This as-told-to essay is based on a conversation with Marty Kausas, the 28-year-old CEO of Pylon, which has raised $51 million from Y Combinator, General Catalyst, and Andreessen Horowitz. It’s been edited for length and clarity.
Pylon was started by myself and my two cofounders, Robert Eng and Advith Chelikani. We went through Y Combinator with a very half-baked idea. Three months later, we raised our $3.2 million seed round from General Catalyst. A year later, we raised a $17 million Series A from Andreessen Horowitz. We just announced our Series B last month.
The team now is around 55 people. At the start of the year, we were 20, so we’ve more than doubled.
Around a year and a half into the company, we went to Seoul, South Korea. It was a nine-day trip, and we rented an Airbnb that we could all be in, which was really fun. We had people sharing rooms.
During the days, we would be working. We set some very ambitious work goals while we were there. During the evenings, we would go get food and try to have fun. One night we went to karaoke. We visited the North Korean border. We bought color-matching — that was the team’s favorite activity, where everyone got their personal color profile of the colors they should be wearing.
We were 14 people, and it cost $42,000. We paid for flights, we paid for the stay, we paid for the activities and food. The only things that were not paid for were if people wanted to go shopping or get food on their own.
We can celebrate our wins in more expensive ways than bigger companies can. At the time, we had just hit a revenue milestone and raised some more money.
Marty Kausas
We’re going to be spending about $150,000 to $1700,000 to go to Hawaii. There are going to be about 50 people who attend. We basically booked out all the spare rooms in a hotel that we could find.
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We’re going to O’ahu, and it’s a seven-day trip. We’re still going to be working normal hours on Pacific Time. The sales team is geared up to wake up at 5 a.m.
We’ve grown so quickly — this is a good opportunity to bring people together and have them focused on the team and the company. Usually, you don’t make the time while working extremely hard to be social with your coworkers. This is going to give everyone the chance to do that.
We have some activities planned, like team dinners. You can choose between parasailing, ATVs, and turtle snorkeling.
For Korea, we made a poll on Slack. The three top choices: Seoul, Bali, and Rome. For Bali, someone started complaining about mosquitoes, so that vetoed it. People didn’t have a strong preference between Italy and Korea, but Italy was going to be twice as expensive.
For Hawaii, we gut-checked with everyone and asked around. Hawaii seemed like an option everyone would be excited about.
Why expensive off-site trips are worth it
Other startups should do more off-sites. If you’re well-funded, then you can definitely afford it and the money’s well worth it.
We have people who come in six days a week now. I think you should reward people really hard work with really great rewards that are not typical of a bigger company.
Think about the word-of-mouth. Our whole team is going to go tell their friends, “Hey, I’m going to Korea for nine days with our team.” They’re obviously going to be like, “That’s crazy. That’s so exciting.” They’re going to look at Pylon and be like, “That’s a cool company to work at.”
That fun is translated to everyone we want to hire or sell to, or will see on LinkedIn later.
Marty Kausas
You’re paying an engineer minimum $150,000, and recruiting them is extremely hard. The cost for this trip to create signal and branding for us to prospective candidates is definitely worth it. It spells out the startup energy, versus being in a big company and working in a machine.
Some people are more stingy than they should be. They might be like, “Let’s not buy certain office snacks because they’re more expensive.” In reality, the real spend is on hiring great people and retaining them.
It’s hard to exactly say, “This many dollars into this type of activity leads to this outcome.” But my vibe-based finance here is that it’s definitely worth it to encourage people — both to stay at or join the company.
