0:09
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0:21
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0:34
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0:49
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1:07
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1:14
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1:34
Welcome to Side Hustle City and thanks for joining us. Our goal is to help you connect to real people who found success turning their side hustle into a main hustle, and we hope you can, too. I’m Adam Kaylor. I’m joined by Kyle Stevie, my co-host. Let’s get started.

1:53
Guys, welcome back to the Side Hustle City podcast. Today we have a special guest. I know we haven’t done a podcast in a while, but I met Jean Valentino a while back at a little political event that we were both at.

2:10
Jean has an exceptional background—very interesting, very similar to what I’ve been into: technology, politics, real estate, all the things you probably are interested in and want to be in.

2:23
Well, we have an expert here to talk to you and explain a little bit about his background. So, Jean, welcome to the show.

2:31
Thanks for having me, Adam. It’s really a joy to be here with you. You’ve had quite a footprint around the nation in different worlds, and the more I got to know you, the more I realized how our pasts align.

2:45
That’s right, that’s right. Just seeing your background, knowing where you’re living, and some of the stuff we’ve talked about… I’ve got a ways to go, Jean, I need to catch up to you! I need a plane, a helicopter, and a big spread up there. It’s almost like… I think you’ve got a ranch or something, don’t you?

3:04
Well, the home’s on the water and we don’t have the helicopter—although eVTOL (electric vertical takeoff and landing) vehicles are coming. The whole concept of aviation is changing.

3:18
Heads up: once we get through web servers and farms, and Elon Musk with satellite stations for visiting as well as web hosting and telephone calls and everything… oh my god, he’s leapfrogging over a lot of these entrepreneurs on the earth’s surface that were trying to admonish him.

3:41
He’s now on his way to embarrassing all of them, as he should. Many of them have stepped on him. From my point of view, I just enjoy tagging along. To your point, like you, I like to just get that surfboard and ride his wave.

4:00
There are a lot of technology enhancements going on that you and I are either involved in or want to ride that I think are going to be the wave of the future in the next 10 years. Very exciting times.

4:13
Just what you were talking about… I mean, it’s one of those things where you see trends, right? You pay attention, you know what’s going on. I think a lot of people that I’ve met and interviewed who are successful see trends before other people, or they can connect the dots somehow.

4:32
I think a lot of people go through life, unfortunately, just not paying attention the way they should. If you just paid attention a little more, jumped on these waves, read a lot, and understood what was happening in the world—and that includes politics…

4:43
A lot of people just want to stay out of politics. They say, “I don’t care about politics.” Well, politics cares about you, right? You’ve got a war in Iran right now; it’s affecting oil prices. Everything’s made out of a barrel of oil.

4:53
These glasses right here are made out of oil—the plastic. A lot of stuff is made out of oil: the asphalt you drive your car on… when the price of a barrel goes up, everything goes up, right? Transportation costs go up.

5:08
So even if it’s food and not directly made out of a barrel of oil, you need to put it in a truck and deliver it where it needs to go, and those costs trickle down. If people don’t understand politics and aren’t paying attention, it’s hard to be an investor, hard to keep track of these things going on, and hard to make money and get over the hump.

5:30
You’re so correct. You said something that I think is key: it’s not necessarily the innovation, but the timing of it in the marketplace with other factors around you.

5:41
I’m not sure Elon Musk could have had success with reusable re-entry rockets 10 or 15 years ago. But as NASA kind of crumbled in the old bureaucracy in the last decade, it was clear that there was an opportunity for entrepreneurs to step up and take advantage of new innovations.

6:16
Speaking of capitalism, look at what’s happening in the stock market right now. They’re begging for innovation. They’re begging for insight and opportunities.

6:33
Now, you’ve got a crowd that came out of the Gen Z era that doesn’t appreciate American history or innovation; they’re looking for a freebie. When I said “tag along” earlier, I didn’t mean in terms of riding the wave of someone else doing the heavy lifting for me—I’ll pay my way.

6:49
I’m talking about individuals coming out of high school and college with some sort of degree where they don’t know where to go for a job. That’s what I think is going to happen. I think we’re going to see a lot of innovation with people like Elon Musk—he’s just the tip of the iceberg—that are going to present opportunities for you and me.

7:18
I invested big time in the SpaceX program. The stock is down a little right now, but I think it’s going to rebound. Morgan Stanley reports something over $300 a share in SpaceX.

7:38
Well, there’s a whole ripple effect you and I were talking about in the marketplace right now. Look at what’s happening with the chip manufacturers that have crashed. Even the chips coming out of Taiwan, and all the manufacturers and innovators over there, are really in the red today as we speak.

8:01
But mark my words, they’re up 300% to 400% since their inception going back two or three years. So I’m not too anxious to throw in the towel just because a lot of greedy individuals in the stock market are trying to short an opportunity that just came to market.

8:23
It’s caused a terrible, misleading sentiment in the marketplace. I think for the prudent investor who sees where the marketplace is going: go out and play a game of racquetball, or go smoke your pipe somewhere and ignore the marketplace for 6 months.

8:47
Watch what happens by the end of the year. I think you’re in for a very pleasant surprise.

8:53
I think so. You can’t really argue with it. Look at the last several years and how things have gone.

9:01
I’m a little worried about the AI boom—it kind of feels like the dot-com thing—but being in the industry using AI, seeing how it’s transformed my own business and increased my productivity, I just don’t see it slowing down. I think it just keeps getting better. Every month there seems to be an update to each one of these models; they’re getting smarter.

9:24
Which scares a lot of people, I think. You know, the whole data center thing… in *Terminator*, Sarah Connor was trying to destroy the data centers that Skynet ran on, right? Yeah, that was her thing. People see that kind of stuff.

9:39
In all the stuff that happens in our government, people always bring up *1984*. There are a lot of parallels. So people try to find things in popular culture that make sense to them and tie into all these things happening in our world.

9:56
But at the end of the day, Jean, you’ve got to worry about yourself. The government’s not coming to save you.

10:04
This is what I talk about all the time on my podcast: you’ve got to make sure you’re paying attention, because nobody else is going to do that for you. Nobody’s going to make sure there’s food on the table for your family, and nobody’s going to help keep your business successful. You’ve got to do that yourself.

10:21
I think that’s something guys like you and I and a lot of other entrepreneurs learned early on in life: it’s up to me to make things happen.

10:45
Going back early in your life, Jean, what led you into entrepreneurship? Was there a specific moment, or was it always in you?

10:55
I have to go back to the early ’70s when I was in high school. I think vividly about my father, whom I respected so much. I was the oldest of four children. We weren’t rich at all—no one handed us anything. He was a radio station broadcaster, if that tells you anything.

11:19
They didn’t make much money. His advancement was becoming general manager of a radio station in Waterbury, Connecticut. At the time, media as we knew it was two or three radio stations in the county, two or three television stations in the state, and cable TV hadn’t been formed yet. You didn’t have this wealth of input coming to you.

11:52
Going to college meant a liberal arts undergrad environment that morphed into some specialty or trade during those four years. For me, it was business with a minor in journalism. During my college years, I studied journalism because my dad became a news correspondent for the Mutual News Radio Network in Washington, D.C.

12:24
Take a look at this mug shot back then: long hair down past my shoulder blades, wearing Farmer John overalls as my normal dress code to business class.

12:41
Let me tell you, I was a different person back then! Liberal? No, I was conservative, but maybe more middle-of-the-road.

13:00
My awakening occurred when I saw my father switch from the Democratic Party to the Republican Party when Ronald Reagan became president. How could you not?

13:12
That was the beginning of my transformation. I began to see that it was important to produce, work, and earn as a reward—not sit on the couch, eat KitKats, and expect someone else to pay my bills. “Adult child support” is what I call it!

13:40
It was a transformation unto itself. We were half-Irish and half-Italian in my family, so we came out of an old Italian work ethic of hard work: 8-hour days minimum, and 10 to 14-hour days were not unusual.

14:09
When I came out of college—having minored in journalism—I was briefly a television broadcaster at a local TV station. But I’ll be honest with you, there wasn’t any money in it. So I realized: if I want all those things in my life, I’d best figure out a way to make more money.

14:46
Daddy had his hands full with four kids, and Mom did too, and I wasn’t about to impose on them for money. I got the message early on: if you want it, go work for it.

14:54
That message transcended my life. I ended up owning a 20-unit apartment building complex with a buddy of mine, and we made some money off that. I said, “Hmm, that’s better than selling advertising for a TV station!”

15:18
Then all of a sudden, I owned a few three-family houses. I decided to let that be passive income while I worked to find out who I was, so I went into insurance. Insurance was a transition for me—a way of building a book of business over the years to build wealth.

16:00
All of a sudden, I realized I wasn’t going to make much money working for the other guy, who was probably going to give the insurance business to his son and daughter. I respected that he would do that, but I needed to find other windows to jump out of.

16:36
While I was at the insurance agency, the auto body shop down the street said, “Hey, we can’t get in touch with you fast enough. We need to be able to know where you are so we can send business your way and trade claims.” We became good friends, and he said, “I’m going to put a two-way radio in your car for you.”

17:06
He built a 75-foot antenna in my backyard on top of a hill with 20 watts of power. Halfway through the project, he stopped and said, “I can’t do it. The United States government shut me off and took the frequency from me.”

17:30
This was 1983 to 1985. He said, “It turns out they’ve got this new thing coming out called cellular telephone in the same radio frequency spectrum.”

17:44
Cellular telephone? What’s that?

17:47
So he turned me over to a guy out of Bloomfield Hills, Michigan, who was putting partnership groups together to invest in an FCC lottery process for cellular telephone.

18:02
After doing a beta test in Detroit, Chicago, and a few key metropolitan areas, the original FCC said, “We’ve got to disseminate this faster throughout the nation.” The only way to do it was to break the nation up into franchise areas.

18:26
I became part of a partnership of 20 people, and we invested in 1,800 different cellular franchise areas around the nation. By the grace of God, on my birthday of all things, the federal government called us and said, “Congratulations, you won the lottery!”

19:00
I said, “Where do I go to cash in my ticket?”

19:04
“Oh, no, sir, you don’t understand. You won the cellular telephone company franchise rights—meaning you own the right to build and own your own cellular telephone company. You’ve got 18 months to do it. Go find yourself $12 million and figure out how to build a cellular telephone company.”

19:27
We had won the area in Central California, smack dab between Fresno to the south and Sacramento to the north: Madera, Merced, Chowchilla, Atwater… the whole San Joaquin Valley and the Santa Clara mountain range.

19:43
There I was on a horse with two buddies and an old-fashioned GPS in my hand, trying to figure out the best location for a tower. We had 18 months to turn on the signal in RSA No. 339 in Central California.

20:12
We got it on 7 days before our 18-month deadline expired!

20:19
Ten years later, in 1996, we sold it for $125 million. That was real good money in the ’90s!

20:32
The government eventually changed its mind—its effort to bring opportunity through a lottery process transformed into a bidding process for, as Bernie Sanders would say, the “oligarchs.” But at the time, there was an effort to let average citizens become part of a system of entrepreneurial opportunity.

21:24
We ended up selling to a firm that eventually went bankrupt, but it made the front page of *The Wall Street Journal* and got absorbed by Verizon in the acquisition process.

21:40
I walked away very happy. My father and my family thought I was crazy at the time because I took $20,000 of my own cash plus $20,000 my wife and I received at our wedding in 1984 to go all-in with $40,000.

22:11
You’ve got to know where people are coming from before you take a shot at where they are. That’s why I take great offense at Bernie Sanders taking shots at Elon Musk, who started in America with nothing.

22:45
We called ourselves Cellular 2000 Telephone Company, doing business as Cellular One in Central California. There was an attempt at a hostile takeover by Craig McCaw of McCaw Cellular. He tried to buy out our shareholders and ended up buying about 25% of our company, though he didn’t reach a majority.

23:31
I became president of Cellular 2000 / Cellular One, and my minority partner was Craig McCaw. We needed them because they surrounded us to the north and south for call handoffs and roaming software.

24:08
One day, I met a gentleman who said, “I’m your new partner.” It turned out he was the CEO of a small company called AT&T!

24:30
So I’m president of Cellular 2000, with the head of AT&T as my minority partner!

24:40
Insane, isn’t it? Riding around on a horse checking cellular signals, using wedding money to invest, and suddenly you’re partnered with one of the top CEOs in the country.

25:05
Eventually, we both got bought out by Dobson Cellular out of Salt Lake City, Utah. They overpaid—$330 a pop, which equated to over $220 million. I had a percentage of that, and that became the seed money for Valentino Holdings.

25:31
Valentino Holdings has since diversified into many things, which gives me the chance to do podcasts like this, contribute on Newsmax and Real America’s Voice, and run for office.

25:54
When Congressman Matt Gaetz left his seat in the Florida Panhandle to consider Donald Trump’s request to be Attorney General, I threw my hat in the ring among 10 Republicans. I came in second or third, and the candidate who won was Donald Trump’s endorsed candidate, Mr. Jimmy Patronis, who was the CFO of Florida under DeSantis.

26:44
As we can see, you don’t run against Trump-endorsed candidates! I think he has a 100% win rate in his second term. I don’t find fault with it—I just wish Donald Trump had the chance to meet me; I think he would have appreciated my background.

27:08
Collector Solutions is another thing you’ve done—working with NCR (National Cash Register). Talk a little bit about that, too.

27:19
Elon Musk was to PayPal what Gene Valentino was to Collector Solutions. Elon Musk was the payer’s solution in PayPal; Gene Valentino was the collector’s solution in payments.

27:50
I went after tax collectors, big centralized accounts receivable billing systems like utility companies and water authorities—where high volume went out—and we wrote the software to connect to their internal management software as the payment engine.

28:20
At first, people were afraid to buy things online or put their credit cards on the internet. People thought putting a credit card online was a communist plot!

29:08
We formed Collector Solutions, built a payment engine moving over $3 billion a year in processing, and secured contracts with the state of Missouri, the state of Illinois, and over 300 counties and utility authorities nationwide.

29:38
We merged with a publicly traded company, which brought us in touch with NCR, and NCR ended up buying us out.

29:53
That became the base. But 25 to 30 years earlier, I was a morning paperboy who mowed lawns afterward, making $20 to $50 a week. I gave half of it to my mother and father to help run the household because we were poor. No silver spoon.

30:41
That was foundational. It taught you that you were a part of something bigger.