• Jessie Ryan

S1 E20 Side Hustles & Entrepreneur Mentality with Josh Eskridge

Updated: Sep 26, 2020


In today’s episode of the Ditto Podcast, I am joined by Josh Eskridge, a successful fashion, beauty and artistic photographer based in Hartford, CT. Josh balances his thriving side hustle and passion for photography with a full-time corporate job as an ethics and compliance officer. We talk about the importance of having a side hustle, and how to balance your side hustle(s) with your day job.

We talk about a lot of different things in this episode, the general theme of conversation being how to be an all around better person, but especially about how it's important to find and stay connected to your “why” when pursuing a side hustle so that you stay motivated. We talk through the importance of using your talents to help people, and how cross-promotion and networking can be integral in building a community of likeminded creative entrepreneurs.

Listen to find out more about Josh and how he balances his life!


2:10 Meet Josh

6:47 How Josh balances his day job with his photography business

10:04 How Josh’s education helped shape him as an entrepreneur

11:15 Balancing a career with a side hustle

14:09 The importance of knowing the ‘why’ behind what you’re doing

18:28 What being an entrepreneur means to Josh

21:00 Figuring out balancing your multiple income streams

23:37 How Josh uses his talent to help people (Chai Lai Orchid)

26:45 What photography means to Josh

27:50 Using your talents for good

28:27 Examples of how you can use your talents to benefit others

34:05 Why Jessie decided to take up hair styling

36:45 Using social media to elevate others and cross-promote

39:30 The importance of cross-promotion

40:50 Some examples of great cross-promotion

44:30 Building a community of likeminded creatives

45:30 Josh’s pandemic project

52:10 Josh’s process when creating his BLM video

55:30 Books that Josh recommends on entrepreneurship

57:20 Navigating difficult comments on your posts, and creating traction with them.

1:03:50 One thing that Josh would tell his younger self


Josh Eskridge


IG - @jeskridge

FB - Josh Eskridge Photography

Boyce McCoy


IG - @mountainburst

FB – MountainBurst

Ariel Perez


IG - @arieldavid

FB - Ariel Perez Photography

Julie Hunter



IG – @juliehunter

FB – Naturally Boudoir

Monique Sourinho


IG - @bee.the.love

FB – Bee The Love

Pratik Naik


IG - @shotbypratik @solsticeretouch

FB – Solstice Retouch – Pratik Naik

Clay Cook


IG - @claycookphoto

FB – Clay Cook

Gary Barragan


IG - @photobygaryb @artbygaryb

FB – Gary Barragan Photography

Other Links and books Mentioned:

Chai Lai Orchid


Books mentioned

Think and Grow Rich by Napoleon Hill

How to Win Friends and Influence People by Dale Carnegie

Listen to the episode now!

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