On Day 2 of the 2015 99U Conference (read all recaps here), Stewart Butterfield, Erin Griffith, and Rob Forbes not only explained how to scale your ideas quickly, but how to do so without losing your mind (though maybe going a little crazy is exactly what you need to do sometimes).

Stewart Butterfield. Photo by Mackler Studios.

Stewart Butterfield in Conversation with Erin Griffith

CEO and Co-founder of Slack // Writer at Fortune

In 2004, Butterfield co-founded Flickr, the online photo sharing site that revolutionized the web. In 2009 he co-founded a gaming studio called Tiny Speck, and from that venture grew what is now Slack. Today, Slack is one of the most rapidly growing communication platforms in the world. In this Q&A with Fortune writer Erin Griffith, Butterfield explained how he was able to take the idea for Slack and build it into a business with more than $20 million in yearly revenue and more than $160 million in venture capital:

• Rid yourself of information hoarding. Butterfield pointed to the fact many of us are connected online for 10 or more hours a day. If we can’t utilize that time to communicate effectively, we’ll have a hard time scaling. Unfortunately part of the modern communication change carries with it bad habits. “One of those is information hoarding,” said Butterfield. Information hoarding is when people feel like the best way to protect their position is to control who knows what and when. “At Slack,” Butterfield explained, “(we) increase the sense of transparency...in a way where people can see into other parts of the organization. That can feel threatening to some people, but it’s usually only threatening when there’s a bad situation. It causes a positive change.”
• Recognize and optimize constraints. “If you back up a little and think about creative practices in general, often it’s about the selection of constraints,” Butterfield said. “In music you have tempo and key, in poetry you have a meter and rhyme scheme...Organizational design is the same: who do we need, how many people, how do they work together, at what point does there need to be another level of management?...Stay focused and continuously optimize.”
• Seek out empathy in new hires. “It’s so easy to fall into the trap of maximizing for some local position...'drinking the stats,'" Butterfield revealed. Instead of hiring for localized positions, Butterfield recommends we pay attention to one key characteristic when hiring: “Everybody needs to know why they’re doing something...The number one quality we look for when hiring is empathy. If you can’t empathize with other people, you can’t do the job correctly.” The way to quickly identify those who can be empathetic, Butterfield explained, is to look for one key trait: courtesy.

Rob Forbes. Photo by Mackler Studios.

Rob Forbes

Founder and CEO of PUBLIC Bikes and Design Within Reach

Forbes founded the hit modern furniture company Design Within Reach, and more recently PUBLIC Bikes. While working his way toward acclaimed success, Forbes explained how he learned a few important lessons about scaling ideas; like welcoming failure, remaining curious, and staying humble:

• Value curiosity over cleverness. “In creative communities we like to show people we’re more clever than curious,” Forbes began, “but I’ve found that being curious and asking questions is something smart people do.” If we approach our work with the goal of being clever, we’re likely to overlook creative (and truly clever) solutions, due to our limited focus on coming across as smart. Instead, Forbes says, we must focus on consistently asking a lot of questions and being willing to explore where those questions lead us.
• Admit you’re a little crazy. Forbes talked about why we should all admit to being a little crazy when starting any endeavor: “Admitting you’re ‘crazy’ can help connect to others who relate.” By putting yourself out there and pushing boundaries when you’re just starting out sends a signal to those who are like you, a signal that states: There might be something here. “Breaking a lot of rules attracts extraordinary people,” Forbes exclaimed.
• Make failure an option. When Forbes first started PUBLIC Bikes, the company flopped (even despite having received a lot of positive coverage in the media). Nine months out of the gate, Forbes handed the reigns over to his team, telling them that “failure is an option.” Now, four years later, PUBLIC has had their first profitable year and raised $1 million dollars. “Serendipity and chance play a lot into our roles,” Forbes explained.

Chris Anderson. Photo by Mackler Studios.

Chris Anderson

2015 Alva Award Winner, CEO at 3D Robotics

Each year 99u recognizes the next great inventor of our time by awarding them the Alva Award. This year the award was handed to author and former Wired Editor-in-Chief, Chris Anderson. His recent success, founding the rapidly growing drone manufacturing company, 3D Robotics, started from a playdate with his kids, some legos, and a bit of Googling. The playdate experiment quickly grew from creating homemade flying robots in his backyard to employing over 275 employees in North American and more than 100,000 customers around the globe, all within a few short years. As he said, "We’re living in an era where regular people can do extraordinary things."

• Choose the best community, not the best technology. When it comes to scaling ideas, picking the right community to be a part of it can far outweigh the benefits of choosing the latest, or seemingly best, technology. “We don’t have to do it all by ourselves,” Anderson explained. Picking the most enthusiastic, involved community members can set you up to work with the people who are most likely to help your ideas and business evolve and grow.
• Learn by doing. Anderson’s first attempt at creating a drone involved Legos and a small processor, and the attempt failed. But it sparked enough interest for him to pursue the idea through online communities. "When you ask dumb questions in public, people answer them, and it liberates people to ask their own,” Anderson said. By asking "dumb" questions, Anderson was not only able to get the answers he needed, but he found himself building a community of likeminded and passionate enthusiasts who began following his work.
• Follow the money. “We need to think smarter about the trends around us,” Anderson stated. “Where is the world going? Let’s design our products for them.” Anderson admits some luck here, in that he simply became curious about the concept of “flying robots” one afternoon. But by staying on the forefront of trends in the field, and focusing on the right community rather than flashy technology, he was able to create a product that consumers wanted while at the same time leveraging resources and existing knowledge. "Go where commodity price and performance trends are the strongest,” he advised.

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We'll be publishing more insights from #99conf over the coming days. Stay tuned!

More 2015 Conference Recaps:

Part One: How to Fuel Collaboration & Innovation
Part Two: Rewiring Your Mindset & Avoiding Burnout
Part Three: Self-Awareness is Key
Part Four: How to Build a Business
Part Five: Tap Into Your Creative Genius
Part Six: How to Change the World