Office Hours: Former Lawyer Turned CEO Diankha Linear on Cultivating Community

Spencer Rascoff

Spencer Rascoff serves as executive chairman of dot.LA. He is an entrepreneur and company leader who co-founded Zillow, Hotwire, dot.LA, Pacaso and Supernova, and who served as Zillow's CEO for a decade. During Spencer's time as CEO, Zillow won dozens of "best places to work" awards as it grew to over 4,500 employees, $3 billion in revenue, and $10 billion in market capitalization. Prior to Zillow, Spencer co-founded and was VP Corporate Development of Hotwire, which was sold to Expedia for $685 million in 2003. Through his startup studio and venture capital firm, 75 & Sunny, Spencer is an active angel investor in over 100 companies and is incubating several more.

​Diankha Linear
Diankha Linear

On this episode of Office Hours, Community CEO Diankha Linear joins host Spencer Rascoff to discuss her foray into the startup world and the strategic approaching to scaling up.


Community is a startup that uses SMS messaging to help Fortune 500 Companies and personal brands turn two-way text conversations into sales.

“Our technology is delivering on like two decades worth of promises in marketing, and that's to deliver customized personal communications to every single customer that you have,” Linear said. “We do that through text messaging.”

The platform uses human assisted AI to scale and customize the text messages you send to your audience.

“So what's wonderful about it is if you send a text message to your audience — let's say you have 200,000 members in your audience — most people sort of tend to respond in very similar ways,” she explained. “You could say something as simple as, ‘Hey, there's going to be a sale on my product, 30% off. What products do you use most or would you most like to see on sale?’ Our technology clusters and segments all of those responses.”

When Linear first joined Community as COO in May of 2021, the platform was heavily focused on working with high-profile celebrities, but she quickly realized that wasn’t a sustainable model.

“We needed it to scale, and certainly not at that rate,” she said. “So we sat down…We looked at the structure of the company—are we even set up right to move up market? Enterprise customers honestly need a more consultative sales process, versus the one-and-done conversations we were having with celebrities."

Linear and her team took a step back and really thought about what their “ideal customer profile” would look like. After months of research, they identified five verticals to focus on that would help them expand their business into enterprise brands.

Linear said the value proposition for enterprise is two-fold.

“One is the data,” she said. “Community is the best and most trusted source—give me a better source of gathering first and zero party data, right? Because you're directly having people text message, and they opt in—sort of sharing in an open way all of their first party data. And then you can curate zero party data that's relevant to your organization. So that's a different value prop that wasn't as important to celebrities and public figures. And then the second value prop is we now have so many integrations that enterprise companies can actually monetize Community very well.”

Community now has integrations with major companies like Ticketmaster, Salesforce and Act Blue. Working as a successful CEO, Linear credits much of her success to her time in the military and to two important lessons she learned.

“One, to prioritize people from day one,” she said. “The second thing is you do have to have a strategy. I should have mentioned that the very next thing I did [when redirecting the company] was getting the structure aligned. I got five people in a room. And we began drafting a strategy. We dropped that strategy the first quarter after I started.”

Given her experience at Fortune 500 companies and smaller startups, Linear said entrepreneurs seeking mentorship should formulate smart questions and then offer to take a potential mentor out for lunch or coffee.

“It would always give me the opportunity to see if there was a good fit,” Linear said. “I think it’s important for someone to feel a natural connection and to want to invest in you.”

And while the mentee will find a lot of value in the knowledge a mentor has to offer, the mentor should not underestimate the value a mentee can offer as well.

“Always remember that there is a certain amount of satisfaction that your mentor gets from investing in you,” Linear said. “So I always do my best to show up as well.”

dot.LA Reporter Decerry Donato contributed to this post.

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