We had the good fortune of connecting with Chris Cunningham and we’ve shared our conversation below.

Hi Chris, how do you think about risk?
This question is my absolute favorite because my entire career has been based on risks. With each of these risk I wasn’t sure of exactly what I was doing or what it would take, but I always just dove right in!

I turned down many top notch companies to take a risk on Cvent. From there I became the youngest manager and the company grew from 200-to 2,000 and went public.

From there, I left my comfy job there to go work for my friend Zeb. (Current founder and CEO of ClickUp) This was a huge risk that paid off well to a social media company making over 500K/month.

From there we took another risk and moved to Silicon Valley and went all-in on a new project management software. Every single advisor told us that this space was too strong and crowded. It took years but we went from 4 people to about to cross 1,000 employees today and a 4 billion $ valuation.

This is why I tell everyone I can to take as many risks as possible, but make sure to be all in!

What should our readers know about your business?
ClickUp is project management software. Project management software is designed to help businesses and individuals track projects, tasks, and schedules. Every company should use one, even if not us haha.

ClickUp stands out because we’re completely customizable. You can work in ClickUp as simple as complex as you’d like, and your colleagues can work how they like best and it’s all cohesive.

We got ahead in the early days by working 18 hour days for years. We pushed out features faster than our competition even if they weren’t perfect. We weren’t afraid to go after a “One app to replace them all”. We were mocked for it early on, but after releasing our Whiteboarding feature we’re getting even closer to succeeding at this mission!

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
Love this question! Elephante is just always a vibe and is my first recommendation because its so fun and the view is unreal. Try to find the right people so you can get into the house parties in the hills. Clubs are cool, but until you’ve experienced a house party in the hills you just haven’t seen LA.

Nobu Malibu and Catch LA are obviously must attends, but don’t sleep on the tasting kitchen in Abbot Kinney as well.

Hit all the hikes and beaches as well and you’re in for an amazing week!

Who else deserves some credit and recognition?
Zeb Evans, our CEO. He’s pushed me every step of the way since college and truly taught me what it takes to work on a different level that most never reach.

Website: clickup.com

Instagram: Cunningham

Linkedin: https://www.linkedin.com/in/chris-cunningham-12755b34/

Twitter: ChrisClickUp

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