10 Things We’ve Learned in 10 Years

Over the past 10 years, Clio Co-founders Jack Newton and Rian Gauvreau have grown Clio from two to 250 employees, and from a new product to something that’s used by 150,000 legal professionals in 90 different countries. Along the way, they’ve learned a lot—about lawyers, technology, and themselves.

Here, Jack and Rian speak about the 10 most important things they’ve learned over the past 10 years.

1. Lead the conversation

Both Jack and Rian believe that leading the conversation around the value of technology and cloud-based practice management has been key for Clio’s success.

“Leading the narrative is really important,” said Jack. “When we founded Clio, we saw right away that the whole narrative around the security and privacy of cloud computing would make or break the company.”

Jack and Rian initially came up against hesitation and apprehension, mostly over perceived deficiencies—promulgated by on-premise vendors—in the security of the cloud, and they knew they had to do something. “We thought ‘we need to lead the narrative instead of being dragged along by it,’” Jack said.

They wrote white papers and blog posts, took on speaking engagements, and even formed the Legal Cloud Computing Association (LCCA) to set standards for best practices around legal cloud computing. It’s been a success: Today, 20 U.S. states have issued ethics opinions that permit cloud computing.

“That is something that we had a direct impact on. But if we were passive about it, we could have seen a very different outcome,” Jack said.

2. Be irrationally optimistic

To build a successful business, Jack argues that it’s important to be optimistic, even if the odds aren’t in one’s favor. “If you’re looking at the odds of a startup being successful, and you still decide to go for it, it’s irrational,” he said. “There are a lot of downpoints that you reach as a founder, and if you’re not irrationally optimistic you’d just give up.

Jack also believes it’s important to have the capacity to infect others with irrational optimism. “In the early stages, I needed to persuade others to bet on Clio, to sign up with us,” he said. “Optimism is always important. There are always challenges, and optimism can always help overcome them.”

For those who struggle to remain optimistic, Rian suggests being mindful about practicing optimism. “I think that people have a tendency to dwell on the negative, and that’s an easy trap to fall into,” he said. “Founders need to be able to find a facet of positivity in even the worst circumstances. Otherwise at times it can get overwhelming, and you can get into a cycle of focusing on what’s not happening instead of what is.”

3. Don’t go it alone

Y Combinator, a company that provides seed funding, advice, and connections to startups in exchange for equity, rarely accepts companies with just one founder into its programs, and Jack isn’t surprised. “A big aspect of our joint success is having each other to lean on,” he said. “The whole idea is when you’re in those lows, you have someone to pick you up and help persevere. That partnership is really important.”

Jack also stressed the importance of finding a co-founder who complements one’s skillset. “For example, sometimes the people who are optimistic and who have a capacity to inspire others have really poor planning capacity. They need someone who is their foil, who is maybe a little more pessimistic, or a little more realistic,” he explained. “You need to find complements to your strengths and weaknesses.”

Both Jack and Rian believe that having a strong friendship prior to founding Clio has been a boon for the company’s success. “Founding a company with somebody is like getting married: It’s a long-term commitment,” Jack said. “You’re going to be spending more time with them than you do with your wife or husband, so you want to make sure it’s a good match.”

4. Be prepared to will your vision into reality

When Jack and Rian look back at how they thought about Clio when they first founded the company, they had a strong conviction that the company would succeed, and Jack believes that vision helped propel the company through its early years.

“Back in 2007, it seemed very obvious that the cloud was going to transform everything, and that there was a huge opportunity for it to transform legal,” he said. “For me, there were enough data points to make that totally obvious, but looking back, the cloud was very much still this emerging, nascent thing at that point, and it was by no means a sure thing.”

Having a clear vision and believing in it helped Jack and Rian overcome the challenges of starting a business, but it also helped them to attract talent once the organization started growing.

“A big part of irrational optimism is having conviction that your vision is right, and having the ability to communicate that vision to new people,” he said, “because sometimes, that’s the only way to get great people to join your company and help make it successful.” For example, Jack’s conviction helped him convince Steven Silberbach, then a VP of Sales at Salesforce, to join Clio.

Rian agreed. “To a degree, founders have to be able to make their own destiny,” he said.

5. Communicate more and more as you grow

On the road from two to over 250 employees, there’ve been plenty of changes to the way Clio operates. Specifically, communication has become much more complex.

“You need to put more work into the act of communicating and aligning people,” said Jack. “That’s almost automatic when you’re at 10 or 15 people. Everybody has a job to do and knows what’s important automatically.”

Rian agrees. “Communication happens so easily when you’re on small teams,” he said. “Everybody knows what everybody else is doing. Very often, everybody is sharing in the common workload, so everybody is wearing a lot of hats. But with companies at scale, like we’re at now, you have to engineer different ways of making sure everybody’s in the know, and that they have the information they need to effectively to do their jobs.

This is where investments in things like company-wide All Hands and Town Hall meetings have come in. Better communication tools, and more transparency (in line with Clio’s “No Doors, Only Windows” value) have been helpful as well. Overall, Rian believes that as a rule, it’s important to err on the side of overcommunication.

“When you think you’re getting tired of hearing or saying something, that’s when other people are just starting to get it,” he said. “Once is never enough.”

6. Do some things that don’t scale

One day, when Clio had about 60 employees, Rian and Jack walked into a common area at Clio HQ and saw faces they didn’t recognize for the first time. They knew right away that they wanted to meet every new Clion going forward.

“Either me or Rian has to be involved in the interview process as a final stage for every person that joins the company,” said Jack. “That was one of our big learnings, and one of our top 10 moments.”

Jack and Rian being personally involved in the hiring process for every person who joins Clio isn’t necessarily something that scales easily. However, as Jack explained, Paul Graham of Y Combinator advises companies to do a few things that don’t scale, when they’re valuable enough to warrant the extra effort.

“I think culture is a side effect of the people that you have in a company, and if we’re not really curating the team, and we’re not personally invested in the selection process for who joins the team, we have no hope of seeing a culture that we’re happy with,” said Jack. “As labor-intensive as it is, I think [being involved is] worth it.

7. Take time to define your values

Jack and Rian are also proud of Clio’s values, and point to them as a key tool that’s helped them successfully scale Clio’s culture. With them, Clio has remained an environment where every employee is encouraged to innovate, share ideas, and point out and take on new challenges.

“The values were all implicit up until about four years ago, when we formally created them,” Jack explains. “I think that was a really key moment in our history and scaling journey. People at Clio had this collective notion of what our values were, but I don’t think we would have scaled to 250 people as successfully as we have without actually having those as a touchstone that people can go to and reference on a day to day basis.”

Importantly, Jack and Rian didn’t create them themselves—a group of people from across Clio did. They believe this has helped ensure that the values resonate with everyone on the team.

“I think something I’m really proud of is that a culture that we were very proud of at 10 people has scaled successfully to 250 people,” Jack said. “And while it’s not exactly the same as it was when we were 10 people, it’s got many of the same traits. It’s an evolution of that culture.”

8. Collaborate with customers

One pleasant surprise for Jack and Rian was how amazingly collaborative Clio customers have been in helping make Clio the product it is today.

When the pair first released the beta version of Clio, they set up an application process for people who wanted to try it, requiring them to request access, attend an onboarding interview where Jack and Rian learned about their practice, and attend a demo of the product.

“These demos were supposed to last half an hour, but they often got extended to an hour, or two, or even three, where the person was giving us real-time feedback on the demo,” Jack said. “I was blown away, because here’s a person that’s billing $200, $300, or $400 an hour spending multiple hours with me and Rian.”

Jack and Rian’s calendars were full every day giving demos of their beta but, looking back, Jack sees this as another approach that didn’t necessarily scale but that was important for the success of the business. “I still think this is one of the game changers for us that was really innovative and made a big difference in terms of how fast we could evolve,” he said.

Today, Clio customers still spend plenty of time with the company, and their feedback has contributed greatly to the success of the product. Rian believes they’re willing to spend that time to build a relationship with a company that’s committed to producing a product that truly solves the problems legal professionals face.

“[Legal professionals] spend all day fighting on behalf of their clients,” Rian said. “The last thing they want to do is pick up the phone and fight with their software vendor. I think there’s a tremendous amount of loyalty there when you can provide good service.”

9. Trust your team

While defining Clio’s values has been important, Jack also believes that trusting members of the Clio team and avoiding too many policies and procedures has played a big part in Clio’s success.

“We were a huge fan in the early days of the Nordstrom Card,” Jack said. Nordstrom famously eschewed a traditional, many-page employee manual, instead distributing a small card that simply asked employees to ‘use good judgement in all situations.’

“I’ve worked for companies that have binders of policies and procedures. But if you trust somebody to do a great job, you’ll see much better results than if you try to prescribe a system of behavior,” he added.

10. Trust your gut and move quickly

Finally, when Rian looks back, he sees not moving quickly enough to hire talented people—or not moving quickly enough to exit those who weren’t working out—as one of the most important things he’d do differently if he could do it all over again.

“Trust your gut,” he said. “Data is important, but not every decision can be based on data, and more often than not, your gut is right.”

What’s next?

The past 10 years have been an incredible journey for Jack and Rian, and looking ahead, they see a positive future for legal tech.

First, Rian predicts that technology will even the playing field for solos, small firms, and larger practices. “I think we’ll see a democratization of the industry,” Rian said. “Solos and small firms won’t have any fewer advantages than those working in big firm environments.”

Jack believes that the foundation has been laid for transformative changes in technology that will advance the legal industry. “The first 10 years [of cloud-based practice management] have been about revisioning what the on-premise solutions of yore provided. The next decade will be about taking things to the next level, and doing things with the cloud that were never possible in the on-premise era,” he explained.

Finally, both predict that as legal tech advances, legal services will become more affordable. “I think that since the advent of the law, access to a lawyer has been a privilege that only the wealthy have enjoyed, and the vast majority of people have difficulty accessing a lawyer. I think tech will have a positive effect in terms of helping people access a lawyer more easily, but also in getting more affordable access to justice.”

Jack agrees. “I think that’s the real driver for all of this,” he said. “The technological transformation we see happening over the next 10 years has a real shot at being the thing that bridges that access to justice gap, because lawyers will be able to employ completely different delivery mechanisms and operate under completely different cost structures than they do today.”

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