Pop Quiz, Monday with Jacob Rupp

Jacob Rupp

The Pop Quiz, Monday is a fun little exam that we love to give to savvy business owners. The examination is not a surprise after all since the interviewee already knew about the questions in advance. However, we can always pretend and have fun with the scenario of a young entrepreneur sitting in class nervously biting on their pencil. They are ready to take a pop quiz on a chapter that they were supposed to read the night before. Instead, they played Metroid all night on their SNES (Oops, this was me in high school). The real purpose of the pop quiz is that this is a fun way to introduce business tips from real-world experiences that you can not learn in a classroom. We want to thank our entrepreneur for being a good sport and volunteering their time to answer a few questions to help our community grow from their knowledge.

I want to introduce you to our guest today who will be taking our Pop Quiz Monday.

Can you please tell everyone your name?
Jacob Rupp

Jacob Rupp
Photo credit: Jacob Rupp

What is your job role?
Founder of Lift Your Legacy, head coach

Tell us about your company?
Our organization helps individuals and small groups uncover their most genuine selves, identify and reach their goals, and create the change in themselves they desire.

What do you love most about your job?
It is highly rewarding to help people who are looking to live a healthier, better life set the incremental changes necessary to begin to improve their lives, and then celebrate with them in their results; maybe its weight lost, businesses built, or peace restored in a marriage.

What motivates you to get up every day and go to work?
My family and my desire to change the world. Providing for my family is crucially important; I want my wife and kids to have the lifestyle and comfort that allows them to live a happy life. I have a fire deep down to change the world, and to create more peace on consciousness in the lives of millions of people.

How do your co-workers inspire you?
I work with a team, but in general, I am more inspired by my clients who go through the difficult work of making their lives better.

How do you have fun at work (team building, pranks, etc..)?
For me, work is, for the most part, all fun. I love interviewing guests for my podcast, teaching teens and collegiates, and helping my clients learn more and break through barriers in their life.

What are some of the challenges of your job?
I struggle a lot trying to identify my ideal clients for coaching, staying organized between the lots of tasks that I have in front of me, and ‘niching down’ as all my coaches tell me to do.

What are some lessons learned from a past project that you can share with us?
I learned how to manage client expectations. Someone felt that literally by hiring me, he would (even without doing the work) have a breakthrough and get the results he is looking for. While it seems silly, it is important to be upfront that no matter what, long term change takes time, and one must not only be willing to invest, but one must also be dedicated to making the steps in their own lives to create successful habits.

What advice would you give to someone who is starting in your industry?
Have a backup plan, a lot of humility, learn your craft, and don’t be afraid of failure. When you are doing work that involves putting your creative self into what you do, oftentimes we take it personally when things don’t work out, and instead of being clinical about what went wrong, we feel rejected. It’s normal–so that’s why having your own coach and support team helps A LOT in the beginning (and middle and end!)

Thank you for taking our pop quiz today. You get an A+ for effort. You can learn more about our interviewee and their business by visiting them on the web:



Author: Ricky Singh, MBA

Editor of The Startup Growth.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.