The Importance Of Being Self-aware With Jessica Kupferman

Jessica Kupferman is an internet and marketing pioneer who is unafraid of new platforms and opportunities. She began her career over 15 years ago, selling banner ads when the internet was considered a fad. In her career, she’s worked with successful small business and some of the largest companies in the world including Comcast, Subaru, Leisure Fitness, and Bank of America. Now, she is one of the most recognised experts in the content marketing industry, currently focused on podcasting media.


Jessica is the co-host and co-founder of the She Podcasts brand where she supports and develops unique female voices in the growing medium of podcasting. Her popular Facebook community boasts over 3,200 members, and she has successfully spoken, hosted events, and gotten sponsorship for her podcasts and events. She was also the host of the very successful Lady Business Radio where she conducted over 150 interviews including notable female entrepreneurs such as Tory Johnson from Good Morning America, Andrea Beaman from Top Chef, and Shark Tank’s Lori Cheek.

In 2016, Jessica launched j/k media agency after seeing the lack of proper representation for podcasters in the media space. Working with her clients, Jessica is able to use her Platform Model to successfully obtain many sponsorship and advertising dollars for her clients.

Jessica is a mother of three, a wife, and most importantly a woman whose talent and passion is helping individuals find their own voices through the medium of podcasting and make a living using that voice.


Jessica’s Key Points


  1. You have to be self-aware.
  2. You have to know how you work best.
  3. You need to know yourself very well.
  4. Know what your flaws are and where your strengths lie.
  5. Be ok with the plan if it changes.


Guest Links



Top Quotes


  • I have a communication’s degree which can go many different ways.
  • I didn’t really know which direction to go because, in my senior year, I had a baby.
  • I always wanted as a kid to have my own ad agency.
  • Almost everyone I know has started their career in banking.
  • I moved to marketing and started selling banner advertising.
  • I sold it to people who didn’t know why they wanted it or where it would click to.
  • I either had a great situation and a miserable boss or a great boss and a miserable situation.
  • I don’t really like selling, I don’t like to pitch and the following up.
  • I wanted to be a graphic designer and let others do the pitching.
  • I would get a job that wasn’t challenging and spend my spare time reading about design.
  • You don’t know how much time you’ve got left, so why would you spend your day doing something you don’t like. I was literally sick to my stomach every day.
  • I went for my other dream that I was afraid to go for.
  • My husband said I had to get a business coach who specialised in ADHD because that’s what I have.
  • The first thing my ADHD coach did was give me two clients.
  • You can overthink your decision until death.
  • There is no better way to learn that “off we go”.
  • I really recommend having a business coach.
  • Plan for what you need.
  • Each project was a learning curve as they came, so I said yes to it all.
  • I always proved low because it was a learning experience.
  • Each morning I did the most important task for that day.
  • When that task was done, I moved on to the next that would further my goals.
  • You’re going to have to be prepared that it’s do or die.
  • There are times when I go on job websites and then think “hell no!”.
  • When the kids wanted to go to summer camp, I just hustled up three new clients.
  • I have to make this work because it’s the only thing I can do without me being miserable.
  • I was overpaid and underworked and it did not feel good.
  • I used the extra hours I had free while contracting to learn new skills.
  • You don’t always have to hit the next step when you hit your goals.
  • I was able to dial my business back to get things done.
  • I know when clients start asking me certain questions, that I should focus in that area.
  • I’ve pivoted quite a bit.
  • I like to change my focus because I get bored of talking about the same thing.
  • I’ve been able to build a life that works for me.


Key Timestamps


  • 0:49 – Miserable corporate
  • 1:56 – My needs at the time
  • 2:37 – My first taste of marketing
  • 4:26 – Losing my mum
  • 6:11 – My perfect reason to leave my job
  • 6:56 – Consulting my husband and planning for my ADHD
  • 9:49 – Tackling each step as they come.
  • 12:42 – The unexpected things
  • 16:43 – True Grit
  • 18:57 – Knowing I could never go back
  • 25:19 – Creating freedom to do what you need to do
  • 27:02 – Adapt your business to what you need
  • 28:59 – Was it worth it?
  • 31:01 – The biggest thing
  • 34:09 – Guest links