This interview series features inspiring female entrepreneurs who have launched and run successful businesses. Through our peers’ experiences, we can learn practical lessons and insights to empower us on our entrepreneurial paths. Crucially, storytelling de-risks entrepreneurship so we believe it is an essential pillar in closing the opportunity gap for female founders.



Firstly, tell us a bit about you. 

I’m Khaleelah Jones, founder and CEO of Careful Feet Digital, a digital marketing agency that created Dime Digital, which automatically writes and designs content and posts it to social media for microbusinesses looking to spend less time creating social media assets. I’m 31 years old and originally from Washington DC, but I’ve lived in the UK for about 7 years now.

I started my career in copywriting, and then worked at a series of startups, including LivingSocial. After working as the head of marketing at WellTok, a health company, and being a part of a team that doubled our user base in six months and secured $18m in Series B funding, I went back to school! I got my PhD at the University of Bristol, and followed that with an MBA at Quantic, working as a freelancer throughout my time in school. After graduating, I launched Careful Feet Digital.


Tell us about your business, how did you come up with the idea?

Careful Feet Digital is a digital marketing agency that has recently undertaken a digital transformation and built Dime. Our goal with Dime is to provide very small businesses the same digital marketing expertise and support agencies and other tools provide larger businesses, at a lower price point (and taking up less time). In doing so, we are democratizing access to quality digital marketing expertise and helping everyone find and share their voice.

I came up with the idea after working as a freelancer throughout my time in university. So many people need high quality digital marketing assistance, but don’t have the time, budgets or knowledge to find and hire agencies or even freelancers. I noticed this gap in the market and decided to do something about it, so Careful Feet Digital was born.


what was the moment everything changed for you? Describe that moment when you decided to fully commit to your idea and the first few steps you took to make it possible.

To be honest, I think I was “circling the drain” of starting the business for several years while freelancing- I had the idea, but was too scared to commit fully, so I’d do a little research here, have an interesting conversation to refine my idea there- but never really took the leap. One day in 2018, I had a life altering conversation with a business coach; I was thinking about becoming a co-founder in a client’s business and wasn’t sure if I was committed. When reviewing my career objectives with my business coach, we really cracked open the issue: I wanted to start Careful Feet Digital and really make a go of it. The next day, I made my first hire and started having conversations with my freelance clients about becoming clients of CFD.


what were the initial challenges you came up against and how did you  overcome them?

Fundraising has been a huge challenge for the business. We are building a big technical product, which takes money to do. I’ve had offers from potential investors, but the terms always seemed off to me: stringent salary cuts, massive dilution of ownership or even the feeling that someone doesn’t really get what I’m trying to do. So, we took on consulting projects, operating as a traditional agency, to fund the build of our technical tool. It doubles our workload but the business is fully in our control, so that’s a worthwhile trade off.


what was the first win that made you feel you were onto something?

The first time I shared Dime with a small business owner and saw her light up, and really get excited about the opportunity to have a great digital presence, I knew this was the right path.


Did you take the investment route for your business or are you self-funded? Can you share some insights on your decision and the process?

We’re self-funded, using the profits from our consulting arm to fund the development of our technical product. The terms of the investments we’ve looked at have just not been what we would want in a business partner relationship. Although one day we may need to take funding, we’re holding off for as long as we can so we can retain ownership and forge our own direction.


what has been your best investment?

The people I work with every day. All of them are simply amazing, and are as dedicated to building this business as I am.


Have you made any mistakes or faux pas? if so, can you share with us?

My biggest mistake has been taking on clients for less than we are worth. I’ve always wanted to make sure that we are accessible to businesses of all sizes, but at the same time, I’ve learned the hard way that if you devalue your services, others won’t value them, either.


what’s your experience of being a woman in the start-up ecosystem and what in your mind needs to change?

When it comes to getting funding, I’ve found the process to be really disappointing: there’s still tons of old-fashioned sexism (I can’t count how many times I’ve been asked what my “family plans” are) and overt racism. But, there are so many amazing networks of women who are supporting one another in business, and I’ve been lucky to tap in to quite a few, such as Ada’s List and the Wonder Women Dinners.


what’s been the greatest lesson you’ve learned since starting your own business?

Have patience and don’t rush things!


Have you had any role models or mentors along the way?

So very many- ordinary women who are killing it in their businesses, such as Ciska van Grootveld, my business coach and founder of I am Groots coaching, and Nousha Watson, the founder of Ethically Woven and an amazing mentor.


with the future in mind, where would you like to be/where do you see yourself in the next 5 years?

I’d love grow Dime into a multi-million pound, international company, helping thousands of businesses every year and attracting the best talent to do that, and keep CFD a booming digital agency. After that, I’d love to start a VC firm that helps minority women raise capital for their businesses.


Can you tell us one of your goals for 2020?

More down time with my husband- I find that I have the best ideas after some rest, anyway.


what can our readers do to support your business?

Two things- one, be part of the rising tide and support female-led businesses, either through your custom or your guidance. Little acts of kindness have helped me so much along the way and I think that can turn into a chain reaction. Second, use Dime and give us feedback. This will help us get better and better!


what books, podcasts or resources would you recommend? 

The Founders Dilemmas by Noah Wasserman was a huge help for me, as was The Lean Startup by Eric Reis. The Monk Who Sold His Ferrari and The Big Leap have also been hugely impactful reads for me in the past year. I’d also recommend a business coach, mine has been utterly transformative in how I view and run my business.


What advice would you give anyone about to start a business?

Be clear on what you want when you set out, but also be flexible and know that’s going to change based on customer feedback, hires you make—just the world of business in general. Clarity, along with openness and curiosity, have been my best allies as I’ve built my business.


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Leah williams

Leah williams

About your author


Leah Williams is the Blog Editor for Found & Flourish, working with Founder Lara Sheldrake to ensure every piece of published content is empowering, inspiring and well presented, just like the women we work with.

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