#BakersDozen is a series of interviews with leading professionals in the fields of law, consulting, finance, tech, and more.

Tell us a bit about yourself and how you came to be in (or a customer of) the legal business?

I went to law school at the University of Cincinnati College of Law after undergrad at Davidson College.  I decided in the summer in between my second and third year of law school that my path was better suited for business leadership than that of a full-time attorney.  So, I passed the bar exam in Ohio, declared myself an inactive member of the Ohio bar, and entered an MBA program at the College of William & Mary.  I have spent the better part of 20 years as a student, employee, employer, and customer of the legal profession.

What do you do for a living right now?

I serve as the CEO of LegalSifter, a company dedicated to making global legal support affordable by empowering people with artificial intelligence

What has been your greatest triumph and your greatest success in the legal services field and what did you learn from each?

Our greatest triumphs lie ahead.  I served as COO of a global safety company for years, so I spent a lot of time employing, managing, and hiring attorneys and other legal services around the world.  At LegalSifter, we are trying to move the profession forward – both for practitioners and customers – with artificial intelligence.  The work that we are doing right now is our/my best work to date … and I can tell you we are just getting started.

Artificial intelligence, the technology that will help lawyers scale, has finally arrived.

 Do you think the legal industry is headed in the right direction, the wrong direction – or which direction?

The challenges in the legal profession are known:

  • Practitioners do not have technology that allow them to scale.  Unlike Sales, Finance, Manufacturing, Development, Customer Service, or any other function in the world that has enjoyed tremendous scale in the past 20 years, Legal does not have access to technology or strategies that allow them to do 2/3/4x the work they did in an hour two decades ago.  Most practitioners will tell you that their most popular tools are Microsoft Outlook, Microsoft Word, and a yellow pad of paper.  I have yet to meet an in-house counsel, for example, that felt like they she had enough capacity for her workload.
  • Law firms are competing for a smaller and smaller market.  With every dollar per hour increase, more and more businesses and consumers are unable to afford the most basic of legal services.  That means that law firms are competing for a shrinking, stagnant, or slow growth market.
  • Lawyers struggle to differentiate themselves and tap into unmet demand.  When a consumer or business goes to find a lawyer, it is incredibly difficult to differentiate the service offerings; many law firms look the same.  I have met many law firms that lament their ability to acquire and grow new clients.
  • The average and in many cases, above average, consumer and business cannot afford the legal services they need.  The number of pro se litigants is growing dramatically in many countries around the world.  Businesses are cutting corners on legal advice.  Lots have been written about the growing “Justice Gap” … as Justice Learned Hand (1951) said, “If we are to keep our democracy, there must be one commandment: Thou shalt not ration justice.”  We are telling law schools to graduate fewer lawyers … but the unmet need for legal services has never been higher.

My take is that the legal profession has plateaued, but is prime to explode in exciting directions for both practitioners, consumers, and businesses.

Who – or what – inspires you – and why?

If inspiration is the catalyst for some objective, then I would say the desire to meet expectations, including my own, is what inspires me.

The best definition of success I have heard in my life is the following: “Success = Meeting Expectations.  The more expectations you meet – including your own – the more success you have.”

I define a lot of my life in terms of whether I met the expectations of my family, friends, teammates, customers, investors, the broader community, and myself.  Striving for that often unattainable objective drives and inspires me.

What advice would you give to the younger generation contemplating law as a career?

Think like a product manager – use people, technology, and process – when solving problems.  The legal profession is in the habit of using people … and only people … to solve problems.  Those that seamlessly weave people, technology, and process together to solve customer problems will find themselves with wildly successful, unpredictable careers.

How ready for change do you think the legal industry is?

When I joined LegalSifter a little over a year ago, LOTS of people ran to tell me that lawyers are change averse.  I do not believe that.  Lawyers are people like any other.  If you understand their pain, show them a better way that works, and make it easy to adopt the new, they will change.  I think that lawyers do not see nearly the number of new, impactful innovations in their professions as do just about other profession in the world.  When they see innovations that work, they will change.  Without those innovations, they will not.

Is more – or different – leadership required? In what ways?

Suppliers to the legal industry need to do a better job of understanding what a lawyer does on a daily basis and where his pain lies.  I have heard a lot from a lot of attorneys who lament the missed expectations of products that they have tried or are forced to use on a daily basis.

Lawyers, General Counsels, and Managing Partners in particular would be wise to invest in operations leadership within their teams.  Dedicating capacity, energy, time, and talent to integrating new process and tools throughout firms and legal departments is not yet a natural act for the legal industry.  Operations investments are a regular course of action for Sales, Finance, Manufacturing, Development, Customer Service, and the like … lawyers would be wise to follow the lead of professionals trained in eliminating waste in process and infusing tools that help teams scale.  Lawyers do not learn that in school, but lots of other people do.

How deep do you think will be the inroads of technology in the industry?

Deep.  Artificial intelligence, the technology that will help lawyers scale, has finally arrived.  It’s the equivalent of a 5 or 6-year-old child today, so it can only be taught to do specific, narrow things.  But it’s learning … and fast.  Before you know it, it will be a teenager, and then a 29-year-old.  A.I. will absolutely be the technology that will replace the yellow pad of paper as one of the favorite tools for an attorney.  It will be incredibly disruptive.  We think that that’s exciting and promising for both practitioners, consumers, and businesses.

In ten years, do you see an industry much as it is – or do you see new players, new technology and an altered state?

We believe that the legal community is similar to the automobile industry in the year 1900.  In 1900, a car cost $2,800 USD (~$75,000 in 2016), took 12 hours to build and required a chauffeur to drive.  In 1908, Henry Ford’s Model T hit the market with a price point of $850.00 (~$21,000 in 2016), took 93 minutes to build, and did not require a chauffeur.  A few years later, the Model T cost $260.00 ($3,500 in 2016 dollars) … changed the world.  The folks that worked for Ford Motor Company sold a cheaper, higher quality, easier to use product … and made more money than the folks who worked for the expensive, lower quality, chauffer-driven cars of 1900.

The lawyers that learn to become software or A.I.-enabled service providers will figure out how to offer 2/3/4x the work in the same hour, drop their price by 1/3-2/3 or more, and will change the ballgame.  Those that get on their A.I. journey now will be more likely to figure this out.  When that happens, the pent up demand for legal services will be unleashed, and you will not recognize the legal industry.

No one knows when this will happen exactly of course, but it feels a lot like 1992 vis-à-vis 1998-99 for those of us who lived and worked through the Internet revolution.

Are consultants and lawyers looking increasingly similar? Should the distinction continue?

Lawyers and consultants operate identically, but for the nuances of the professions.  Always have been … they both often offer expertise and advice to decision-makers.  The training and certifications are different between a lawyer and a consultant, and that should not change.  As a consumer and employer of legal services and consultants, the lines are often unclear.

I am a big believer in non-lawyer ownership of firms.  The innovation, investment, and problem-solving that non-lawyer ownership would bring to the profession would far, far outweigh any assault on fiduciary standards of care.  I think smart minds could mitigate many the risks of non-lawyer ownership.

What are your thoughts on the increasing availability of data to guide client-side procurement of legal services?

The more information the better.

Lawyers offer a credence good – “a type of good with qualities that cannot be observed by the consumer after purchase .. making it difficult to assess its utility.”  Typical examples of credence goods include dental services, automobile repairs, dietary supplements, and legal services. (Investopedia, 2016)

I suppose all goods start as credence goods … until they are no longer credence goods.  Information about the usage and effectiveness of goods become more transparent with time.  That tends to be a good thing for innovation, satisfaction, pricing, and for the best suppliers, profitability.

Lawyers have typically regulated to keep non-lawyer investors out but that’s a two-edged sword these days. What are your thoughts?

See my answer to #11

What’s the one most significant factor that will drive change in your view?

Pain – consumer, business, or practitioners – and solutions that solve the pain.

We all used to go to Blockbuster to rent our movies … until virtually overnight for most of us … we didn’t.  We did not realize that we had a pain around driving to a separate store for picking out and returning our movies until we figured out that Netflix through the mail was a better solution.  Suddenly late fees, time, and gas savings became more and more annoying, and we jumped.  The industry changed.

Are we seeing the demise of the “profession” and the real emergence of the “business” of law?

The profession is not in demise.  It’s plateaued.  It needs an infusion of operations / process leadership and technology, just like every other profession and function in the world.  That talent is not likely to come from within the legal profession alone; people are not trained to think that way.  (I know, because I have been to both Law School and Business School.)  The entire legal profession is taught in school to work from stare decisis; it’s geared to work from the past and not the future per se.  That’s a little unfair, but the training of lawyers curbs innovation relative to other professions.

What do you consider is the greatest challenge facing the industry?

The growing justice gap in the world due to the unaffordability and often unnavigable nature of legal services.  The law holds societies together.  When people cannot access it, society breaks down.  The profession must solve this problem.

What do you see as the greatest opportunity for the sector looking forward?

Unleashing the pent-up demand for affordable, easy-to-use legal services.  It’s an enormous opportunity for the entrepreneurial-minded lawyer.

Do you think law can improve its track record on diversity and inclusion? How?


How? Diversity and Inclusion should be a core value, not an initiative, of the profession and its practitioners.  (LegalSifter is going to take a thoughtful look at its core values in the coming weeks / months.  We will have a stated core value that comments on diversity and inclusion.)

Having a core value on diversity and inclusion means that an organization will consistently and constantly seek out opportunities to drive more diversity and inclusiveness throughout the enterprise.   Every significant strategic decision should be made with an eye toward diversity and inclusion.  It should be part of the every-day vocabulary within an organization.  When that happens, people at the highest and lowest levels of an organization and eventually, a profession, will figure out all the cool innovative ways to achieve the diversity and inclusiveness objectives that most people strive to achieve.

Will the current regulatory framework around law help or hinder it in the future

Non-lawyer ownership is hurting the growth of the profession.  Period.

Who do you think are the greatest influencers on the industry these days?

I am a fan of James J. Sandman – http://www.lsc.gov/james-j-sandman – people would be wise to listen to him. https://www.youtube.com/watch?v=iNyfrBFEe8M – good video of his keynote at the FutureLaw 2016 conference in the summer of 2016.

The law holds societies together.  When people cannot access it, society breaks down.  The profession must solve this problem.

If you had to do it all over again, would you? Or what would you do differently?

I want to move harder and faster toward innovation in the back half of my career than I did in the first half.

I have had the privilege of working in three companies who were dedicated to disrupting the status quo with innovative technology that served a broader purpose.  I have had tremendous role models in my life.

If I do my job, my fourth company – LegalSifter – will disrupt the status quo in a way that benefits consumers, businesses, and practitioners, serve a broader purpose, and create a global A.I. brand that is known for meeting expectations.  That will take decisive leadership from me.

If a law firm was a startup pitching for investors, would you be an investor?

Only if it had a story around scale.  The law firm that tells a story of people, process, and technology … of software/technology/A.I.-enabled products … is one that I would bet heavily on for long-term success.  The law firm that does things with service-only products and smart lawyers would not get my money.

Wildcard Questions

If you weren’t doing this, what would you be doing?

Probably another startup.  I have unknowingly prepared for this role my entire life.  It suits me.

What would you like to be known for?

Leading with intelligence, integrity, courage, and good humor.

What’s your favorite hobby or activity outside of law?

Activity: Having a meal with my family and playing sports

What’s your favorite sports team?

Kentucky Wildcats (basketball), Pittsburgh Steelers (football), Pittsburgh Penguins (hockey), and Pittsburgh Pirates (baseball)

Whats your favorite city?

I have many favorites, but Pittsburgh, Pennsylvania … and Melbourne, Australia

What’s your favorite food?