Building an Effective AI Moat with 4x Founder Gaurav Oberoi CEO of

Gaurav Oberoi is the CEO and co-founder of, a generative AI in the legal space. He is a 4x founder and was also a former VP of Product and survey monkey. Gaurav joins Ryan to talk about how to tactically create a mode with AI, how to get the best product market fit and the importance of time to value and demonstrating high-value ROI early on.

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  • makes software that helps companies accelerate the entire contracting process. They bring AI and acceleration to every part of the process.
  • Linkedin is a great social platform to leverage, you can put content out there that provides value and also notifies people of your business at the same time
  • It’s essential to focus on delivering a very high-quality product with high ROI otherwise having a good referral engine is useless.
  • Positive feedback isn’t all you need to build a product, you need commitment from your early interest clients as well as the ability to read between the lines and push for the harder feedback that isn’t always immediately obvious.
  • AI is quickly becoming more sophisticated but it still has a lot of limitations such as when something has been done incorrectly or where more context is needed.
  • When using AI you need to teach it your personal rules, all the context it may need, generate guard rails and remember that it will constantly be evolving and you are driving that evolution.
  • If you want to grow a start-up then you need to show high value quickly, the faster and more clearly you can show the ROI the better.


“Our software is all about any kind of document process that needs accelerating”

“Nowadays the most powerful social network for b2b companies is LinkedIn”

“It’s not really when people have paid that you’ve got success, it’s really when you see repeat usage that you know it’s working”

“Having significant data about users and their activity is a significant mode”

Ryan Staley

Founder and CEO

Whale Boss 

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo:

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