I’ve gotten a bit of grief from friends and colleagues for starting a series of blog posts on lessons I learned from my time as a musician and composer that I now use every day in my capacity as a legal technologist, then building to the announcement that I’m starting my own consulting company, and then immediately dropping off the face of the earth again.  I will come back to that series shortly, I promise, but as you can imagine I’ve been all consumed with the new company for the last few months.

As I write this, I am sitting on a train from New York to Boston to attend the College of Law Practice Management Futures Conference, where I and Geek #1 will be inducted as fellows.  Toby and Casey are already fellows, so we’re quickly approaching Phase 2 of 3 Geeks World Domination, (ed. – First rule of 3GWD: We don’t talk about 3GWD, Ryan!) but my 4-hour train journey gives me a bit of time to reflect, regroup, and rewrite.

The interesting thing about starting a company in the midst of a series of posts about lessons from a past life, is that it makes me think a lot about how I’ll use the lessons I’m learning today in my future endeavors. Here are a few lessons I’ve learned in recent weeks that I’m planning to keep in mind as I go forward.

1) Approach new opportunities as if you know nothing.

This has been really easy in the last few months, because while I know a quite a bit about what Sente Advisors does for our clients, I started the company knowing very little about actually running a company. Knowing nothing, and knowing you know nothing, allows you to sponge up experience and gain an understanding very quickly.  In some cases, knowledge – or the self-perception that you are knowledgeable – can blind you to new learning opportunities.

2) Starting a business and working for yourself, is like having 2 jobs and no income.

I had been a freelancer for years when I worked as a musician.  I often held multiple jobs and temp jobs, and I scraped together income to pay for my music habit. So I figured working for myself would be kind of like that.  I joked for the first month or so that I was finally unemployed again.  But the reality is owning your own business is like having 2 separate jobs.  One is the job you want to do; the work that your company was created to do, and the other is actually running your company.  Oh, and for the first few months, you won’t have any income.  Good luck!

3) Don’t be afraid to ask for help.

It’s easy to get into the mindset of ‘it’s us against the world’ when you’re starting a new business.  But you’ve got friends, former co-workers, fellow startups, and even former employers that will likely offer guidance, support, and if you’re lucky, even office space. People that have started their own companies know how difficult it can be and, in my experience so far, they are eager to help others succeed too.

4) Surround yourself with smart people that have compatible and complimentary skills.

This is probably the most important lesson of all.  Don’t do it alone.  When I was first thinking of starting a company, I thought I’d just ‘go out on my own’.  Thankfully, I had a few people that liked my idea and said, “would you be interested in working together?” I can finally announce my partners in Sente Advisors.

Shashi Kara, formerly VP – Solutions Consulting at Neota Logic, is the Chief Technologist at Sente.  I’m pretty good with technology.  Shashi’s better.  And tenacious, and frankly a bit OCD.  He’s currently meeting with vendors daily building out our sandbox of legal innovation tools.  (Also, he came up with the name Sente when I was hopelessly stuck. Anyone want to hire Super Magic Legal Techno-Wizards?)

Dan Pryor, formerly Sr. Consultant and Account Manager at HighQ, is the Chief Revenue Officer at Sente.  In addition to being a smart and talented technologist in his own right, Dan is commercially minded in ways that Shashi and I never will be. Without Dan’s skill in managing the pipeline, negotiating contracts, and speaking in a British accent, Sente would just be another techno-nerd consultancy struggling to make ends meet.

The primary extra-technical skill that I bring to the table is my interest and ability to get up in front of large groups of people to talk about technology and try not to make a fool out of myself.  While that is quite a useful skill to have in general, it turns out to be a lot less helpful than you’d think in the early stages of starting a business.  I have the utmost respect and admiration for solo consultants, solo lawyers, or anybody trying to do anything by themselves, but having a talented team of people with a diversity of skills and capabilities who can shore up each other’s weakness and further strengthen the company’s core offerings is a much better way to do things.

At least, in my admittedly limited experience thus far.

Photo of Ryan McClead Ryan McClead

Ryan is Principal at Sente Advisors, a legal technology consultancy specializing in innovation strategy and cross-platform solutions and support.  He has been an evangelist, advocate, consultant, and creative thinker in Legal Technology for more than 15 years. In 2015, he was named a FastCase 50 recipient, and in 2018, he was elected a Fellow in the College of Law Practice Management. In past lives, he was an Innovation Architect, Knowledge Manager, a Systems Analyst, a Fashion Merchandiser, and Theater Composer, among other things.