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Lessons from a lawyer who started a tech company

I’ve focused on customer discovery, developing technical skills and learning to sell because so many entrepreneurs suffer by lacking these skills.

6 min read



When I founded CaseFleet in early 2015, I wasn’t a first-time entrepreneur. While we continue building CaseFleet software to help litigation attorneys prepare their cases for trial more effectively, I previously started a law firm in 2011 with one of my law school colleagues.

We succeeded in growing the firm from just two attorneys to a respected employment-litigation firm with associate attorneys, staff and a substantial profit margin. Starting a law firm straight out of law school was brutal and required working a lot of nights and weekends to make it a success, but that challenge pales in comparison to the challenge of founding and running an early-stage SaaS startup. CaseFleet is now a year old, has a strong product and is acquiring new paying customers each month.

I’ve learned a tremendous amount in the past year about business and myself, and I’d like to share a few lessons that could prove extremely helpful to other entrepreneurs and founders.

1. Do customer discovery

Most entrepreneurs — including me when I was starting CaseFleet –are champing at the bit to start building their product and getting it in front of users. But this is absolutely the wrong way to start your new business, no matter how well you think you know your market and future customers. In fact, an entrepreneur’s knowledge or assumptions about a market or a customer segment can be dangerous to the extent that they get baked into a product or strategy at an early stage before being tested.

A better strategy, which I learned from excellent programming at Atlanta’s Advanced Technology Development Center, is to start by investing your time in rigorous customer discovery. This process involves meeting (in-person, if possible) with a large sample of people who might theoretically be users of your product or service after it is launched. The meetings don’t count if they are with friends or others who will be inclined to tell you what you want to hear.

Instead, you’ll want to meet with strangers so that you can learn about their actual problems (not just the ones you think they have) by obtaining real-life stories about their experiences, which will help you understand what they need and how they are motivated. During the process you are not selling or asking for future orders, but your meetings could lead to sales or beta agreements down the road.

The customer-discovery process is so extraordinarily valuable that you can (and should) continue using it to gain insights even after your product is launched.

2. Learn to code

My next recommendation for entrepreneurs pondering a new tech startup is to learn something about the technology that will power your business. Unless you have a swimming pool filled with gold coins, you may need to help build part of your product yourself. By acquiring some coding skills, you can save an immense amount of money for your startup.

For example, in the early days you may be able to support your development team and help them be more productive by writing unit tests or handling your HubSpot or WordPress implementation. Even if you don’t, it’s damned helpful to have some understanding and appreciation of what it takes to build your product.

Plus, learning to code opens the door to meeting lots of software developers. One of the first things I did when I began learning Python and Django was attending meetups for developers using the same language and framework. Indeed, I met one of my co-founders at a meetup that I attended for both recruiting and learning purposes.

There are a number of free-to-cheap services to start learning, such as tutorials on building a web application with Django or Ruby on Rails at sites like Treehouse.

3. Learn to sell

Most people I know can think of nothing more dreadful than reaching out to a stranger in an attempt sell a new product or service. Many of us don’t have a favorable impression of salespeople, and we don’t like to think of ourselves becoming one. But if you’re a founder, and especially if you’re looking to be the CEO of your business, you not only need to change your attitude towards selling — you also need to learn to sell.

This was a particularly rude awakening for me. As an attorney who handled employment cases on behalf of individuals, potential clients (mostly folks who had just lost their jobs) were continually beating down my door from the day I opened my practice. I was spoiled, and rarely had to risk rejection to get a new client. So when we launched our first product at CaseFleet and realized it was me who would be selling it, I got a little queasy. Still, like most entrepreneurs who seem downright attracted to difficult and frightening challenges, I started sending emails and making sales calls.

Even after mustering the will to sell, I hated my new role in large part because I got my butt kicked — until I found a good sales training program (Sandler). I now have a method for selling that helps me to focus on the right potential customers and move through the sales process in a low-pressure and mutually beneficial way.

Unless you’re a gifted and seasoned salesperson, I suggest that you begin learning to sell right away because selling is one of the most important job functions of a founder and CEO.

4. Just 3 pieces of the puzzle

There are dozens of other lessons I’d give to would-be founders, but I’ve focused on customer discovery, developing technical skills, and learning to sell because I see so many entrepreneurs missing one or more of these areas and paying a heavy price for it. In contrast, those entrepreneurs who master all three areas should experience a smoother and more profitable early period with their businesses.

Jeff Kerr, a former litigator, is the CEO and co-founder of CaseFleet. Learn more at

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