Season 1,

63: Paying Taxes PROPERLY as an Entrepreneur with Joe Saul-Sehy

June 30, 2017

This is an essential topic to cover because paying taxes is something all entrepreneurs and self-employed people have to do. Making a lot of money is great, but you have to plan for paying taxes. This includes putting money aside, keeping track of expenses, and working with a seasoned CPA. In this episode, Joe offers great advice that will hopefully save you time, money, and hassle.

Joe Saul-Sehy is the creator and co-host of the award-winning Stacking Benjamins podcast, one of the top personal finance podcasts in 2016. Joe is a former financial advisor (16 years) and represented American Express and Ameriprise in the media. He was the “Money Man” at Detroit television WXYZ-TV, appearing twice weekly. He’s appeared in Bride, Best Life, and Child magazines, the Los Angeles Times, Chicago Sun-Times, Detroit News and Baltimore Sun newspapers. He’s also appeared online in more than 200 different places, including and

Time Stamped Show Notes

[4:30] Having no background with money education, Joe was hired by a friend as a financial advisor for a firm. His first year he made $85,000.

[6:20] Since a license is not hard to get, be sure to hire a financial advisor with at least 10 years of experience.

[9:20] Now knowing how taxes work, Joe didn’t know he had to keep track of every business expense, he wasn’t withholding money. When a CPA told him how much he would have to pay, he got angry at him.

[11:07] Being debt free is good but he owed over $20,000 of taxes. Had to think of a plan to pay.

[13:46] Joe’s thought were, if I don’t pay, I’ll make more money and pay later. Didn’t file taxes for two years and didn’t know about the failure to pay penalties.

[16:15] On the second year, he earned more money but didn’t put any away. At month 21, letters from the IRS started coming, after 4 or 5, Joe decided to look for help.

[18:35] Found a much better CPA who also was a counselor. They made a payment plan, filed paperwork to have some reductions and he was learning had taxes work.

[22:24] For his mistakes, Joe had to pay about half more than what he would’ve if he had filed on time.

[23:30] Learned to build income streams to make money in different ways and had better money management systems.

[23:04] Everybody makes mistakes and we don’t talk about those mistakes, but some don’t learn from them. Follow a process and talk about money.

[28:08] Failing Forward Segment

  • What is the bottom line reason of this failure? – “I didn’t know how the rules work, when I do things now I make sure I know the lay of the land. Do some basic homework before you do anything.”
  • What is the single most important lesson they and you learned from this? – “Not the mistake that I made but learning the lesson afterwards. Whenever I get payed to take a percentage in put it in a tax fund. Automate.”
  • What are the major ways you protect yourself from future failures? – “Know how the rules work, have people that are more knowledgeable than you.”
  • Who do you turn to when you need help? – “Roger Whitney, a CPA buddy who’s great, Of my co-host in the podcast and my coach for over 20 years, Mary Lou.”
  • What advice would you give to someone in a similar position? – “Don’t bury your head.  There’s this great quote from Jack Welch when he was at GE and he said something to the tune of: Don’t confront reality the way you wish it were, confront it the way it is.”

[34:55] late thirties mentor wrote a note leaving to do something else he like what he was doing but didn’t love it build up a pile of money other mountains to climb Everest twice, sold my business at 40, went to school to become a teacher. Financial stuff light way entertained learning by play

[38:55] Connect with Joe at and find him on Twitter @AverageJoeMoney.

[40:12] Joe’s final thought: Pay the IRS and learn from my mistake. Get good help on your corner and keep listening to this podcast.

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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