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About the Creator

I’m Jon Gross and I’m glad you’re here.

As part of my personal and professional development journey, I am leveraging over 10 years as a CFO, M&A Professional, and Startup Generalist Operator into writing / speaking on my experience and learnings along the way.

I have seen a lot of good and bad operating at all 3-levels of business (board/investor/C-Level, manager level, high output individual contributor) and hope you enjoy!

LinkedIn Follow me on LinkedIn

Those closest to me would describe my personality as...
positive, upbeat, competitive, detailed, and efficient. Sprinkle in a bit of humor too depending on who you ask

When I'm not working you can find me...
playing any sport I can find, learning something new, hanging out with my wife and dog, watching standup comedy, playing cards/board games with friends, and/or enjoying a cold brew coffee

Topics of particular interest...
the intersection of tech/digitalization with legacy markets, including ways to reduce stress and making life easier for everyone, including vertical SaaS, insurance, finance, healthcare, and education; M&A and Entrepreneurship Through Acquisition (ETA/SMB); Miami Heat basketball, European soccer

My current goals are...
becoming a more consistent, thoughtful writer and communicator (this website is part of that), taking better care of my body (drink more water, exercise 3x/week, etc.), and setting better boundaries which will allow me to set and keep more consistent routines

Quote that resonates with you today...
while many years ago now, my high school yearbook quote was “a day without laughter is a day wasted”, which remains true today

*** Special thank you to my mentors, colleagues, influences, and parents. I would not be where I am without your support along the way

What's the Deal

From growing pains to capital gains — skip the scars and get straight to the real deal on building, scaling, and investing. Straight to your inbox.

The content herein reflects the views and opinions of Jon Gross and guest contributors and does not reflect the official views or statements of any current or prior employers.The content herein is the property of Jon Gross. and may not be used, reproduced, or scraped without express permission, including but not limited to for the purposes of training artificial intelligence models.

© 2025 Jon Gross. All Rights Reserved

© 2025 What's the Deal.

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