Ask Holly How is a culture-first business consultancy founded on the principle that successful entrepreneurship resides at the intersection of self-evolution, business growth, and the creative pursuit.

Holly works with Creative Entrepreneurs who are building locally and growing globally. They are risk takers by nature, with an expansive mindset for growth, who are driven by a sense of possibility. By catalyzing culture change, constructing a stable infrastructure, unifying teams, and clarifying the company vision, her clients gain creative freedom, financial prosperity, and a clear path towards generating their legacy.

Since launching Ask Holly How in 2012, Holly has worked with over 1000 businesses through her private consulting and business growth program. She has a rich background as a professional ballet dancer, Board-Certified Music Therapist, medical researcher, bassoonist, VP of Operations and Finance, and former Visiting Professor of Business at Pratt Institute and former Faculty Member of Rhode Island School of Design. She holds a degree in Music Therapy from Berklee College of Music, A Certificate in Pre-Medical Sciences from Columbia University, and a Graduate Certificate in Religions of the World from The Harvard Extension. Holly is the host of the Cultures [w/n] Capitalism podcast and she is at work on her first book. Holly is also the 2nd place winner of the 2023 FemMullet Champ Competition. Each of these pursuits has allowed her to shape her approach and philosophy to helping entrepreneurs grow their businesses without sacrificing their souls.

holly howard
Holly Howard — Principal


There are 5 guiding principles that drive this work to ensure you’re working towards creating a healthy company.

We engage in nuanced collaboration
We provide intimate accountability
We embrace flexibility inside of structure
We create simplified not optimized systems
We deliver clarity within context

Why How?

Alexandra Fine
Dame Products — NY, NY

Holly has touched so many aspects of Dame. She has guided Dame through Business planning, cultural changes, infrastructure development, leadership development... and so much more. Since working together my business has tripled in size and raised $4M. But what I have found most valuable is my improved values alignment. She helps you stay grounded so everything else can soar.

Alex Daly
Daly — NY, NY

When peers ask me for business consultant recommendations, I tell them: “Hands down, Holly. She changed my life.” And it’s true. Holly has been my guardian angel in exploring, finding, and cementing the mission, values, and culture at Daly in its many iterations. We have built operational systems together, hiring plans, financial models, growth paths, dream client lists, and so much more. Holly isn’t just a consultant, she has been a partner and a friend, and with her guidance, we have almost grown by 40% in size and revenue in just the last year. I am grateful that I found her, and am lucky to be on this continued career journey with her.

St. John Frizell

I met Holly Howard in 2013, when Fort Defiance, my restaurant in Brooklyn, was at a crossroads. We were still recovering from Hurricane Sandy, burdened with debt, and I was exhausted. Holly showed me that I wasn't alone — that there were lots of creatives like me trapped in businesses they started that they didn't know how to run properly — and that there was hope for all of us. Under Holly's tutelage, Fort Defiance became a powerhouse, increasing revenue and profit year after year. She introduced me to ways of thinking about business that were entirely new, and converted me from a frustrated bartender into an efficient operator. I opened the restaurant Gage & Tollner in 2021, and thanks to Holly's advice on securing investment, creating culture, and sound business planning, we raised $1.3M in private equity and close to $500K in regulation crowdfunding, and the business is now a wild success.

Jen Pywell
Greenpointers — Brooklyn, NY

Big thanks to Ask Holly How for helping me create a selling plan for my former business Greenpointers. All small business owners should think about a business plan and GET HELP! Working with her gave me confidence and showed me the true value of all my hard work. It also increased the profit of my sale to almost double of an offer I received before working with her! When I come up with another business idea she is the first person I am going to call!

Tone Johansen
Sunnys Bar — Brooklyn, NY

I am an artist and musician that stumbled into the bar business. It is the love of what I do that makes me an artisan. Today, thanks to this class, I take better care of the systems that support my bar. Thank you, Holly, for making me understand that being poor doesn’t make me more authentic. It just makes me poor. And although money still is not my primary motivation, you helped me recognize that it is a necessary tool to keep my business healthy. I am proud to think financially and to not just pretend the scary “business of business” doesn’t exist and hope for the best. On the days when sisyphean tasks pile up, you start to wonder where your freedom went. Now, because of this class, I have lots of obvious goals that pull me out of that day-to-day and keep me excited about the future.

Stephen Tracy and Harry Doull
Keap Candles — Kingston, NY

When we first met Holly we were exhausted and struggling to grow our company and growing afraid of what might happen next. Holly helped us get to the bottom of and resolve the fears that were blocking us. With her mentorship, we were able to refine our vision and values, and restore our enthusiasm and confidence to move forward with inner clarity and ambition. Over time Holly has helped us reflect on and improve almost every aspect of our business and culture — from our pricing model to our hiring practices. In the two years since we began working with Holly, we’ve almost doubled our sales (despite a pandemic in the middle), achieved profitability. More significantly, the health of our company culture has transformed, benefiting our employees, our customers, and ourselves. Holly achieves all this through asking the right questions, as opposed to giving rote answers. Perhaps the most brilliant thing about our work with Holly is a genuine sense that we have grown as humans in the process. We are now better equipped to run our business in future, and on a deeper level, to navigate the complexity of our own personal lives.

Sara Berks
Minna — Hudson, NY

Working with Holly these past four years has been a business and life changing experience. She has a way of understanding the person behind the 'business owner,' and guiding them to know and understand their own strengths and embrace their weaknesses. We've worked on everything from Business Planning to Infrastructure Development, Culture Change, Marketing, Financial Planning, and Executive Coaching. She also joined my team on our first team retreat, guiding us in a workshop for goal setting for the next year, and a few years later leading us through a communication workshop after we experienced a lot of change, growth, and transition. Sometimes I joke that a guiding principle of how I lead is 'What Would Holly Do,' but it's honestly really true. Holly has taught me to slow down and pause before jumping into problem solving, the importance of structure, and that difficult conversations can only lead to better.

Hunter Craighill & Zach Fried
Craighill — Brooklyn, NY

Working with Holly has been transformative for our business. With her guidance and support, we've learned to keep perspective on the countless small tasks calling out for our attention on a daily basis, and focus ample time and energy on developing processes and systems that will allow us to continue growing into a calm, stable, mature company. We've worked with her on business planning, infrastructure development, personnel systems, financial planning, and marketing planning. Her approach is holistic, and grounded in a framework that always goes back to our core values. It makes it easy to know when we're being true to our vision, when we might have strayed, and how to course-correct. More than anything, working with Holly has been empowering. She has set us up to trust ourselves, know when to seek outside guidance, and continue charting a self-directed path for healthy growth, both personally and professionally.

Catherine May
Maison May — Brooklyn, NY

Running a small business is incredibly rewarding yet challenging and often lonely for its leader. Over the course of the years working with Holly, I realized that she has an un-matched ability to embrace and understand deeply all aspects of what it takes to be an entrepreneur and therefore, she is truly able to assist me through not only the lows, but the highs that came with the task. It takes incredible strength and self-exploration in her part to master that in a way that is not only empowering but no intrusive in what must stay the leader's process to achieve his goals. And she does it always with a smile...

Rebecca Bullene
Greenery NYC — Brooklyn, NY

Working with Holly transformed my business and helped me to become a better manager. Holly helped me prioritize my time and energy to become more efficient and a more savvy sales person of our services. She helped me to take a hard look at our numbers and make the right decisions to shed the parts of our business that weren't working and focus on those that were. Working with Holly helped me to get a better understanding of how we could be more profitable and what kinds of clients we should be targeting to grow our business while also helping me understand what kind of staffing I'd need to put in place to reach my goals. She also made introductions to financing partners to help expand our business and other local business with aligned interests. Working with Holly over the course of two years doubled our revenue and made me a much more effective manager. I can not recommend her services highly enough!

Dave & Mel Morris

We began working with Holly at a pivotal moment in our retail business when we were unsure about important next steps - selling, closing, expanding or re-envisioning. We needed to delineate and evaluate our best options. Holly provided the direction and a platform for exploration that allowed us to discover what our strongest and most effective paths ahead were, inspiring us to rethink our next careers based on our skill sets despite the scary unknowns that were part of that decision. Ultimately, she helped guide us through the structure and terms of the sale of our business that allowed us to pursue and achieve quality of life goals. She gave us the tools to build new business models and encouraged the questions that brought us the clarity to make our most informed decisions. Most of all she is the team member we’d always wanted: smart, engaged, and a force for bringing out the best in you by building on your strengths.

Brent Young
The Meat Hook — Brooklyn, NY

When we started The Meat Hook, we focused our efforts on creating the best butcher shop in town, mostly fueled by beer and whiskey. However, we didn’t take the time to focus on the structure of our business, and the organization we were creating. Holly helped us define our roles and responsibilities, clarify our relationships, be better leaders, and get on the same page. Our shop is now managed better, with clear managerial roles, and expectations. Everyone’s job easier just knowing what is expected of them, and how they can succeed. Now we’re drinking to relax, rather than out of stress.

Lauren Haynes
Wooden Spoon Herbs — Georgia

Wooden Spoon Herbs would be so far from where we are now without Holly's support. Through Infrastructure Support and Financial Planning (among other services), our work together allowed us to grow 71% in the first year working together. Her Executive Coaching ensures that I have the skills I need moving forward to think outside the box and maintain profitability. Holly is an invaluable advisor of the Wooden Spoon ecosystem. She is the best in the business.

Rebecca Atwood
Rebecca Atwood Designs — Charleston, South Carolina

The Business Growth Program shifted everything. I was just going along bit by bit before the class and wasn't looking at my business with a bigger plan and goal. I started to have a process for vetting these bigger ideas and figuring out how to make them attainable. It made me realize that my job was to not just create the product but to create the business, the company, the culture. I had to think bigger—and actually more personally. Figuring out values that were important to me personally, but relevant to what we were doing was a huge step. Getting clear on that made it easier to think about what kind of company I wanted to build, what experience I wanted for our customers, and also for my employees."