I’m often asked how I stay motivated in trying to move my multiple endeavours forward. In addition to sweating it out at the gym, a lot of the motivation comes from reading the interviews I’ve conducted on the blog.
To help start the new decade with some insight and inspiration, check out this interview with Sophia Ruffolo, co-founder and CEO of femmebought.
From the femmebought website:
femmebought is an online directory of women-owned businesses but we are so much more than that. We’re a community that empowers more women to reach to the top; a community of smart, driven and passionate advocates who take action towards levelling the playing field.
1.What made you decide to go to law school and become a lawyer?
My grandfather was a lawyer fighting for people who couldn’t afford legal services. I inherited the desire to help people. My first summer after law school I worked in the courthouse in Chicago helping gain orders of protection for domestic violence victims. Later I went on to establish the pro bono legal programs for a global financial institution.
Helping people is in my DNA.
2. How did the idea for femmebought transpire?
Stacee, my co-founder, and I wanted to spend my money more deliberately and with purpose. The idea was to spend our money on women’s businesses. It inspired our friends to do the same. The first time someone told me they hired a woman from the directory I jumped up and down – I was so happy. Today we have 600 directory members and limitless possibilities.
I also really wanted to foster a sense of helping each other up. Our latest t-shirt designed by Stephanie Chinn embodies our mission. It’s of two women helping each other up to build a sign that says “Support Women-Owned”.
3. Did you encounter any obstacles when you went full-time with femmebought? How did you overcome them?
It’s been an incredible journey of ups and downs. Every time the air deflates from my balloon I turn a corner and find the air filling back up.
Funding is a big obstacle. It’s hard to find the dollars when you do the income thresholds are hard to meet. Navigating the application process is very complicated. It’s why we do so much funding education and the events are open to everyone.
Changing how I viewed myself was hard. Shifting from a successful lawyer to a baby business owner made me feel lost.
4. There are so many cities around the world that are entrepreneurial. What made you decide to focus on Toronto, Chicago and Tel Aviv as community hubs for femmebought?
They each have three things in common:
1) I already had a network
2) There are extraordinary women building businesses
3) We were welcomed with open arms by the entrepreneurial and corporate communities
5. What business book and/or podcast are you currently reading/listening to /recommend?
Venture Deals for a second time. If you’re seeking funding, read this book. We gave it out as a prize to women entrepreneurs at our last Girls Just Wanna Have Funding event.
Editor’s note: I first met Sophia at the aforementioned event. I highly recommend attending this event if you have the chance.

6. What advice would you give to someone who is looking to take their side-hustle to full-time?
Go for it!!! Do you have passion, drive, and vision? If yes, then do it. It won’t be easy or cheap but it is incredible to build and run your own business.
7. Whenever you feel overwhelmed, unmotivated or unfocused – what do you do to get back on track?
My partner in life is my biggest support system. Some days I feel like a failure and an imposter. He props me up and reminds me – Sophia – YOU’RE A CEO! Don’t worry if you don’t have that support system, femmebought will prop you back up!
8. Now that a new decade 2020, has begun, what is in store for femmebought?
Building a business is going to become more affordable for the femmeboughtfam thanks to incredible perks and packages that are coming.
Member access to one another for tips, help and advice just grew thanks to our members-only Facebook group for our paid subscribers.
If you’re curious about expanding into the Cannabis + CBD industry you’ll enjoy our upcoming Demystifying Cannabis for Women Entrepreneurs event in Chicago and Toronto.
9. Who are 3 female entrepreneurs that you admire/look up to and why?
This one is hard. I admire so many women entrepreneurs and want to emulate the qualities they have. Here are three women investor entrepreneurs I admire –
Vicki Saunders who founded SheEO, creating a membership for women and using the fees to give women-owned business loans. That’s pretty fantastic.
Arlan Hamilton who founded Backstage Capital started a fund to back Black, LGBTQ, Hispanic and women founders and has a great podcast.
Sheena Brady who founded Tease Tea and the Founders Fund providing early-stage women business grants.
10. How can entrepreneurs determine whether they should seek funding and financing options vs bootstrapping?
Come to the next femmebought Girls Just Wanna Have Funding event or watch our livestream on Angel Investing – www.femmebought.com/events It’s a good introduction to thinking about how to fund your business.
Spoiler alert – sometimes you’re better off giving back the check.
11. What is your definition of success?
Every time a woman joins the directory, every time I introduce a woman to an investor, every time I hear that a woman was hired from the directory – that’s a success.
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