New York’s Coolest Couple: An Interview With Abie And Leandra Medine Cohen

A glimpse into the lives, family histories, and brilliant ideas of some of the coolest people I’ve ever had the honor of interviewing.

Leandra Medine Cohen is the founder of the iconic fashion blog Man Repeller, a witty, honest, and massively influential lifestyle publication which was included in Time Magazine’s 25 best blogs of 2012, author of ‘Man Repeller: Seeking Love, Finding Overalls’, and founder of The Cereal Aisle, Leandra’s newest hit blog. Abie is a former financial adviser at the largest private bank in the world, Switzerland’s UBS bank, and the cofounder of early stage venture capital firm Centre Street Partners.

I’ve never interviewed two people at once before for Time Well Spent, but I couldn’t be happier that the first time was with Leandra and Abie, and you’ll see why. People go their entire lives without meeting anyone who views the world in ways as compelling and sound as they do, so it’s a remarkable thing that I not only got a chance to chat with them, but that I also get to share the conversation with all of you.

To keep up with Leandra and Abie, subscribe to The Cereal Aisle, follow her on her beautiful instagram, and visit the Centre Street Partners site here!

For Abie—

My first question for you has to do with your personal history. I don’t think there’s a better way to find out who exactly someone is than asking about where they came from. For example, I remember watching season two of the Sopranos I think it was and thinking that it was less compelling than the season prior, and I couldn’t figure out why, until I realized that the series protagonist, Tony, had a falling out with his therapist and hadn’t been to her office in at least a few episodes. His therapist’s office was an anchor supporting the entire character, and in turn the entire show, and all he ever did in that office was talk about his family history. The more he talked about the past the easier it became to understand Tony’s present and predict his future, we understood him more or less perfectly and it was beautiful. Can you share a bit about your family history, where they came from, where they’ve gone, what they did there, and maybe how that all shaped you? 

My whole family is Syrian Jewish – all of my relatives emigrated from Aleppo between 1900 and 1915 and ultimately settled in the Gravesend and Midwood sections of Brooklyn. I don’t know very much about my ancestors' lives before America but I do have friends who can literally trace their lineage back to King David who lived ~1000 BCE, which I find remarkable. There is a lot written on the community at large but I’ve missed learning about my specific family. It’s something I’m curious about, in particular relating to general religiosity level and professional interests. 

My family on both the maternal and paternal sides is very big and everyone lives in either Brooklyn or Manhattan. To give context on what I mean by big: last month, an aunt on my mother’s side hosted a Chanukah party and we counted 93 family members (including significant others) to have sprouted from my maternal grandparents, who were there celebrating with us.

As far back as I’m familiar, my mother’s family started in the retail business before they moved into real estate in the 1960’s. My grandfather works with his three sons (my uncles) and most of the male grandchildren (my cousins) and impressively, they all get along really well. I credit this to what I think is one of my grandfather’s leading principles – to live within your means. 

My dad’s family on the other hand also started in retail. They launched a retail pharmacy chain that still exists after an opportunity that took my grandfather to Louisville, Kentucky didn’t pan out. My father was actually born in Louisville – he came up in the family business before moving into finance after selling the family company in 1992. 

When I was growing up, my life revolved around four things: family, work, religion and community. And within the community, the four are intertwined – family is also work because you’re working with your family and religion relates because so many in the community believe financial success is attributable to faith in God.

I would say that growing up so deeply ingratiated in the Syrian community shaped me in ways I probably still am not conscious of. There is the Jewish community, and then there are pockets of communities within that community. The Syrian community has thrived in America to such a degree of magnitude that many other Jewish immigrant communities have made attempts (and in some instances succeeded) to emulate the model. Early on, I understood that I belonged to something, and was accepted by something that a lot of other people didn’t have. If at first that gave me a sense of entitlement, I think it is shifting to become a benevolent confidence. 

I’d also say the community is at the crux of my own internal battle – when a societal construct that is proven to work is laid out so clearly for you and you find yourself curious about other paths and even choosing uncharted terrain, a lot of complicated feelings come up.

Second question for you is: what does your routine look like these days, from working on Centre Street Partners to parenting to supporting and loving Leandra? 

I am and have always been very disciplined about my routine – it’s one of the few traits I can say with confidence are innate to my character and is, I think, the reason I’ve also always been a rules follower. Only recently have I started to question this trait in myself. Is it better to ask for an apology over asking for permission? Ten years ago I’d have absolutely answered no.  

My life today gets broken up into two finite parts: work and family with some room for myself around the edges – I wake up at 6:15 AM, spend a few minutes with my phone and then sit up for a 20-minute meditation. I started practicing transcendental meditation eight years ago and have been rigorous about keeping to this practice. After meditation, I get breakfast started for my kids while Leandra readies them for school – this 45-minute window is great family time for us. After they leave for school, I prep for work and either go to my office or a breakfast meeting. Lately I’ve been running around the reservoir in Central Park and aim for 3x/week before the kids are up.

Centre Street Partners is a venture capital firm focused on investing in founders at the earliest stages of building technology companies. I run CSP with my partner Jonathan Kerstein. I spend a lot of my work time in meetings with founders and investors, I am an aggressive networker. This is a quality that I brought with me from my career as a financial advisor at UBS. I had a rule back then to make 15 new relationships a week and I’ve carried it over. 

I usually head home around 6pm to meet Leandra and the kids for dinner and bedtime. Leandra and I will then catch up for a little before I head back to my computer for clean up and deep work. I do my best thinking and reading from 8-10pm while I’m riding out the fumes from my day. I usually get to bed around 10:30pm. 

During the week, I spend what I consider efficient quality time with the kids. An hour in the morning and an hour in the evening and I read to them almost every night before bed.

Can you share a few thoughts on the importance of fathers in the lives of women? I think fathers get discounted a lot these days as something defunct, but when your daughters grow up I’m certain they’ll disagree. And personally I think fathers are responsible for some of the most foundational parts of a decent life, like making life fun. I read a study recently on the “caring contexts” of parenting, or the split functions both parents have in childcare, with mothers spending most of their time on “managerial activities,” focusing on scheduling, dressing, feeding, bathing, etc., and with fathers having focus on recreational activities, or things like reading stories and playing sports and attending events etc. Fun, safety, stability, support, fathers do a lot and I don’t think they get enough love for all of it! What do you think about the importance of fathers? 

I definitely agree that it’s important for the children to have two different experiences from each respective parent. Leandra and I definitely play different roles for our kids' emotional and intellectual development. Leandra is more of an emotional support tool for them. While they’re just 5 years old, I can already imagine the stereotypical teenage drama they’ll bring home. Leandra is really good about letting them freely get their feelings out. I believe I offer more stoic path options. I’m often less emotional but still convey a sense of safety, stability and acceptance through the routines that I set and the even keeled approach I take to them. Overall though, I would definitely say Leandra is the fun parent. 

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For Leandra—

A common theme runs through some of your writing on Substack about losing your identity in your kids, husband, and routine, and I’ve been wondering if there’s also some element of this loss of identity happening because of the unspoken demands from your audience and the internet? More than ever it seems that deviating from popular ideas carries harsh consequences, but for figures in the public eye there’s an even more piercing version of this—it’s the inverse end of parasocial relationships, the audience holds the object of their love captive by way of their expectations. It’s a very weird thing! The brilliant author Tim Ferris has a blog post that’s related where he describes what it’s like becoming a public figure and suddenly there are tens of thousands of people who want to see you conform to their idea of you, who he had to then navigate his life around. Does the internet chip away at the edifice of your identity? Are we seeing your true self? 

This question is timely – I have been spending a lot of recent thought on the concept of generosity and how we expend it. To a degree, I think even the most miserly among us are generous with something: time, money, expectations, resources, compliments, judgments, even our senses of self. Most of the time, when we think about who is generous and who is greedy, it seems like we assume that they who are most selfless with their material possessions are also the most generous, and to a degree, this is true, but there is such a breadth of ways that a person can demonstrate their own generosity. 

One thing I realize about myself is that I’m very generous with my energy. Historically, I think it’s even been to a fault. I have a tendency to match my energy to the energy that is around me – be that high like with excitement or thrill or even anger, or low – like with sadness or pain or humiliation. I think I’ve always been this way, but have not been aware of it, and wonder if it is part of the reason that I tend to take it personally/get so hurt when energy that is my own isn’t matched. It’s an intimately familiar let-down. It’s also much more comfortable for me to meet and match low energy – possibly because I try to avoid the letdown. 

I’m not entirely sure – but when I look back retrospectively at my writing and my career at Man Repeller, it feels like I spent a lot of my time…feeling around, looking for energy, taking the temperature of the culture around me and using it to inform how I felt and what I wrote. I didn’t know I was doing this then though – and as such, don’t think I realized there could have been a difference between the energetic pull of what was around me, and what I, Leandra, actually felt. It created a lot of internal confusion.

So to the extent that the internet could chip away at the edifice of a person’s identity, yes, absolutely, it can. It has! My writing for Man Repeller was entirely wrapped in trying to figure out who I was – I wrote my way through my 20’s, trying to get a handle on where I was going, which often presented possibilities of who I could become based on the various directions that revealed themselves in the writing. And this, I think, was very unmooring, and created a desire for stability that had me clawing into whatever surfaces I could find. 

The newsletter is something else – it’s an expression, I think, of the surface I found once in private, a surface that really has always been here, even though it got shrouded in expectation. The newsletter is a reminder of who I am when I’m either not consumed entirely by the roles I have chosen to play in my life as: a devoted mother and committed partner and loyal daughter/sister/friend, or when I’m trying to reconnect with who I am under the roles. 

Now that I write this all out, I think it’s the very reason I have intentionally chosen not to anchor my writing in pop culture/what’s happening “out there” the way I used to, why it sort of exists as this other thing. It’s my energy when either I’m bathing in it or trying to swim back towards it, and it’s something I love to share.

I want to talk a bit about a related topic: your cancellation. Reading about it reminded me of this idea I like called the Gossip Trap. The idea is that, before the development of formal hierarchies like monarchy or electoral politics, early human societies self-organized through pure social pressure; shame, gossip, and virtue signaling shaped the prehistoric governance landscape. Human life was a popularity contest played at the expense of the more generative activities of civilization, like art or invention. Something similar is happening now: social apps have reinstated prehistoric village dynamics where no one is permitted to mind his own business since everyone is keenly aware of it, and everyone here becomes fair game for behavioral policing and character attacks. We’re all forced to either subordinate our interests to status games or get treated as social defectives by moral opportunists, and it’s not healthy. It seems like your work undeservedly bore the brunt of this, so my question is—How do we build an internet that avoids the Gossip Trap? What might it look like? Some examples I’ve thought about are “internet tenure” based on age of account creation and engagement generated by posts, which would prevent mobs from banning tenured accounts, mandatory anonymity like on the infamous 4chan, or obscuring the status of individuals as instagram has done by hiding likes to remove incentives to moralize and cancel. 

Is building an internet to avoid The Gossip Trap the goal? I’m not sure if that addresses the human condition that underlies it. I’m not even sure that the internet has reinstated prehistoric village dynamics so much as it has reactivated them at scale. Because even when witch trials and high school lunch table dynamics weren’t being re-enacted online, they were still clawing people out of their own integrity in more private settings. So I’m much more curious about what it is about shame or gossip or virtue signaling that unites us so potently. Does it actually unite us, or just make us feel united because its power makes us all feel so alone? 

My hunch is that we’re so driven by shame because it is one of the most impermissible human feelings, so it activates a lot of energy – and when it starts to creep in, it’s almost like our most urgent human need is to shut it down. “Avoid it at all costs, even if that means tagging someone else who may or may not deserve it.”  And when they are successful, it’s almost like we find relief – and then we cover ourselves in the morality clause, signalining virtuousness as a proof of concept that we are better than the bad, as if this will protect us from experiencing the impermissible feeling.

The truth, at least as I have experienced it, is that in some way we all build at least elements of our personalities on never accessing the core wounds that have hurt us, and we become so terrified every time we feel ourselves getting closer to them. 

I think about this in the context of my own parenting sometimes, and what triggers my own acting out. What motivates me to abandon the inner-calm that I tell myself I will maintain when I’m with my kids. Usually, it is some impermissible feeling from my past: some way I felt misunderstood or unheard or deeply helpless. A close mentor and teacher of mine once asked when I was telling her about an outburst: what painful feeling are you trying so hard to avoid in yourself that you’ll actually make them feel instead? It totally reoriented the way I think about treating people. Is any feeling that is actually my own worth trying so hard not to feel for myself that I actually give it to someone else? 

I genuinely don’t know that we can have an internet without the gossip trap as it stands now. I think our institutions depend on the gossip trap to survive and succeed. I worry that avoidance will just create a dark underbelly, criminalizing what I believe is genuine misunderstanding or guidance. So maybe what I’m really saying with all of this is that I believe in the potential of the individual much more than I do the institutions. That the individual, who at scale becomes the collective, is the key that informs how society runs – how the institutions get built and what they do. But I also don’t think we’re there. I think too many of us, whether wittingly or not, are invested in upholding the current institutions. 

Is family more important than social justice? We in the west have a deeply abstract sense of morality, we want an end to all injustice, all inequality, and so our compass is drawn less toward family and almost exclusively toward institutions, which have been effective at transforming society in ways that families can’t accomplish. At the same time though economic and social reform are mostly immaterial to human welfare, we subsist almost entirely on close connections, which sounds a bit romantic but still true. With family we can bear anything, be happy with anything. So, which is more essential: concentrating on social justice and the institutions which create it, on family, which is a near universal source of contentment across time and culture, or is there a middle ground? My dad’s Nigerian background tells me family is more important than the entire world, how does your Turkish-Iranian background inform your thinking on this question? 

I don’t think the stakes here are truly family vs. social justice. I think for many people who don’t grow up with a profound sense of family, social justice work becomes their sense of family, and there is something beautiful about the force of human will that can enable us to look for and find that connection later in life. 

But it can also be really dangerous – as we have seen play out en masse across the political spectrum over the last decade, with special emphasis on the last 3-5 years. 

In my own experience, nothing is more important than family. With the exception perhaps, of one’s own sense of self: the extent to which you or I or anyone knows we are living honest lives based on the compasses of our respective senses of integrity.

My suspicion is that you and I both feel strongly anchored in the notion of family because of parallel immigrant values that raised us, because of the sort of heroes journeys that our families  probably endured. 

Leaving one place for another, whether traumatically (the way my mom left Iran) or by volition (the way my dad left Turkey) necessitates a massive growth spurt that tends to reconnect you with The Important Things. I mean, I think this is true – it also depends on whether the immigrant in question has not just a vested interest but an urgent and primal desire to build a new life. 

And I think for many people who leave where they’re from and settle somewhere new, there is this period of coming completely undone before you can put yourself back together. I know this was true for my parents, who in addition to navigating this new country, were also navigating each other from regions so close and seemingly similar yet genuinely worlds apart. And when you do put yourself back together – or at least when my parents, and especially my dad, did – the way you’re constructed is reinforced by this hugely durable binding and the binding is typically a set of values. Family, hard work, honesty, generosity – they’re different for everyone but they’re baked into the texture and the fabric of what raises you.

One thing I have been thinking about lately, possibly because I have young kids and am therefore so close to the elasticity of the human mind, is how beneficial it could be to study the immigrant communities that have settled and thrived in America, to better understand what has underwritten their perseverance and resilience. What facilitates their endurance. I suspect that alot of what is there can help inform how our schools think about their role in the lives of our youth – in what becoming ours kids’ anchor of values can do for them and their families. 

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Q’s For Both Leandra And Abie—

How do you raise your kids around the effects of being affluent? I think about things like “luxury beliefs,” or beliefs borne out of never really having to engage with the practical realities of life, which include opposition to things like policing or standardized testing or even monogamous marriage, and how these ideas signal an underdeveloped value for the opportunities and institutions that make life stable for most people. It worries me that my kids might think in these strange ways because ideally they won’t have to work as hard as I do. How do you work around this and ensure that affluence never separates kids from planet earth? 

Leandra: This might be a bit off topic, but: one thing I think about a lot as it relates to affluence is luck. I believe there are two kinds of luck – transferable luck and nontransferable luck. Nontransferable luck is like the set of conditions that existed when you were born. These can be broken up by traits you were born with (such as a baseline intelligence) and the environment you were born into (wealth, a loving family). 

The environment you were born into makes pruning the traits you were born with either easier or more challenging. If you hit the jackpot with both – so you were born into an environment that nurtured the healthy evolution of your raw traits, it is likely that your non transferable luck has facilitated the manifestation of a good amount of transferable luck, which is the result of what you make with the non transferable luck. It relates to your question in that I think to a degree part of our environmental nontransferable luck has kept us anchored in our traditional Jewish values, led us to send our kids to the same Jewish schools we attended, and in many ways, I actually believe also mirror the immigrant values that you and I were probably both raised with. To me, the religious north star – a sort of dependency on the possibility that there could be something greater out there than what is apparent to the naked eye on this plane – creates a pretty significant impediment that makes buying into luxury beliefs more difficult, no matter the level of affluence.

Abie: The blessing and the curse of being part of a community is the legacy of norms that are born out of these communities. Within many of the religious Jewish communities, the concept of luxury beliefs simply cannot hold a candle to cultural mandate, with the culture being informed by rabbinic values.

How do you guys feel about childhood internet exposure as parents? Do you want to limit it like Steve Jobs or is there some benefit to free internet use that most parents should consider? 

Leandra: I really don’t think about it that much, I am much more consumed by teaching my children discernment. Either way at some point they are going to be exposed to everything I don’t want them to see, so to me, helping my kids build the kind of character that knows how to discern and set limits is the real task at hand. Second to that is building enough trust between us that they feel like they have someone to turn to when they’re just not sure.

Abie: I secretly hope that no one wants an iPhone by the time my kids would ask for one (how the iPhone becomes no longer necessary is a conversation topic you should cover Sotonye!) But knowing it will probably still be a major part of our lives, I feel that exposing our kids to the internet incrementally – before it's completely in their control – is very important. 

Growing up, I had a close friend who wasn't allowed to watch TV and whenever he’d come over, he would sit in the front of the TV and just stare. When we got older and he was able to buy himself a television, he became obsessed and it hurt his social life pretty badly. I want to avoid a situation like that so we’ll start slowly introducing the internet to them and not make it a novelty. 

You’ve both built successful businesses, what are some practical tricks you’ve learned during the process that may be helpful to anyone building a business today? For example, while trying to build my own blog, I learned that a huge volume of content affords more chances for a single post to go viral than the sheer quality of any single post. I had always believed that quality was more important than quantity but was very wrong, and this is a rule that can be applied across domains, like in music or vlogging or even in startups where a high number of cold calls and emails may afford more chances to secure funding or other unforeseen opportunities. What are some ideas you guys have learned over the course of your successes? 

Leandra: I think about the lessons and tricks I’ve learned from a less pragmatic vantage. Those tips seem to change depending on the cycle or season I’m in and I think the information that I tend to retain long term is really the wisdom that comes out of life experience. And for me, the key insight as it relates to building a business has definitely been to stay close to myself. What you need most as a business leader is clarity of mind. And every choice you make when you’re in that position of leadership is genuinely an invitation to walk one step further away from or closer to yourself. I can’t understate the importance of staying close because that is the well from which clarity springs.

Abie: Find an amazing partner to work with. I spent five years at UBS without one and regret it. I started Centre Street as a solo practitioner because I couldn’t find the right partner to launch with. After launch, a close investor friend introduced me to Jonathan and then he and I went through a relatively quick but in depth courting and diligence process and formalized the partnership mid-fund. It’s extremely helpful to have another person to share insights with, to strategize with and to push. We hold each other accountable in ways that are tricky to do for yourself. Of course though I know this advice isn’t one size fits all, so maybe the better thing to say is: know your limits, and troubleshoot against them. 

My final question for you guys is: what role does Orthodox Judaism play in your lives, and are you wanting your kids to be observant? As the only black person in the United States who has borne the yoke of the mitzvot (half joking) this question is one of the most important to me!

Leandra: I grew up in a Sephardic Jewish home and went to a modern orthodox Jewish day school and the guiding principle at home was: don’t get in trouble at school, but explore whatever questions you have at home. I think this was smart on the part of my parents – to give me and my brothers the room to build and examine our own relationships to Judaism while also providing us with a rich tapestry of decidedly biased information to sift through as we were considering it. I plan to give my kids the same flexibility and freedom to decide for themselves what makes sense. 

The one thing I’d say is that even though my parents were less strict about technical religious observance, they were rigorous about our upholding tradition and maintaining close ties to our heritage. Friday night after sundown (the beg of Sabbath) is and has always been non-negotiable family time. I’ve always lit candles with my mother to welcome in the Sabbath and to spend a moment honoring the lives of the women before us who brought us here; the food we eat and ate was always derivative of Persian Jewish and Turkish Jewish cuisine, the way we prayed when we did go to synagogue was practiced in the style of our Middle Eastern roots. There are a few examples of how tradition plays out in my life and the rituals around them that have provided a sort of safe container, or movable sense of home that I am always eager to return to when I’ve got out exploring too long.

Abie: I almost completely agree with Leandra. The Jewish piece is a big part of what made us so compatible while we were dating. It’s a foundation that enables me to feel comfortable that our relationship will evolve over time and strengthen during stressful situations.

Though my own relationship to practicing Judaism has changed a lot and will probably continue to change, I have no qualms about sending our kids to Modern Orthodox day school. But one thing I didn’t get, which I’d really like to give, is a push to question more existentially what’s being taught. I never knew I could ask potentially threatening questions about the system without there being major ramifications from school or my family. But the way I see it now, there are so many flavors of practice and that’s okay – you have to be able to ask so that you can find yours. I’ll support them as long as they understand why we raised them with this foundation, even if it differs from the ultimate decisions they make. 

For more of Leandra and Abie, subscribe to The Cereal Aisle, follow her on her beautiful instagram, and visit the Centre Street Partners site here!