How To Get Into Wine

Summary

How To! with Mike Pesca

Episode: How To Get Into Wine
Date: June 2, 2026
Host: Mike Pesca
Guests: Ross Novi (TV director/AD, aspiring wine enthusiast), Joel Stein (wine writer, author of “The Corrupt Wine Writer” Substack)

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Overview

This episode explores the intimidating world of wine—how to learn about it, enjoy it, and not get lost or feel out of place among aficionados. Listener Ross Novi wants to transition his casual, sometimes problematic, wine drinking into something more “erudite and classy.” Mike Pesca invites wine writer and former Time columnist Joel Stein to guide Ross (and listeners) through demystifying wine culture, selecting good bottles without breaking the bank, and cultivating genuine enjoyment rather than anxiety or status-seeking.

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Key Discussion Points & Insights

1. The Anxiety and Status of Wine Culture

• Wine’s Reputation: Mike opens with observations about wine’s “snooty” reputation, the confusing barrage of advice, and how it can feel like a minefield for newcomers ([00:07], [03:11]).
• Ross’s Motivation: Ross admits his interest is partly about not embarrassing himself and being able to “push back” in sophisticated company:
  “I feel vulnerable. I like being the person who can then make fun of someone for their lack of knowledge about something.” ([03:23] – Ross)
• The Gatekeeping: The group discusses how wine, like collectibles and luxury goods, creates club-like barriers via knowledge of labels, vintages, and proper storage ([04:05], [05:38]).
• Restaurant Strategies: Ross and Mike playfully debate the classic ‘second cheapest bottle’ trick and how everyone tries to “game” the system ([06:18]).

2. How to Start: Mindsets and Misconceptions

• Price ≠ Quality: Joel Stein directly challenges the myth that more expensive wine is always better ([15:04]): “There are a lot of things going on with wine pricing that don’t necessarily have directly to do with quality… I wouldn’t go by price in many things, like most luxury goods.”
• Label Appeal & Tools: Ross admits to buying wine based on label design, a habit Joel gently pokes fun at ([19:44]), but also says it’s okay to have fun with presentation.
• The False “Drink What You Like” Cop-Out: Joel says,
  “I actually don’t think you should drink what you want. […] You want to try a bunch of different stuff … some stuff does go better with certain foods.” ([11:11])

3. Practical Advice for New Wine Drinkers

• Buy by Region, Not Grape/Label:
  “Instead of grapes, focus more on place.” ([18:14] – Joel)
  Discovering less famous regions—Portugal, Spain, France’s Loire—can yield great, affordable wines (<$20).
• At Stores/Restaurants, Start with Price Point:
  “A sommelier almost always appreciates it if you say, ‘Hey, I don't want to spend more than $60 or whatever… I want something interesting or weird.’” ([16:02] – Joel)
• Don’t Fear Wine Pros:
  “The guy at the store knows things. Right? […] If you give them a price point, that takes away your whole fear of the discussion.” ([31:11] – Joel)
• Liberation from Optimization: Ross voices the “pressure to optimize” every choice, but Joel suggests focusing on trying new things—and not obsessing over mastery or status ([24:27], [32:12]).

4. Tasting Together: Demystifying the Experience

• Joel’s Cellar Tour: Ross marvels at Joel’s not-overly-organized “cellar” (really, a garage holding 600 bottles) and enjoys a tasting journey across three bottles—white, red, and dessert ([22:05]).
• Affordable Finds: They taste a $15 Portuguese white (well-liked), discuss accessible options, and reiterate good value often comes from lesser-known regions ([23:00]).
• Celebrating Enjoyment Over Expertise:
  “The lesson I’m learning is the best thing is to know people who know things and then lean on them.” ([31:03] – Ross)
• Dessert Wine Discovery:
  Ross enjoys a dessert wine, calling it “magical” and “everything I would want to enjoy from wine” ([30:59]), to which Mike jokes about “dessert chicken.”

5. Reframing Wine Knowledge and Status

• You’ll Never Know It All:
  “Just learning the restaurants in your city is hard. Imagine if you had to learn the restaurants in every city around the world … these are dynamic things.” ([26:04] – Joel)
• Wine Community Gatekeeping: Joel suggests that outside of the “high end,” most pros are welcoming—not intimidating ([27:20]).
• Taste is Malleable: Ross shares that in blind neighborhood tastings, cheap wines (“Two Buck Chuck”) can win, and our ideas of “good” or “bad” are shaped by exposure ([28:14]).
• Downsides of Expertise: Joel remembers:
  “Don’t start getting into wine because you won’t get any more enjoyment. You’ll just have to pay more for that enjoyment as time goes on.” ([28:53], quoting Mario Lemieux)

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Notable Quotes & Memorable Moments

• On Motivation:
  Mike: “It’s not a chemical dependency, it’s a chemical opportunity.” ([02:08])
• On Wine Anxiety:
  Mike: “Wine is really fraught. There are a lot of landmines with wine.” ([04:37])
• On Competition and Collections:
  Joel: “Are you guys just, like, showing off your baseball cards? Like, what is this all about? ... Yeah, we’re just measuring dicks here.” ([17:34])
• On Tasting Notes:
  Ross: “The red that he poured is one of those wines that you go, oh, oh. So that’s like a. That’s like a good wine. Like, it just feels like a different weight class.” ([29:41])
• On Wine Enjoyment:
  Ross: “Again, like it’s everything I would want to enjoy from wine. It’s different, it’s delicious, it’s all these things.” ([30:48])
• On Gatekeeping vs. Helpfulness:
  Joel: “The guy at the store knows things...We think of them as the enemy, the sommelier and the guy at the store. But they’re not. If you give them a price point, that takes away your whole fear of the discussion.” ([31:11])

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Important Timestamps

| Timestamp | Segment | Content | |-----------|--------------------------------------|-------------------------------------------------------------------------------------------------| | 00:07 | Opening remarks | Wine’s mystique and social baggage | | 03:11 | Ross’s vulnerability | Motivation: not to be embarrassed, desire for status | | 06:18 | Restaurant tactics | “Second cheapest bottle” problem | | 10:01 | Joel Stein introduction | Joel’s Substack and wine philosophy | | 15:04 | Price vs. quality | Wine pricing myths debunked | | 16:02 | How to buy in restaurants | How to approach sommeliers and price-oriented conversations | | 18:14 | Region over grape | Focus on regions for better value | | 22:05 | Wine cellar tour & tasting | Joel’s 600-bottle garage, white wine from Portugal | | 24:27 | Ross’s self-reflection | Motivations—pleasure vs. optimization | | 26:04 | Impossible mastery | You’ll never know it all | | 28:53 | Enjoyment diminishing returns | Quoting Mario Lemieux on the cost of “taste” | | 29:41 | Noticing a “weight class” | Tasting a high-quality red | | 31:11 | Demystifying wine professionals | Advice: store owners are allies, not adversaries | | 32:12 | Final advice and attitude shift | “Get weird with it. Try different things.” |

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Takeaways for the Aspiring Wine Lover

• Don’t be intimidated: Most wine professionals want to help you find something you enjoy at your budget.
• Start with your budget and seek interesting regions: For affordable, great bottles, look beyond California’s famous wines.
• Embrace experimentation: Tasting new things is more valuable than chasing “the best.”
• Release the pressure to optimize: “Get weird with it” and enjoy wine as part of life, not just a status symbol.
• Remember: Even aficionados still get pleasure from cheap or unexpected wines. Expertise is a journey, not a requirement.

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For more tips and practical guides, visit Joel Stein’s “Corrupt Wine Writer” Substack or listen to future episodes of How To! with Mike Pesca.

Transcript

[Joel Stein]

Don't start getting into wine because you won't get any more enjoyment. You'll just have to pay more for that enjoyment as time goes on.

[Mike Pesca]

Bottled poetry, Sunlight held together by water. Beer is made by men, wine by God. Martin Luther said that. And so many amazing things have been said about wine, you assume they're all true because you know, in vino veritas. But wine is also a snooty, snooty affair, or can be. And I find the most annoying thing about wine advice is this when they tell you, but the real rule of thumb is just drink what you like. Uh huh, sure. Like that won't get you mocked at the club or even de club. But what's an inspiring wine lover gotta do? Ask an inophile because they will tell you about the nose, the notes, the, the legs. Eventually you'll get to the wine itself. I have made my peace with my status with wine. I am a beer guy. So like Martin Luther says, I'm a man's man. But a lot of us want to be into wine. And unlike almost every other consumable, there are big hurdles, real or perceived. I am here on how to, to answer the question how to get into wine. And asking the question is this guy.

[Ross Novi]

I'm Ross Novi. I work in television as a director in first AD and I also do a lot of AI production tools lately. But one thing that AI hasn't been helping me with is, you know, how to pick the right wines, going to parties, sometimes in restaurants, and how to transform what is admittedly probably a drinking problem into something a little bit more erudite and classy.

[Mike Pesca]

Oh, so okay, I thought that you were this innocent lamb who just wanted to know about wine, but you're looking to cover up a problem and using a well known how to podcast to do so.

[Ross Novi]

Well, I wouldn't say cover up a problem, I would say just reposition my problem into more of an advantageous situation. Yeah, so yeah, covered.

[Mike Pesca]

Right, right. It's not a chemical dependency, it's a chemical opportunity.

[Ross Novi]

I'm glad it's a podcast because I'm shaking a lot right now because it's, it's 12 o' clock and I haven't had my Cabernet Sauvignon yet.

[Mike Pesca]

So what, where are you, where are you on the wine knowledge continuum? Where would you put yourself?

[Ross Novi]

Well, in some ways I probably know more than some people because I actually when I went to college I took a course on wines and it's famously the most failed class in the Ivy League, because seniors take it in a giant auditorium and we learn about all the varietals and all the regions, but mostly you're getting buzzed with each pour of the wine. And so I should have this knowledge, but instead I would just get kind of hammered and then go to the liquor store and then actually got into trying different brands and flavors of Mad Dog 2020. But I feel like I should know more. I'm 55 now. You know, I want to be classy, like George Clooney or Hannibal Lecter, you

[Mike Pesca]

know, do you want to get into wine because you really like wine, or do you want to get into wine so as to not embarrass yourself around people who really like and no wine?

[Ross Novi]

Yeah, I think you put your finger on it. Like, I. I feel vulnerable. I like being the person who can then make fun of someone for their lack of knowledge about something.

[Mike Pesca]

Not the other way, but also in your world. In much of the world, wine is an entree point, a currency. You have to say, speak it to some extent to show some level of sophistication. It's also table stakes for conversation because so much conversation takes place over dinner. There is this phrase, dinner conversation. I think it comes from there.

[Ross Novi]

Yeah. The fact that it also has vintage years makes it difficult to access. That's just an extra level of making it opaque that I think.

[Mike Pesca]

Right.

[Ross Novi]

You got to know the label, and then like, oh, what a schmuck. He got the 2022. Didn't you know there was a drought in, you know, the east of France? And, like, that's not right.

[Mike Pesca]

No. Wines like baseball cards, maybe a lot of collectibles have a year component. I haven't thought about this.

[Joel Stein]

Art.

[Mike Pesca]

I guess art has periods. Yeah. Okay. So maybe when you're collecting wine or collecting baseball cards or collecting comic books, you're staking your claim to that era.

[Joel Stein]

Yeah.

[Ross Novi]

And there's a lot of ways to lose, to make a mistake going back to, like, what we're talking about. Right. So there's just.

[State Farm Announcer]

Right.

[Mike Pesca]

Wine is. Wine is really fraught. There are a lot of landmines with wine.

[Ross Novi]

Oh, by the way, did you. I hope you stored the wine. Right, Right. Because you can totally get up because it was in the sun or it was too cold or it was too warm or. Oh, and then we're going to talk about pairing. But I want to just have that minimum where I can push back and go, hey, hey. I know, I know a little bit. A solid base to work off of. That feels secure.

[Mike Pesca]

Right. You're bringing me around because, you know, as you might know, Ross, I'm a bit of a skeptic and a pushback artist, and so I'd be dangerous with a little knowledge of wine. Probably more dangerous with a lot of wine in me. This is really, really fascinating. Also, what you're pointing out is of the consumables, it is the one with the most ways to go wrong, it would seem. I wonder if you think that's built into the snobbiness of wine to. In order to make some seem more expensive, you have to carve out all these potential downsides and all these ways to do wine wrong.

[Ross Novi]

Oh, I think so. Like, any, any. Any activity that you have to have this, this gate that, that people have to get through to. To join the club, you know, like, you know, you're developing your character for D and D, or you're just, just, you have to know this extra knowledge, otherwise you don't know. And so it's like a little test you have to go through each time you want to talk about it, to have a real conversation about it. And then if you don't, then you just become like. Like me. And you just go, I don't know. It's like, seems like a good price. Or, or how about this? When you go to the restaurant and you know that they. Everyone wants to get the cheapest bottle among a million of people, right?

[Mike Pesca]

Right.

[Ross Novi]

So you then, you know, they upcharge that the most. So then you get the second cheapest bottle. Trying to outthink them. But, you know, they probably thought of that too. So then you're like, I don't know what to get.

[Mike Pesca]

I have read that the most popular bottle on the menu is the second cheapest.

[Ross Novi]

Right? Right. So we're so clever. We have thought, no, no, they got us any even worse.

[Mike Pesca]

So right now, what are your favorite. What are your favorite wines?

[Ross Novi]

Now, I like reds. I like Cabernet Sauvignons, I like Rioja because I had a semester in Spain and that makes me think back to that. And it has a unique flavor that feels like it brings me back. So it's nice to have a wine that has, like, that emotional resonance, which I appreciate. So I don't know, I try things, but ultimately it's more price based and label based. If the label looks classy and looks nice, that appeals to me.

[Mike Pesca]

If you have one goal short term and one goal medium to long term, about your en ophilia, can you articulate those goals for me?

[Ross Novi]

I think just elevating you know, I hope I'm not coming off as a caveman like I understand.

[Mike Pesca]

Quite the opposite. With your summer abroad and your Cornell education and your diamond Denali, I'm glad

[Ross Novi]

you're picking up on all that. I'm selling it hard. What is it? Humble bragging? I'm really trying. I'm.

[Joel Stein]

No.

[Mike Pesca]

Well, I don't know about the modifier before brag, but go ahead.

[Ross Novi]

I've got the shakes, man. I'm a drunk. I need this. I need this, Mike.

[Joel Stein]

Yeah.

[Ross Novi]

I just want to elevate my working basic knowledge. Right. So. So. So when you go and you look for things, you just. Just. You're doing something a little more than just drinking silly juice or sleepy juice, you know, something a little bit better.

[Mike Pesca]

In a moment, the man. Of all the experts in the world, we are going to pick one who I am going to say is perfectly suited and will meet Ross where he is. And the reason I say this is he's actually sitting next to him. Right? We return in a moment. The wine seeker meets the wine merchant. Or at least the wine expert. Stay with us,

[Joel Stein]

Jesus. No more love.

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[Joel Stein]

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[Mike Pesca]

We're back with how to. We just met Ross. He has some goals around wine. You know, not to get a headache, maybe to get a buzz, but really to be able to have some grounding so he knows a bit about wine so he can have that conversation so he could not feel. I don't know if foolish is the word, but a little less than when he's hanging around with deeper inophiles than himself. And so who better to pair Ross with as one would pair a pheasant with a 1987 Burgundy, than this gentleman?

[Joel Stein]

I'm Joel Stein, and I produce a substack called the Corrupt Wine Writer.

[Mike Pesca]

And why corrupt Joel?

[Joel Stein]

Oh, if you Send me your wine. I will review it and I will give it a good review.

[Mike Pesca]

Does putting the corruption in the title really just get you off all ethical hooks?

[Joel Stein]

No, I think living in 2026 gets me off of all ethical hooks.

[Mike Pesca]

Yeah, but if I did substack called the plagiarizing journalist, would all bets be off? Would that work?

[Joel Stein]

Yeah, I think you could do that.

[Mike Pesca]

Now, Joel, I don't know if you know people like Ross or actually literally Ross, but when people get in touch with you who read your column, is this among are his reasons, among the reasons why people want to get into wine?

[Joel Stein]

But I was listening to both of you. You were both so sweaty and status conscious that it was an ick factor. It's just wine, guys. It's like food. Like, it's the idea that this is like owning a super yacht or something. It's not going to propel you into the varsity blues class just knowing a little bit about wine.

[Ross Novi]

Yeah, of course. Of course a guy like that would say a thing like that.

[Joel Stein]

It's what you said you didn't want people to say, right? Like, just drink what you want. I actually don't think you should drink what you want. But, but I do think that it's not, it's to me, I like food, I like restaurants, I like wine. They're all basically the same thing. And you know, you can't memorize everything about every restaurant in the world that's ever existed. And you can't do the same with wine. You could just, you know, if you know the difference between red sauce Sicilian and like, I don't know, you know, Tuscan, you know, grilled meat. It's like, you know a little bit about Italy and you know the difference. And that, that seems like that's interesting and that might help you, but some people don't even want to know that and they just want to, like, eat Italian food.

[Mike Pesca]

Well, you say you don't actually think that people should just drink what they want. I've. I've read, I've glean the subs, the subtext of your sub stack. It's drink what I want. But what do you really mean by that when you say people shouldn't drink, just drink what they want? Well, I just always drink what they like.

[Joel Stein]

There are always these quizzes like, what. What's you. You know, you're supposed to fill out what you like and they'll tell you the perfect wine for you. And that's just like, I don't know, it's like, I guess you could find the perfect restaurant for you. But yeah, no way to live. Like you want to try a bunch of different stuff. And some stuff.

[Mike Pesca]

Right.

[Joel Stein]

Some stuff does go better with certain foods. It just makes sense, you know, even if you don't think, if you think about beer, if you think about juice, if you think about like you just wouldn't match certain things because it would taste bad. And it's, it's worth having some idea about that.

[Mike Pesca]

Yeah. Milk and peanut butter. Tell me about your wine journey. How'd you get into wine?

[Joel Stein]

Well, in a sweaty, status seeking way, I like, I was around 30 and I was like thinking I want to be an intolerable old person, so I want to learn about classical music and wine. And for the wine part, I actually started with dessert wine because it's easy, it's delicious, there's not much of it. And then learn from there.

[Mike Pesca]

Okay. That's how you got into wine. What was your. So where were you? What was your baseline before you decided to be a classical music guy, an intolerable old person. Add in the wine, what you know about wine. What kind of wine drinker were you?

[Joel Stein]

I wasn't much of a drinker. I guess I. I had been up to nap a couple times, so I knew that kind of like big California punch you in the face wine and I liked seemed more interesting to me than other alcohols I had.

[Mike Pesca]

And then were you doing this as because you're a writer? Were you doing this as a project that you were going to write about or more personal improvement? Not improvement, but more for the personal aspects.

[Joel Stein]

Yeah, yeah, no, just personal aspects. I mean, I've wound up doing some food writing and some wine writing because I'm interested in it. But no, it wasn't like I wasn't going to write a book or something.

[Mike Pesca]

Did your wine knowledge and appreciation proceed linearly or were there jumps things that maybe you drank a certain wine and that just opened your eyes and opened your palate and things were never the same again.

[Joel Stein]

Kind of the opposite because I remember the first time I had a sip of a really expensive wine. It was an old Margot. Wasn't that old. It was a Margaux. And I expected it to taste like super wine, just like everything about wine times 20. And instead it was, it was just like really balanced and really nice. And I was like, oh, that's not, not what I expected at all. And maybe like chasing, you know, some kind of great wine experience isn't really what I'm after. I'm just after like Enjoying this as part of my life.

[Mike Pesca]

So what do the newbies say they're looking for from you in your newsletter?

[Joel Stein]

You know, I think they're just hoping to learn about wine by reading it. But if I write something like here are the wines to buy at Costco. That. That's always a hit diet.

[Ross Novi]

I go by his guide when I was at Costco. I look each time and definitely go by that.

[Joel Stein]

Oh, yeah, because wine. The one thing you guys were saying that I would push back on is you were kind of equating how much a wine costs with how good it is and trying to find a way around that. I think wine is one of those things. And I also think there are a lot of things going on with wine pricing that don't necessarily have directly to do with quality. That may have to do with, like these wine. Real estate, for sure in California makes wine much more expensive here. There's just a lot of other things to take into account. So I wouldn't. Well, I wouldn't go at price in many things, like most luxury goods. Right. Like if you're buying a purse or something.

[Ross Novi]

But that's the fear I have is then when you're looking at something is the price. It doesn't correlate necessarily. But then how do you figure out you get nailed with a $30 bottle of junk.

[Mike Pesca]

Okay, so give me a piece of actionable advice so I don't get ripped off. In fact, let's not think of it like that. So I can get a good, affordable bottle of wine I might not have otherwise known about.

[Joel Stein]

Look, it depends. One thing you guys talked about is a restaurant. If you're buying a bottle at a restaurant, I think a sommelier almost always appreciates it. If you say, hey, I don't want to spend more than 60 bucks or whatever it is, I want something that's really interesting or weird because I like to do that at a restaurant because I can go buy normal stuff at a store and they'll. They'll be so excited. Anyone can buy super expensive wines. And if I'm going to a store, under $20 is a great space for getting really good, interesting wines. Like, don't get a California cab for that price because they're. They're very expensive now. But can you get like, great Portuguese and Spanish wine? So what would you say? Great French wine?

[Ross Novi]

What would you say to someone at.

[Joel Stein]

I would always start with your price point. Like, don't. And I also don't think when you go to someone's house and you're worried about them judging you. There's so many wines in the world. You said, like, so many vintages, they're not going to know. Just get, like, an interesting wine. The Pebble Beach Food and Wine Festival has this dinner before the festival starts where you have to bring a Magnum that's worth, like, more than $5,000. And they have this dinner and I get, I. They drive you there into some house they've rented, and literally, like Walter Mansky, Thomas Keller were cooking dinners that no one even wanted to eat because they just wanted to, like, show off their wines. So I turned, I. I told them I wouldn't say who it was, but I was sitting next to someone who was. Remember the guy who owned the Washington Redskins?

[Ross Novi]

Dan Snyder.

[Joel Stein]

Dan Snyder. Dan Snyder. And I was talking to him and the guy next to me, I'm like, are you guys just, like, showing off your baseball cards? Like, what is this all about? They're like, yeah, we're just measuring dicks here. And I was like, oh, there's a collector aspect to this. But that's for, like, Dan Snyder. For the rest of us, like, just, like, look for regions that aren't as expensive. Like, you're not going to buy a burgundy for under 20, but there's plenty of, like, wines in the Loire or, you know, other parts of France that are really interesting that you can get for under $20 that are really good.

[Mike Pesca]

Do you have any insight as to the best way to orient yourself in a non Napa situation?

[Joel Stein]

Yeah, if you do want to learn, and again, you don't have to, but if you do want to be able to tell the difference between, like, you know, different cuisines of France that, like, you know, not all French food's the same. And seeing where Burgundy is and what the grapes of Burgundy are, and, you know, it's a little bit of work, but, like, instead of grapes, focus more on place.

[Mike Pesca]

Well, guess what? And this doesn't always happen on how to. But Joel and Ross are speaking to me from the precipice of Joel's wine cellar. So when we return, we do some talking and some drinking. Back in a minute.

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[Mike Pesca]

We're back with how to. We're joined by Ross, who would like to know a little bit about wine. And Joel Stein, who knows a lot about wine, invited Ross over and there's going to be some bottles opened and some wine exchanged. So Ross, what did you bring to the table today?

[Ross Novi]

Well, I, I brought a bottle of Dao. Dao, pronounced right.

[Joel Stein]

I always wondered. Yeah.

[Ross Novi]

D A O U. Cabernet Sauvignon, like I talked about earlier, has a nice classy label. It.

[Mike Pesca]

Label, yes. Ross is really into the label.

[Ross Novi]

Well, it's, that's how I get an idea. You know, I don't like the ones where they have like, like Snoop Dogg on it or like people in jail and stuff. Like that's not more the Dodgers. I have a wine.

[Joel Stein]

Yeah, yeah.

[Ross Novi]

Not into that. I mean this has like a nice serif font. Oh a classy.

[Joel Stein]

I'm familiar with Dao. I don't think you got a great price.

[Ross Novi]

Said I saved like 50% and then you get the bonus if you buy me.

[Joel Stein]

There were five Beatles once.

[Ross Novi]

Well, yeah, I mean it's been known to hallucinate. But anyway, I feel like I saved a little bit and it feels like an upgrade from my usual station and I wanted to impress him. I would have taken the label off if I was really smart. But he's going to know anyway. Let's be honest. He's an expert.

[Mike Pesca]

But I think this points out something Joel was saying is that you are too price oriented. You like the label and that's fine. But your definition of might this be good is you asked chat GPT is this a good value for the money?

[Ross Novi]

Yes.

[Mike Pesca]

And that's not the way to go.

[Joel Stein]

I don't like that. So Dow is a, is a manufacturer that makes a lot of wine. This is a big, they have a huge plot of land.

[State Farm Announcer]

Right.

[Ross Novi]

So I up. So this is, this is classic.

[Joel Stein]

No, this is fine. You'll be at a corporate party and the guy behind the bar is going to be pouring this for sure. This is going to be up there and so it's, it's going to be fine. It's not going to be great. Exciting, great.

[Ross Novi]

Sounds like a fun time plan.

[Mike Pesca]

We got a corporate party. Tell me more. So what do you got? Okay, counter. You see his Dow and you now

[Joel Stein]

Ross says he likes red so that my immediate desire is to give you white. Is that Wrong. How do you feel about whites?

[Ross Novi]

I can. I can drink white.

[Joel Stein]

Do you like sparkling whites? Do you like.

[Ross Novi]

I prefer not sparkling.

[Joel Stein]

Not sparkling.

[Ross Novi]

Yeah, but I know. Yeah, but it's omakazi. Like, you know.

[State Farm Announcer]

Okay, okay.

[Ross Novi]

Let the chef tell me what I should have.

[Joel Stein]

And I know you like dessert wines.

[Ross Novi]

Yes.

[Joel Stein]

Okay.

[Ross Novi]

But not at 12 o'.

[Joel Stein]

Clock. Really? I was gonna open a fun dessert wine.

[Ross Novi]

Okay, let's do it.

[Joel Stein]

Okay, but how much time do we have? Should you open a white and a red or just go to red and dessert?

[Mike Pesca]

Let's go white. Let's do it all. Describe Edward Murrow esque on the top of building during the London blitz. Describe his wine cellar. What are you looking at there, Ross? Physically, is it down? Is it downstairs? Is it in the room you're in? Tell me about this.

[Ross Novi]

We're in his garage. It's this downstairs garage that has this walk in space. Not large enough that you would want to drink in there, but it has shelves all around, about four, four levels high. And so it feels like 250, 300 wines in there.

[Mike Pesca]

That's great.

[Ross Novi]

Yeah, yeah. And it's not labeled. It's not lab, which my instinct was I would want to organize it more. But he just.

[Joel Stein]

It's like close to 601.

[Ross Novi]

I'm not good with numbers. 600, so. But it's. It's enough that I looked at it this morning and was like, I don't know if I could ever finish. I know it feels like there's a little pressure that's building. Like at some point you gotta.

[Joel Stein]

I would also recommend. Don't get a corkscrew any more complicated than this. Okay. I've never had this. This was sent to me, but I know it's a 15 bottle of wine and it's from Portugal and it's not quite as cold as you would like.

[Ross Novi]

It's okay.

[Mike Pesca]

So this is a white from Portugal. Am I wrong to think Portugal is no more known for its reds?

[Joel Stein]

They do both. Most countries do.

[Mike Pesca]

Yeah.

[Ross Novi]

This is delicious. And I like this temperature box. This is great. Yeah, this. So this makes me angry in a

[Mike Pesca]

way because like, so you can get

[Joel Stein]

good wine prices for Portugal.

[Mike Pesca]

But where did you get this?

[Joel Stein]

But that's the thing. Don't focus on like this because it's not like, no offense to the nice people that sent me this, but it's not like some super special wine. It's just like you can get from different regions of the world better deals.

[Mike Pesca]

Ross, you said it makes. What did you say it makes?

[Ross Novi]

Me angry just that his access to those better choices. Right. But I mean, I'm being facetious because he has knowledge, you earn knowledge. And that's what the benefits of that. But, you know, it's just that you'd also know. And I guess that's part of the frustration with any of these opaque things is, you know, there's a better answer.

[Mike Pesca]

But Ross, I want to, I do want to ask you this. You at least have articulated some notions of being interested in wine for what they might call external reasons, when perhaps the best reason to be into wine is that it just pleases you. Now, can you do a self assessment and strip away all the jokes? Do you think that's accurate or are you mostly into wine for the reason of you'd like to like wine?

[Ross Novi]

First of all, I feel naked, so thank you. No, I, I think there's a truth to that. And maybe I've been leaning a little bit into that as well. But I sure, I do think there's a legitimate. You can enjoy wines of different price points and all of that. And I'm not looking to tie my status to it. And it's not like I get really upset if you get a bottle of wine that maybe you wished it was better. It's just, maybe it's like there's just so much to know in the world and there's so many things that, yeah, I can know that and pick that up and you can learn to specialize. But I drink a lot of wine and I enjoy it and just, you know, that there's more to. To learn. But you can do that in a thousand directions in your life. And so it's a little frustrating. And maybe I'm not answering it, but I feel like it's. Maybe it's a more global frustration that, yeah, I can know more about that and I don't need it to feel special, but I just would always like to be optimizing my choices. And I think that's. But there's a pressure to optimize everything in my life always. And maybe that's what I'm feeling.

[Mike Pesca]

But to be fair to you, if there is something about wine that makes people feel defensive, I don't know if it's inherent, I don't know if it's cultural around people who like wine, but I do sense that as the non wine drinker, when I approach wine, I was making all these jokes maybe out of a sense of defensiveness. And is that, I don't want to say inherent. Do you, Joel, think that that actually is going on. And does it need to go on with wine? Is there a way through that?

[Joel Stein]

I think the idea that you could learn everything about wine is particularly ridiculous because, look, just learning the restaurants in your city is hard. Imagine if you had to learn the restaurants in every city around the world, right? And then, you know, these aren't stable things. You learn the name of this winery, someone else buys it, it's got a new name, it's got a new wine maker. These, these are dynamic things. It's not just the weather of the year. These are, these are businesses that are changing over time. So imagine trying to learn all the restaurants in the world, all the chefs who ever worked there when they were good, because you can buy old wine, right? And the other thing is, old wine isn't better wine. Old wine is just different and most people don't even like it. So don't focus on thinking the year. You know, old wine is going to be something you love.

[Mike Pesca]

To be fair to Ross and what he was articulating, Joel, is there anything about the wine industry or the people who are the cask keepers, which is what they call gatekeepers within the wine community, I've just coined that, that plays into this, that makes it so a person like Ross will say, you know, I'm made to feel inadequate when I approach this as opposed to welcomed.

[Joel Stein]

I mean, on the high end, I think there's some of that. But I think that's true with a lot of what are now called luxury goods, whether that's clothing or, you know, walking into a clothing store can feel like that. Walking any. Into anything that's filled with people of a different economic status than you can feel weird in a capitalist society. But I think in general, if you go to a wine store or a restaurant, they aren't trying to make you feel that way at all.

[Mike Pesca]

But, you know, I always wonder if it's worth putting in the time to, to refine my palate. It's, you know, the curse of knowledge. I once took a scotch tasting class and now I can only drink really good. That is really expensive scotch. So same with wine. What if I like the mass produced stuff, the cheap stuff? Am I better off, in fact, being educated out of that orientation?

[Ross Novi]

We once did a neighborhood wine tasting and we had blank labels to see what people thought and that we had a range of wines and Two Buck Chuck ended up, I think, if not winning, then second, which. It's not good, it's juice, it's not bad, but also our tastes, you know, are trained on things. Just like we watch certain shows and we. Certain things we're used to, and so then we like them more. I think. I think that's part of it.

[Mike Pesca]

So is it that the cheaper wines don't actually taste cheaper unless we know we're trained to think of them as cheaper.

[Joel Stein]

So I remember watching, like, a hockey thing, and Mario Lemieux had a sweet wine collection, and he said, don't start getting into wine because you won't get any more enjoyment. You'll just have to pay more for that enjoyment as time goes on. I think that there's truth to that for sure.

[Mike Pesca]

Yeah.

[Ross Novi]

And when you.

[Joel Stein]

When you go to a winery, like, these are people who are farmers and they're working in agriculture. So that feels even less intimidating, except on the very high end. Should I go get a red?

[Mike Pesca]

Yeah. And so the guys got a red.

[Joel Stein]

So American wine, it's hot in California, and Americans have a certain personality type. And so American Cabernet Sauvignon tend to be big and loud and punch you in the face, which can be super fun. Right. So I think this will be a little more intense than that one.

[Mike Pesca]

The guys liked it.

[Ross Novi]

The red that he poured is one of those wines that you go, oh, oh. So that's like a. That's like a good wine. Like, it just feels like a different weight class.

[Mike Pesca]

And tell me, how much. How much are you drinking? A sip here and there.

[Ross Novi]

Well, I, you know, I have a problem, so I'm. I'm. I'm drinking it all. Tiny pores. I know it's a little stingy, the pores so far.

[Mike Pesca]

Yeah.

[Ross Novi]

Are you a spit bucket guy or.

[Joel Stein]

I never use the spit bucket. I should use the spit.

[Ross Novi]

It seems so antithetical. I can't, like, I can't accept using the spit bucket.

[Joel Stein]

I know.

[Ross Novi]

I almost get mad at actors when on set, they, like, spit it out. Like, I'm like, come on, keep eating.

[Mike Pesca]

And then they moved on to dessert wine.

[Joel Stein]

This is one of my favorite wines in the world. So this will go. Even though it's dessert wine, you could. I would drink this with chicken.

[Ross Novi]

Yeah. I mean, this is, again, getting into, like, this is magical.

[Joel Stein]

This is what wine I think this is.

[Ross Novi]

Want it to be like, it's really.

[Mike Pesca]

I drink it with maybe a dessert chicken, a candied Cornish hen.

[Joel Stein]

So I did buy this at auction. You can buy things on auction now easily and cheaply.

[Ross Novi]

That sounds terrifying. Like, I was. I almost going to buy a car on auction. You should see what they're selling at auction.

[Mike Pesca]

How is it? How is it, Ross?

[Ross Novi]

Again, like it's everything I would want to enjoy from wine. It's different, it's delicious. It's all these things. And it's also. I'll never have this on my own.

[Mike Pesca]

But why do you say that? Like Joel has given you some advice on how to get there?

[Ross Novi]

No, it's great. It's, it's wonderful. And I think the lesson I'm learning is the best thing is to know people who know things and then lean on.

[Joel Stein]

But the guy at the store knows things. Right?

[Ross Novi]

That's true, that's true.

[Joel Stein]

Like we think of them as the enemy, the sommelier and the guy at the store. But they're not. If you give them a price point, that takes away your whole fear of the discussion. Right. It's just like I want a good wine under 20 bucks. I want a good wine under 15 bucks, whatever it is. Then you can have a really nice discussion with someone who wants to share their expertise without worrying that they're going to screw you up or upsell.

[Mike Pesca]

So but Ross, going back to the advice he gave, do you think there is a chance you may reconsider your conception or your misgivings going in? In other words, might there be a recalibration of your attitude towards the entire endeavor?

[Ross Novi]

Yeah, I mean it's really helpful to hear the demystification of it and just to recenter that like again, it's a food good and it's just like not to put too much pressure on it and just to experiment. I also love his advice which is just get weird with it like and try different things.

[Mike Pesca]

Joel Stein was a writer and columnist for Time in the LA Times and is the author of Man Made and indeed Defense of Elitism. But here he was very much a man of the people. He is the author of the Corrupt Wine Writer on Substack. Joel, thank you so much.

[Joel Stein]

Thank you.

[Mike Pesca]

And Ross Novi works in TV and is working on himself and how he could become a better and more principled and exalted in a file or at least to not worry about the labels and the, the prices and just to enjoy some wine. Ross, thank you so much.

[Ross Novi]

Thank you.

[Mike Pesca]

If you like what you heard today, please give us a rating and a review on Apple. We have two ratings from since I took over the show. I think, I think we'd like more and we'd love your questions because we'll make segments out of it. How to make a great apology. There is one. We have experts standing by. Email us at how to at Mike Paul and on my other show, my daily show, the Gist. Today I will be talking to a future how to guest. His name is Simone Stolz. Off and on How to he's going to guide someone who's trying to decide between passion and stability in a career. On my show, he's talking more explicitly about his new book, how not to Know the Value of Uncertainty in a World that Demands answers. That's Simoni Stolzoff on the Gist and what the information age has done. Yes, it's helped, you know, eradicate some diseases. It's helped us improve technologically as a society. But this influx of information has often just made our lives more anxious. How to is produced by Jeff Craig and Cory Warra. Michelle Pesca puts the can do and How To Charles Duhigg founded the show and to motivate us, he has taken to snapping castanets and stomping loudly on the floor. I asked him to explain I had

[Ross Novi]

a semester in Spain and that makes me think back to that and it has a unique flavor that feels like it brings me back.

[Mike Pesca]

It's very motivating. I'm Mike Pesca, back every week answering your questions of how.

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