Richard Rossi 5:23
Well, it was extremely profound. They both were Jews escaping Hitler and my mom from Austria, my dad from Italy, they immigrated to the US in the in the 1940s, got married had me 13 years later, they separated when I was in the third grade and I lived in the one of the richest towns in America and I was one of the poorest kids in that town really had almost nothing but I had a mom who loved me, and was 100% committed to me maybe 200% committed to me, and made sure that even though She had little to nothing. I had everything I got to go skiing trips, and I got to do sailing lessons and I got to feel just like a regular kid in, in the school system there in Greenwich, Connecticut, but it taught me a lot about sacrifice. I really was in every sense of the word, the sole focus of her life.

Jeremy Weisz 6:23
What did she do?

Richard Rossi 6:25
Well, she really was just she, she was a mom. But before that she was an artist, a graphic artist. And when she came to the US and got married, that she really became just just a great mom and I hate to say the word mom because just mom because every mother is a working mother. And it’s

Jeremy Weisz 6:48
like the hardest job. I mean, asking involved is insane.

Richard Rossi 6:54
And it is, it is an incredibly noble profession. So she Really we relied on the little money that we got from my dad every month and we just soldiered through and then went together to Washington DC when it was time for college,

Jeremy Weisz 7:11
you know, were some of the things that you learned from her. Because I know that she’s a big inspiration to you.

Richard Rossi 7:19
Well, you know, I learned positive and negative things. On the positive side. I learned about the power of love and commitment and there was no question it was total is absolute. There was incredible sacrifice every day. There was so many things that she could have done with the paucity of money that we had, but instead she decided there’s all kind of go to me I was at I was her hope I was her inspiration. I was her focus. And that was amazing. I also learned later in life when I reflected upon it about the the the power of survival because her parents died. Her sister died her aunt died. She was devastated. David, she never recovered. And as I thought about it later in life, I realized you probably never went through a day. without suffering. She didn’t really make that super obvious to me. But death and suffering, we’re always in the picture with her. And I think in a lot of ways, she just kind of white knuckled her way through life, this, there’s some people that because of their psychological makeup, they can get over it and live a great life. And there’s some people that just can’t get over it. And she just was one of those people that was knocked to the ground and couldn’t totally get up afterwards. But she certainly did everything to be a great mom. Yeah, it seemed like she put on a strong

Jeremy Weisz 8:39
facade for you. No matter what, right?

Richard Rossi 8:43
No doubt and on the negative side is also I think the was kind of the same thing which was I was the total focus I was the person that she was thinking about working with and, and in the science, directing every day, and that was suffocating right so and, and what I learned as a kid was how do I work around that? How can I be a normal kid? Have my friends go out Have a drink every once in a while, do some things that are naughty without disappointing her some pressure. Yeah, enormous, enormous pressure and it wasn’t even hidden. It was like, okay, Richard, I’m alive because for you, it’s the only reason why I’m like, Oh, great. So but no pressure there. What I have a Jewish mom. But what I learned was, how to kind of just get around that and with my own kids. It taught me a lot about you know, when to hold, when to fall, when to push when to hold back, and how much to get involved and how much to allow them to make their own decisions and mistakes.

Jeremy Weisz 9:48
There’s one story that sticks out to me that you have told about your mom’s candlestick holders, which I think demonstrate this whole way exactly what you’re saying.

Richard Rossi 9:59
Yeah. There’s really nothing that demonstrates as well as that. So, as I mentioned, we’re super poor, super, super, super poor. And one of the things that I wanted to do is play in the school band. I wanted to play the flute. But that was there was no money for a flute period. So she took the only thing that she had left from her parents, which was a set of silver candlesticks, took the train into New York City went to a pawn shop and pawn them so that we could have enough money to rent by the total rent floof. And every month, she would take the train in New York to pay the interest so that they wouldn’t sell those candlesticks. And I got to play the flute. I was never very good, but I got to play it. And it was just another thing that I wanted to do to be a real regular kid and she made every sacrifice to make it happen. And she eventually recovered those, those candlesticks and they’re down in my living room. dining room right now. But that’s a real microcosm. My mother for sure. sure

Jeremy Weisz 11:00
that it was easy.

Richard Rossi 11:02
And a lot of ways she lived a very tragic life. Because when when something like world war two hits when you lose your entire family, there are consequences and they were with her the rest of her life.

Jeremy Weisz 11:16
Yeah, I mean, I can’t even imagine. Right. And how old was she when she came over? She was in her early 20s. Yeah. 20s just uprooting leaving your whole family and leaving them behind them. Never seen them again. You know, it’s just

Richard Rossi 11:29
Well, there’s also survivor’s guilt, right. So she tried to get them to come with her and they wouldn’t they it was the classic thing if you read about World War Two people stayed behind because they thought it wasn’t going to get worse. And then no idea how much worse it actually was going to get. By the time they realized that they couldn’t get out.

Jeremy Weisz 11:46
Yeah, I think you know what, you’re one of the main inspirations for your eventual business. Helping high achieving students was from your mom,

Richard Rossi 11:54
right? Oh, absolutely. No question about it because she Well, look, she died when I was 24 years old, and only a few miles from here. And I was sitting by her bedside when she died. And before she died, we had a conversation where I said, Tell me what you want from me. You have sacrificed everything. What do you want? And she said, Well, I want you to help people. And I thought, Oh, this is going to be that hard. I can be a doctor, I can be a social worker, whatever. And she said, No, no, I want you to help people. And at that moment, I realized she was actually referring to manatee. And I remember so clearly Jeremy thinking at that moment, well, that’s never going to happen. And yet, as time has gone on, I really feel like I have had an impact and that she would be proud of me.

Jeremy Weisz 12:48
That is amazing. And you have continued to live I want to give people the just a quick timeline over your jobs and careers, because it’s pretty diverse to start, and, you know, I knowing in college, you know, after college what you did, but I know, you know, you didn’t have a typical college experience where, you know, you had to put your way through Georgetown. And so you would, you know, you to work your way through and at night. And so, you know, over that, that time period, right?

Richard Rossi 13:23
Well, I came to DC, I enrolled in Georgetown University at that time, we were still getting money from my dad, both for tuition and for child support. And I volunteered up on the United States Senate for my senator. And it’s interesting, because back then, in the early 70s, if you looked at, like, Who were the most respected institutions, the first were firefighters, and the second was Congress. And if you look at it now, the first is firefighters and Congress is actually the opposite. But back then they were held in high regard and I volunteered for my senator, then a year later The checks started, stopped coming in and my dad moved to France and my mom had no sellable skills here I was, we were destitute. I mean, as in literally, we would nothing, not even to buy a sandwich. So I went up to my Senator, Senator awake and I said, Sir, I need a job. And God bless him. He said, I’ll give you a job. And, and he did. And I worked in the Senate for nine years after that, and took eight years to work my way through Georgetown at night and also support my mom who died four years into that,

Jeremy Weisz 14:35
hmm, do you think that this has driven you? Like, do you run from that, you know, like, just like his journey so much to be make a difference to be successful?

Richard Rossi 14:47
You know, well, yes. And no, I mean, I’m, when I reflect back on it, a lot of what happened to me was taken advantage of opportunities were presented to me for better or worse, and No successful person, if they’re being honest, will discount the role that luck plays and being in the right place at the right time. And I took advantage of that when it presented itself and then tried to maximize the opportunity. But honestly, it was only decades later that I reflected back on the conversation I had with my mom and I connected. The fact that she had asked that of me to the fact that I thought, wow, maybe I’ve actually achieved that it was pretty monumental, because it wasn’t in my conscious mind.

Jeremy Weisz 15:33
Yeah, it was in the subconscious. Yeah,

Richard Rossi 15:35
yeah, for sure.

Jeremy Weisz 15:36
Your entrepreneur journey started with a software business.

Richard Rossi 15:41
It did. And in fact, I never thought of it as entrepreneurship. I didn’t know what that word meant. It seemed like a very highfalutin word to me. I was just a single guy who is judgment proof and didn’t have a possession in the world and came up with an idea of creating a computer system for political campaigns to handle all their fundraising and their and their filings for the government. And thank you letters and all the rest that really didn’t exist at the time you were ahead of your time. Yeah, yeah, everything was done out of a shoe box and three by five cards. And I just knew a guy was a good friend of mine, who is a programmer and I there was a guy in worked in the office who was willing to fund us. And I was like, you know, let’s just see what happens. And off we went to start our first business.

Jeremy Weisz 16:29
And so what happened?

Richard Rossi 16:32
Oh, my God was miserable failure. And the reason is that we were never able to produce a stable product. And we were never really that great at marketing. And boy, did I tell you, you do this for a while and you get your MBA the hard way? You really do. You learn what it means and how and what it takes to really succeed and survive through not succeeding and failing, right? And so at 28, or 29, it was it was, as my first journey into what I later learned was entrepreneurship. And I want to emphasize the fact that there was no big aha moment where I said, All right, I’m getting on this ship, and I’m going to take this amazing journey into the entrepreneurial world. I was just this young kid going, what the heck, I’ve been doing this a long time. Let me try this. It just never occurred to me that it was any sort of big deal.

Jeremy Weisz 17:27
Yeah. You saw like a pain point problem, and you just went out to solve it.

Richard Rossi 17:31
Yeah, it was a big problem. It was Yes, yes. Before the introduction in the PC, so we actually built it on a small mainframe computer, mini computer, they were called back then.

Jeremy Weisz 17:43
You know, Richard, other many things. How I try and describe you. One of the terms that I always describe you and I tell other people about you is he’s a direct mail genius. Okay. And you learn from political directions. Mail. And I want you to talk a little bit the first mailing you did for the business.

Richard Rossi 18:08
Well, after that my business Yeah. So after my first company failed, I did some consulting for the political parties in Washington, especially the Republicans, and a high dollar donor program called the republican Senatorial Committee $5,000 a year per person. And at that time, I learned from one of the masters of direct mail, who worked for the Senatorial Committee, what that even meant, and I got to work on this incredible package where we actually took a boronia which is like an envelope us for a mailing for a wedding, and we actually engraved it and we actually calligraphies it and put heavy card in there and all the rest and invited people to join the Senatorial Committee, and it was a phenomenally successful full package what I today would call a shock and awe pack. It just was one of those things you couldn’t not open we send it certified mail. It was just, it was a it was a barn burner. I mean, you just looked at that thing and there wasn’t a chance in the world you were going to throw it away. And I learned a lot from that. And I learned and that has always been my specialty has been the so called shock and awe package. And then I learned about how to locate mailed to the right people and the Republicans. We had two great packages one two great list sources. One was called Big Buck hunters with Bing and the other the other was this grapefruit company in Florida called Frank Louis grapefruits, and it just turned out that if you bought expensive grapefruits by direct mail from Florida, you are republican period. And so how

Jeremy Weisz 19:54
did you figure that out?

Richard Rossi 19:55
Oh, I didn’t. But the guys up in the in the committee did The answer is they bought and tested hundreds and hundreds and hundreds. Wow. And then we found some

Jeremy Weisz 20:06
great quotes equals Republican. Absolutely.

Richard Rossi 20:10
Franklin is great for it. I don’t know if they still exist, but they were great grapefruits, by the way.

Jeremy Weisz 20:17
So I want to hear about your first million you spent 20 $500. But before you talk about that, what’s your favorite lumpy mail? shocking all you’ve received and or sent out? So you talked about one of them? What is there any that you’ve received personally, or that you’ve sent out that stick out to you is cool, shocking all

Richard Rossi 20:35
packages? Oh, yeah, it’s actually I wish I had one right here. I haven’t downstairs but it’s what I’m doing right now, which is the video brochure. So basically, it is a looks like a little brochure book, a little book. And it can be several different sizes, but you open it, and there’s a video screen in there, good quality and a speaker and it just begins playing So think about it, you take this thing out of the envelope, and it’s thick, and it kind of demands to be inspected. And you open it up and it just starts playing. And in this case, it’s my face. And it’s my voice and it’s good quality. And I’m talking directly to you. That my friend is pretty damn awesome. And they’re individually recorded for each recipient or whatever you want. Okay, whatever you want. In my case, sometimes I depending on the value of the mailing, I’ll do one that’s personalized to you. In other cases, it’ll just be a mailing for people like you. Hey, you know Jeremy, you’re a high achieving kid who wants to be a doctor. I know you’re in high school right now. And I think there’s something you need to know about. Oh, wow, that’s me. Right. Our video as we know from TV and from cable is massive.

Jeremy Weisz 21:52
Yeah, so it matches the shock and awe with a real personal touch with the video.

Unknown Speaker 21:58
It’s an and the other thing is, of course, Like,

Richard Rossi 22:02
the things that work the best are the things that people haven’t seen before. It used to be direct mail in general just killed it because you weren’t getting that much direct mail. Then it was certified mail, and it was Federal Express. And we’re always looking for something that just kind of shut, just kind of shakes you out of your, you know, day to day stupor, and you go, Oh, wait a minute, I gotta pay attention to this. And people just don’t really, I mean, have you ever gotten a video brochure?

Jeremy Weisz 22:28
Once? Okay,

Richard Rossi 22:30
so it’s not that often, right?

Jeremy Weisz 22:32
No, no, not at all.

Richard Rossi 22:33
So you do take the time and actually focus. And that’s what we as, as people who market I don’t think of myself as a marketer. I think of myself as someone who is really good at doing what it takes to actually make the revenue and that happens to be marketing. I’m not someone who does it for other people. I do it for me.

Jeremy Weisz 22:54
Um, have you received anything, personally, or has Lisa received anything that sticks out that is impressed you.

Richard Rossi 23:03
Yeah, I think one of the anytime there’s an really interesting object in there, I mean, one of the things that that you’ll read and persuasion or pre suasion, child Dinis work is that you know, you give before you ask. So I got a clear two, but about a year ago, and have a label on it, you can still see everything inside and inside was a little bear as a really nice bear. And then there was a letter wrapped around the bottom. So when you get it, the question is, are you throwing the little bit? Are you going to take the little cute bear and just throw it in the trash? Of course you’re not, you’re going to open it up and take the bear out. Right? So that was very, very good. And then of course, what do you have the bear? What do you have, you have something that I gave you. So now boy, psychologically, there’s a sense of obligation even though it may sound like it doesn’t work. The psychological aspect of pre suasion it’s extraordinarily powerful because it’s built into our psyche. since we were little kids. If you get something you say thank you.

Jeremy Weisz 24:07
Hmm, the first mailing 2047 20 $500 What happened?

Richard Rossi 24:13
Oh, it wasn’t 2500 was only 500 per person. So I had my myself and my partner. So it’s actually $5,000 we had. And basically we wanted to start a company that would bring kids to DC to learn about democracy and citizenship and leadership. And we were going to mail the the principals of schools and we decided to do it through direct mail. We got a list of principles. And I said, Oh, I remember that package that I did up at the Senatorial Committee, and I did what we call stealing smart. I basically knocked the package off and made this beautiful shock and awe baronial package with gold foil and something that looked like calligraphy. And so on so forth. We dumped it in the mail. And that was it, Jeremy. I mean, that’s all the money we had if it had failed, we were just gone our separate ways. But it didn’t let it ride. Well, yeah. And it worked. It worked big time. And the thing that’s so incredible about that package is it is never stopped working. Well, that package has been mailed in one form or another for 30 years, and believe it or not, has produced over $1 billion dollars in revenue. And if I took the original package mailed in 1986, and I put it next to the package, this mail today, you go, Oh, that’s pretty much the same package. Right? So it goes to show you the power of an incredibly effective mail or advertising campaign it can produce from it. And the most important message for everyone that’s watching is don’t ask expect this to happen to you. Usually it’s going to take dozens of tries before you find that combination of words and images and lists and all the rest. That actually gets people to open up their wallets and give you money. But we just lucked out. We completely like that. And we build a really big small business on now.