I love America more than any other country in this world, and, exactly for this reason, I insist on the right to criticize her perpetually.

— James Baldwin

I believe we find the truest embodiment of the American Dream — in the soul of black people in this country.

The belief we can work our way to equality, praise, and understanding.

It is in this belief that there is a false comfort. We design a new reality. Around work and achievement as our salvation.

On constant display to show that we are truly exceptional. Whether that is your parents making you perform at the family barbecue or walking into your 20th venture pitch within a week…

From an early age we are conditioned for the stage of what it means to be black.

Be leery bout your place in the world
You're feeling like you're chasing the world
You're leaving not a trace in the world
But you're facing the world

Weary by Solange

I would say I grew up in the Poconos, somewhat sheltered from my own blackness. I knew blackness as my family, some friends, and beautiful role models. Not as otherness. The otherness would be told to me, in pieces.

The first time I was told about my blackness was in kindergarten. When my crush came to class and said “my mom said we can’t date because you’re black.” My young naiveness responded “that’s weird because my mom is white and my dad is black.”

For the record, my mom isn’t white. She’s Dominican. Just a light-skinned. My father would correct this mistake swiftly (you can laugh here, it’s funny).

The next identifiable moment of being told I was black would come continually on the golf course. I grew up playing competitive golf since the age of 5. Tiger Woods was everything to me. During the summer I would essentially live on the golf course.

Once I was in 8th grade, I played on a summer tour in Lehigh Valley. As the only black kid on tour, I stood out in every way. From my peers on tour it was truly, all love. Perhaps because it’s always been cool to hang out with the token. From the eyes of youth, perhaps they truly saw me as one of them. It certainly felt that way at the time, I certainly behaved that way at the time. My blackness was rarely a subject between my peers on tour. But it was consistently a reminder from the space itself. From the older members of the country clubs I competed at. Mostly looks, and only once called a nigger.

A while ago I was reminiscing with a friend from high school about our gifted & AP class. How diverse it was in racial, gender, and 1st generation composition. It would be here again that excellence for the sake of progression would be celebrated and pushed amongst friends. Truly believing, despite our older peers, that we could have multiple classmates within the same year go on to Ivy’s. That we would win every award across our district. And we would achieve all of these things together.

It was both so obvious and natural to us. As we went to state competitions and national conferences, looking like a college brochure… that this is how it should work. This is what separated us, from our peers at school. Why we would achieve everything we said we would achieve. That we were different, it was written all over us. I had written it all over myself.

And — not speaking for my classmates — it should have been obvious how naive I still was at the time.

I remember the night I got accepted into Wharton early decision. I had come home from a Georgetown interview. It was December 12, 2012. 12/12/12.

I sobbed. Because I had proven it to everyone. That it all paid off.

Something I didn’t necessarily appreciate at the time, but realize how instrumental it was to my adolescence — was that my parents never said I couldn’t do something. I think because of this, I don’t have memories of feeling uncomfortable in spaces I walked in.

Getting to Penn was biggest test in this upbringing. It wouldn’t be until after my sophomore year, after my finance internship in which I learned I hated finance — that I realized I valued something different. I wasn’t sure what it was, it was incredibly unclear at the time. But it started me towards something else. And concurrently for the first time ever, I doubted who I was.

I would design my own major going into junior year. Get introduced to tech and Peter Boyce at General Catalyst… and many other wonderful moments that directed me to where I am right now.

But in the spring of junior year, I had a very new experience in being reminded of my blackness.

After a party, my girlfriend and I were getting into an argument while walking to my apartment. It wasn’t too late into the night and we were essentially on campus. When we had turned a corner I was stopped by two police officers, and then out of no where was circled by 4 more.

I realized in that moment, wearing a black tee and black jeans… that I wasn’t anything but a black man surrounded by 6 police officers. Getting asked questions about a disturbance I was supposedly causing. That they were called because a young woman was crying loudly. It was peacefully resolved, I walked back to my apartment with my girlfriend in shock. She was now crying for completely different reasons.

Side note: if you’ve ever partied at Penn on a weekend, there are young women drunkenly crying all the time. (you can laugh here too)

I’ve only had two full time positions at companies since graduating from Penn, not tied to building my own products. My time at JUMP Bikes being the longest one.

It was at JUMP that I would be reminded of my blackness in both obvious and nuanced ways. My manager criticizing how I talked through my work, not the work itself. Calling me entitled for pushing for certain projects. Being the youngest employee on the team, and the only black employee not tied to local operations (bike mechanics, pick ups, etc) — this presented other quieter challenges. But the loudest moment came when a white designer said nigga rapping along with music playing.

I looked around to see if anyone else had heard what I had just heard… I would leave two weeks after that incident to join Dreams. My last stint before teaming up with Luca on Eternal.

I return to my JUMP experience a lot, because in every way it was what I was used to. Being the youngest, blackest person in every room I entered. Speaking out and pushing for what I wanted to achieve. Yet, nothing seemed to go right for me there.

For the first time it wasn’t a reminder from the world that I was indeed black, or my safety coming into question — but instead an active block to be excellent.

The double edge sword of black excellence is the understanding that to be great you must believe you are different, but in believing you are different you create an otherness not only from the crowd but at times communal blackness.

This is just a piece of the racial trauma that is woven into this country. So often to achieve while black, is to also stand alone while black.

But to stand alone while black, in America… is to be in danger.

Your excellence does not save you here. And the idea of excellence in the presence of hatred and injustice, does not always weather the storm.

I love being black.

I noticed I’ve grown somewhat numb to these injustices… and in recognizing that, I’ve been allowing myself to feel the pain again. The events of the past several days have led me through pain, and reflection.

I thank you deeply for spending time reading some of my reflection.

If we haven’t talked in a while, know that I love you.

I don’t do edits really, so excuse typos and things that don’t make sense.

Thanks so much for giving me your attention. I hope it was worth it, if not… unsubscribing will not hurt my feelings, and will give you back time you literally cannot have back.

Much love.

Image Credits:

1 — James Baldwin

2-6 — All pulled from Kendrick Lamar’s music video “Element”

That could think of dreaming and getting a glimmer of God
I be dreaming a dream in a thought
That could dream about a thought
That could think about dreaming a dream
Where I can not, where I can not
Less morose and more present
Dwell on my gifts for a second
A moment one solar flare would consume, so I nod
Spin this flammable paper on the film that my life
High flights, inhale the vapor, exhale once and think twice
Eat some shrooms, maybe have a good cry, about you
See some colors, light hang-glide off the moon

— Seigfried by Frank Ocean

There is a sort of fetishization in tech — believing you might call out what the future holds for the collective rest of us. The particular manifestation of the thousands of decisions that go into the form of the product in your hand or home. We do this so often that we tend to miss the initial kernels of that which we are claiming to be aware of its future state.

I’m not saying that it isn’t good or useful to have an opinion on where a community, technology, or the world at large might be headed. In fact, I believe it’s incredibly important to have an understanding of cultural waves and machinations. But it’s important to understand the widening cone of future possibility.

We may agree that in 10 years X will be common place. Knowing the proper details of how X might be constructed is impossible. However, on Twitter we see many people build followings by saying very broad things about X that give no actionable insight whatsoever.

🌀 @HipCityReg

Pseudo-insight formula: [insert current event] will be when [popular thing to talk about] changes Why? [obvious, over generalization of a reason no one disagrees with] [start list] - [widely successful company] for y [non-directive encouragement to watch the space or do it]

March 28th 2020

3 Retweets46 Likes

Below is a crude representation of the “cone of possibility” I drew for a previous Twitter discussion.

In the present we have a much higher chance of understanding a key detail or two about a particular need or form. And I want to say that that is enough. That’s all you really need. The idea is to stay on that through line drawn in the center of the cone. That comes with a mix of hunches — being pointed in the right direction — plus intense prolonged focus.

Two weeks ago, I was talking to Luca about something I wanted to tackle in a few months. And he slapped me through facetime.

“Reggie, you’re being stupid. You have 5 things to tackle today alone. You have to direct us on some key product questions and you’re telling me about something months away. I don’t care dude.” — it was something to that effect.

The lesson here: walk the line.

The only way we can truly focus is by being here, now.

Sometimes I hate writing about product / business / etc — because often times it comes back to extremely fundamental base understandings. You have limited resources, and your job as the ceo/product leader is to sequence the energy of your team in the most impactful way.

That’s it.

This reminds me that something I believe is incredibly undervalued in early stage product development is strategy. Strategy is about designing focus. Specializing to open the door for flow. This focus, like a game system, compounds one strategic advantage into 5 new potentials of play. In which you are presented with our familiar challenge…

Walking the line.

I don’t do edits really, so excuse typos and things that don’t make sense.

Thanks so much for giving me your attention. I hope it was worth it, if not… unsubscribing will not hurt my feelings, and will give you back time you literally cannot have back.

Much love.

Credits:

1st Image — Midnight Gospel, a Netflix Animated Series

2nd Image — Crude sketch done on my phone

3rd Image — Evan M. Cohen

I walk with my girlfriend to our train station. The F on York. It’s the last stop on the F train that’s in Brooklyn before you emerge on the other side — East Broadway in Manhattan.

Usually when I walk to the station there’s a homeless man right at the entrance. A silent friendship, where if I have a few singles in my jacket pocket I’m sure to give it to him. He holds it to his chest and flashes a smile. I return the nod, say “alright boss”, and hit my heart twice. Like I said, a friendship.

A couple of months before social distancing, my guy wasn’t there. I had no one to ask about his whereabouts. I’m sure to many, his presence or lack there of hasn’t even registered. He isn’t part of their reality in any meaningful way.

I have this short story idea around a new pair of AR glasses. In which our protagonist selects his filters and begins his new reality. After an encounter with an angry homeless person, he decides to filter them out as well. And the story would continue down this path — getting darker in some ways, but hopefully pulling to light some unpleasant truths that we already choose to filter out daily.

This past week I’ve been thinking about constructing realities a lot. Not in a lofty metaverse style way. But in the understanding that to a certain extent, we are presented with and make a multitude of choices that allow us to see the world in a certain light. Of course there will always be shocks to our individual systems — the very nature of externalities. However, the truth of modern American life is that there is no one shared reality. And this is a psychological privilege in some senses… that we can continually choose to reinforce what we believe living is… and how we might share in that experience.

I write entirely to find out what I’m thinking, what I’m looking at, what I see and what it means. What I want and what I fear.

— Joan Didion

The construction of any reality comes down to the values this reality will sit on top of. We encode values into any system we design. The translation of these values, from the very moment it moves from the first person to the second — will warp. Like a game of telephone, how far off might we be by the time it reaches the 1,000th person. It doesn’t take too much time for “All men created equal…” to become something-else entirely.

Ultimately, I think everyone wants to feel that their basis for reality translates well between those within their view. Maybe this is the essence of presence. The reason many said “that’s not my president”. The inability to recognize the presence of someone that cannot fit their reality, which is to say that their perception of the individual’s values are so far from their own… how could it possibly exist within the same space.

I’ve noticed, the examination starts to become an intellectual exercise. I think this is why the attraction to Tiger King was so strong. Look at these people, all twisted in every different way. So far from my reality. We consumed them. Countless hours straight. Meme’d and profited off of the narrative.

In a way… this might also be at the core of Keeping Up With The Kardashians. Documenting these alternative realities for our own consumption, dialogue, media machinations. Maybe Paris Hilton is the OG of modern reality construction — maybe she’s the future as well with her VR DJ Club.

To wrap this up, in the shower today I was contemplating the nature of language during the product development cycle. What are we ever really communicating, and subsequently trying to communicate through our products. If actually, the creator wants to communicate anything. How common is it to hear a creator tell a story that goes something like — “well we wanted to do this, but then this other thing made us more money and we just keep going until it doesn’t”

What even is that… it legitimately doesn’t compute in my mind. Perhaps this is my reality being confronted by others… maybe this is my short coming on display here now.

I used to get spanked a lot as a kid. Mostly because I think the disrespect I showed to my parents was rooted in never yielding what I believed was true. Until the very last swat. In a way… this is what fundraising is. Getting smacked around while refining the details, yet unwilling to compromise on your vision of the world. How it is, how it ought to be.

This notion, of how it ought to be. This is where creation starts — or at least where it should start. Plenty of people are happy to complain and be a hater. I have little patience for that.

I attempt to live simply and deliberately. Setting values that we can collectively build around. Creating a language that might be shared. Delivering products that embody this and improve another individual’s reality daily.

I don’t do edits really, so excuse typos and things that don’t make sense.

Thanks so much for giving me your attention. I hope it was worth it, if not… unsubscribing will not hurt my feelings, and will give you back time you literally cannot have back.

Much love.

I think words are one of our lowest forms of communication. Music, sound, food, dancing are nonverbal forms of communication. We get so wrapped up into words. We got to make things that are speechless. We have to make things that leave people speechless. We have to make things to the level where no one can say anything.

— Kanye West

I didn’t think it was possible to love Kanye — in what he means as a public figure — more, but somehow his GQ cover interview did just that. (link)

There’s a lot to unpack, and I’m not going to cover all of it. But I do want to work through my core belief around Kanye’s pureness of “unfiltered creation”.

What do we think of when we think of Kanye West?

George Bush doesn’t care about black people. His MAGA hat. Him standing on top of a table in the Apple store. His proclamation of being both Jobs and Walt Disney.

All these come to mind as Kanye, potentially more than any other artist, has the gift of demanding attention for his ~acts~. It’s a self generated gravity. Where every act radiates with a force that pulls us back. Even if we hate him for it.

Everything I’ve ever done has been an art piece, because I’m an artist.

Any action. Any word. Anything. Even this conversation right now.

— Kanye

Beyond any other description you could ascribe to Kanye, the word I continually comes back to is “creator”. He simply exists to create.

The music birthed Yeezy. The music combined with Yeezy birthed Sunday Service and a renewal of faith. The combination of these things birthed his new project in Cody, Wyoming.

And there is a privilege to this as well. That he can choose to construct the reality of his projects — both off of the fame of himself & despite the consequences one may have thought to result from certain actions.

Throughout the entire piece we see the constructed reality of Kanye. If he parks one way when entering a new venue. His car is magically turned around, pointed to his next location by his team. There is no, inconvenience. Nothing saying, at this point, “no, you cannot do this Mr. West.”

The only thing that falters Kanye’s ambition is how much he registers the vocal critique of certain audiences. And as long as he compartmentalizes that critique, he opens his psyche up to whatever he believes he can construct — with the help of others he appreciates. The rarity of this, as a black man, cannot be overlooked. We cannot strip away the complexities that identity brings when we discuss Kanye and everything he does and represents.

This reminds me of a moment I had while walking around Clinton Hill last year. I was walking behind a black mother and her young son. The mother was on a phone call with someone, and had just hung up. She then looked down to her son and expressed the very harsh reality that was tied to that phone call. I chuckled, thinking of the fact that many black parents don’t hide realities from their children. That that particular luxury does not exist for them.

But then I started thinking about what this forced maturity does to the mind. Does to that child’s imagination of what their life might look like. Already burdened down with realities well beyond their years. I thought about my own childhood. Growing up in the Poconos, my parents affording me whatever reality I wanted to construct for myself. And the result of me being the only black kid in many arenas of my life until I got to college.

Kanye has restructured his reality to not be blocked by the impositions others might try to throw at him.

You don’t want me to rap, only produce? Too bad

You don’t want me to make clothes, only rap? Too bad

You don’t want me to start my own center for new living, only make clothes? Too bad

You know what it is? Farming. Farming ideas. Planting seeds. Fashion Week and the internet is the soil. This is the seed. If I don’t show, then I never plant the seed. But the thing is, people say, “This is Kanye West, and we love the huge trees that you have given us. We want to come to your garden to see your trees.” And when they come, they just see dirt.

— Kanye

I’ve written a lot about the difference between process and residual. Process is the visible nature of planting seeds in the soil. Residual is enjoying the trees, the grove if you’re lucky.

Kanye is a master of visible process.

Recording “Through The Wire” with a jaw that was wired shut. Updating The Life of Pablo (his best album) multiple times across platforms after release. Scratching entire works, leaking them, and then recording a new album within a couple weeks and making that the official work. Recording on his iPhone. Making album art on the way to the live show.

And now we get to see it on another scale in Cody, Wyoming.

Will this center become the new Black Mountain College? (h/t Nikita for sharing this wave)

Perhaps more importantly — what does this location tell us about where the new edges of cultural experimentation might be headed? Do we need an exodus in order to bring new creations, new thoughts, new forms… that’ll breathe new life to our cities?

In an increasingly dematerializing world, I don’t think we fully understand the ramifications to the psyche due to the continual abstraction of what we produce. This is probably why remote work never sat well with me… if what I produce (software) is already abstracted, please give me physicality with those I’m producing with.

I simply find it very attractive to think about living in a place like Cody, in order to pull back and test what new consumption may inspire new production.

A lot of people are celebrities because they’re vibrating at such a high energy. They’re just stars. I felt that me and James always had that connection. That first time I talked to him, I was literally screaming at the top of my lungs about how important it was for us to work together.

— Kanye

I wrote months ago that all creation is spiritual. From which there was nothing, there is now something. To feel, consume, meld as part of ourselves. In the most beautiful times — extend.

The visible process of Kanye elevates so much discussion around expression and production. And we wrestle… publicly over the nature of his actions.

Let me state clearly — that I do believe that there are gaps in Kanye’s overall logic. That some of his support is misguided, and is hurtful to other causes. And he’s allowed to do all of these things in his God given autonomy.

But most importantly what I have taken away — from both my fandom and observations — are a few core principles that apply to every creator.

• Chase people you find talented with exceptional fervor, and force them to collaborate with you

• Now that you have these people, bring them together, isolate them — and push. The Mac team would go to Hawaii. MBDTF was recorded in Hawaii. Eternal went to Beacon — there is clarity in getting away together

• Publish and record everything. People don’t remember most L’s. Your big moments outshine them. — both of these are refining as the creator

• Take, combine, & reform from everything you consume and are attracted to

• Don’t try to look too far in too the future — you can paralyze yourself

I don’t do edits really, so excuse typos and things that don’t make sense.

Thanks so much for giving me your attention. I hope it was worth it, if not… unsubscribing will not hurt my feelings, and will give you back time you literally cannot have back.

Much love.

Let’s put a nice bow on this experiment.

A year ago I made an anonymous twitter account called “Tech Twitter Bachelor Board” — where I simply tweeted a list of people that made the list. It was one of those things that I didn’t think too much about, I thought the idea was hilarious and I did it.

• People have a love / hate relationships with lists

• They like it when they make good ones, and have a social obligation to support their friends if they make it on

• It’s incredibly shareable

• And even if you don’t want to publicly support it — you’ll complain and share it privately… so the job is getting done either way

This last point proved to be the most right. Although the tweet itself didn’t go viral by any means… the engagement & buzz that circled around it were undeniable.

Shortly after the tweet was live for an hour, Taylor Lorenz had dm’d the account. As far as social experiments go — I had made it. But I was anonymous. A very private joy, although a handful of friends guessed that it was me. And I eventually conceded the truth.

I shut it down quickly. Changed the handle, and used it for a new experiment in my free time.

Fast forward to this past Friday. I’m sitting in my apartment, maybe on my second drink and I get a text from a friend.

Coyne messages the group “Maybe COVID has cooled off enough for me to start tweeting out lists of hottest men over 40 in venture capital.”

An obvious joke to my previous Twitter account. Combined with — let’s call the other person in the chat BOYBOY — BOYBOY egging that this was the best thing I’ve built in my product career (ouch!), my tipsy self was pushed over the edge.

Within 30 minutes I had the site up and running through Universe. BOYBOY was giving me copy suggestions, and everyone was throwing names out as to who should be on the list. There were some debates, but really just trying to make the whole thing splash.

Then it was ready. But obviously I cant tweet this thing out. That’s not how this works. Enter BOYBOY. They suggested going through something people already have mixed feelings about. VCBrags & FounderBrags.

I dm’d them asking not to share my identity. VCBrags didn’t share it. FounderBrags did. And it was done. It was out there — and it was growing.

In one night and a full day, we’ve received 30k+ hits and still going. Some tech-glitterati retweets. Subscribers from A16Z, and more.

Yesterday, during my government excused walk. A writer from Forbes reached out. The groupchat was conflicted so we elected not to say anything at all. But we got a fun story — LINK. Right now the story is tracking at 7k+ views.

Put up a “product” in under an hour. Find a channel to distribute. Make it inherently shareable by instantly including people with high spread. That’s one way to do it.

I wanted to share the story because, I think overall it’s just fun — but could have easily gone south fast. We start messing with the list just because we can. Put voting in. There’s a lot of paths that just aren’t fun + I simply don’t have the time for.

But I do think there’s a lot of interesting things that have come out of this.

• People did subscribe, either out of morbid curiosity or genuine interest… they want to see if it could be useful — and in tech gossip is always useful :p

• People did reach out to guys on the list / follow their accounts — everyone wants to be told, what the best is

• Guys did ask to get put on the list

• Guys were genuinely flattered — something something the patriarchy something something — I don’t think most guys view themselves as “beautiful” and to be told that is something special… I didn’t think I was attractive until one specific moment after college… it be like that sometimes

I could write more, but I think this is a good stopping point. I hope nobody took this too seriously. That it was an enjoyable moment overall, and took your mind off the constant onslaught of the macro-climate.

Much love.

I don’t do edits really, so excuse typos and things that don’t make sense.

Thanks so much for giving me your attention. I hope it was worth it, if not… unsubscribing will not hurt my feelings, and will give you back time you literally cannot have back.

Much love.