Episode 141: Transitioning From Military Service to Entrepreneurship With Phil Randazzo

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Phil Randazzo AmericanDreamU

Phil Randazzo

Phil Randazzo started AmericanDreamU.org to help Veterans make the transition from military life to entrepreneurship.



Listen to how you can transition from a structured work environment, like the military or even Corporate America, to working on your terms.

Phil talked to us about the challenges Veterans leaving the military now face. He also discussed some of the similarities between leaving the military and a job in Corporate America for the entrepreneurial path.

Phil is a serial entrepreneur and author who has been helping Veterans since 2003 when he first hosted a “pro-troops” rally in Las Vegas. Before starting American Dream U, Phil founded DefendingFreedom.org, which raised over $2 million for veterans and their families.

AmericanDreamU provides military members interested in learning more about entrepreneurship with online resources, trainings on bases and mentors.

Phil did not serve in the military himself, but felt called to give back to those who have done so much for our country.

Programing Note: This is a special episode of UnStuckable in honor of Veterans Day.  

UnStuckable, along with The Daily Travel Podcast and the DudesDay podcast, encouraged 45+ podcasts to dedicated one episode to the story of a Vet during the week of Veterans Day. Listen now at VoicesForVets.co

Key UnStuckable Takeaway

Entrepreneurship is all about collaboration and teamwork!

Most military members don’t consider entrepreneurship when they leave the service because they don’t feel prepared for that type of career path. Little do they know, the military instilled them with two of the most important qualities to become a successful entrepreneur: collaboration and teamwork.

Most successful entrepreneurs start their business by finding key partners to compliment their strengths and weaknesses. Working with a partner or team is critical to the the development and growth of almost any business.

Quick Action to Get Unstuck

Develop a good morning routine!

Several of our guests have discussed the importance of starting your day with a set morning routine to help you get the most out of the rest of your day.

Phil provided two suggestions to start your day off right:

1. Don’t wake up to your phone. Don’t use your phone as your alarm clock, use an actual alarm clock instead. In fact, don’t even put your phone in your bedroom when you go to sleep at night. This will reduce your temptation to check email or social media as soon as you wake up. Phil recommends not touching your phone or laptop during the first hour of your day.

2. Accomplish your most important task first thing in the morning. If you can get your most important task done first, no matter what happens during the rest of your day, you’ll feel less stress and more satisfaction throughout the rest of your day. Eliminate distractions until you get your most important task done and even consider not checking email or social media until it’s done.

UnStuckable Quotes From Phil

“These guys are going to be leading our country in 20-30 years, and I’m really excited about that.”

“I sure hope I break even on this deal because I could sure use the money.”

“I can tell a story more about my failures and what I learned from them than I did with my successes.”

“Don’t work on your weaknesses.”

“Every venture that I tried doing on my own failed.”

“Your mind will only search for things you tell it to search for.”

More Habits & Actions

  • Work with a mastermind group. Seeking out people with similar interests or those who are pursuing the same goal as you is a great way to learn more and develop better insights. A good mastermind group can motivate you to continue working when you are overwhelmed or provide you with ideas when you are feeling stuck.
  • Review old information. It can be very beneficial to go back and reread books on a topic you want to learn more about or if you need a refresher. More often than not you’ll gan a new perspective on the same information the second or third time around.
  • Identify your strengths. Everyone has their own unique strengths and weaknesses. You need to identify yours and learn to play to your strengths. Don’t waste time trying to improve your weaknesses because you’ll just end up with strong weaknesses. Focus on what you already do well and try to find a way to utilize those skills effectively.
  • Take action on what you have learned. It is not enough to read books and take notes on them. You have to take the information you learned and put it into action. This is the best way to fully understand the concepts you read about and understand them for your own unique needs.

Phil’s UnStuckable Lesson

In today’s lesson, Phil gave us three recommendations for how to start making a big transition in your life.

1. Know Your “Why”

As you consider becoming an entrepreneur, the most important question you can ask yourself is “Why?”

What would you do if there was no cost attached or no risk? What are you passionate about?

If you don’t have a strong “why,” you may not be able to push through those inevitable bumps in the road to success.

2. Build Your Network

Once you clearly understand your “why,” you’ll want to start seeking out people who are doing what you want to do.

Surrounding yourself with other entrepreneurs and like-minded individuals will motivate you. Find people who have accomplished the thing you want to do and ask them for advice. Most people will be honored and want to help you out.

Talk to people who are doing what you think you want to do. You need to understand the downside of your “dream job”.  Get an honest perspective about what that potential career path might really be like versus the version you have in your head.

Lastly, consider offering to work for someone for free. If you can provide value to someone at no cost to them, it just may lead to other opportunities in the future.

Networking is something you need to be doing constantly and you should never stop. Devote at least one hour a week to networking with people, no matter how well your job or business is going.

3. Start a Side Project

Before you pull the trigger and quit your job or leave the military, start a project on the side.

Here are some of the benefits of starting a side project:

  • You can still rely on your current income source and save more money to fund your transition. Think of your current employer as one of your initial investors.
  • You can test your idea and validate it to see if it’s a viable business idea or if it’s something you will enjoy working on over the longterm.

It may be hard to find time to start a project as you are working full time, but doing even just a little bit each day is a start. Carve out a small chunk of time each day and by the end of the week you’ll be amazed at how much you actually accomplished.





Start With Why

Example of a Human Resume

Pat Tillman Foundation

Think and Grow Rich by Napoleon Hill

Outwitting the Devil by Napoleon Hill

Winstreak App

Questions & Feedback

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