Episode 7 | Communicating your vision with May Habib (CEO, Writer) and Gaurav Misra (CEO, Captions)

Fund/Build/Scale

Successful entrepreneurs must translate their personal visions into something tangible enough to attract employees, investors, and eventually, customers.

There are best practices for product management and software pricing, but how do you make yourself persuasive (and authentic) enough to convince someone else to risk their time and money on your idea?

I interviewed May Habib (CEO and co-founder, Writer) and Gaurav Misra (CEO and co-founder, Captions) to learn how they use a mix of hard and soft skills to maintain a clear and strategic vision that informs everything from recruiting to GTM strategy.

We also discussed methods for finding investors who understand your space, building a team, and why “rarely is the first idea the right idea.”

Here’s a full episode breakdown:

Part 1: May Habib, CEO and co-founder, Writer

• "This was going to be just a much more interesting product." [03:27]
• Writer's original founding "team is pretty together from early days." [5:45]
• "In 2020, I don't remember spending a lot of time on the AI behind the AI." [6:11]
• When May recognized that she’d connected with investors who shared her vision [8:30]
• "The benefit of the full-stack approach is really becoming pretty obvious for people who are spending time with enterprise customers." [12:11]
• "I don't see myself as a storyteller, I see myself as decent at picking up signal from noise and explaining that to people." [13:03]
• "I do care a lot about design, about brand.... it's always been a very visual company." [16:07]
• "If I was just meeting somebody, they got a slightly different deck in the first meeting." [19:06]
• "Even ‘til the Series A, I think I looked down on people who were active on LinkedIn." [20:03]
• "I think enterprises are getting fatigued." [23:01]
• "If it's AI, show, don't tell, because the capabilities are so wild that you can really blow people away." [26:42]

Part 2: Gaurav Misra, CEO and co-founder, Captions

• "We want to come up with a lot of different ideas in this space and what gets us excited." [33:32]
• "We talked to a lot of people to help solve that creation problem that we were trying to go after." [36:34]
• Why social media is "a really good way to actually test startup ideas" [38:20]
• Investors were enthusiastic about shifting strategy, but "the hard part was to convince yourself." [39:55]
• "It's really important to have an investor who understands the space inside and out." [41:29]
• "The hardest part has been, what do we actually want to do, and what did we see actually working?" [44:35]
• "I don't think of myself as a natural storyteller. I think it's something that I had to learn a little bit more of." [47:00]
• Why Gaurav is still Caption's 'chief storyteller'" [49:42]
• The importance of aligning your overall vision with PMF [51:16]
• "As the company grows, the vision does become more and more crystal clear" [52:10]
• "Once people try the alternate solution, they should never want to go back to the original." [54:30]