Season 1,

95: How to Lose Money by Running a Million Dollar Company with Jim Brown

December 21, 2017

Jim has led two companies from $1 million to more than $10 million and one from $1 million to zero. He has started eight companies and been a part of several others. Some have been wildly successful and others, well, not so much.

But all of it has empowered Jim with lessons on what works and what doesn’t, and helped him become one of the most highly sought after sales coaches in the tech community.

Time Stamped Show Notes

[3:55] After Compendium was acquired by Oracle, Jim pent 10 months while looking how to transition his way out.

[6:20] Ego was the main component in wanting to find a company to start and raise a million dollars in venture capital, which he did in 57 days.

[7:31] Maintaining a house takes a lot of time and work. Jim wanted something that could take care of that so the idea of an app was born.

[9:32] Taking investor confidence media coverage as market acceptance, Jim later found that those are completely different things. People would download the app but never used it.

[11:24] The app wasn’t really solving a real pain for the homeowners and some of them, couldn’t afford to hire the services offered, so they opted to do it the traditional way.

[13:17] Looking for a problem to solve, Jim went on to ask the people who already outsourced those services and talked with them.

[15:00] Most homeowners already had someone taking care of the maintenance of the house but wanted the pain of having to pay 10+ different vendors separately go away.

[16:35] All of a sudden a new company named Porch came out with more than 20 million dollars raised. Jim reached out to the CEO looking for an acquisition but the deal felt through.

[19:17] As he felt it, Jim feared telling his team that he failed. And when he told them, they all wanted to stay and figure how to make things happen.

[21:29] After selling everything to liquidate as much debt as possible, Jim started to tie that filure to him, personally. He made it his identity.

[23:48] Having gone through this much needed trial, after telling the bad news to his investors, more than half of them asked him what he’s doing next, as they were willing to write another check.

[25:00] After some digging with his therapist, the issue was that he needed to stop caring about everyone thinks of him and focus on who are the people that really matter. So Jim is finding himself again.

[26:44] Failing Forward Segment

  • Why did this failure experience happen to you? – “Ego. It was all about me. I wanted to raise the money, I wanted to build the application that I wanted to exist. Didn’t care about my customers. Didn’t care about what the pain’s they actually had. I was doing it for me, and that’s why I failed.”
  • What is the single most important lesson you learned from this? – “You have to solve a real problem for your customer. And if you don’t have a way to solve a problem and extract money, you don’t have a business.”
  • How do you protect yourself from failing in this way again? “I don’t think you do completely protect yourself from failure. I think you do need to be willing to take risks and be willing to try new things.”
  • Who do you turn to when you need help? – “It depends on what the situation is. I’ve now started to compartmentalize all the different roles that I have in my life. I’m a dad, I’m a husband, I’m a business owner, I’m a friend. I have to identify which role is currently failing an I find the right support system for that specific role.”
  • What advice would you give to someone in a similar position? – “One of the things that helped me is the separation of identity versus role. Inputs versus outcomes.”

[32:40] It’s hard to admit failure so that’s why we only concentrate on the successes. But our failures is what really teach us how to move forward.

[37:11] The Sales Tuners Podcast gives entrepreneurs ways to see what might happen in their journey and helps them with techniques to success.

[38:56] Download the Sales Tuner Workbook at: to set smart goals and actually achieve them.

[40:00] Jim’s final thought: “You will never get anything in life that you don’t ask for, so start asking.”

To hear this episode and many more like it on your mobile device, you can subscribe to How To Lose Money via iTunes or Stitcher.


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