Matthew Prinn

Knowing the buck stops with you is both exhilarating and scary – and both those factors add up to a strong motivation to outwork everyone.


Matthew Prinn is a Boston native who loves the city he lives in. He is a loyal fan of Boston based sports teams the Celtics, Red Sox and Bruins, and is the proud owner of a Boston Terrier dog. Professionally, Matthew has over 20 years of business development experience helping companies drive revenue and implement marketing strategies.

Matthew attended a local college, Boston College Carroll School of Management, where he completed a BS in Business Administration with a marketing and accounting double major. He shares his alumni with his older siblings who also attended Boston College.

Mr. Prinn has worked his way up from the bottom, first starting his career in a mailroom. After graduating, Matthew packed up everything he had and drove across country to Los Angeles, to pursue his dream of a business career in the entertainment industry. While he didn’t have much, his motivation and unstoppable determination granted him access the mailroom of a talent agency in Hollywood.

Matthew Prinn describes his time in the entertainment industry as follows:
“It was a great way to start a career because nothing is handed to you, and everything is earned. I started in the mailroom making less than $300 dollars a week while working 12-16 hour days 6-7 days a week. I had colleagues in the mailroom program who had graduated from Harvard, as well as colleagues who didn’t have a college degree. It didn’t matter where you came from, whoever worked the hardest and produced the best results got promoted. You had to outperform your peers to survive and move up in the company. If you didn’t excel, you were gone and gone quickly. The cutthroat environment was a great training ground to build a strong work ethic as a foundation for my business career.”

Mr. Prinn was promoted to the level of Junior Talent Agent before deciding to begin the new challenge of working in the legal marketing industry at Latham & Watkins.
As a marketing coordinator working for Latham & Watkins, one of the world largest and most profitable law firms in the world, Matthew developed strong skills in project management and branding.

The time came for Matthew Prinn to head back to his northeast roots to spend time with his friends and family. Over the next few years, Matthew worked for several companies developing strong business and marketing strategies in addition to website maintenance, research projects, and advertising campaigns. His hard work and expertise led him to join the business development team at K&L Gates. The company grew tremendously during his tenure. Mr. Prinn ultimately reached the position of Director of Business Development where he was responsible for creating and sustaining long-term relationships, using market research to identify key targets, and redesigning the firms pitching process so better results were achieved.
Matthew also became a master in Request for Proposals (RFPs) during his time as the Director of Business Development.

As the legal market evolved into using preferred panel providers as the favored process of hiring a law firm, Matthew used his expertise to oversee hundreds of RFPs a year where he worked with senior partners to execute winning responses that generated millions of dollars in income for the firm.

After gaining an immense amount of knowledge about the RFP process, law firm pricing strategies and how to use the RFP process to reduce outside legal counsel spend, Matthew Prinn started his own consulting practice in 2018.

When not at work, Matthew loves spending time with his friends, and his family – especially his niece and nephews. Matthew Prinn also loves spending time on the water boating and is an avid photographer.

Where did the idea for your company come from?

I spent the last nearly 20 years marketing/selling legal services to buyers. Working with hundreds of lawyers on business development initiatives gave me a real strong insight into the best practices and obstacles to avoid when trying to expand the work we do for clients or to convert a prospect to a client. I also gained extensive experience working with my colleagues in other departments to develop a real strong understanding of law firm operations. About five years ago I took over the firm’s global RFP response process. This allowed me to see hundred of RFPs each year and to become an expert on the process and how to use them to win new business. I had an up-close view of the evolution of legal procurement and legal operations and saw first hand the successes they were able to achieve in getting more value from law firms. I saw an opportunity to capture market share for corporate counsel at companies who did not have the resources to hire a full-time in-house procurement or legal operations full-time employee. With my unique insight into law firm operations – it allows me to manage the RFP process more effectively to drive value for the dollar for my clients.

What does your typical day look like and how do you make it productive?

As long as I am doing work that I find intellectually stimulating, I’ve never had a hard time making the day productive. But give me a job sweeping floors, and I would probably be terrible at it. Nothing too special in my daily routine beyond walking the dog, working out and going to work.

How do you bring ideas to life?

When it comes to ideas, I’m a believer that in order to come up with a good one, you need to come up with a lot of bad ones too. For me bouncing ideas off trusted colleagues is the best way to flesh out if the idea will sink or swim. However, sometimes the best ideas are when everyone tells you they won’t work. I’ve always been a “failure to plan, is planning to fail” type of person so for me it all starts with making a list.

What’s one trend that excites you?

I think the recent trend of more people entering the “gig” economy and creating more jobs where you are your own boss is really exciting. The fact that more people can work remotely and customize their work/life balance is a great development.

What is one habit of yours that makes you more productive as an entrepreneur?

Knowing the buck stops with you is both exhilarating and scary – and both those factors add up to a strong motivation to outwork everyone.

What advice would you give your younger self?

None of it would be fit for print – but I would have knocked some sense into myself numerous times.

Tell us something that’s true that almost nobody agrees with you on.

Vegetables are terrible for you.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I think this quote sums it up nicely. You have to jump off the ledge at some point even if you don’t know what’s below. “Nothing will ever be attempted, if all possible objections must be first overcome.” — Samuel Johnson

What is one strategy that has helped you grow your business?

It’s not what you know; it’s who you know. I was never a top student, but when I walked into a room, I always tried to make as many friends as possible because you can never have too many friends in life. Some of my best business connections have resulted from random introductions, quick beers or just being friendly with people.

What is one failure you had as an entrepreneur, and how did you overcome it?

Lack of experience, but sometimes you just need to wing it.

What is one business idea that you’re willing to give away to our readers?

An application that deletes text you have sent that you wish you could take back.

What is the best $100 you recently spent? What and why?

A bottle of 10-year-old Scotch for someone who helped me out when I really needed a helping hand.

What is one piece of software or a web service that helps you be productive? How do you use it? is pretty cool. I’m a list and planner, and it makes project management in business or life much easier.

What is the one book that you recommend our community should read and why?

“A Dog’s Purpose.” It really gives you a good perspective to view your life.

What is your favorite quote?

“A coward dies a thousand deaths. A soldier dies but once.” – Tupac Amaru Shakur