Guests: May Habib, (CEO, Writer ) and Gaurav Misra (CEO, Captions)

Every entrepreneur has some idea of what they want to build and how it will eventually create value.

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

There are plenty of best practices for product management and software pricing, but how do you make yourself persuasive (and authentic) enough to convince someone to risk 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 maintain a clear and strategic vision that informs everything from recruiting to GTM strategy. 

Writer is a full-stack generative AI platform for the enterprise and Captions offers creators a suite of AI-powered creative tools, which means they’re working on different sides of the street. But if they can convince enough people that AI-driven content generation is more efficient, these companies will help change the way we communicate.

I talked to Gaurav and May individually to learn more about how they formulated their initial design and marketing strategies and the frameworks they’ve developed over time to keep refining their value propositions. We also discussed methods for finding investors who understand your space, building a team, and why, in Gaurav’s words, “rarely is the first idea the right idea.”

With a total running time of one hour and one minute, this is the longest episode I’ve done so far. As much as I’d love to pluck every golden nugget for this summary, this strike was just too rich. Instead, I’ll share two quotes that stood out after editing the transcript:

May Habib:

Today, we were on-site at a customer, a CPG company [with] globally recognized multiple brands. And they've got this problem where the legal review of ads takes literally weeks and weeks and weeks. And so we built an app in real time on the Writer platform in their office where they uploaded an ad and it told them whether the dog was too overweight for the laws of that country. Those are actual laws. And it was just — they were blown away, like, “holy crap! “ And that's what you can do with a full-stack generative AI platform. And so if you are launching a company — show, don't tell, if it's AI. Show, don't tell it, because the capabilities are so wild that you can really blow people away showing them.

Gaurav Misra:

Don't start by just going and raising money. Start by putting pen to paper and just creating a first version of something. It doesn't have to be the idea that's going to be the company forever. But you want to at least create the first version of something that you can show investors and get them excited. Maybe you can even show it to people. And you'll get a lot of feedback very quickly on like, whether, you know, whether people like it, whether it's useful or not, right, and investors will give feedback as well. And so I think it helps quite a bit with even just showing investors that you have the ability to actually create, right at the end of the day and put something in people's hands, right, which I think is the biggest blocker at the earliest stage.

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 company’s 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]

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