Raising capital is crucial for startup success, as it can determine whether a company scales or fails.

Shankar learned that fundraising success requires one strong commitment ('love') from a VC rather than multiple positive signals ('likes').

The experience reinforced his belief in the importance of experimentation and an exploratory mindset in business, especially when stakes are high.

With a16z's investment, Everlaw expanded to serve over 1,000 customers and generate nine-figure annual revenues, marking a pivotal moment in the company's growth.

Initial pitches attracted interest but ultimately led to rejection, largely because VCs lacked an investment thesis in legal tech and were doubtful about the market size.

The pressure to secure funding made it difficult for Shankar to take risks; he felt compelled to perform well in every meeting, which hindered his ability to innovate.

After numerous rejections, Shankar realized he needed to shift from refining his pitch to experimenting with new approaches.

He restructured his pitch by using analogies from familiar industries and focusing on his vision rather than detailed product features, which resonated more with VCs.

This new approach quickly garnered attention, leading to a term sheet from Andreessen Horowitz (a16z), marking a significant milestone for Everlaw.

In 2015, the legal tech market was still emerging, which made fundraising particularly challenging for AJ Shankar, who faced skepticism from venture capitalists due to his lack of legal expertise and a strong founder reputation.

Despite having a strong product and generating over $2 million in annual revenue, Shankar encountered 29 rejections during his Series A fundraising for his startup, Everlaw.