Leonard (Lenny) Shostak AKA: Hardy Brooklyn

As Box of Rain’s founder and principal, I coach a wide range of diverse individuals, including those still trying to figure it all out—be it in life and/or business. Over the course of my life, my own personal and professional missions have continued to evolve. It’s thrilling to share the singular mission into which those two separate missions have merged:

I am change agent specializing in helping people understand who it is they truly are, explore who they truly want to be, and develop and implement a strategy on how to get there from here.

Being confident in who you are is the gateway to wonderful relationships—with others, but, more importantly, with yourself—and a great life!

I’m Leonard “Lenny” Shostak, a fun-loving, successful serial entrepreneur who has bootstrapped several of my own businesses while still finding plenty of time for family, travel, live music, and nightlife. My guiding principle is the vital importance of human creativity. Whether it’s music, visual art, performance, an idea, or an invention—or something we haven’t even heard of yet!—I am passionate about helping people tap into themselves.

In addition to having what some would call “a well-developed sense of humor,” here’s a list of just a few of my experiences and certifications. I am or have been a/an:

* Eagle Scout, tech expert, and FIFA-certified youth soccer referee;

* life-long learner and trained in life coaching, Dale Carnegie, the Sandler Sales method, Landmark, wilderness first aid, and more;

* active member of Toastmasters (since 2006) and currently am a “Competent Communicator”;

* leader of workshops, trainings, and team-building activities for numerous organizations;

* presenter of live workshops and webinars on boundaries and consent;

* trained in improv with UCB East;

* performer in live on-stage sketch comedy, burlesque, and the Moth storytelling competition; and appeared in several television series and independent films;

* model for life drawing, body painting, and photography;

* produce a live variety event series in New York City (when social distancing is not in effect); and

* always searching for “What’s next?”—be it for me, my friends, my family, or my clients!


  • Achology Certified Life Coach
  • Transformation Academy Happiness Life Coach—certificate in progress
  • Certificates in New York City Mental Health First Aid—Youth and Adult
  • Toastmasters Confident Communicator
  • FIFA, US Soccer, AYSO & PSAL Certified Soccer Referee
  • UCB East Improv 101, 102, 103
  • Sandler Sales President's Club
  • Dale Carnegie Workshops
  • Certified Novell Engineer
  • BA, Computer Science, CUNY Queens College
  • AS, Liberal Arts, Nassau Community College
  • Eagle Scout


  • Actor, model, performance artist, and event producer
  • Started the first young advisory board for the American Cancer Society, Brooklyn Chapter
  • Expert witness in New York State and federal courts
  • Founder/owner of Box of Rain LLC, 2007-present
  • Outward Bound team-building workshop facilitator
  • Seminar presenter, American Management Association Annual Conference
  • Instructor, Continuing Education, CUNY Queens College
  • Founder/principal of WebHostNY LLC, a boutique web hosting firm
  • Business Development Consultant, Averweb Inc.
  • Founding partner/owner of L&D Computer Consulting, 1992-2008
  • Assistant Manager, Hunki's Pizza/Ackerstein Caterers

If you want to explore who you are, who you want to become, and how to get there from here, I hope you will contact me at: