Season 1,

76: How to Lose Money by Answering a Question with Robert Graham

August 20, 2017

How can answering a single question cause you to lose money? If you want to learn how to handle yourself in common business situations, this episode is for you!

Robert is a software engineer turned entrepreneur. He has run the gamut graduating from Georgia Tech at 20 to interning at Google NYC to writing a sonar system for nuclear submarines. Robert somehow went from being an engineer to writing, self-publishing, and selling a book about cold calling. He loves learning new things and being a jack of all trades but master of none. Lastly, Robert is the host of the personal finance podcast Your Money Over Coffee.

Time Stamped Show Notes

[1:05] An engineer turned entrepreneur working on products and things has answered a question that cost him thousands of dollars.

[3:09] Cold calling is was a necessity for Graham when he had to sell a software. That trained him for something he never considered.

[5:55] A question in a job interview can cost you thousands of dollars depending on how you answer it.

[6:59] Just out of grad school with a paid internship, salary negotiation was not considered.

[8:34] Doing research after grad school, Graham went on to have a job in a security company, where he got the job but learned about the importance of how to answer: How much did you made at your last job?

[10:22] Answering that question or not is valid but you never know what the employer would do with that. An offer based on that leaves the interviewee at a disadvantage for negotiation.

[12:09] Not wanting to stay any longer at the research lab, the security company was a jump from that job but not the best.

[14:13] Despite not being the best offer for the job, Graham took it and stayed there for a couple of years.

[16:33] Despite having to take it, the job wasn’t the best as it did not allow Robert to have more responsibilities.

[17:30] More money could mean a different relationship with the company but in the end, the job wasn’t great.

[18:19] Failing Forward Segment

  • What is the bottom line reason of this failure? – “I just didn’t think negotiation was an issue for an engineer. I didn’t understand that other people were paid to do this, to hire people and outnegotiate them to pay less for labor.”
  • What is the single most important lesson you learned from this? – “Negotiation comes up in everybody’s lives all the time. Everyone should have some negotiation skills and when it comes to things as cars and job it could make a difference.”
  • What are the major ways you protect yourself from future failures? – “I think it’s important most of all to be prepared. So you can read some books about negotiation, you can practice negotiation. Be prepared.”
  • Who do you turn to when you need help? – “I’ve developed some relationships over time with some other people in similar arcs in their entrepreneurial careers or their business careers.“
  • What advice would you give to someone in a similar position? – “You can always play for time and not answer a question.”

[28:16]  Be prepared for the questions that you hope they don’t ask.

[33:17] You can listen to Robert’s finance advice on the podcast Your Money Over Coffee at and contact him on

[36:15] Robert’s final thought: “Know what you’re worth, know what the thing you’re buying is worth and be prepared and know what relationships are worth.”

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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