056: Hillary Gadsby – best selling author, founder of The Boss Box and StilettoGal



In this episode I chat with Hillary Gadsby – an event and marketing dynamo and co-founder of The Boss Box. Hillary is also a best selling author and founder of StilettoGal.com, a multi-media company for women in business.

Check out how Hillary created the buzz for the Boss Box, overcoming the difficulties female entrepreneurs face when starting their businesses and how she found the drive to pursue her businesses and brand to create a movement rather than just a product.

1:30 – Welcoming Hillary to the show, background on her, and background her businesses and how they got started.

3:48 – Personal relationships being key to sales and business connections.

4:54 – The importance of collaboration.

6:13 – Challenges in building A Gadsby Affair, particularly without a professional mentor.

8:20 – The process to bring on partners and contractors.

9:37 – Why she didn’t have a mentor early on and how that led into her passion to mentor other women.

10:36 – The added difficulties female entrepreneurs face when starting their businesses and how Hillary dealt with them.

13:26 – Hillary’s moment of realization that she could leverage her experiences to help others through the Stiletto Gal.

15:30 – The challenge of getting people to open up and be vulnerable in an interview or conversational situation; how Hillary goes about addressing that.

18:23 – How Hillary found the drive to pursue her businesses and brand even through difficult times.

20:27 – More details on The Boss Box and creating a movement rather than just a product.

24:04 – The ways Hillary sees women doing business differently.

25:15 – The level of collaboration in the community that she’s building and what the key point of her mission is.

28:14 – Hillary’s feeling of being called to do this work and some developments coming to the Boss Box.

30:42 – How Hillary’s approach to helping people is different and addressing the “get rich quick” schemes out there.

31:42 – The importance of authenticity in her work and the challenges she’s facing with the Boss Box.

34:23 – Understanding what a position needs to do before hiring someone to do it.

36:42 – The “buzz” you get from creating businesses and feeling a pressure to get better.

38:55 – Continually being a learner and looking to others’ experiences.

40:22 – Deciding to make the Boss Box a quarterly delivery.

42:45 – The questionnaire.

46:34 – Learning more about Hillary and her businesses.


Resources and Links Mentioned:

The Boss Box

Stiletto Gal

A Gadsby Affair

Business Forums International


The Stiletto Gal Facebook, Twitter, and Instagram

The Boss Box Facebook, Twitter, and Instagram