an Emmy-winning baseball analyst and color commentator,

and a very successful entrepreneur.

He stars as a guest judge

on a new episode of the popular show "Shark Tank,"

which you can now see on demand and on Hulu.

Here is Alex Rodriguez!

Hey, Alex, welcome back to "The Tonight Show."

Thanks for coming on.

You were on our show back in April,

which was pretty early on in quarantine.

So thanks for coming on then.

Who'd thought we'd still be here nine months later on Zoom?

-It's crazy, Jimmy. It's always so great to see you.

I see you've upgraded -- you're now on your set.

I've upgraded to my bar. -[ Laughs ]

-That's how long this has gone on.

-That's exactly where most people are, yeah.

Yeah, you were in your office last time, right?

-Yeah, I'm still in my office.

[ Both laugh ] I made it a bar.

-Exactly right.

I have so many things I want to talk to you about.

But I was very curious,

'cause you were in Times Square for New Year's Eve.

I saw you guys with Ryan Seacrest,

and Jennifer was awesome -- her performance.

Happy New Year, by the way. -Same to you.

What was it like to be in Times Square with no people?

-Jimmy, it was crazy.

I've been to Times Square a million times,

but to be there where -- no fans on New Year's,

I mean, it seems like for the last hundred years,

you've millions of people out there,

and hopefully, God willing, for the next hundred years,

you have millions of people.

But Jennifer killed it. It was awesome.

But Jennifer did have a great slide.

I thought that was my job. [ Laughs ]

-Dude, yeah, yeah.

I'm used to seeing you sliding, yeah.

She had one of the best slides.

It was -- I mean, whatever she does always --

she does it the best, always goes everywhere.

I just saw you guys are gonna be --

you're headed off to Washington. -Yeah.

-She's going to be performing at the inauguration.

-Jimmy, it's been such a crazy year for her --

I mean, so amazing, so many blessings.

But to think, in the span of 12 months,

she's done the Super Bowl, New Year's,

and now the inaugural -- it's unbelievable.

And what's interesting is she's most nervous

about Washington, D.C.,

because of the responsibility.

And she wants more than anything, like all of us,

to bring people together, to inspire.

And, you know, music and sports does that better than anything.

And she has something really cool.

You're going to be surprised. You're going to love it.

-Really? -You're going to love it.

-'Cause she always does -- alright, good, good, good.

I don't want to know. This is so good.

Hey, 2021 --

do you think you guys are finally going to get married?

[ Chuckling ] What do you think?

-You know, we tried twice in 2020.

-I know. -We got bit twice by COVID-19.

-Yeah.

-You know, they say in baseball, third time's the charm.

So let's -- let's...

-There we go. -Let's hope it's...year.

-Alright, good.

I want to talk about the new season of baseball.

What can you tell us about the upcoming season?

-Well, I'm excited. I mean,

we're supposed to start Opening Day, April 1st.

Baseball and sports -- I mean, we just need it so much.

We saw football this weekend -- it's so much fun.

But, again, music and sports bring people together

more than anything around the globe.

And Commissioner Manfred just said

that he expects a full season --

not sure what the fan situation will be.

But Yankees are on fire, Mets are on fire.

It's gonna be an awesome year.

And I can't wait for 162, a full season.

-Right? Yeah. People like seeing you.

I mean, that's why -- I mean, I see you on "Shark Tank,"

because you're -- you know what you're talking about.

You've built a giant business empire.

Is it -- Have you always been into business,

or is this a thing post-sports?

-Yeah, ever since I was 10 years old,

I've had two big kind of goals, as --

I call them the two B's -- right? --

baseball and business.

And I wanted to be like my father, an entrepreneur.

He also loved baseball.

And I've studied it for a long time.

We're lucky we have an incredible team.

We've done some awesome things in 2020

through a very, very difficult time.

We've given tons back to the community.

-Yeah. -But we're happy

we're taking a public company, hims & hers,

one of the great telemedicine companies that we have,

going public.

And then, we're taking another one public later in the year.

So it's been a very active, busy year.

We've been growing a lot,

and excited to do more and give back more.

-Why do you like doing "Shark Tank"?

-I like it for several reasons.

Number one, I feel like, on Friday nights,

America is getting their MBA in business.

That's number one. -[ Chuckles ]

-Number two, it's done a lot of social good.

It's deployed over $100 million, over 25,000 jobs.

My daughters, Natasha and Ella,

ever since they were, like, little, little, little girls,

I always used to make them pitch to us

and tell us about their business ideas.

-Alright, I'm trying to think of any ideas I can pitch you,

'cause I always try to pitch you ideas.

I have one idea for a silent glass.

So, if you're having a cocktail,

I don't want to hear the ice clink around, you know?

Alright. That's one idea.

But I don't know how you do it or if anyone needs it,

but, hey, I like options.

Do I have any other bad ideas?

I have an idea for Oreo. -Okay.

-I think Oreo should come out

with cookie dough in the middle of the --

instead of the creme filling.

If Oreos... -Okay.

-Would... -You're getting warmer.

-Okay. [ Both laugh ]

Alright. I'm trying to think -- Oh!

Then I thought of another cookie idea

where the inside is powdered milk.

So, when you eat the cookie, it turns into milk and cookies.

It's gross -- never mind. Okay.

I want to -- [ Laughs ]

That was the reaction -- -You saved the worst for last.

It was great. [ Both laugh ]

-That's the reaction I want to see, man.

I want to show everyone a clip.

Here's Alex Rodriguez in "Shark Tank."

Take look at this.

-So there's two rules in investing, as I see it.

Rule number one is don't lose money.

-Right.

-Rule number two is don't forget rule number one.

-Yeah. -Okay?

So I'm going to make this investment

as convertible debt. -Okay.

I'm going to offer you $200,000 for 20%.

When you hit your 1.8... -Mm-hmm.

-...it will convert into equity. -Okay.

-That's my offer. -Okay.

-You understand the dilution of that.

-I do.

-Alex Rodriguez, everybody!

Catch him in an all-new episode of "Shark Tank,"

now on demand and on Hulu.

Alex and I are playing the "Singing Whisper Challenge"

when we come back.

It's going to be fun. Stick around.