He Sold His First Business At 22 And Just Raised $50 Million To Take On The $450 Billion Legal Tech Industry

Reuven Moskowitz has started and sold multiple companies. His latest venture has raised over $50 million to advance technology for law firms. They’ve got some incredible case studies and are changing what’s possible for lawyers.  

Moskowitz recently joined me for an episode of the DealMakers podcast. We talked about buying and selling companies while still in college, the top challenges for entrepreneurs, balancing your optimism, and the future of law.  

Listen to the full podcast episode and review the transcript here.   

Entrepreneurial Spirit  

Reuven Moskowitz was born in South Carolina but spent most of his younger life being raised in Brooklyn.   

Both of his parents were immigrants. His mother, a medical professional found her way to America from Algeria and then France. His father was the first of his family to go to college and graduate medical school. His family landed in American after surviving the horrors of  Auschwitz.   

Reuven grew up with this mentality of persevering, being a self-starter and being able to make something out of nothing. Anything is possible, but if you want to get something done, you’ve got to just get out there and do it.  

Ideas & Execution  

Reuven’s first startup was born from a very simple idea. OneReceipt was a receipt aggregator tool that gave users rich insights into their spending. Pretty soon the business was acquired by eBates. Moskowitz was still just 22 and in school.  

It not only gave him a taste of what’s possible with technology but how great companies can be successful with very simple and rarely unique ideas. It’s all about the execution and stepping up to do what others have only thought about.   

Discovering Legal Tech  

A family friend asked Reuven to come help at his law firm. He wanted to build it out, scale the firm and improve operations and customer acquisition.   

He joined the Long Island firm and found the industry completely fragmented. Processes, marketing, platforms, communication, nothing was integrated. Most law firms remained very small because of this.   

He discovered Salesforce. Then gained a lot of traction helping this firm become a leader in its practice areas. He saw a great impact to be had.  

Reuven then took a detour into tech with his second startup. The iPhone with a camera was just coming out. He saw an opportunity. He saw the opportunity to create a mobile business around this. Penguin was born. Their app MoPho quickly became a market leader in this space.   

Just a few months in they were in licensing talks with companies like HP and Walgreens. They sold the business to Shutterfly. They are still using the app to make hundreds of millions in revenue.   

Reuven found great learning experiences while serving as a director at Shutterfly. He had great access to executives who taught him a lot. He says this was far more valuable than the profits from selling the business.   

A part of this exit deal also allowed him to go to Columbia law school and become a lawyer.  

Litify  

Columbia got this entrepreneur thinking about how to implement technology in the legal industry again.   

He attended various industry events. Then on the last night at a conference in Puerto Rico, he met   John Morgan and that night would change everything. They talked about how they could take his giant firm and scale it even further. How they could leverage several differentiated brands, put the right systems and technology in place and even extend that to other lawyers and legal firms.  

Startup Litify was born. Leveraging this technology John Morgan’s firm is now 3,000 employees strong and clearly a big name in the business.   

Other early adopters had been longing for a solution like this. They sold $3M of licenses in the first year. Double again their second year. And they are on track to grow over  120% this year.

This allowed them to raise over $50 million from great investors such as Tiger Global. Storytelling has played a key role in this. This is being able to capture the essence of the business in 15 to 20 slides. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

The Challenges Facing You As A Startup Founder  

Reuven clearly knows something about startups. While he may make it look effortless, he acknowledges that all will face challenges and hard days.   

These include:  

• Product-Market Fit – You won’t get far without this and paying customers
• Finding a big enough opportunity to justify your effort and investment
• Maintaining customer success as you scale
• Developing company culture as you scale headcount fast

Litify has seen its team grow by almost 200%. For hyper-growth startups like this, culture may just seem organic in the beginning. Moskowitz says that as you grow and have remote teams and offices you’ll have to be even more deliberate about creating culture.  

For most founders, letting people go can be one of the toughest moments. Of course, if entrepreneurship was easy, everybody would do it.   

Deciding its time for employees to move on is s hard to do. That’s true whether they just reveal themselves not to be a good fit after hiring, or they no longer fit in your company now that it has grown so much.   

It can be disruptive to teams and the company, but as Reuven has learned, it’s a decision always best made firmly sooner rather than later. When you know, you know.   

Listen in to the full episode to find out more, including:  

• The future of legal tech
• The key parts of innovation that law firms need most
• How to balance optimism and realism as an entrepreneur
• The importance of saying no
• Mastering long sales cycles as a startup
• How to contact Reuven