Ask The Business Lawyer launched in 2008 in New York City, provides entrepreneurs and small business owners with straight-talk legal to bolster your business.

‘Ah ha’ moment that led to launching the business: It came in the summer of 2007, when I had to reinvent the business I had. Too many nights of waking up at 3 a.m., railing at the gods, because business was lousy. My 12-year-old law firm had little growth opportunity and was based on a model that could never become self-sustaining. My business partner and I fought regularly and bitterly. I had reached the point where it wasn’t enough to be “just” a lawyer. During those 3 a.m. “vomit-out” journaling sessions, I recognized that every four years, I’d reach a point where I’d throw my hands up in desperation and say “That’s it!! I’m through!!” But the fear of the abyss that lay on the other side was too great. So I’d find a way to re-tool, re-configure, re-vamp the business in some small way … and that gave me the illusion of progress. That early August dawn, I realized that I was about to begin my third, four-year cycle. I looked in the mirror and said, “I am absolutely not repeating this pattern again!” So I set about dissolving my law partnership and creating a multi-faceted business that had meaningful opportunities for multiple streams of income (especially passive income).

Ideal customer: Entrepreneurs and small business owners (especially women) earning up to $10 million a year who have started and grown (or are growing) their companies by the seat of their pants — and are ready for a trusted advisor success team to bolster their business. 

First customer or client: I told anyone and everyone that I had reinvented my business. I wrote about it and created information products about it. I spoke about it and confessed my mistakes. Business owners appreciated the candor.

Measuring success: In part, by what I give back to the entrepreneurial community. Some might see awards as a form of self-promotion, but I view them as the community letting others know they perceive me as a valuable resource. Early successes include being named:
• The U.S. Small Business Administration’s 2011 regional Women in Business Champion of the Year
• Forbes’ Top 30 Women Entrepreneurs to Follow on Twitter
• Top 30 Business and Entrepreneurship Blogs by Women (via She Takes on the World)

Biggest struggle: Making the leap from practitioner to business owner. It took me long enough to grasp that I was not a business owner if the entire business revolved around me. Nor could I rely on my brainpower alone. My first step was to form a solid team of advisors to fill the gaps. The challenge has been in creating the systems and model that can function without with me, and that is scalable for growth.

Surprise!: How much is involved in starting, running, and growing a business. They never taught us this in law school.

Promoting sales: I’ve been myself, instead of the stuffiness and pompousness that business owners have come to expect from lawyers. I enjoy educating and communicating. I hate unnecessary power trips. I love a good laugh. When it comes to demystifying the law for business owners, I know I need to be a translator. So I let that shine through. My website and social media communications take the same approach.

What you wish you would have known: First, that I need to begin with the end in mind. What’s my exit strategy? What do I want the business to do for me? I wish I had had my feet held to the fire so that I could have been really clear about that. I started (years ago) with the naïve exuberance of “Yay! I’m in business!” — without setting performance benchmarks. If you can’t monitor it, you can’t change it. Second, that I need an outside, objective team to really move forward as a business. Not just the odd marketing consultant here and there to tell me how to network more effectively. And not just to rely on “internal” team members, like business partners. You need someone (preferably, multiple people) who will hold the mirror to your face and force you to address what you’d rather not see.

What keeps you up at night (business wise!)?: Unproductive worrying. As a lawyer, I’m a “trained pessimist”—taught to look for the pitfalls and “what ifs.” Rehearsing difficult conversations with staff (in my head), wondering if I have a strong enough system for monitoring work flow and wrestling with time frames for achievement.

Ever tempted to throw in the towel and just get a job?: Who isn’t? After years of sticking your neck out on a daily basis, the thought of not having to deal with business management responsibilities sounds like a vacation. I couldn’t do it, though. First, I love the fact that my time is my own. Second—and it’s the reason I started my own business years ago—I wanted to control my own destiny. I’ve never been very good at office politics. And I want unlimited potential in my income-earning capacity. Besides, where’s the security in working for someone else these days?

Biggest goal: Ramping up the online portion of my business so that it generates enough traffic and revenue to ensure financial freedom. I will do this through SEO techniques, increasing community outreach, beefing up my affiliate program, possibly launching new digital products—and, of course, moving the right players into place to implement it.

A few good tips: For any web-based business, a website/blog is a work in progress. Always set aside enough money to revamp it periodically to take advantage of changes in the online world. Unless you’re in the website development business, delegate development to others who really know what they’re doing and meet their deadlines. And as it’s a valuable business asset, make sure you have the right agreements in place to protect your IP.

The absolute best part of owning my business is: that I control my time and destiny.

If I had to start over again, I would: have planned better for my exit and developed an outside advisory team from the get-go.

I never imagined: getting to the tipping point would be so difficult.

If standing on a rooftop facing crowds of aspiring or struggling small business owners, I would shout: “When you earn your own money, you have power, independence, and options. Choose freedom!”