[Veteran Entrepreneur Series] Empowering Veterans With Purpose & Entrepreneurship With Phil Randazzo

Phil Randazzo is the Founder of American Dream U, a nonprofit organization dedicated to helping military service members transition into successful civilian careers or launch their businesses. Since its founding in 2003, American Dream U has provided educational programs and mentorship to over 16,000 veterans and their families, featuring guidance from top entrepreneurs and business leaders. 

Beyond his nonprofit work, Phil has authored several books, including Mission Next, Funding Your Bigger Future, and Shark Talk. As an entrepreneur, he maintains business interests across healthcare, compliance, and franchising industries. He has been recognized for his service with honors like the key to the City of Las Vegas and a commission on Nevada’s Veterans Services Commission.

Here’s a glimpse of what you’ll learn:

• [03:11] Phil Randazzo discusses the mission of American Dream U
• [05:25] Why traditional transition programs often fail veterans entering civilian life
• [06:40] The journey of Combat Flip Flops’ founder and the role of meditation in emotional healing
• [09:27] Phil reflects on his personal struggles with identity, anger, and emotional suppression
• [13:33] How seeking relief through events led Phil to deep integration and self-awareness
• [21:43] Less You, More Life and its message of presence and purpose
• [25:45] The origins of American Dream U, starting with wristbands and wounded warrior support
• [30:57] Free online classes and mentorship available for veterans and spouses
• [33:06] How Phil personally funded the nonprofit and built support through strategic donors
• [37:25] Clarity Council’s approach to reevaluating life choices through quarterly reflection
• [41:59] Missy’s story of transformation and the life-saving impact of community and connection

In this episode…

Many veterans struggle with transitioning from military to civilian life, facing uncertainty, emotional upheaval, and misaligned career paths. Standard programs often push veterans into roles that mirror their service jobs without exploring their passions or personal growth. But what if the transition could be a transformative opportunity to rediscover purpose and design a life that truly fits?

Social impact entrepreneur and leadership mentor Phil Randazzo shares how identity challenges, suppressed emotions, and outdated belief systems can hinder veterans from fully integrating personal growth. He offers insights into shifting from seeking external relief to practicing internal integration — through tools like meditation, storytelling, journaling, and self-reflection. Phil emphasizes the importance of releasing inherited emotional patterns, cultivating awareness, and building community for sustained change. His journey of emotional awakening, marriage transformation, and helping over 19,000 service members provides a roadmap for creating lasting impact and self-discovery.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz interviews Phil Randazzo, Founder of American Dream U, about empowering veterans through personal transformation and entrepreneurship. Phil discusses his turning point, strategies for sustainable change, and the power of community. He also explores childhood belief systems, how transition impacts family dynamics, and the importance of integrating lessons rather than chasing relief.

Resources mentioned in this episode:

• Phil Randazzo on LinkedIn
• American Dream U
• Combat Flip Flops

Special Mention(s):

• Breaking The Habit of Being Yourself: How to Lose Your Mind and Create a New One by Dr. Joe Dispenza
• Awareness: Conversations with the Masters by Anthony De Mello
• Essentialism: The Disciplined Pursuit of Less by Greg McKeown
• Play It Away: A Workaholic’s Cure for Anxiety by Charlie Hoehn
• The Biology of Belief: Unleashing the Power of Consciousness, Matter, & Miracles by Bruce H. Lipton
• The Honeymoon Effect: The Science of Creating Heaven on Earth by Bruce H. Lipton PHD
• The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday
• Never Eat Alone, Expanded and Updated: And Other Secrets to Success, One Relationship at a Time by Keith Ferrazzi and Tahl Raz
• Shine: How Looking Inward Is the Key to Unlocking True Entrepreneurial Freedom by Gino Wickman and Rob Dube
• Rocket Fuel: The One Essential Combination That Will Get You More of What You Want from Your Business by Gino Wickman and Mark C. Winters
• The Gap and The Gain: The High Achievers’ Guide to Happiness, Confidence, and Success by Dan Sullivan and Dr. Benjamin Hardy

Related episode(s):

• “[Veteran Entrepreneur Series] Working with Donald Trump and the Impact of Winning The Apprentice with Kelly Perdew of Moonshots Capital” on the Inspired Insider Podcast
• “[Veteran Entrepreneur Series] An Emphasis on Expanding Business with Charles Moyer Founder of Badass Beardcare” on the Inspired Insider Podcast
• “[Veteran Entrepreneur Series] From Small Startup to Thriving Ecommerce Business with Michael Eldridge Founder of Safety Glasses USA” on the Inspired Insider Podcast
• “[Veteran Entrepreneur Series] Why Persistence Pays Off with Mike McKim Co-Founder of Cuvee Coffee” on the Inspired Insider Podcast

Quotable Moments:

• “I had literally become a dog no one knew they could pet.”
• “I was making her one and only life miserable, like she was in fight or flight.”
• “I wasn’t looking for a cure. I was looking for relief.”
• “We need to remove the old furniture — the beliefs.”
• “We’re always going through transition. Like there’s not one transition in our life.”

Action Steps:

1. Prioritize internal integration over constant external solutions: Without integration, personal growth efforts fade and result in only temporary relief.
2. Rewire limiting beliefs from childhood: Recognizing and reframing unconscious beliefs enables healthier behaviors and emotional freedom.
3. Build a support system through community: Genuine connection fosters accountability, resilience, and lasting personal transformation.
4. Reflect on how you leave transitions: Your exit mindset often shapes how you enter and succeed in your next chapter.
5. Recognize you’re already there: Embracing the present fosters confidence and clarity, breaking the cycle of constant dissatisfaction.

Episode Transcript

Intro: 00:00

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz: 00:22

Dr. Jeremy Weisz here founder of inspiredinsider.com where I talk with inspirational entrepreneurs and leaders. Today is no different. Phil Randazzo of American Dream U, could check them out. AmericanDreamuU.org.

Phil Randazzo, before I formally introduce you, I always like to point out other episodes of the podcast people should check out, since this is part of the Veteran Entrepreneur series we had winning The Apprentice with Kelly Perdew. I know you know Kelly actually of Moonshots Capital. Also Charles Moyer, founder of Badass BeardCare, and he talked about expanding his business. We had Michael Eldridge of the founder of Safety Glasses USA and Mike McKim, co-founder of Cuvee Coffee. So check those out.

Just some amazing stories of, you know, not only the hard things about entrepreneurship, but, you know, veteran life and some of the challenges and things they had to overcome to get there. Before I introduce Phil, this episode is brought to you by Rise25. At Rise25, we help businesses give to and connect to their dream relationships and partnerships. How do we do that? We do that in two ways.

One, we’re an easy button for a company to launch and run a podcast. So we do the strategy, accountability and the full execution production. Number two, we’re an easy button for companies gifting. We make gifting staying top of mind for clients simple, seamless and affordable. You just send us an address list of your people.

We send a campaign of gifts for them for years to come. Phil, we call ourselves the magic elves that run in the background and make it stress free as possible for companies to build amazing relationships. And I found no better way over the past decade to profile the people and companies I most admire, and also send them sweet treats in the mail. So check it out at Rise25. I’m excited to introduce Phil Randazzo, founder.

He founded American Dream U in 2003. American Dream U is a nonprofit that’s helped more than 19,000 military members, civilians and entrepreneurs successfully navigate life transitions, and they do this through world-class education, mentorship and entrepreneurial training. They’ve supported thousands in moving from service. Or I guess what, Phil kind of like stuckness sometimes into a purpose-driven career and venture. And after more than 2001 on one conversations, Phil actually discovered a common thread that something could be hidden in our subconscious that often holds us back.

And so, Phil, thanks for joining me.

Phil Randazzo: 02:49

Hey, appreciate you Jeremy. It’s awesome.

Dr. Jeremy Weisz: 02:52

Let’s start off and just talk about, I’ve heard about American Dream U for many, many, many years through, you know, some of the past speakers like Brian Kurtz and Jordan Harbinger and many other people. But just tell people about American Dream U and what you do. And I’m going to pull up the site as you do that.

Phil Randazzo: 03:11

Yeah, I appreciate that. Appreciate that. Yeah. All those guys are just amazing. And we’ve been super blessed with phenomenal individuals who have been willing to give up their time to come and share at military bases.

And so what we discovered, Jeremy, and it was in 2012 that transitions can be difficult, right? And in the military, I’m not a veteran. I want to make that very clear. But a lot of conversations is that some of their future endeavors are chosen for them, right? Based on their skills, where they live, what they do.

You know, they have a very rigid routine when they’re especially when they’re getting ready to deploy for any type of military situation. And so what we found is that when they’re getting ready to leave the military, military has great people running an okay program, the transition program, but they’re kind of siloed in a box, right. So if you do logistics in the military, they suggest you do logistics when you get out. If you do whatever it is tech, cybersecurity, you’ve got these, you know, these backgrounds that allow you to sit in a basement and listen to chatter and make decent money. But is that what they really want to do?

Right. And I’ll give you a quick story. As at Fort Benning, Georgia, with Brian Kurtz, we’re having a conversation around, you know, what’s next. And there was this big job fair and JBL hunt was like, yeah, we’re paying these young soldiers 50 grand to come out and drive trucks. I was with the young Army Rangers name is Trevor Shirk, owns a great business right now.

I’ve kept in touch with him, gosh, for close to 15 years. And he literally said, you put a guy who’s driven a truck, right? Overseas, Iraq, Afghanistan, wherever he’s going to blow his brains out, right? Because you’re just going to put him in that same situation. And so the guy from JBL hunt was just stunned.

And I remember Brian Kirk just kind of looking around like we were always kind of an awkward moment. But that’s again, that’s just what they feel is the best for these individuals. And so we.

Dr. Jeremy Weisz: 05:18

See the logic, right? I mean, this is you know, you have these skills and keep doing it.

Phil Randazzo: 05:25

Yeah. Right. And so we through the help of a guy and a good friend named Clay Baer, I don’t know if you know Clay. He’s a brilliant marketing guy, spoken at, I don’t know, a dozen different events. We sat down and kind of whiteboard and we’re like, okay, what if we allow them to choose their own adventure?

Like, what’s next for them? So we created this great option, right? If you want to be an entrepreneur, we can help support you. We’ve had, you know, everyone from combat flip flops to grunge style to gold rock to black rifle coffee guys, right? Like you can learn from some of the best entrepreneurs on the planet.

But there’s something holding them back from allowing them to take that, quote, risk, right? Like, I remember we were at the Pentagon and they were saying, listen, you know, if you these guys want to become an entrepreneur, they have like a 4% chance of making it. Right? So they’re already putting it in those that want to become an entrepreneur in their minds that over the next five years, you have a very small percentage of chance of making it. So we want to enter that conversation before they have that conversation.

Does that make sense, Jeremy?

Dr. Jeremy Weisz: 06:35

100%, yeah. Yeah. Talk about combat flip flops for a second.

Phil Randazzo: 06:40

Yeah. So Griff is the founder. Two, seven, five Ranger guy. Awesome individual. I’m not sure how I met him.

He was referred. He got out of the military and he’s talked publicly about that. And he said that he found some addictions to help him kind of deal with what transition looks like. And so he also said that the Army was no longer, you know, paying him to work out. So he got out of shape, gained a ton of weight, had some addictions.

You know, as he and I have talked about, he was trying to escape his world, not the world. And one day he woke up and we were scheduling. He was going to come speak and he sounded different. And I’m like, hey, Griff. I’m like, you sound different.

He goes, yeah, I did a meditation today and I. I’m happy. And I’m like, all right, if we can figure this out in the next five minutes. While you’re happy off of meditation. Well, ended up being you read a book called Breaking the Habit of Being Yourself, doctor Joe Dispenza I just come back from a doctor, Joe Dispenza we spent probably two hours on the phone talking about how to rewire our thoughts and be able to create something new.

And he is an incredible individual and he actually in combat flip flops, was on Shark Tank and ended up getting a deal with Mark Cuban. So he’s partners with Mark Cuban. And so we’ve been like I said, we’ve been blessed to have some incredible entrepreneurs like you’re looking at here at Scott Man, Lieutenant Colonel Scott Man, Green Beret. He has a play called Last Out. And he is found healing through sharing through storytelling.

Right. And that’s a healing process, right? Like you’re a doctor and you get people on your table when you are fully practicing. And we had all this stuff stored in their body and they had no way to release it. And one of the ways that Scott has shared with people is releasing it through storytelling.

Does that make sense? Yeah.

Dr. Jeremy Weisz: 08:42

No, I mean, I love when you talk about this because I’ve heard you talk in some other videos. And the old Phil, I don’t know how old far back we need to go would have dismissed this as like, this doesn’t work. I mean, listen, this is I come from the chiropractic universe, so, like, there’s a lot of stuff I’ve heard that most people would think is even more kind of out of this, you know, woo woo than. But there’s the varying degree there. But what flipped in your mind, at what point were you like, okay, like, I need to start visiting this stuff and looking at some of these things where maybe I would have thought, oh, this is woo woo.

This isn’t for me. Meditation, storytelling, this kind of thing.

Phil Randazzo: 09:27

Yeah. No. Great question. I think it was 2016. I was kind of in American Dream U in the transition space, pretty strong.

And I was showing up in one way when I was publicly facing another way, when I was by myself. And another way around my family, right? I took my wife, who I’ve been married almost 34 years now, has taken her for granted. And what happened, Jeremy, is that my whole self-worth was based on how well I was doing, comparing that, how well I was doing to how old I was. Right?

And I had this big delusion of time. I should be further along than I am, right? And I should be doing much better than I am based on my time.

Dr. Jeremy Weisz: 10:17

And I’ve never thought that fill for myself. Never.

Phil Randazzo: 10:19

Right? Right. And so what I uncovered was in my beautiful wife. She’s like an angel. You know, she was born into this world knowing she had to deal with me.

I had literally become Jeremy, a dog no one knew they could pet. Right? I’m a big guy, you know? Six, four, six, five. At the time, I was 255, and I was a man’s man.

And, you know, I was looking for reasons to get angry, right? The person in front of me didn’t use her turn signal. Angry. Wanted to choke him out. Right.

And so when you’re a dog, no one knows they can pet. If I had a good day at work, I’d roll, roll over, and let my family pet me. If I had a bad day at work, watch out. I would chew their face off. Not physically, but mentally, right?

Like I was, I was having a really difficult time. And when I shared that story with a lot of veterans, they’re like, dude, you’re in my kitchen, right? Like, we’re all spun up and we’re just we just got this anger inside of us. We don’t know how to do it. And so my wife basically said, 80% of the time, you’re a great guy.

20% of the time you’re unpredictable. I don’t think I can take that anymore. So I had to make right. I had this big awakening. And the other realization I had, Jeremy, is that, you know, they say we have this one and only life.

Well, I was making her one and only life miserable like she was in fight or flight. So that’s when I started getting a little woo woo, and seeing people behave in such a way that I wanted to behave. And I was surrounded by 400 amazing American Dream Youth speakers. Some of them behind the scenes were a certain way, and some of them in front of the camera were a different way. And so I really was looking for those individuals who were happy for the sake of being happy, not tied to any comparison or game.

Does that make sense?

Dr. Jeremy Weisz: 12:06

Yeah. I mean, EO Entrepreneurs Organization, I feel like with our forum group that comes up over and over again, kind of what you said, and at least I’ll speak for myself of like I always think about that, right? Okay. Based on how old I am, you know, what should I be further? I always think I should be further along than I am in various aspects, right?

I’d love to hear what you did. Right. So you okay? You made this realization. It’s.

I feel it’s hard to change, right? Because I’ve been a certain way for decades. So I’m curious on that. I do want to say, one of my friends who has one of my entrepreneur friends who has road rage, I read them this quote. This is my favorite quote by George Carlin.

Now, if you’ve heard this quote but has you, it says, have you ever noticed that anybody driving slower than you is an idiot? Anyone going faster than you is a maniac? So that’s I sent that to him. He laughed. Because he’s definitely has some road rage.

But talk about what are some of the things you did to put in place, because again, you’re surrounded by all these amazing entrepreneurs. You’ve had a lot of entrepreneurial experience over the years. What did you do to then go, okay, I had this realization of taking my wife for granted and maybe, you know, spending less time or more time on certain things. What did you do?

Phil Randazzo: 13:33

Yeah. Well, one thing is that I had this awakened moment, Jeremy, that I wasn’t looking for a cure. I was looking for relief. So I was part of, you know, Joe Network and Dan Sullivan, strategic coach and mastermind talks and blah, blah, blah, like all these great things. Been to all these workshops.

I’d get super excited, Doctor Joe Lipton, and then I’d come home and I’d just get triggered and it just wasn’t working. And so what I realized is, I was just looking for relief. And for me to go to events, for me to go to workshops. I got that relief. I was in a community.

No one knew my backstory. They didn’t know. I just lost my shit with my kids and my wife and all this kind of stuff. And so I could kind of be myself in a way, but not myself. And then.

The cure to me was, I don’t think we can ever fully get a cure was to integrate what I had learned before jumping into the next thing. And I know people, and I’ve worked with a lot of people where they’re just running from one release to another relief to another relief and never integrating. And the biggest thing I learned, Jeremy, was that I had to dissolve everything that wasn’t me. And there was a lot of things that I was still living in this context that I’ll give you a very quick example. So never asked a girl out in high school.

Super low self-esteem, right? Like I had to use my humor. And, you know, some girls thought I had pretty eyes, like I had to do. I had to go for anything to try to get attention. Like, wasn’t me.

And I met my wife in college. We dated for a while. We ended up getting pregnant because that’s what you do when you’re in college. You don’t have any money. She was the oldest of eight kids, the most religious Catholic family on the planet.

And I thought that she was only with me because of her religion and the fact that we had a kid. Anything she did to show me love or connection, I was like, no you don’t. You’re only doing this because of your religion. No you don’t. Right.

There was always something tied to why she was doing what she was doing. And so my belief running around was I wasn’t needed, I wasn’t wanted, and I was a burden. It wasn’t conscious. It was unconscious. So I was running around trying to get attention, foot on the gas.

All along when people gave me attention, I’m like, no, you don’t mean it. And so I had to just understand that that wasn’t true. She was with me because she loved me and she saw behind all of that nonsense. Does that make sense?

Dr. Jeremy Weisz: 16:22

100%.

Phil Randazzo: 16:23

Right. And so all these people are great. Whether we partner with Tony Robbins. Last year, we did some in-person military veteran events. It was amazing.

And, you know, we’re jumping around. We’re having this great connection. And then the guys fly home on a Sunday, and then their wife tells them, why didn’t you take the trash out on Wednesday before you left? And they fall right back into their old patterns? Right.

And they immediately all these great wirings they had, it goes right back to where they were. So I’ve always been curious is how do we keep the fresh snow on the brain so that we can, you know, have the awareness and build our own tracks versus all these tracks that, you know, it’s our parents left us furniture in our room, in our head. It’s just there and we’re trying to put in new furniture and there’s no room. So we need to remove the old furniture, the beliefs. Right?

Like, I know I was put on this planet, Jeremy, because my dad. Sweet guy underneath everything but Sicilian, born in Sicily, angry, violent. Everything. My grandfather, I heard, was even worse. Great-grandfather, even worse.

And so I believe I’m here to break that chain of anger, of violence and my great, great grandkids. I had this conversation with Greg McEwan, who wrote a great book called The Essentialism, and he talks about our great, great grandkids who won’t know our names, but they will inherit who we are. And I don’t want right, my great, great grandkids not to know my name, but inherit the anger, the resentment, all those type of things. And I saw it in one of my kids, actually, in all my kids in different ways. And I could see it.

And that broke me. That was part of the change, and I couldn’t tell them how they should be. I had to show them how they should be.

Dr. Jeremy Weisz: 18:11

What did the integration look like for you then?

Phil Randazzo: 18:15

One is for me, the big thing, Jeremy, is I was always trying to get there. And there is no there. I was already there. Right? Like, I’m not as successful as Tim Ferriss.

And we’ve had seven billionaires. Grant Cardone has spoken a handful of times like all these people, right. They’re running around their private planes. And, you know, I’m praying to get an exit row at southwest just so I can have a little extra legroom. And it was just I was trying to be somewhere.

And I just came to a realization is that we’re all already there. We just have to recognize it. And so it’s.

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