CEO of Wishlist
"I have no respect for the status quo"
Dan Kasper is the CEO of Wishlist, an employee recognition software company, where he has overseen 345% growth in the last three years. Prior to Wishlist, Dan lead the Trust & Safety team at Airbnb after transitioning from the military where he served for six years in Special Operations within the NAVY. He is a leader, fighter, and a believer in advancing humanity through technology.
You served our Country in Special Operations within the Navy. What exactly was Special Operations and your role within the group?
Special operations are smaller communities that exist within all branches of the military. Their focus is a little different than what you typically read about. The conventional forces traditionally go in with planes and tanks and all guns blazing while, in the special operations community, we went in, conducted our objectives, and got out without much notice. Within special operations I specialized in explosives. I worked specifically with Seal Team 5 and led their explosive operators.
How did you go from Explosive Specialist to Trust & Safety at Airbnb?
Well I really had no idea what the heck I wanted to do (after the military). I thought I wanted a big name firm like JP Morgan, Boston Consulting Group or McKinsey. Then I ended up getting connected with this transition program called The Honor Foundation. It’s essentially an executive coaching program for Special Operations personnel that are transitioning out of the military.
They really taught me take a step back and think through what I really wanted and what my strengths are. They showed me that working in a big corporation is actually the opposite of what I should be doing. I realized I belong more in the tech space and I got connected with Airbnb and ended up getting a job on their Trust and Safety Team.
What is Trust & Safety at a Tech company?
Trust and safety is pretty common in the sharing economy world. Similar to Lyft or Uber, Airbnb has to make the platform safe for its users. They have a proactive side that works to identify certain behaviors on the platform and it'll either let them through as good behaviors, or it will reject them. The portion my teams handled were the ‘maybes’ of which the system sent to people to provide human input. My role was to build the teams in North America and Asia Pacific to be able to review those cases and process all the behaviors in order to make the platform safe..
How was the transition from the military culture to the tech environment?
Honestly the environments have been strikingly similar. Both are fast moving, use new technology, global, high risk, high impact, and build teams with people from various backgrounds. So the concepts are actually very similar and the skills that I was able to build in the military have translated well into the civilian sector. I think the transition is one that was less daunting than I had originally thought.
Have you had to change your approach since joining Tech?
I always adhere to the same principles – ownership, resilience, critical thinking, decisiveness, communication, and strength. But I adapt my approach to fit the environment.
Communication is obviously critical in the military. Does the same apply for Tech?
Absolutely, it's the core to all high functioning teams. I'm big on ownership, so I hire people smarter than myself, which it's pretty easy to do, then I give them a mission and a vision of what we're trying to build. Then I set them free to accomplish their mission, our mission, in the most effective and efficient way possible. So communication isn’t, “I'm going to sit there and monitor what you’re doing.” Rather, I say, “Here's what we're trying to accomplish, here’s your objectives, go do it.” In order for that to happen effectively, I need strong communication.
After Airbnb you became VP of Operations at Wishlist. What brought you to Wishlist?
My mission in life is to push the human race forward. The way I want to fulfill my mission is by intertwining technology and humanity. I was able to find an organization that really aligns with that vision. I'm super passionate about what we're building and the impact our technology is having on people and teams.
You became the CEO just two years after joining. Did the military prepare you well for your first CEO role?
It really did. Within special operations, you don't have a billion dollar boat, you don’t have a multi-million dollar plane. What you do have is people, and you have technology. So the concepts that made me successful in the military are the same things I'm using to build Wishlist. I just use them with a different approach. A lot of it is how to build successful team, how to work with people, how to leverage technology, make decisions, and how to implement solutions using data.
What do you think CEO’s get wrong about their role?
My role is that I work for my people. That's it. What some leaders get wrong is thinking they have no boss. That couldn't be more wrong. Real leaders are responsible and accountable to their people. Period. Take the traditional hierarchy, that's a triangle, and flip it upside down. Every single person sitting out there, I'm accountable to. I work for them. I tell them that my job is to fuel their success. I don't make this company. They do.
Another thing leaders typically get wrong is unproportionate amounts of talking to listening. Successful leaders listen more than they talk. Talking is selfish. If you want to be a good leader, listen to your people, make what's important to them, important to you. Finally be authentic. Be human.
What’s been some of your main objectives as the CEO?
I’d put it down to two main objectives:
1. Leading with and connecting everything to a why. Cultivating surgical intentionality to spark every idea, ignite every person and fuel every solution.
2. Creating a culture of performance. We’re not here to compete, we’re here to win. Getting the right people on the team who are uniquely positioned to take us to the next level is a must have but difficult transition.
How do you build a culture of performance?
This may sounds strange, but I encourage our people to fall. I say Fall over Fail because that assumes that you're going to get back up. But it's essential because if you’re never failing, you’re never trying anything new, and if you’re never trying anything new then you’re going to become obsolete. It’s a process. No one likes to talk about it but guess what? It's real, it’s raw, and it's important to grow. People are gonna make mistakes. I make plenty of them all the time. It's just a matter of how do you learn from that? How do you get back up? We have built an environment and a culture of a team that encourages you to try new things.
Wishlist has grown a lot recently. What’s been your secret?
There's a Zig Ziglar quote that comes to mind – “You don't build a business, you build people and the people build a business.” We are building a rockstar team and then we are also focusing on the problem we are solving.
Is that your favorite quote?
It's a good quote but my favorite is actually from Apple Computer back in like 95’ when they had that think different campaign.
“Here's to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently. They're not fond of rules. And they have no respect for the status quo. You can quote them, disagree with them, glorify or vilify them. About the only thing you can't do is ignore them. Because they change things. They push the human race forward. While some may see them as the crazy ones, we see genius. Because the people who are crazy enough to think they can change the world, are the ones who do.”
That motivates me every time. Let's go do it and get after it.
On the note of getting after it, what’s a habit that you’ve instilled that has gotten you to where you are today?
Doing what I'm saying I’m going to do. It’s just so core and foundational because it feeds into trust. And trust is one of the most foundational elements of any relationship.
What’s something you learned from the military, that anyone can incorporate into their life?
Resources are finite. You have what you have. The key to winning is quickly taking what you have and creatively adapting it to solve your problem instead of dwelling on lack of resources. As my main man, Bubba Sparxxx said back in ‘08, “losers make excuses, winners make it happen.”
Order of Time by Carlo Rovelli.
Any productivity or time management hacks?
I try not to book my calendar more than a week, or two, out. Otherwise company priorities shift, yet I would still be bound to a calendar working on projects that would be outdated in impact by that time.
How important is it as a leader, to have advisors and mentors around you?
It’s essential. Every person is a teacher and every person is a student. The more I learn, the more I realize I have so much more to learn. I want to be challenged, I want to be pushed, and I want to learn. I think it's critical no matter what phase you're in, to be vulnerable, share what's on your mind, get people that will hold you accountable, and push you to achieve your goals.
You’re a mission oriented person, how do you see the next 5 to 10 years unfolding? What are you hoping to accomplish?
It’s hard to look that far ahead but I was talking to my mentor and he asked me “Dan, what’s your Ethos? Successful organizations have an Ethos, what’s yours?” So I took some time and wrote mine out –
I'm a fighter. I have no respect for the status quo. I inspire others around me to create lasting change in themselves and find success no matter their challenge or environment. I choose to win through the unity of people, unimagined technology and unrelenting resiliency. My legacy will immortalize through galvanizing the actions of others and bonding mankind.
I want to inspire others, build teams and create lasting change on this earth, while doing things that are now thought impossible. When people say, “You can't do that”, or “That's impossible” – that fuels me. In 5-10 years you’ll find me working on a solve to something we now consider only a dream.
Lastly, how do we bring more veterans into the tech and business world? Are there programs entrepreneurs should rally around?
There are numerous programs, but a lot of it is just taking time to talk to vets and hear their story. Today's military is made up of independent thinkers. They have a huge amount of impact and decision ability. At young ages, they're in charge of massive budgets. All components which are essential to successful businesses. So just take time to hear their story. Ask questions. Don't be afraid to take a gamble on somebody who's coming directly from the military. They know how to make things happen with few resources.
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Dan Kasper, leading his team in service of our great country