Fulfillment Found

Inspirato inside counsel Kasey Johnson discusses startup culture

For a lawyer, the move from an outside counsel role at a law firm to a corporate counsel role at a startup is more than a role reversal, it’s a complete culture change.


Kasey Johnson, who works in an office on the periphery of the open bullpen of Inspirato’s Sugar Building office in downtown Denver, notes how obvious the differences are to anyone who’s been in a traditional law firm environment. She became vice president, legal at Inspirato in mid-2018 and had a quick adjustment to the different environment at the company. 

Inspirato could be oversimplified as the ultra-luxury version of a short-term rental business. The company finds high-end luxury rentals and hotels all over the world for its members to vacation at. Its staff, at a glance, is diverse, young and plugging away at computers in an open workspace. Johnson said the office has lots of snacks and happy hours on Thursday, and the high-energy environment and fun office culture is probably different from most corporate environments, much less a law firm.

And Johnson said that environment requires a change of mindset for a lawyer to fit in.

“I think your goal as the general counsel is to help push the business forward, which is an ideology shift. Instead of the instinct to say no, my instinct is always to try to find a way to say yes,” Johnson said. “And then I go back to my office and think, ‘O.K., how am I going to make this happen?’”

For instance, Johnson might have to figure out a way to make an important partnership happen in the face of pushback from the other side. Inspirato’s members expect luxury lodging and elite service when they pay to be part of Inspirato’s club. Some of the vacation homes made available to members are worth multiple millions of dollars, and homeowners are often billionaires. When drawing up agreements, those homeowners might have extensive revisions to the template documents.  

“I have to make that assessment,” Johnson said. “We really want this partnership, we really want this home in our portfolio, our members have been requesting a home at X location, let’s make this happen. I’m going to say yes, here. … But then let’s be prepared for what this could mean for us on down the line.”

Other parts of the job are a big departure from Johnson’s law firm experience as well. She started her career in private practice at national and regional firms in the Denver area, and she said she honed her legal skills doing commercial litigation for clients ranging from Fortune 500 companies to startups. Going from working as outside counsel for startups to actually working at one was a “complete 180,” though. 

At a law firm, she said she might have previously spent a full week working on a 45-page brief to submit to a court. Now, she’s rarely in her chair long enough to write a brief, if at all, within a given week. Instead, within any one day she might have 10 to 15 different issues in front of her ranging from employment disputes to consulting with the company’s board on strategy to doing contract negotiations with owners of property across the globe. Her role is much more versatile, though she said she gained the skills necessary for that job by doing different types of law in private practice. 

Her current role has her advising every business unit at the company on a daily basis almost, and she sees the value she can provide to the company. “They love to seek my counsel, they use it, they value my counsel, and it’s been a really rewarding experience.”

She notes several other changes about her transition in-house. Not worrying about billing is a big positive. As outside counsel, she spent a lot of time tracking hours and worrying about how a client would react to a bill.  “Now I’m the one reviewing the bills,” she said. And she applies a lot of that knowledge to her job now as she considers whether she would have billed for certain things and how. She expressed the importance of value for time — is someone billing for several hours of proofreading on a memo in order to get it perfect when they might otherwise have gotten good work with a few typos for a lower cost.

One other highlight in her job ties in closely with the fact that she’s no longer billing time. She still has busy days, but she spends more time on the work that she feels matters more. That spills outside of work hours as well.

She has two young children at home and said she’s more able to be present while she’s with them. 

“I can’t be any more fulfilled than I am currently. And I think that’s in large part due to the fact that I’m fulfilled when I’m here,” Johnson said. “And then when I’m home, I’m truly home. I’m not feeling like I am beholden to my phone. I don’t feel like I need to be working all hours of the night. I’m not on the road nearly as much as I once was, it’s really nice to have found a place that I can build my professional career but also have a measure of sanity and balance that I hadn’t previously had.”

— Tony Flesor, [email protected]

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