meetings, the younger employees--over time--will feel empowered to act on their own.

In short, the lesson is not to blow off meetings when you're busy. It's to stay disciplined about them, especially because meetings can provide a loose communications structure, around which employees feel free to operate. "You have to stay disciplined," says Wolfe, "to feel free."

Published on: Sep 10, 2015