Episode Summary

Holly is joined by Jennifer Mackey-Mary in-studio this week to discuss her business, Everyday Style! As a seasoned retail professional, she left corporate life behind when she had her first daughter, and hasn't looked back since! What started as an individual wardrobe consultancy business has grown to a massive online styling membership that includes customers on SIX continents around the world.

Jennifer says she's an open book, and she could not be more correct! She shares some of the toughest lessons learned throughout her 12+ years of business, including her biggest regret and what she would do differently today. She also walks us through how she scaled her service-based business and how she converted her business from in-person workshops to an online membership empire.

The Everyday Style goal is to help women feel comfortable and confident in what they're wearing without breaking the bank or taking too much time in the morning! Every woman can be stylish, no matter her age, shape, size, or life stage, especially with the help from Jennifer and Everyday Style!

In this episode you’ll learn:

1:08 Holly shares her insights from 50+ episodes talking with entrepreneurs, as well as her own experience as a business owner

3:40 Holly previews Jennifer Mackey-Mary's background and business before welcoming her on the podcast

4:55 Jennifer Mackey-Mary joins the podcast and shares the purpose behind her business, Everyday Style

7:50 The "f-word" that is NOT allowed in the Everyday Style community, and the "s-word" that is!

9:05 Jennifer jokingly refers to herself as "the idiot who tried" and how that has carried her through starting her business to today

9:40 The start of Jennifer's business as an individual wardrobe stylist to help contribute to her family income while still having the flexibility to take care of her kids

11:15 Spent $100 dollars on a logo and website, it wasn't pretty, BUT it was functional!

12:50 The importance of finding a pain point and solving it for your ideal client

14:40 Jennifer's goal of becoming "5-mile famous"

15:40 How she spent ZERO dollars on marketing her first 3-4 years but still continued to grow her business

16:45 Jennifer shares the biggest mistake she made as an early business owner, and what she learned from that experience

23:50 The importance of trusting your gut for the bad AND the good, it works both ways!

24:55 How to scale a service business

26:15 What is a capsule wardrobe and how that became an integral part of Jennifer's business

28:00 The biggest pivot Jennifer made in her business when she moved from Washington D.C. to Minneapolis, MN

29:24 Rebranding her business and finally creating a professionally made website

31:35 Jennifer's biggest REGRET she has with her business and her advice on how to avoid it

33:50 The major difference between in-person business interactions and virtual-only and how to bring your personality to an online community

34:52 Corrine Crabtree episode mentioned!

35:18 Jennifer's quarterly customer feedback process that is KEY to her success

37:05 Jennifer breaks down why she created a membership-based business and all she has learned after starting one

42:40 Membership business model does NOT equal passive income

45:50 The average email list to membership conversion rate

47:05 Jennifer's biggest lesson learned during COVID, hint: feelings are NOT data!

49:45 How memberships allow you to stop reselling to the same customer, and instead evolve with your ideal customer

51:05 What's next for Jennifer and Everyday Style and her focus to make sure her core business is running smoothly before looking to grow or launch something new

58:11 Fashion sustainability, how Jennifer was impacted by the documentary "Brandy Hellville &...