Holly Rachel of Rachel + Winfree Consulting: “Access to capital”

A community/mentorship of other women founders that provides support for new or aspiring women founders. There are communities like this, industry foundations, online communities, etc. I recommend aspiring women founders check these groups out. Having a group of people that understand the challenges you face can make all the difference. As a part of our […]

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A community/mentorship of other women founders that provides support for new or aspiring women founders. There are communities like this, industry foundations, online communities, etc. I recommend aspiring women founders check these groups out. Having a group of people that understand the challenges you face can make all the difference.


As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Holly Rachel, cofounder of Rachel + Winfree Consulting, a data analytics consulting firm based in Nashville, Tennessee. Rachel + Winfree Consulting provides data strategy design services to small and medium businesses, as well as data career coaching services to those wanting to advance their careers in data. Holly is a native of St. Louis, Missouri, and resides in Nashville, Tennessee.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

My business partner Lena Winfree and I noticed that small and medium businesses were sorely lacking in their ability and understanding of how to use data. We decided to use our backgrounds in STEM and data analysis to help make data simple for business owners.

Can you share the most interesting story that happened to you since you began your career?

In 2019, we were nominated as Startup of The Year by the Greater Nashville Technology Council! That was such an exciting and inspiring time as entrepreneurs.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Honestly, entrepreneurship can be such a rollercoaster, usually we are laughing to keep from crying. Lol!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I absolutely want to shout out my business partner, Lena Winfree! Entrepreneurship can be a very lonely rollercoaster, and we have both leaned on each other when things get tough. It certainly makes a huge difference to have a partner you can depend on.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I really enjoyed The Hard Thing About Hard Things because I found it very inspiring, and it helped me reframe challenges as necessary events to move me and my business forward.

Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?

“Let other people tell you ‘No’” has been a very important quote for me in the past year or so. So often, it’s easy to talk ourselves out of opportunities, or to tell ourselves that we aren’t prepared or knowledgeable enough. It needs to stop! Let other people tell you no. You will never know for sure until you try.

How have you used your success to make the world a better place?

I am certainly trying! I believe that our recent offering of Data Career Coaching is helping to encourage more women and minorities to get into or advance their careers in data. As we know, more diversity in the field produces more innovation, and better products/tools for all of us.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

As with most issues, I think that there are multiple contributing factors. Some of these factors include lack of support to manage family responsibilities, limited access to capital/investment funds, feeling un/underqualified, overthinking, and more.

Can you share with our readers what you are doing to help empower women to become founders?

Lena and I have always been extremely supportive of any woman who comes to us to discuss being a founder of her own business. I believe that us simply existing in the technology/data space as African-American women can be inspiring and encouraging to other women. We also use our influence on boards, and as co-organizers of the Blacks in Technology Nashville chapter to encourage more women and minorities to get into tech, and possibly become founders.

This might be intuitive to you but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

There is a lot of growth happening now in business, and especially in tech. There is absolutely no reason that women should be left out of this! We are half of the global population, and should be represented as such in every industry. Women have ideas and perspectives that can change the world, and those ideas should be given the chance to grow and develop.

Ok super. Here is the main question of our interview. Can you please share 5 things that can be done or should be done to help empower more women to become founders? If you can, please share an example or story for each.

  • Access to capital/investment funds to start or grow their businesses
  • Community/family support to manage family responsibilities such as caring for children or elderly family members
  • Access to education — around the world, 132 million girls are out of school. Having access to an education allows girls to understand their options and make better choices for themselves. Some of those choices will be to become founders of their own businesses.
  • More representation of other women founders that aspiring founders can learn from and be inspired by
  • A community/mentorship of other women founders that provides support for new or aspiring women founders. There are communities like this, industry foundations, online communities, etc. I recommend aspiring women founders check these groups out. Having a group of people that understand the challenges you face can make all the difference.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

As a black woman in tech, I feel that it’s very important to get more black people into tech, and help more black people advance their careers in tech. There should be a way to connect black tech talent with black founders, and other companies that want to hire diverse talent for their teams. That’s something we hope to spark in the Nashville chapter of Blacks in Technology.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I’ve been following Dan Price’s journey with Gravity Payments, and I love his approach to business. It seems that he’s very fair and equitable to his team and wants them to be successful as individuals as much as he wants the business to be successful. I love that way of doing business and try to incorporate it into my own daily work. It’s important to make sure your team feels valued and well compensated, not just because it improves the success of your business, but because as humans, we all deserve to be appreciated and treated well.

How can our readers further follow your work online?

Readers can connect with us via our LinkedIn Page, on our website, and on our social media accounts.

Website: RachelWinfree.com

Twitter: @RachelWinfree

LinkedIn: https://www.linkedin.com/company/rachel-and-winfree-consulting/

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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