Holly Howard

My career path has not been a straight line, and for that I am so grateful. I have been blessed to pursue all of my passions in life from performing as a ballerina, to publishing medical research, to working as a music therapist and to participating in a few recording sessions on the bassoon. I am a graduate of Berklee College of Music in Boston as well as Columbia University in the City of New York.

So how did I end up as a small business adviser? I can vividly remember the day I realized that the way a business operates can make or break it. It was 2009 and at the time, I was neither an entrepreneur nor a manager, I was…a waitress. I was working at one of the busiest brunch restaurants in NYC. It was a Friday; I had just finished a busy shift and was told that my paycheck would have to wait because there was no money in the bank. I asked myself, how could a seriously bustling restaurant not have money to pay the staff on time? Something did not add up and my curiosity about business operations had been sparked.

And so began my journey. Soon thereafter, I was promoted as the first manager of the restaurant. Eventually, I rose to become Vice President of Operations which included two restaurants and a farm. When I was promoted to a management position I didn’t have an MBA, and with a ton of student loan debt already accumulated, I knew that an MBA was totally out of the question—so I taught myself.

Over the next three years, I streamlined all of the systems within the company from hiring and training staff, to ordering and inventory. I standardized all of the protocols and procedures that allowed the business to operate day in and day out. The results were larger than average growth rates for the company, increased productivity and significant decreases in the cost of goods as well as employee turnover. I implemented employee benefit and development plans that were models for the industry and were so impressive in fact that I was asked to testify about them at a congressional briefing in 2010.

In that environment I was blessed with total autonomy and freedom to develop my own philosophy of business operations. Looking back on that day in 2009, I see so clearly how the absence of systems, standardized procedures and organization can handicap even the busiest businesses and most well meaning entrepreneurs.

In May of 2010, I found myself sitting in a hotel in Vienna talking management philosophies with my father, a seasoned CFO. I had an “ah ha” moment as we were exchanging ideas: I said to myself, I want to be the Peter Drucker of my generation with a focus on small business. His emphasis on respect for the worker, his insight on the importance of community and, most importantly, his message of keeping it simple resonated deeply within me. Upon returning to New York I founded my company and started working with private clients.

In 2013,  I created and launched the From Artisan to Entrepreneur® Business Growth Program based on the need I saw to bring creative entrepreneurs together within their community to learn, build relationships, and create realistic plans for growth.  That program is currently being taught at Industry City in Brooklyn under the name, Plan for Growth, in a partnership between Southwest Brooklyn Industrial Development Corporation and J.P. Morgan Chase.

I am fully committed to bringing clarity to the way your business operates and to reconnect you to the original inspiration and joy you had for your business in the first place. My goal is to deliver to you unbelievable value.  In addition to advising small businesses through Ask Holly How, I have writen a small business advice column for Brooklyn Based, teach the From Artisan to Entrepreneur Business Growth Program, and am the founder of the Small Business Book Club at McNally Jackson.

I am committed to:

  1. Rolling up my sleeves and working with you to find out what’s keeping your company from operating successfully.
  2. Creating a plan necessary to make your business operate efficiently.
  3. Implementing with you new practices and systems and developing the organizational structure needed to keep them running.
  4. Inspiring the leadership necessary to keep your business growing.

And, I keep the promise that I make to you so you can realize all of the potential your business has to offer for yourself, your employees, your customers and your community. Just ask my clients →

I believe it is the small inspiring businesses in our communities that define our quality of life in those communities. It is my life’s mission to support the promise and genuine experience each small business can offer so they can remain gathering places for sharing love, livelihood and social innovation.

Change your business
Change your life
Change your community
Ask Holly How


Holly is ready to help you transform your passion into a profitable, inspiring and thriving small business. If you have any questions for her or if you’re ready to get started, drop her a line: info@askhollyhow.com

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