What happens when you try to fund and scale a legal tech company in one of the most rigidly regulated industries in the country? In this episode, Todd Richheimer shares how he grew Lawfty into a tech-powered personal injury platform that has generated over 55,000 cases and nearly a billion dollars in recoveries.

From taking his first client calls on his cell phone to surviving a last-minute funding failure, Todd speaks openly about scaling, leadership evolution, and what the legal world looks like as regulation and AI collide.

Takeaways:

• Finding the Right Co-Founder in the Hamptons: Todd met his Co-Founder, a former MIT engineer, in the Hamptons. They spent a year working on ideas every Saturday before launching Lawfty, combining Todd’s legal background with Mike’s technical skills.
• Building with Complementary Strengths: Todd surrounded himself with people who could help him see around corners. He emphasizes that knowing your weaknesses and recruiting to fill them is the most impactful thing he's done as a Founder.
• The Power of Shameless Outreach: Todd started the company by emailing every contact in his Gmail account. With no product and no revenue, he relied on personal relationships and a willingness to ask for help to land early clients and supporters.
• Leading with Empathy and Integrity: Todd acknowledges his struggle with letting underperforming team members go, especially when they're good people. Instead of defaulting to layoffs, he focuses on reshuffling and preserving relationships where possible.
• From Answering Phones to Scaling Teams: For over a year, Todd personally fielded every intake call. That hands-on experience shaped how he hires and builds processes today, and made him intimately familiar with every part of the business.
• Navigating Capital Constraints Without Venture Money: Due to legal restrictions, Lawfty couldn’t raise institutional equity. Todd had to get creative with structured finance, high-interest loans from individuals, and careful debt planning to scale the company.
• Legal Tech’s Big Bang Moment: Todd sees the convergence of AI and regulatory change as a generational opportunity for the legal industry. With non-lawyers now allowed to own law firms in more jurisdictions, he believes the space is finally ripe for innovation and scale.

Quote of the Show:

• "Standing up for individuals always felt right to me… so I didn’t necessarily care about the personal view that people had." - Todd Richheimer

Links:

• LinkedIn: https://www.linkedin.com/in/todd-richheimer-esq/
• Website: https://www.lawfty.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Lawfty

Chapters:

00:00 Intro

01:41 The Importance of Complementary Skill Sets

02:41 Finding a Co-Founder in an Unlikely Place

03:44 Building Lawfty: From Idea to Execution

06:19 Challenges and Strategies in Team Building

09:29 Navigating the Interview Process

12:47 Understanding Lawfty’s Business Model

16:26 Early Customer Acquisition Tactics

20:57 Fundraising Journey and Lessons Learned

26:38 Scaling as a CEO

29:31 The Legal Tech Revolution

32:09 Challenges in Legal Services

34:52 Building a Tech-Enabled Law Firm

37:14 Overcoming Industry Stigma

42:35 Fundraising Challenges and Solutions

47:01 Personal Journey and Entrepreneurial Drive

54:12 Advice for Aspiring Entrepreneurs

56:48 Outro