Skip to main content
turnaround sign, outdoors

Work Worth Doing: How Jason Long Turned Around A Death-Bed Company & Sold It For $14 Million Dollars

In this listen-to-learn discussion on the Share Life podcast, I'm chatting with repeat guest Jason Long. This will mark his fourth appearance on the podcast!

After getting together recently for some Korean BBQ and hearing the conclusion of Jason Long's CEO journey, I asked him to join me on the podcast to share his insights on the journey of transforming a dying company into a multi-million dollar deal.

Jason is a serial entrepreneur who normally launches and runs his own companies. But, several years back, an opportunity arose to turn around a medical software business. He walked into the hellish scenario and transformed the business and people in it. And he was transformed in the process as well. In this episode, we talk about the situation and the lessons learned.

Conversation Highlights

  • How Jason Long stumbled into this CEO opportunity
  • Blindsided by the wreck of the business he walked into and the business horrors he discovered once he started leading the company
  • Advice for someone who has stepped into the hornet's nest
  • From losing several hundred thousand dollars per month to cash flow neutral
  • A revolving door of CEOs making compounding mistakes
  • How Jason changed from having an emotional connection from the company to the people
  • Seeing companies as another tool in the toolbox towards a designated goal versus having a personal relationship with the business - looking at a company like a machine instead of looking at it like a person
  • Being clinical and empathetic
  • Being foolish about managing funds when environmental forces are so volatile
  • Navigating outside forces that can drive or affect the business — in positive and negative ways
  • Sorting out the absolute nightmare scenario and why the company was not dead
  • Transforming a massive and archaic software system that is unusable
  • Being transparent about the company and what was going on
  • How the little things matter and how specific things make a difference - a business as a sum of its parts
  • How to have courage in a situation of distrust
  • Metering transparency based on what people can handle so they don't depart out of fear
  • Getting rid of the bad apples to transform the business culture
  • Being managed versus being led
  • Culture, threats, examples — disappearing communication
  • Evidence that hope is justified - not just talk, but real change
  • Reality painted against the background of hope and seeing the path forward
  • Important work worth doing and making a difference in people's lives

Watch or listen to our conversation below.

Connect With Jason Long

Listen To This Discussion

Click here to listen in on Podcasters by Spotify directly, or click play below to immediately begin streaming.

You can also find this discussion on Pocket CastsItunesSpotifyGoogle Podcasts, and wherever you listen to podcasts under the name, Share Life: Systems and Stories to Live Better & Work Smarter or Jason Scott Montoya.

Watch This Conversation

Click here to watch this discussion on Youtube directly, or click play on the embedded video below to begin streaming the interview.

Click here to subscribe to my Youtube channel.

Click here to find this video on Rumble.

Podcast - Listen To Learn, Jason Long

  • Created on .
  • Last updated on .