Interview with Yitz Applbaum
Yitz Applbaum is an investor and businessman who is the founder of MizMaa Ventures. He is Jewish Insider's wine columnist.
Scotch and Cigars
Contents
Max Raskin: People probably always ask you about wine, but I want to start with hard liquor. How do you take your scotch?
Yitz Applbaum: Always, always, always straight up.
I drink mostly cask strength — anywhere from 50 to 65 percent alcohol. I rarely if ever cut it with water. Sometimes, if the alcohol burn is too overpowering, I'll cut it with an eyedrop of water. But very rarely.
If you drink really beautiful, high alcohol scotch, a little bit of water does open up the nose. But you're talking about a teardrop.
MR: I find it is easier and tastes sweeter and more caramel-y the more water that’s in it.
YA: No, you're just drinking the wrong stuff. It's that simple.
MR: I like Laphroaig. Is that good or not good? And Octomore. The peatier the better.
YA: Both are wonderful, but I hope by the end of this interview to introduce you to some truly great scotches
MR: But you say that's sacrilege to put water into that?
YA: It is. Given the predilection of your palate I would strongly recommend to you to try Lagavulin for the elegant peat and smoke you favor, and Talisker for the sea salt and iodine you crave. You will not need to cut either with water or ice.
YA: If you were a first-time cigar smoker who wanted to smoke something very beautiful, then I would recommend a Trinidad Robusto, a Cuban cigar that I like very much. This Robusto has a lighter flavor too; it's easier to smoke. I also very much like the Arturo Funete brand – the best non-Cuban cigar family in my opinion.
MR: For someone who's only drank Jameson in their life, and they wanted to try a nice scotch, what would you recommend?
YA: If you want to start your journey in really wonderful scotches — and no one says you have to buy a $1,000 bottle. A brand I love to drink a lot of is called Mortlach. You can buy age ranges from 12-year-old to 30 and upwards, the liquid is very beautiful. And I find it's one of the great equalizers because it's affordable, it's attainable, and it's really good as a starting place.
MR: For someone who has never smoked a cigar, where would you recommend they start?
A Material World?
MR: How do you balance your gashmius [materialism] and ruchnius [spirituality]? You are interested in material — in the physical world and aesthetics and taste and things that please you. But I know you also have strong political and religious beliefs.
YA: First of all, I don't let them control me or own me. I own them and I control them.
MR: The material?
YA: Yes. I don't yearn for anything that I have to have. I don't chase after anything that I can't really afford. And so it's never that it's a have-to-have or need-to-have.
The second thing is that a lot of my gashmius helps my ruchnius. I'll give you an example. I have one of the top 10 kosher wine collections in the world. You know what I do with those wines? I have huge Friday night farbrengens. I do lots of Shabbos meals.
I don't collect anything for the sake of collecting.
But my wine and my whiskey and my cigars, which are the three things I like— I share, I drink, I trade. It’s around friendship, it's around community, it's around enjoyment.
MR: I want to dig a little deeper on that — it would be one thing if you just hired someone to buy the stuff for you and you devoted no mental energy to it. But you have considerable intellect and at least part of it is occupied by the names of vintages of good scotches. That must be some serious compute power. How do you justify that? Or do you think it helps you relax?
YA: That's a great question. I can't answer you. It's a hobby. It's a passion. It's an interest with an end result.
My dad was a big stamp collector. When he died, I don't know who inherited it. But I can tell you — for every dollar stamp, it was worth 20 cents. His passion was stamp collecting.
He was a rabbi, but he stamp-collected and there was zero practical benefit to it except for the fact he was a perfectionist and he loved doing it. I can see him sitting there using these tweezers, picking the stamp up, putting it into the plastic. I couldn't do that for 30 seconds. I have ADD, I'd go out of my brains.
MR: Did you ever talk to him about it?
YA: Not that I remember. I should have.
People, Places, and Things
MR: So I’ve noticed that on the one hand, you very much go with the flow and when a new opportunity presents itself, you are all over it. But on the other hand, you seem very structured and regimented. I wonder: how do you balance those two things? How much of your day is set and how much is spontaneous?
YA: I think what happens is I get very excited very quickly about a lot of things, but it's usually driven by people. If I see a great deal but the person doesn't energize me, I probably am not going to say, "Oh, let's go look into it and make connections." But if it's a really good deal with people who I want to get to know or who are experts in their space or doing something really creative or different, then I get very, very energetic about it.
And then what I'll do is I'll introduce them to people. This is always a win-win situation in that I'll introduce it to smart people who can both opine on whether it's a good deal and if someone else wants to invest, then it's a win-win situation because I got confirmation and I did everyone a favor.
MR: How do you actually organize your day?
YA: It's a couple of things. I do everything on yellow or white legal pads [shows pads divided into three columns].
MR: What are those columns right there?
YA: They are: People I need to be talking to, projects I'm working on, and places I'm going. The metrics in my brain are around people, places, and things I need to accomplish.
On projects, everything is weighted. I spend time on my funds. And I spend time on my companies and I spend time on my boards. I figure out how to prioritize things daily and weekly, always trying to get to where I want to go.
MR: Can you tell me what's the last thing you crossed off your list if you feel free to share it?
YA: Of course. It's very mundane because I'm taking a train from London to Edinburgh. I simply booked my train back and forth. I’m flying by plane to Islay for the opening of the Port Ellen Distillery and then I’m taking a plane back to London for Purim and then I'm taking a train back to Edinburgh for some barrel tastings. And so I simply had a couple of logistical things to do that I crossed off.
MR: Do you have a secretary?
YA: Yes, but she doesn't do my scheduling. She's been with me for 20 years and does all my financial stuff, but all my scheduling I do myself.
MR: That's very interesting to me is that you do all your scheduling.
YA: Part of it is I don't like to let go. Part of it is that I change my mind so frequently, so I just end up doing it myself.
MR: Do you use technology for organizing your life or are you more a pen-and-paper guy?
YA: I'm more pen and paper, but I use Microsoft Exchange. My calendar is second to my Bible study. There are few things more important than the calendar.
MR: Someone like you has a just enormous — both mental and physical — list of contacts. How do you keep track of it? It is high-tech or low-tech?
YA: That's more high-tech. I have people in categories in Microsoft Exchange. So if I'm going to New York, I'll run through my New York contacts and ask, "Okay, who should I be seeing?"
MR: Is it just organized by location or are there other categories?
YA: Yes, I’ll categorize by limited partner, general partner, VC, Young Presidents Organization, for instance.
MR: How many people are in your contact book?
YA: About 7,000.
MR: Wow, that's a lot. When you meet someone, are you fastidious about updating it?
YA: Not as fastidious as I should be, but yes, I'm pretty good at it.
MR: Are you as fastidious as you used to be?
YA: No, no, no. Everything, I'm less.
MR: Really?
YA: Yeah. It’s not even that I'm slowing down. I get up at six o'clock and I go to bed at 11 o'clock and I can be in three cities in the same day. I don't tire or slow down from a physical perspective, but from a mental perspective, there was never a time when I didn't do two or three things at the same time. I can't really do it anymore. Focusing. I need to focus. I can't be sitting talking to you now and doing email and be on the phone at the same time. I have to focus.
Zooming Out
MR: Do you have unscheduled chunks of your day just for reflection and thinking?
YA: Pre-COVID — and this is either good or bad, I can't tell you — I never, especially if I was traveling, ever had an hour that wasn't scheduled. There was no way I would be in a city and not have a meeting every hour or hour and a half. Most of them were meetings I wanted to have. Sometimes it was just prospecting, but I always did that.
COVID taught me that I can a) have downtime and b) do Zoom calls. It taught me that I don't always have to see someone face to face. I can do calls. This sounds simple now, but it surely wasn’t back then.
So now I mix my day, even when I'm overseas, I'll do Zoom calls. That mixture has given me more time to have some downtime because the Zoom calls never go the full length. I don't have any travel time between meetings. I don't have traffic.
So a long answer to your short question is: I do not take scheduled mental breaks but I do take some time to plan and think.
MR: What did you mean when you said you did “prospecting.”
YA: Just new people to meet, new contacts because I'm never raising capital, but I'm always raising capital. Not necessarily for our funds but we’re always thinking about raising for our companies. I have a company I'm working on now that I think is going to be the biggest company I ever was involved in. It's called Orca.ai and it's Mobileye for ships.
Digging Deep
MR: Have you ever done therapy?
YA: I've done therapy two or three times in the last 25 years. It has always been short-lived and not successful. Not because I don't share, but because there is something buried deeply inside of me. My mother died when I was 16 and I am not sure I ever really absorbed that properly.
MR: How did your mother die?
YA: She died of cancer. But very quick — six weeks from diagnosis to death.
And no one's been able to really prove to me that they can dig in deep enough to expose what's the real issue. Maybe I've just never gone deep enough or with the right person, or not spent enough time digging. But I continue to try.
MR: Is there something particular in your behavior you want to fix or just in your personality that you want to understand?
YA: The latter. I am happy with my life and where I am. But I would love to understand more, just because I think I can be a better person.
Listen, I'll sit and talk to you for three or four hours one night smoking a cigar, and I'll learn so much about myself and you and see things that I never saw before because you're able to bring things out in people. That happens to me from time to time and I love that. So if there's more to me, I'd love to know it.
MR: Do you have a lot of friends?
YA: I do have a lot of friends.
MR: Do you think you have too many friends?
YA: I don’t think so. However, since I turned 60, I’m focusing more on spending more time with fewer people.
Applbaum Variations
MR: What do you do to really unplug?
YA: I hang out with buddies. I listen to music. I love classical music, Hassidic music, and country & western.
MR: What's the last classical music you listened to?
YA: Bach — the Goldberg Variations.
MR: Is there a version you listen to?
YA: No. My older brother is an expert's expert. He can listen to a piece, and not only tell you the piece, but probably tell you who's playing it.
MR: Would you call yourself an introvert or an extrovert?
YA: I'm an extrovert.
MR: Do you get energy being around people?
YA: Yes, very much so
MR: What about your wife?
YA: Oh my God — a super introvert.
MR: Since you host so much, I feel like Shabbos for you might not be as relaxing. Is Shabbos a day of rest for you?
YA: So Friday night, often not, because Hilda cooks, prepares, and I do the wine. Friday night with guests is our favorite meal of the week but I am not sure it is always relaxing. Fulfilling yes, relaxing — less. Shabbos we tend to meander our own way, go to shul or not, and have a quiet Shabbos lunch – very, very relaxing.
MR: What's the first niggun that pops into your head right now?
YA: [Sings “Hakodosh Baruch Hu”] — it’s a Dedi Graucher song.
MR: Do you watch TV?
YA: Pre-COVID, never. During COVID we started watching Netflix — Fauda, Outlander.
We're watching something now called The Wire about Baltimore.
Starting COVID, Hilda and I had dinner every night together and watched an hour of TV. We worked all day, but at night we watched an hour of TV and now we do that at home.
MR: So I’m going to say a statement and tell me if this is true or false — it seems like COVID was good for your personal life.
YA: I'm not allowed to say yes, but it was very good for my personal life.
MR: I think I asked you this when we first met, you probably way surpassed your dreams of how much you wanted to earn in life. Do you have a temptation to just check out and either study or do the equivalent of going to a Buddhist retreat?
YA: I do, and then I quash it. I could do it for a week.
I’m going now to Edinburgh to barrel. The rarest barrel I've ever bought is a 1982 Brora, 42-year-old. It's from a closed distillery. I go with a couple of friends and that is to me like a Buddhist meditation retreat.
MR: Will you bring your phone?
YA: I'm never without my phone except for Shabbos.
I went with one of my dearest friends, Greg Wolfond, a hugely successful entrepreneur in Canada, and he took me up to see the Aurora Borealis, but he didn't tell me the phone wasn't going to work. I had hives and I went through a withdrawal for a day, but it was three days and I did it.
MR: But Shabbos you probably love?
YA: Oh yeah. I love it. Three-day yontif doesn't affect me at all.
MR: Do you care about clothes at all?
YA: I don't care how I look that much, but I have nice clothing, mostly because my wife buys me really wonderful clothing.
MR: What’s an example?
YA: Oh, I love Loro Piana. I love the fabric. I love the way it looks, the way it holds. I own very little of it, but what I own I wear on special occasions.
MR: Do you floss?
YA: Yeah, of course — every night.
The Wall
MR: Do you believe in God?
YA: Very much so.
MR: When you need things, do you pray for them?
YA: Absolutely.
MR: What's an example of something that you pray for?
YA: I'll tell you a story. I'm chairman of the Western Wall Heritage Foundation — the tunnels under the old city…I'll take you on tour.
One time I was down in the tunnels and Rabbi Rabinovich, the Chief Rabbi of the Holy Sites and the Western Wall, asked me what I was praying for, and I told him my aunt was sick. And he said, "You don't only have to pray when people are sick. If you want a new car or you want something good to happen, pray for it. Otherwise, the relationship you have with Ha-Kadosh Baruch Hu is always a one of ‘I'm in pain. I'm in need.’"
So I pray when I go to the Kotel, I pray for my kids to be good people, more grandchildren, things you would imagine…sometimes a new car or sometimes something is wrong or a deal is going bad. I believe in the power of prayer for sure. I try not to be frivolous about it, but I do believe in the power of prayer.
MR: Do you have a morning reading routine?
YA: I do. I do not read enough books. That's one of my big flaws in life. But I love the FT and the Wall Street Journal. So I am a news junkie. I go online.
MR: What’s the last book you read cover-to-cover?
YA: There's a wonderful book — The Hare with Amber Eyes — it's about pre- and post-war Vienna about a collection of small little dolls and they were handed down from generation to generation.
MR: And then what are you reading now?
YA: I just finished a book on tape on the House of Rothschild. I love history of people who've been successful. But I'm not in the middle of a book right now.
MR: And what about Jewish study? What does your Jewish study look like? Do you have a set time?
YA: Of course. Every Sunday for an hour I study Mishnah, I study Gemara.
MR: Where are you holding right now?
YA: We're holding in Makkos.
Insurance Salesman
MR: Do you have financial tips for young people?
YA: First and foremost, life insurance in general is the most important financial tip I can give anyone in the world at any age, but surely if you're young. Either second-to-die insurance, but if you're not married, then just regular insurance.
The other thing is the power of saving. Even when we first got started, and had very little money, we always took the maximum amount we could and put savings into our 401(k) No matter what. We lived less well, as long as we always took out that money that was tax-free or matched.
MR: In Jewish marriages it's called not second-to-die insurance, it's called second-to-kill.
YA: Exactly.
MR: It feels like the money's overlaid on top of all these other interests for you and it doesn’t actually seem that important. I guess my question is why do you keep doing these things?
YA: I ask myself that. I don't know. I am scared. I don't know what I would do otherwise. I have this talent — I put people together. I meet the right people. I know how to make the right connection. I like to invest. I'm just not sure what I would do.
MR: What are things that pop in your mind as things that you would be interested in?
YA: Well, that's the problem. I know I would like to study Judaic studies and read more autobiographies. I love to travel, but since I travel so much for work, I would need to figure out how to do non-hectic travel. I am just not sure if I am capable of slowing down. I suspect age will help me get there.
MR: What about teaching?
YA: Something is going to convince me that it's time to stop and do something else. I haven't figured out what that is.
I want to write a book on mentorship. To me mentoring is really important. And I both had mentors and mentored people.
Mentors and Mentees
MR: Who were your mentors?
YA: I had a remarkable mentor — Marty Stein, who was vice chairman of Bank of America. It took me six months to get a meeting with him…I was selling Israeli software.
I got to Marty. It's four o'clock in the afternoon. Five minutes into the interview he says, "Oh, and where'd you grow up?"
I said, “Flatbush.”
He picks up the phone, he calls his wife, and for the next 24 minutes we talk about Jewish geography we talk about this, we talk about that. It's one minute to go. He hangs up. I say, "Marty, my boss is going to kill me. I got to talk to you about some business here."
He said, "Yitz, I'm not buying anything from you. How can I buy from you? Talk to my five direct reports and go establish relationships with them."
And he's been my friend 40 years. When I started my company, he became the chairman.
Dr. Max Weiss, the former Vice Chairman of Aerospace was a guiding light to me in both business and how to treat people with dignity. Senator Norm Coleman is someone I look up to so much and has taught me an enormous amount about politics and doing things the right way. I have been really blessed in this part of my life.
MR: Who are some of your mentees that come into mind right now?
YA: I have some wonderful, wonderful young men who I've worked with. Grant Silow. He's extraordinary — honest and focused and dedicated and a great human being. To me the most important, quality in a human being is hakarat hatov — gratitude.
MR: What do you mean by hakaras hatov in this context?
YA: It is sort of like the saying paying it forward. When you help someone or do something good for a person you expect nothing in return. It’s part of your mission in this world. When you mentor someone both the mentor and the mentee need to feel as if they are learning, growing, enjoying the relationship. It can’t just be one sided – from the mentor to the mentee. With Grant I always feel as if I am learning and growing by being friends. Hakaras hatov to me is becoming part of the family.
MR: So it seems that teaching is totally up that alley.
YA: I'd be very good at it. I'd love to do it. I've done a little bit of that here and there, but what do I teach? And where do I teach it? And how do I teach it? And when do I teach it? To whom do I teach it? You know what I mean?
MR: I think people like you when they write books — people who are doers, who don't necessarily want to sit down — I think the way to do it is you sit down once a week with a tape recorder with someone and you talk to them and then you transcribe it. That’s how John Sexton did his book baseball.
I think if you gave yourself the time, you would come up with ideas that you don't even realize that you have. I think you would be capable of writing a really deep book on mentorship that you don't even know what you would say about it right now.
YA: Do you know Rabbi Dardik? Judah Dardik?
MR: No.
YA: He's someone you should know. He's our rabbi. He was our rabbi in Oakland. He lives in Israel now and he's a tremendous ilui.
I've talked to him a lot about this, and he thinks that there are things that I can do and he can help me around mentorship to really put it in the context of doing, of sharing, of giving, because I'm very much a doer, less thinking, more doing. And if I thought a little bit more and put it into the doing, I think the doing would be better.