How I came up

My grandfather, a carpenter, bought land and sold it to his kids, so I grew up with my extended family on the same block, on the top of a hill, in the woods of Connecticut. Early memories of sledding on the street because we lived so far out that the plow came rarely, and hot cocoa.

Two older twin cousins, we’d spend most of our time playing imagination games, sock puppet show, Janet Jackson dance routines. We’d watch scary movies in their basement, go on long hikes alone or with a dog through the woods, caught salamanders, made tree house forts, and played kickball with paper plates. We’d swing on their swingset or pogo stick near the shed. Every summer blackberries and wild raspberries grew. It felt something like how the berenstein bears lived.

My grandmother lived with us, she taught me all the crafts I know. And she’d stay up listening late to Red Sox games on the radio. She’d take me to church in the small town she raised my mother and would squeeze my hand extra tight during the ‘our father’. She volunteered to serve coffee and donuts and was a staple at the Christmas and Easter-time bazaars. She’d create Christmas tags and ornaments and hand made Barbie clothes from the scraps of her own dresses she made, and baked cookies. We’d sit 8 hours at a stretch at a bazaar or a tag sale, and I’d be responsible for making sure the display was stocked and I’d make change. I remember she gave me $100 of the profit to buy a tv with a vcr, so I could tape snl and watch it on Sunday mornings. 

My mom worked two jobs and in high school she traveled for months at a time. She worked every Sunday because you got paid time and a half. She worked the same job for 46 years and when her company was bought out by a private equity company, she was demoted and not inconspicuously they made her job more difficult and more intolerable. It’s cheaper to install self check out or hire part time labor with no health benefits than pay someone who has benefits.

My dad patched together jobs, but always played the drums in a band. They’d practice Rush and Led Zeppelin at full blast in our living room, the floors shook. He later recounted how he never “made it big” because he didn’t believe in himself, but he also never stopped playing his kind of music despite it all.


My mother got me tested when I was 2 or so with a psychologist for gifted children. Today I call it neurodivergence, but then it was just called “off the charts”, especially for me on spatial reasoning. The report said I was well rested (code for un-coached by an overzealous parent) and suggested that my intelligence would catch up to me, and eventually I’d learn at the same pace as everyone else. But that’s not really how neurodivergence works, it was just what was understood in 1988.

My mother would become my advocate at school, lobbying the superintendent to hire a gifted and talented teacher and paying for summer school with a third grade teacher who taught part time. Dee Daniel’s just retired and she was the first and only gifted teacher in my hometown public schools for over 30 years. Mrs Cannito has since gone legally blind but we keep in touch by letter. She still lives at the same ranch home where I sat at her kitchen table writing essays. She probably still has the yellow shag carpet too. 

My mother would also enroll me in computer classes, with three other kids I’d go and play learning games. I had a Socrates learning machine at home and my dad, who was managing a book warehouse, driving a forklift at the time, brought home copies of all the loose children’s books, like white fang and moby dick.

Computers and later coding helped me think as fast as my brain worked. I could type or click and it was a great anxiety release. I got a digital encyclopedia and Carmen San Diego (which came with my first ever almanac and book of maps) and the Incredible Machine.

My mom worked on Sunday’s and my dad played out on Saturday night and my grandma went to her own church, so Sunday’s were my time alone. I’d wake up and fix myself a bowl of ice cream or Cocoa Puffs and pop in the cassette I had recorded snl on the night before. I watched the last few years of will Farrell and Tina fey, and the start of jimmy Fallon. I loved the idea of high stress yet play pretend, anything could happen.

After snl the Sunday morning news shows would come on and I’d have nothing to do but get engrossed by the political theatre. As a child that saw the world in black and white, I didn’t understand how such big decisions could be made or points argued with so few facts or data so obviously skewed. It bugged me and I developed a political opinion about it and would argue with my uncle Ronnie, who ran a small painting company that did commercial developments like hotels and hospitals. He’d complain about taxes and I’d argue for social welfare policies. He’d dismiss me as young and naive which I suppose I was, but I still hold the same political views.

My mom drove with me to visit colleges. I think she would have loved to go to college, but it was a different time then and she didn’t have the same opportunity or support at home. So we didn’t really know what we were doing, but I knew that the best school I got into was in DC and that felt like a good choice.

I had interned with senator Dodd, famous for the Dodd-Frank act at his local office in Connecticut. His chief of staff was my uncles friend and my mom asked for a favor to give me the exposure. Work at local offices aren’t like the DC offices where bills are reviewed, mostly the staff are fielding calls from parents adopting children from abroad, tips about fraudulent business activities, and people looking to make sure the senator knows their opinion. I’d open the mail, answer the phone, and take notes to update case files. Once a month, the chief of staff, Mr Mann, and I would take a meeting with a specific constituent who would rant about 100 different subjects in 30 mins, and I took the notes.

When I went to DC, I had a leg up on an internship at the Capitol, but it was unpaid so I’d work the night shift at the university key depot to loan keys to kids locked out of their dorm rooms. But, I got a badge and access to the Capitol underground train system. I’d mostly proofread docs and answer the phone for the chief LA, but it wasn’t unusual to see senator McCain in the elevator. I’ll never forget the war scars that man had on the back of his head, you’ll never see on tv. 

I’d go on to string together a series of internships at k street lobbying firms, with the goal of getting a much coveted chance of working for The Brookings Institution. I’d get my first break the last semester of college, another unpaid internship but this one with the potential for full-time future employment.  I worked for Matt Fellows and I did a literature review on every book written on low income banking. He’d leave the next quarter to found a lending business for minority families affected by predatory lending … and I was left without a partner advocate and didn’t get a job offer. I’d graduate and start doing temp work as the financial crisis of 2008 made it almost impossible to find a job and then I got an offer to join the Urban Institute, Justice Policy Center, in May 2008.

I didn’t know much about criminal justice and criminology as a discipline, but I learned on the job. I learned to code SAS then GIS then after two years, got the call up to the Brookings Institution. I remember part of the interview was a take-home prompt, and I slept under my desk at work and showered in the office gym, because I didn’t have a laptop at home. I got the job and spent two lovely years there, learning from the best. 

That was the last “job” I had, now ten years ago.

Chat GPT is trained by man

Chat generated pre-trained transformer, otherwise known as ChatGPT is “pre-trained” meaning it is not unsupervised. The law and policy to set boundaries and clarify responsibilities will not come soon enough. The machine will act on parameters of popularity and speed, reinforced by its users. We know that computers are not yet trained today with enough data about minority faces and over-indexes for convenient, simplified nationalist opinions. Without supervision and analytics the power structures that are in place today, that train and supervise these systems will reinforce and strengthen these human tendencies

The quiet part out loud

Some people get it and some people don’t. We have to show up more and put extra money into black founder deals because every step of the way, they will face bigger, tidal forces against them - lower valuations and less available money, bc they can’t count on the people who “can’t get comfortable” but can’t say why exactly. 

In this moment, you can enrich yourself further by doing what you’ve always done with non-minority founders…  or you can equip the generals with the munition they’ll need for a hard battle. But that is your choice. 

Financial services is rigged to structurally advantage some, not because they are better. I’m not black, but I’m also not blind.

I’ve spent my life running the numbers on structural inequality, and I believe black people who say it exists, and I’ve held the hands of its many victims in moments when there’s just nothing left to say to make it better. Speaking out is not a sign of our company’s weakness, because having the numbers is an illusion - even when you have them, they aren’t enough. There’s always another excuse other than saying the quiet part out loud - it’s because you’re black. 

Let me also be clear that I don’t expect to see a coming to Jesus moment on racism in this country, but operating in silence or trying to operate within this system is the wrong move. When I see something, I say something. Now is the moment when VC should step up and lean in for the community. 

The arc of justice is long and I know that those that chose to be on the right side of history, will get the deal flow that’s coming, because the groundwork for generational, transformational wealth among black people is happening, with or without VCs. 

🦋 🦋 🦋 🦋

Creation is the act of distilling and repurposing the source material of your experiences and the way you repackage that content is the art. if you believe the biggest returns come from innovation, then diversity investing is a mathematically logical and lucrative endeavor. I have come to believe that “pattern matching” is not the way… 

The scientific and logical mind runs the risk of forgoing the influence of the spiritual that surrounds us. In Product, I hear “I need to know the why”, but the answer should not always be quantified… a gut feeling, a sign you interpreted, should be weighed as valuable inputs. If your grandmother came to you in a dream or a series of butterflies flew past your window, listen to the direction the wind wants to take you. It’s okay to come back and counterbalance these influences with logical certainty but limiting ourselves only to quantifiable inputs seems like a mistake.

Echos of subtle ideas repeating are easy to miss. Noticing connections and seeing where they lead is the process. It’s not conviction or consensus, it’s spiritual intuition that makes products great art.

Get up

My uncle used to throw snow in our face when we fell down and didnt get back up quickly enough. most people are like holy shit, that's awful, but they miss the lesson he explicitly taught us -- dont get caught having too much self-sympathy, and learn how to get up quickly.

Or, as my dad likes to say, "so you got punched in the face, that was plan A." 

Or another Rick Nadeau one is,"... be like a rabbit, Carey. You see the rabbit it pops up out of nowhere, it doesnt burrow down one hole and when it rains, it drowns. No, it builds multiple escape routes. Just pay attention to the rabbits and be like the rabbits." 

Right now, in this market, this advice and training is so helpful. In the bear market, I get to flex. To me it shows the dog in the fight of the person, when you're backed up in a corner, that reveals their willingness and ability to be great.