Beyond the Uniform

Beyond the Uniform is a show to help military veterans navigate their civilian career. Each week, I meet with different veterans to learn more about their civilian career, how they got there, and what advice they'd give to other military personnel.
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Beyond the Uniform



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Jan 16, 2017

“I didn’t start it with being a company in mind. I knew it was possible to make money but I didn’t know how or how much. My goal was to make my $125 back. My goal beyond that was to have date money - maybe $100 a month to take my wife out to a nice dinner. And it took seven months to make my first $100… and then after that it just took off. And I’d say that within two years I had replicated by day job income."
– Ryan Guina

Ryan is the Founder of Cash Money Life & The Military Wallet - two websites that focus on helping people better manage their finances by offering informational articles, tips, tutorials, and product and service reviews. He has run these sites for over nine years and been featured on publications including The New York Times, The Wall Street Journal, and LifeHacker. He started out in the Air Force, where he served for six and a half years as an Electrical-Environmental Specialist. After transitioning from the military, he worked at BearingPoint as a Management Analyst and then at the Computer Sciences Corporation as a Business Process Modeler. In addition to running his websites, Ryan currently serves in the Illinois Air National Guard.

Todd is the Founder of Kill Cliff, maker of the recovery drink with the same name. Kill Cliff has about 40 employees and makes continuous donations to the Navy SEAL Foundation. Todd also serves as the CEO at BAM Worldwide, the leading provider of cash management technology for small to medium transportation companies. He is also the Founder & Chairman of Triserv Appraisal Management Solutions, a real estate appraisal management company. Todd started out in the Navy, where he served as a SEAL for four years. After his transition from the military, he held a variety of positions at Kroll Associates, United Rentals, and Jacobs Private Equity.

In this conversation, we cover a lot of topics, including:

  • How Ryan doubled his income in just two years by doing something he loved
  • Financial advice every veteran should hear
  • The emotional struggle of looking for a new job and identity
  • Resources to help veterans start their first company and advice on how to make it happen
  • And much, much more…

Selected Links

  • Ryan's sites:
    • Cash Money Life -  a personal finance and career journal with tips about money management, career topics, small business, increasing credit scores and more
    • The Military Wallet - Personal finance for military, veterans, and their families. Updates for GI Bill, VA Loans, veterans benefits, military discounts and more.
  • Wordpress - An essential component for creating your website
  • Books
    • Big Magic: Creative Living Beyond Fear - this was one of my recommendations but I think it's really essential reading for creative, artist, or entrepreneur. The audiobook version is really fantastic.
  • Conferences
    • FinCon - financial media conference
  • Podcasts
    • Pat Flynn- smart passive income - anything digital marketing, apps
    • Entrepreneur On Fire - JLD, very top level but doesn’t dive as deep, good for inspiration
    • Tim Ferriss - what makes people tick and tricks they’ve used to be successful
  • Other

Show Notes

  • 2:00 Ryan’s background
  • 2:47 - Ryan’s decision to leave the Air Force and how he approached this decision
  • 4:31 - How Cash Money Life & The Military Wallet were born
  • 5:47 - How Ryan has kept his company running for over seven years
  • 8:25 - What it was like to maintain a full-time job while also growing his business on the side
  • 9:40 - Ryan’s initial job search that landed him at Bearing Point, and advice on how to approach this
  • 13:20 - When Ryan made the decision to jump in and work full time on his own company
  • 16:30 - An overview of Ryan’s sites, Cash Money Life and The Military Wallet
  • 18:13 - How Ryan knows the topics to write about each week, and how he breaks down his time
  • 19:16 - If Ryan’s time were a pie chart, how he divides his time each week
  • 21:30 - Ryan’s advice to other veterans considering starting their own company
  • 24:04 - Ryan’s advice around growing your audience once you have started a company
  • 26:00- Integrity, and the importance of maintaining this in your relationship with your customers and community
  • 27:05 - One of the most challenging moments in Ryan’s 10 years of running his own company and what he learned from this
  • 29:30 - The concerns that come with starting your own company and Ryan approached this
  • 30:45 - How Ryan’s work at Computer Sciences Corporation and Bearing Point helped him in starting his own company, and advice on whether or not to dive directly into your own company
  • 33:58 - How Ryan continues to learn as he is growing his own company and recommended resources for aspiring veteran entrepreneurs
  • 35:45 - Books and Resources Ryan would recommend to veterans
  • 37:15 - Ryan’s advice about finances and what he has learned with working with veterans and their finances for over 7 years
  • 40:30 - An overview of the concept of a “Master Mind Group” and how Ryan went about creating his group
  • 44:00 - Final words of wisdom