This guest is amazing. His confidence and ability to help others change their lives shines through in his words as he discusses a wide array of topics of interest to the soul of any entrepreneur.

What Do I Want PDF  |  Personal Assessment PDF | Recommended Reading List

With a common-sense approach that would put the edgiest person at ease, Cash Flow Diary podcast guest Aaron Walker has a lot to say about living with accountability and purpose. This phenomenal and highly successful businessman and entrepreneur is also a business and life coach who helps men explore the meaning behind their objectives, and then helps them achieve those goals with greater focus and balance for improvement across all areas of their lives and relationships. This guest is amazing. His confidence and ability to help others change their lives shines through in his words as he discusses a wide array of topics of interest to the soul of any entrepreneur. Aaron talks about how we can create a roadmap to those things we desire and what that requires of us, particularly as men. Listen as he shares his story of how he grew to be the man he is today. Raised in a family with a hard-working father and “never say can’t” mom, young Aaron learned leadership skills that would stick with him through his life. He decided early on that he would be an entrepreneur. He didn’t call it that at the time, and it wasn’t something everyone was doing, but it sure suited Aaron. In fact, he has been at the helm of several impressive entrepreneurial endeavors for more than three decades! In this fascinating, introspective interview, Aaron talks about all sorts of things, including essentialism and what that means in our world today. There’s so much good information in this episode that you might want to listen to it more than once! Don’t take our word for it. LISTEN NOW

Show Notes


On this episode of Cash Flow Diary, J interviews Aaron Walker who is a highly successful business and life coach for men. In his work Aaron has inspired many through his leadership, mentorship, and consistent pursuit of excellence. He helps men explore the meaning behind their objectives, as well as achieve goals with a greater focus and balance for improvement across every aspect of their lives and relationships.

Episode Rundown:

[03:45] Aaron’s origin story

[06:28] Pawnshops

[11:47] Generational work ethics

[16:53] The entrepreneur rollercoaster

[19:16] Top 3 books

[23:00] Contributing to the life of men

[25:08] Apply for a free one-on-one session / J’s episode insight

[27:44] Men acting like men

[32:14] How to grow

[36:46] The 5-10 year plan

[38:39] Definition of ‘grit’

[40:36] Contacting Aaron

[45:37] Advice for new entrepreneurs


Main Questions Asked:

  • What is your opinion on work ethics and generations?
  • What is necessary for an entrepreneur to build something that lasts?
  • Knowing what you know now, would you have started being an entrepreneur at all?
  • How did you learn to deal with the entrepreneur rollercoaster, and what can we do to prepare?
  • What are your top three books?
  • Why contribute to the life of other men now?
  • What would you say to someone thinking ‘What can I do to grow?’
  • Do you really have to do a 5-10 year plan?
  • What is your definition of ‘grit?’
  • What is your advice for someone considering becoming and entrepreneur? 

Key Lessons Learned:

  • Fail fast, fail forward, and fail frequently.
  • Some people are creator/developers and not maintainers.
  • If you have the talent to make money, look for opportunity to help others.
  • If we want to have things tangible, then sacrifices have to be made early in marriages.
  • Entrepreneurs not only create value for the customer but also create jobs for others.
  • It’s important to get rid of the non-essentials and focus on what is vital.
  • You will be the same tomorrow as you are today, except for the books you read and the people you meet.
  • A goal once attained becomes a responsibility.
  • Take one measurable action toward one of the goals you have set for yourself.
  • Clarity leads to power and the power to do two things, 1) decide 2) act.
  • If you are a success at work and you do it at the expense of your family, you still end up a loser.

Preparing for the Entrepreneur Roller Coaster

  1. Start Reading More
  • You aren’t going to go to bed and wake up smarter! Make sure you read every day.
  • Aaron reads 2-4 hours a day
  1. Start Building Relationships
  • Aaron spends 60-90 minutes a day writing letters and emails of empowerment, encouragement, and making check-in calls in order to build relationships.
  1. Create Margin In Your Life
  • This involves time, as well as money, so you can build a buffer and be prepared for the roller coaster.
  • If you are prepared financially, you can ride out the dry times.
  • If you have margin in your life from a time standpoint, you will have time to read, learn, and do better.

Aaron’s Top 3 Books 

  1. How to Win Friends and Influence People (Dale Carnegie)
  2. Essentialism – The Disciplined Pursuit of Less (Greg McKeown)
  3. Business Brilliant (Lewis Schiff) 

Men Acting Like Men

  • A lot of men don’t take notice of the value of other men in their lives, and the relationships can be forged.
  • Sometimes it takes a tragedy for men to wake up.
  • Don’t let it take a disaster in your life to realize the value of pouring yourself into other people.
  • It is possible to be a ‘servant leader’ to your community, families, organization, and careers.
  • When you invest in other people and help them achieve their goals and milestones, your life is better as a result of it.

Success and Grit 

  • The overriding theme to successful businessmen is grit.
  • Aaron defines grit as sheer determination and perseverance. Remember: “Can’t couldn’t do it and could did it all.”
  • Don’t aim to do 15 things average. Rather, aim to do 2-3 things really well.
  • Always write your goals down, make it measurable, and incorporate dates.

Thank you for listening! If you enjoyed this podcast, please subscribe to the show in iTunes 

Links to Resources Mentioned

View From The Top

Iron Sharpens Iron Groups

How to Win Friends and Influence People


Business Brilliant

Halftime – From Success to Significance

Click to Tweet

Are you ready for the entrepreneur roller coaster? Find out 3 ways to prepare w/ @VFTCoach & @CashFlowDiary cashflowdiarypodcast.com

Why is it important to create ‘margin’ in your life? Find out w/ @VFTCoach & J Massey of @CashFlowDiary cashflowdiarypodcast.com

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