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A 36-year-old CEO who sold his first startup for $1 billion explains how to build authentic relationships as an investor, founder, or employee

Nov 3, 2019, 21:00 IST

Justin Kan, from Y Combinator, on stage during the 2014 TechCrunch Disrupt Europe/London at The Old Billingsgate on October 20, 2014 in London, England. (Photo by Anthony Harvey/Getty Images for TechCrunch)Anthony Harvey/Getty

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  • Regardless of whether you're a VC, founder, or employee, if you want to build meaningful relationships, you need to be authentic.
  • There are three main areas in which this applies: your relationship with yourself, investor-founder relationships, and internal employee-driven relationships.
  • Justin Kan, CEO of corporate law startup Atrium, sold his first startup for $1 billion.
  • He and Jason Boehmig, founder and CEO of legal contracting startup Ironclad, weighed in on how they've seen people build authentic relationships across the startup world on separate episodes of "The Twenty Minute VC" with Harry Stebbings.
  • Click here for more BI Prime stories.

Whether you're a VC, founder, or startup employee looking to make it in the industry, experts agree there's one word to keep in mind as you build the relationships that will help you achieve your goals: authenticity.

Though the term has become a buzzword of sorts, actual authenticity means being genuine to who you are. Being able to attain full authenticity with others means first knowing yourself and what you stand for - and according to serial entrepreneur Justin Kan (current founder and CEO of legal startup Atrium), therapy can be an important tool in bolstering the personal development needed to fully know yourself.

"I first started seeing a therapist seven years ago when I was really stressed out about being a founder and I was feeling a lot of guilt," Kan, 36, told Harry Stebbings on an episode of "The Twenty Minute VC" podcast. "So I broke down and I found someone. It was very helpful to me."

Kan is a founder and investor with more than 15 years of success in the startup space. He sold his first startup, Twitch, to Amazon for $1 billion, and has raised millions in VC funding for Atrium. He thinks of therapy like coaching: It helps him process what's going on in his life and discover more about himself.

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As Kan once mentioned in a series of tweets reflecting on 2018, he was able to tell his friends, family, and coworkers how he really felt by discovering "the power of being vulnerable," or authentic to his actual feelings.

Social interaction can't be easily automated, so developing the right mindset to navigate situations is key.

This is where knowing yourself takes center stage: Only you can position yourself to best start a project, and then communicate with others to run that project smoothly, according to Dr. David Deming, director of the Malcolm Wiener Center for Social Policy at Harvard Kennedy School.

It's important to "put yourself in somebody else's shoes and coordinate with them so that the two of you can work together," Deming told Harvard's Graduate School of Education. "That often requires knowing when to be a leader and when to be a follower, knowing when you're the data specialist in the group versus when it's time for you to be the writer or the presenter."

Navigating investor-founder relationships

Jason Boehmig, CEO of legal contracting startup Ironclad, follows a sister approach to vulnerability when interacting with investors: He tries to "drop the bulls--t."

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In a different episode of "The Twenty Minute VC," Boehmig told Stebbings that he advises founders get to know exactly who their investors are outside of the business.

"Life is too short to work with people you just don't enjoy being around," Boehmig said.

For founders testing the value add of VCs, Boehmig suggests going as far back as pre-investment to see how helpful people actually are. There should be a balance, however: VCs shouldn't be making critical business decisions for founders. Even though it's natural for new founders to be awestruck by experienced VCs, they have to maintain agency over their own business.

Though Boehmig has worked with experienced VCs himself, he says his previous Wall Street career taught him that even very smart people can be wrong.

"I've never felt psychologically swayed to change how we operate," he said.

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Building relationships within a company

Startup culture is defined through public risk-taking, but when things go awry, CEOs should be transparent.

"People should form a group, form connections, where they can be truly vulnerable," Kan said. "It's really great to have a support network to talk to."

Boehmig knows what he needs from internal relationships within Ironclad, so he hires accordingly. This goes back to his "life is too short" philosophy: He wants to surround himself with genuinely driven people.

Successful employees are nice and laid-back on the surface, but there's a hunger underneath. Ironclad's sixth employee didn't have a college degree and started doing data entry for them for $10 an hour. She was so thoughtful and humble and motivated that Boehmig kept promoting her.

She's now head of the support division.

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"I'm a big believer in letting people show and improve the caliber of their work," Boehmig said.

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