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How to Succeed in Business: Tips From a Superstar Business Attorney

Gary Ireland and I are together in a mastermind group, which is a great opportunity to get to know a colleague well. He works with executives, helping them manage employment transitions.

These transitions are challenging. Gary has great insight into how to turn professional and business challenges into successful outcomes. I’m delighted to bring him to you today.

David: How did you arrive on your current path?

Gary: I come from several generations of lawyers; my parents are both therapists and my father was a psychologist and worked for NASA in human factors and in a private practice problem solving. Working with my family growing up, I have been able to see people in difficult situations embrace change and be able to overcome adversity to move forward in a positive direction. When I first began practicing law, I began working as a commercial litigator with a focus on bankruptcy. Early in my career, as a sole practitioner, I worked with a client embroiled in a fight against Chrysler, who had fired him based on his age. We won at trial, and when the manufacturer appealed, we won on again appeal in the Second Circuit.

For over 20 years, I have focused on representing executives and the various companies they have created. In addition to representing individual executives, I enjoy the energy of working collaboratively with entrepreneurs and start-ups and the businesses they create. I work closely with management to save money by making smarter legal decisions, streamlining administrative proceedings and avoiding liability, while maintaining the focus on positive aspects of the business.

David: What does your typical day look like?

Gary: Depending on family and professional obligations, I try to start early, sometimes as early as 5 am, and start by working on a project that needs immediate attention and on a short timeline. By starting my day early, I can preview, organize and prioritize, before I return phone calls and put out fires.

David: What traits do the most successful people share?

Gary: The most successful people I know have a personal mission, an ability to embrace and thrive under changing circumstances, have a balance between their professional and family lives, and they listen.

I had the honor of knowing and collaborating with Jim Burke, the former CEO of Johnson & Johnson, who proactively removed Tylenol from the shelves in the wake of a cyanide poisoning, a case taught in every business ethics class today. Jim was able to overcome deep adversity and help the company and brand to thrive. When he retired form J&J he went on to lead the Partnership for a Drug-Free America, partnering with advertising agencies in a high profile media campaign to save lives. I worked with Jim on an environmental project we were both passionate about and learned from his collaborative style, integrity, humility, and principled leadership.

David: What are some of the hardest truths to face up to in business?

Gary: Like most the businesses I represent, I need to work smarter, not necessarily harder. There are many ways to approach situations; listening to a client and finding out what is important to them and then being cognizant of their needs and wishes while working towards their goals. You cannot be everything to everyone; I encourage my clients to hire consultants to handle specific matters so that they can focus on their businesses. I encourage clients to be organized, keep costs and overhead down and do something to improve everyday – whether it be reading a book, taking continuing education or meeting with a mentor – and to market their business at every opportunity and to everyone.

David: What are some of your own professional development challenges?

Gary: I am always trying to refine the systems in my office to work more efficiently. I work with other professionals who are experts in their fields and I try to embrace new technology and continue learning through continuing education seminars to become more streamlined and acting as a model to encourage my clients to do the same.

David: How are you working on them?

Gary: I have mentors in both the business and legal fields with whom I work with on a regular basis. In addition, because I work closely with individual coaches and consultants, I appreciate the value of these professionals. I ask for help when I need it and enjoy working with others towards a common goal, whether the goal is tackling a legal issue or moving forward toward a business target with a client. Of course, I very much like people, particularly the clients I have the privilege to work with.

To learn more about the Law Offices of Gary Ireland, go to www.irelandlaw.net, or contact Gary at gary@irelandlaw.net or (212) 991-5468.


What do you think of what Gary has to say? Let us know in the Comment Section below.


About the author, David Shriner-Cahn

David is the podcast host and community builder behind Smashing the Plateau, an online platform offering resources, accountability, and camaraderie to high-performing professionals who are making the leap from the corporate career track to entrepreneurial business ownership.


  1. Shahab on 04/23/2014 at 1:56 PM

    This is great advice. Regardless of your experience level, we can all benefit from working with other like-minded professionals in various fields and cultivating relationships with anyone and everyone that can help grow our businesses.

  2. Paul Marshall on 04/24/2014 at 12:52 AM

    Some great insights on how collaboration enables creativity and business synergies…always admire those who are driven, personable, and can lead from the front.

  3. Angela Watts on 04/24/2014 at 9:24 AM

    Gary is smart, articulate and fighting the good fight. He is an inspiration and role model for sure.

  4. David Shriner-Cahn on 04/24/2014 at 10:39 AM

    Shahab, Paul and Angela, I couldn’t agree more. Those around us who lead with integrity and strong values garner great respect — and are very inspiring.

    Who are some other role models you follow?

    What other traits inspire you?

  5. Heather on 04/26/2014 at 5:28 PM

    I am greatful for knowing Gary and gain insight and excelent advice every time we talk. He is great at pinpointing peoples personal missions and helping the develop a action plan to reach their goals. And he knows the law – what more could you want in an advisor!

  6. Elisha on 04/27/2014 at 3:41 PM

    This is an excellent summary of what to look for in business advice from your lawyer:
    Integrity, Knowledge, and sometimes as important, Humbleness.
    I love that you’ve worked with or had some business dialogue with some of the biggest companies and can share that knowledge with your clients!

  7. Norm Sanyour on 04/28/2014 at 7:58 AM

    Very interesting commentary from someone who has clearly been around the block a time or two. Could benefit from more interviews like this one.

  8. Mark Utke on 04/28/2014 at 8:41 AM

    I have had the pleasure of working with Gary on several legal cases involving high profile clients. Gary treats every client with equal importance. Very interesting article.

  9. James Hamilton on 04/28/2014 at 1:55 PM

    Gary is a good man to have in your corner when it comes to employment law and executives who are looking to make that next move but just aren’t sure how to proceed. That’s why I haven’t had hesitation recommending Gary and his legal services. And this is coming from another attorney.

  10. David Shriner-Cahn on 04/28/2014 at 3:09 PM

    It is a pleasure to be colleague of a professional who is so well respected.

  11. Leslie Tilles on 04/28/2014 at 4:46 PM

    Excellent interview of Gary Ireland. Gary and I have worked together to advise a mutual client regarding her employment issues. Gary listened as the client detailed her experiences at work. Gary offered great insight and excellent legal advice to this client. Gary has extensive employment law experience. He takes a very hands-on approach when advocating for his clients.

  12. Stuart on 04/28/2014 at 5:14 PM

    I’ve had the pleasure of working with Gary on a number of transactions. He’s always well prepared and able to add insight to a transaction that no one else had come up with previously.

  13. Catherine on 04/28/2014 at 5:30 PM

    Great interview and sound advice from a real superstar. I’d love to read more, he should write a book!

  14. Dolores Kelly on 04/28/2014 at 11:53 PM

    Your Comments*

    Gary is the ultimate professional as well as a loyal friend. Hardworking, creative and just smart–any organization would be lucky to have him!

  15. Thierry Sighel on 04/29/2014 at 12:57 PM

    There are no words that can describe how I feel about knowing Gary Ireland.
    Either as human being or as a professional, he is just incredible !!

  16. David Lewison on 04/29/2014 at 4:24 PM

    I’ve known Gary for about 20 years. His best trait, in my opinion, is how direct he is. He tells it like it is even if the message is difficult. Too many advisors dance around a problem when taking it head on will work best.

  17. Stephen Shaw on 05/08/2014 at 2:13 AM

    Gary has dedicated his career to sticking up for the little guy by advocating for the underdog. It’s a vital part of the system; someone has to put forth the effort to keep the powerful honest, and Gary has the unmatched desire and ability to do so.

  18. Matthew Loera on 05/28/2014 at 4:45 PM

    As an executive headhunter working in Silicon Valley, I have needed Gary’s advise and counsel on a number of issues. Also, my C-level clients have benefitted from his insights and attention to detail. Gary is a major asset to my firm, and by extension, to my clientele.

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