Lawyers don't want to be anyone's tech guinea pig. Still, legal tech startups looking to break into the industry aren't out of luck. It's not impossible to overcome attorneys' skepticism and garner initial investment, though the path is far from easy.

A cold email to then-Fenwick & West venture partner Ted Wang about the intersection of technology and law got then-Notre Dame Law School student and future Ironclad Inc. co-founder Jason Boehmig out of Indiana to Silicon Valley.

The email requesting a 15-minute chat with Wang led to a position in 2012 at Fenwick & West's Series Seed, a service that streamlines the production of legal documents for startups' fundraising and product development.

Boehmig was able to meet his network through Fenwick & West, which included one of Ironclad's eventual first investors, Jesse Beyroutey of JA Ventures.

To be sure, while some startups are lucky to have investors in their network, many still have to seek out funding after launch. And Luminance Technologies CEO Jason Brennan noted lawyers' skepticism places a lot of pressure on a first impression. "The legal industry isn't one that's very forgiving," Brennan noted. "You get one shot—if you go in with a vision or dream and if you fail, that might be it." Innovative success, however, leads to a positive perception in the market that spurs investor interest, he added.

However, Richard Mabey, CEO and co-founder of contract collaboration platform Juro, noted blog postings and other thought leadership was a powerful tool in gaining a name in the industry. Still, startups also need to rely on their already established networks and work to create new ones.

"To some extent, I think some networks you just have from working in the industry and some you earn, outreaching to people cold and asking for 15 minutes of their time to learn about the pain points and challenges," Mabey said.

To be sure, legal tech providers noted the steepest challenge in building a startup is developing a product lawyers will buy. Once a startup develops a solution, it pitches the service to prospective clients and they grow their clientele if the tech solves a challenge. A growing consumer base attracts investors.

Still, while revenue drives investors' interest, it's still difficult to get noticed by investors in the first place, said Evisort Inc. co-founder and CEO Jerry Ting.

Ting and his fellow Evisort co-founders initially emailed and sent LinkedIn messages to venture capitalists who invested in software as a service enterprise technology systems like Evisort. But they gained little traction with that approach, Ting said.

"At the end of the day the firms that invested in us were done through referrals from mentors because there's a credibility through referrals," he said. "If you have someone that has run a company before or sold a company and has a lot of trust in your company, [the recommendation] is valuable."

But while the road to initial outside funding is paved with hesitancy and rejection, legal tech funding isn't immune from discrimination that plagues the broader tech funding market.

In June, LawSites Blog spoke to Court Buddy co-founder James Jones Jr. about being a Black legal tech entrepreneur in an industry that only has 2.3% Black founders, according to a 2018 report.

In 2019, Jones and his wife and Court Buddy co-founder Kristina Jones gave up their company to an initial investor to pursue other goals. But the investor pitches leading up to Court Buddy's $1 million fundraising in 2017 was still fresh in James Jones' mind, according to the podcast. Jones described the common startup stories of constant pitching and rejection that was served with an undertone of racism that Court Buddy couldn't avoid.

Court Buddy was faced with venture capitalists moving the criteria for investment, a VC washing his hands in the middle of a pitch because he couldn't believe he'd shaken the hands of a Black person and not fitting a preconceived image of a Silicon Valley entrepreneur, Jones said.

"If you look at the makeup of San Francisco and Silicon Valley they're looking for a certain type of entrepreneur but if you don't fit that mold you'll have an uphill battle," Jones told LawSites Blog. Still, by 2018, Court Buddy raised an additional $6 million, which Jones noted was somewhat easier because of their previous funding.

"When you raise a round, it's a signal to the market that you've somewhat derisked the market."