Taking the Leap

Jess is the founder and executive chairman of inDinero, a business that runs thousands of companies' tax, accounting, and finance operations. She is also the Co-Founder and Chair of Astonishing Labs and founding partner of MahWay. This venture builder creates innovative, industry-changing billion-dollar businesses that improve the world. She earned her Associate of Arts from Bard College and her Bachelor's in Computer Science from the University of California, Berkeley. She is in the Harvard Business School President’s Program and a Young President’s Organization (YPO) member. She enjoys flying her commercial multi-engine pilot's license in her spare time with an instrument rating. She started her first business in high school and was has been on the cover of Inc Magazine and was recognized on both Inc. and Forbes Magazine's "30 under 30" superstar entrepreneurs. Her combined companies have a value of over one billion dollars.

Show Notes:

  • Jess's entrepreneurial journey started at 13 because she knew she "did not want to work for anyone else."
  • She started a business to solve her own problem and then used it to solve others.
  • Barnes and Noble was her first mentor as she was pulling books off the shelve to learn about business. She realized early how important it was to learn and grow and later get mentors and coaches to help her build her business.
  • (11:45) Business got easier as it got larger and scaled. The hardships of the early days will not last forever.
  • (14:30) Don't compare yourself to others...you are in competition with yourself. Focus on your "next step" and your journey!
  • Jess likes the ratio of focusing 80% on the next 45 days, 10% on the next quarter, and 10% on the next one to five years out.
  • (15:50) "People consistently overestimate what they can get done in the next 30 days but underestimate what they can achieve in five to ten years."
  • (17:15) Entrepreneur communities are super important to support each other on your journey.
  • (18:45) The real challenge is our mindset and attitude. Most entrepreneurs have an understanding of what needs to happen next. 
  • (24:25) The greatest growth comes from taking advantage of the latest trends! How are you going to leverage AI? 
  • (26:10) Time blocking is a productivity hack that people can use to accomplish more. Elon Musk does this.
  • (30:00) What is the difference between the entrepreneurial vs. employee mindset? First, the biggest difference is you have to have a sense of ownership. Everything starts and ends with you. Second, you have to be optimistic at all times. This also bleeds over to your personal life. Third, you need to grow yourself constantly. How do you evolve as a person and leader?
  • (32:15) "There is no such thing as work-life balance. As an entrepreneur, your business is part of you. You don't have spouse life or child life balance...they are a part of your life."
  • (37:00) How do you have an optimistic attitude when things are going wrong and during a crisis? 
  • (41:00) If you have never taken a leap in your career or life, you are probably not pushing the boundaries enough.
  • (43:00) When Jess moved from software to biotech, she knew it would be a ten-year investment and she had to be willing to be uncomfortable and start all over. Being an outsider allows you to see things that others may miss, push the boundaries, and be innovative.
  • "The more you learn, the more you are able to learn new stuff and it becomes exponential." Examples are Steve Jobs and Elon Musk
  • (48:00) Jess gives insights she has about the future based on her research and investments.
  • (51:45) If Jess had the ability to give a State of the Union Address to the American people what would she say?

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Creators & Guests

Robert Dickie
CEO, Author, Entrepreneur, Investor
Mitch White
Freelance Audio Engineer, 2011 Recording Connections Certified Audio Engineer
Tristin Dickie
Nashville Fellows Program 2022, Marketing Assistant for Affinity Technology Partners, Professional Photographer freelancer. Go VOLS!

What is Taking the Leap?

Taking the Leap Podcast hosted by Robert Dickie III discusses changes in our global economy impacting the way we work and live. For young professionals starting their careers, mid-career professionals navigating changes and late-career professionals thinking about starting an encore career, Robert and his guests discuss the global economy, technology, workplace developments, and all the latest changes impacting our professional lives.