Angel Investing

My first angel investment was in 1999 in UPOC, where I served on the board. The concept was before its time, and there were people on the board who couldn’t see it and didn’t do their job. The founder wanted to bring in a CEO, and the person the “majority” of the board chose was a huge mistake; it was like watching a train wreck in slow motion. The person whom the founder and I wanted was nixed. I might be going out on a limb here, but I am pretty confident that the business would have had an entirely different outcome if they had chosen him.

After this investment, I began to focus on angel investing broadly. It was 2007 and the beginning of the second stage of building internet businesses. I developed a financial thesis and started to put capital into the entrepreneurial world, primarily supporting female, Black, and brown founders. I have a few white men in there, too, but they are a different breed in a good way. Fast forward, I invested in over 150 companies, sat on multiple boards, was extremely founder-friendly, and along the way, I created many lasting relationships and learned a shit ton.

During this time, I spoke to investors doing the same thing as me or wanting to make angel investments. This type of investing is high risk. Companies evolve, and all of my investments were the company’s first capital raise, so the chances for success with zero institutional investors sitting around the table are lower. Now that I have stopped angel investing, I will likely see a 4-5% return on all the capital I put out there. More than likely, it was because I was so early in the game of the start-up world.

I saw this full-page ad in NY Magazine the other day. Now, investing appears to be mainstream. Even YCombinator has over 10,000 applications a year; roughly 2% get accepted to the accelerator. The good news is that each accepted applicant receives a chunk of change to help them build and prove their concept.

I have seen that ideas are everywhere, and sometimes cash can be flush, but it is all about execution. That means building a cohesive team, making bets, and evolving daily. The idea that someone could pitch to a group of “legendary” VCs on television for ten minutes and become the next unicorn doesn’t add up. What exactly does legendary mean? The VCs I know are not spending time filming for every Wednesday episode.

This has been going on for some time, beginning with Shark Tank, and some could say that most of the accelerators are a bit sharktanesque. It is not easy to be a generalist these days, as it was when I began investing. Now, committing to a vertical with a thesis in an area is what I would do if I were starting today. Although every company has the same issues at the beginning, you do have to understand the space.

Investing is never going away. I wonder how many people will lose their shirts and how many people already have lost them.

Women and Sports

We have watched the NCAA Sweet Sixteen for as long as I can remember. Over the years, women’s basketball has become more fun to watch. This year, the games were incredible. If you have not paid attention, Caitlin Clark, who played for Iowa, is not only one of the greatest female college athletes of all time but also the scoring leader for the entire NCAA.

Title IX mandated gender equality in sports 40 years ago. We are seeing the impact rise to the top. This year, the Liberty games had the highest attendance in the league’s history. The playoffs were packed. We took our kids to Liberty games when Becky Hammond played, and the stands were far from filled. Seeing these games now filled to capacity is amazing.

This list shows the top female players in the NCAA. Many of these women will go on to play professional sports with sold-out games. Caitlin Clark will be paid over $76k a year while her male counterpart will make $10.5m, roughly 140% less than her male peers. When will that change?

I understand that paying players has to do with attendance, sponsorships, etc., but as we begin to see crowded arenas for the female teams, I hope the owners make the salary changes quickly and show why.

Seeing the Olympic tracksuits for women, where they are expecting all women to get a good bikini wax to wear them, points once again to promoting the sexuality of women and not their athletic ability. This statement says it all.

Lauren Fleshman, a retired U.S. world champion runner, had some harsher criticism to share. In an Instagram post, Fleshman wrote, “I’m sorry, but show me one WNBA or NWSL team who would enthusiastically support this kit. This is for Olympic Track and Field. Professional athletes should be able to compete without dedicating brain space to constant pube vigilance or the mental gymnastics of having every vulnerable piece of your body on display. Women’s kits should be in service to performance, mentally and physically. If this outfit was truly beneficial to physical performance, men would wear it.” She added, “This is not an elite athletic kit for track and field. This is a costume born of patriarchal forces that are no longer welcome or needed to get eyes on women’s sports. … Stop making it harder for half the population @nike @teamusa @usatf.”

All women in sports, particularly the ones succeeding at a high level, should be financially rewarded for their hard work and skills, and certainly it is time to stop sexualizing female athletes.

Karen Blondel, Public Housing Advocate

Karen Blondel has lived in Red Hook for over four decades and is a true Jill of all trades. Looking to learn about climate justice, local organizing, structural engineering, or the best pilsner in Brooklyn (Strong Rope Brewery)? Karen’s your girl. You’ll likely find her hanging out in Coffey Park when she’s not helping navigate tenant questions or finding a marching band to play at the next Red Hook West get-together.

I am thrilled that Karen sits on the Public Housing Community Fund board. She is a force of nature. I am honored to spend time with New Yorkers who care passionately about this city.

Karen is the “mayor” of Red Hook. We all need more Karen Blondels in our lives and our cities.

Grenfell, In the Words of Survivors

I had the pleasure of speaking with the executive directors at London Public Theater a while back, who were bringing Grenfell to St. Ann’s Warehouse. It is finally here. They invited me to see the opening night on Sunday. It is a short run, and I highly recommend getting there before it closes.

If you do not remember, Grenfell was a 24-story public housing building in London that caught fire in 2017, and 72 people lost their lives. This play is similar to a documentary, and based on a book, going back in time, meeting the community, hearing the stories, and understanding how this happened. It was a typical day in their lives.

If you know nothing about how buildings are built, you will have a bit of insight after you leave. Due to lax restrictions and little oversight, the shoddy, flammable products were used to construct this building. The company, of course, thought they could get away with it, although they have yet to be charged. The government takes a long time to process things like this. Today, the building sits empty, with a huge green heart looming over London.

Every time something awful happens and research is done on why, why is it that executives of companies know exactly what they did was wrong but let it go regardless? Each time, human lives are at risk, but was it because it was public housing they didn’t care so much? We have seen this movie too many times.

At least the ex-housing chief, Rock Feilding-Mellen, apologized for the lives “shattered” by fire. He says this will haunt him for the rest of his life. Yet it was not up to the deputy leader and cabinet members to question the information they had, and they believed that the company they were purchasing cladding from would not sell the government products that were a huge fire risk.

The performance is a slow crescendo of the day. We get to know the neighbors and the people, and above all, these people live in public housing and are the backbone of our communities. Anyone living in an urban area, such as NYC or London, to think otherwise, you are fooling yourself. Teachers, public servants, childcare workers, bus drivers, restaurant workers, and I could go on living in public housing, which is the center of our city.

See the play. It was exceptionally well done; it draws you in and will stay with you.

What Took So Long?

Government money is tight, and it began to get worse when Reagan took office. As leaders in the world, we can still help others financially when they need it, but doing right by our own citizens should be a priority.

The recreational cannabis roll-out in NY has been a bumpy ride, to say the least. Supposedly, the crackdown on illegal dispensaries is starting to take place, but as always, we will see what gets accomplished. I won’t rest until Empire Flower is closed for life.

Each legal dispensary has worked incredibly hard to follow the rules set forth. I am sure none of us thought that our biggest competition would be illegal stores. I breathed a sigh of relief to see this sign randomly placed at the bus stop finally. FInally! What took so long to do this is beyond me; more PSAs must be done. It is not a huge cost, and it is government leadership that we are all hoping for. This is at least a step in the right direction.

Lastly, the Hochul administration has passed a budget allowing Adams to remove the supposed 2500 illegal shops ( I believe there are many more ). He believes he can close them all up in six months. Let’s see. When Empire Cannabis Club is closed, that will be the moment all the legal dispensaries will applaud. It is time.

Hospitality Pathways Auction

I have been involved with many non-profits led by people who want to make a difference. Sometimes, they replicate what others are doing in the same city; sometimes, they grow into something unique, and other times, they never get off the ground. Hospitality Pathways is unique because it was started by someone who wanted to give back after spending her entire career in hospitality and to share her knowledge with others with the hope that she could help others end up in a career that she loved: hospitality.

We supported this last cohort through The Public Housing Community Fund, and I enjoyed speaking to this past group. We support programs like Hospitality Pathways that help NYCHA residents find careers. Sometimes, finding a job and feeling confident about going and interviewing for that job is not easy for many. You can’t be what you don’t know.

What happened is unprecedented. For the last cohort of 20-plus people, over 700 people applied. That speaks loud and clear that what Beatrice (the founder of Hospitality Pathways) has created is a gift to the community. At Gotham, we have hired incredible people from the last cohort and plan on hiring more.

Of course, the biggest issue is funding. If this was a company and not a non-profit and over 700 people clicked to buy, the investors would come pouring in, but looking and asking for money from foundations and people is a whole other ball game.

And so, Hospitality Pathways is raising money through an auction. The capital raised goes directly to someone sitting in the next class, who will be hired with new knowledge to enter the world of hospitality; many of them will work in cannabis, an industry that has only begun to grow in NYC. I can tell anyone that the people we have hired at Gotham have been wonderful. Many have been with us since the start, and some have been given promotions. That is an impact I always feel good about.

Please bid or give. We do, we have, and we are huge fans.

Last Day in Montgomery, Alabama

This morning, we went to the Farmers Market Cafe. Everywhere we ate, people would ask if we were from Montgomery. Perhaps it was just an icebreaker in a town of less than 200,000.

An egg and cheese biscuit sandwich and a pancake to share was the call. Good coffee, too!

One of us came in a day later, so she had not seen the park, which is an absolute must, so we dropped her off while we headed to a farmers market. This one is open on Tuesday, Thursday, and Saturday. We were told that it was much busier on Saturday. FYI, nothing here is regulated. There are signs at every farmer’s booth noting that the products (jams, soups, pickled veggies, etc.) were not made in a government-regulated location, so you are on your own.

We met a few of the locals. This woman was lovely, and we bought her local sweet, delicious strawberries and freshly shelled pecans.

The tea man was great. I bought two teas for the summer months: fresh ginger root and Georgia peach.

We picked up our friend and visited the National Memorial of Peace and Justice. Here you can take pictures. This museum is dedicated to lynching victims. Once again, the names, the stories, and the art all give a powerful punch to the gut. You enter the structure that has large rectangular pieces of iron hanging over an outlined rectangle that the hanging piece could fit into if it dropped.

Each piece is etched with a lynching victim, the year it happened, and the city/county and state. These are only the people that they can find through massive research.

You can hear water as you pass all the hanging structures, which get higher as you walk through.

When you turn the corner, there is a wall that rotates water, which I thought must represent the tears shed. It is an ode to the names of people they will never know who have left no history.

As you continue through the mile loop, I looked back at the new section of graves in front of me and the large lynching structure behind me. The chosen materials have begun to patina throughout the museum, which lends itself to the long, dark, covered history of slavery.

It was our last stop, although we did call in an order to Martins Restaurant for some more fried chicken. This time, the place was packed. While we waited, we got a glimpse at the gravy, potatoes, macaroni and cheese, and heaps of fried chicken serving the locals.

This trip has taken me a few days to process. I now look at the world with a completely different set of eyes. America’s horrifying history of targeting Black people who had been kidnapped from Africa has left trauma in our country that still reverberates today. These Legacy Sites are a step in the right direction that more of this country and the world need to see. Our history is what too many would want us not to believe. That must change. Everyone needs to bare witness.

Montgomery, Alabama, Day 2

We had breakfast in the hotel and plotted our day. We always check out the local art. I had found two spots, and we started our day at one of them, the Alabama Artist Gallery, located on the first floor of a very tall Government building. There are a bunch of enormous government buildings but few people on the streets, which made us ask multiple questions that were never answered.

What we found at the gallery was an installation of the local high schoolers’ work, many of whom had been given colored ribbons. Seeing what kids at that age make is definitely insightful. This was one of the pieces, a ballerina’s slippers.

The next stop was Freedom Sculpture Park. It is pure luck that this park opened a few weeks ago. The big opening is June 19th; although you can visit the park now, you can not take photos except for a few locations. This is the journey’s start, and I was allowed to photograph this.

The park is set on 17 acres on the banks of the Alabama River. The landscape consists of trees typical of the South, with branches up high, creating shade from the heat. The reality of American history is about to hit you in the face. The attention to architectural and historical detail is awe-inspiring. Commissioning art from a slew of American Black artists today who use their medium to feel the generational trauma that they have endured next to etched iron stories of slaves is gut-wrenching. It is also brilliant because even if you do not take the time to read every piece of information, although we did, you just have to see the artwork to understand the agony these people endured and how inhumane it all was. Each museum is consistent with the art installations, historical factual stories, and personal narratives.

The committees that worked on this and the donors who gave have left us all a gift that can help change how we discuss race in this country. Every 9th grader should go and see this museum; it would be game-changing, and you can’t help but leave with a different set of eyes.

Montgomery was the major center of slavery; at one point, over 65% of the people who lived there were enslaved. We walked through the circular path around each of the art pieces, telling the history of the slave trade, beginning with the transatlantic passage of those kidnapped and then sold into bondage.

At the end, we were allowed to photograph this 43-foot by 155-foot sculpture etched with each slave’s name that was recorded somewhere, many were not.

We needed lunch, so we went to Capitol Oyster Bar, which sits over a tiny marina amid scrap metal yards. This place is legit, and there is live music many nights.

Oysters are from the river down in the South. They are big, creamy, and not so briny. I like them raw, but the way to eat them down there is fried, so we did.

After lunch, we had time to sneak in at the Southern Arts and Makers Gallery. True local art. We each bought something before heading to the Legacy Museum. Again, no photographs.

We were lucky throughout the trip that few people were visiting the Legacy trio, which allowed us to take it all in. The museum sits on the spot where enslaved people were taken before they were auctioned off. Each spot is self-guided, so each story is told as you move through the museum. They mirror each other so people stay on their side; it is replicated. It is super smart for crowd control.

Again, these places take no prisoners, and they shouldn’t. The first room is dimly lit, with one path down the middle. On both sides is a moving picture of waves crashing up and down, making visitors feel like they are on the boat. As the water drops down onto the sandy banks and pulls back, multiple sculptured heads in obvious agony are installed there. And then the journey through the Legacy Museum begins.

The rest of the rooms tell stories from the slave trade to mass incarceration and police brutality. Interactive stories about people in jail, including a few short films, are also featured. This museum exposes the reality of Black history in America. At the end of the visit are two extensive galleries filled with works of Black contemporary artists that point directly to their generational trauma from slavery. It wasn’t expected, and making sure that art is part of the story is ingenious.

We left and sorely needed a drink. What a day. We hit up the bar and then the Central restaurant across the street. It is a new spot that probably brings people from outlying areas into town, which is good. Personally, I prefer the local spots that haven’t changed in decades.

The last piece of the Legacy trio is tomorrow. What a day.

Montgomery, Alabama

I traveled to Montgomery, Alabama, with two friends this past week to see the Legacy Sites. These three sites are the brainchild of Bryan Stevenson, the Founder and Executive Director of the Equal Justice Initiative. I am sure there are many others to acknowledge, but he leads the charge.

In 1989, Stevenson, then 29, moved to Montgomery and began the Equal Justice Initiative to guarantee legal representation to every inmate on the state’s death row. He has dedicated his life to defending injustice in the criminal justice system. Everyone should read his book, Just Mercy, a Story of Justice and Redemption.

After seeing the Legacy Sites and reading this book years ago, I believe Stephenson is a national treasure. We need more people like Bryan Stephenson.

I am going to spread this trip over three days of posts. We flew in Tuesday afternoon and grabbed a rent-a-car. It is not a big town, but you do need a car, and I did not see one Uber. Our first stop was Chris’s Hot Dogs, established in 1917. The last renovation, including the grill, was probably in 1950.

Next door, There Is A God In Heaven.

We went with the classic hot dogs and fries, you have to. There are hot dogs under that sauce, I swear.

I do like to get to a local farm where they teach agriculture to the community. The town felt empty, and the farm was empty. Eat South Farm located at the ends of a large parking lot might have school groups but it is not easy to get in the office, no stair.

We moved on to the Rosa Parks Museum. We were one of five people there. The museum is really well done. It tells a story that would relate to a 6-year-old or an 80-year-old. Impressive. The story is about how Rosa got fed up and refused to move from her seat on the bus to give to white people, which launched the civil rights movement, starting with people boycotting buses. I know the story well, as this was part of our kids’ curriculum growing up, as it should be.

The hot dog did not do the trick, so we went to Martins Restaurant.

A local family spot for some of the best fried chicken, fried okra, collard greens, coleslaw, and, of course, sweet Tea on the side.

We had to walk into Winn Dixie, the local grocery store, to see a bit of local flavor. I have never seen these eggs in our NY grocery shop.

We stayed at the Trilogy Hotel. The hotel is a year old but has some history, as everything does in Montgomery. It was built by the Threefoot Jewish German family, who migrated to Montgomery in the 1800s through Ellis Island. Unfortunately, the building was built in 1929. It then went through several owners, preserving history by sitting there vacant. It was rebuilt by Ascent Hospitality, which partners with the largest hotel groups, such as Marriot, to build hotels that make sense in 2024. Impressive job.

The chicken was a snack, so dinner and a drink were needed. We had a drink at the hotel and met a variety of friendly people at the bar, most of whom were doing work in Montgomery. Then, we headed down the street to Moe’s Original BBQ. It is a chain across the country, but they do have fine ribs.

As we have all learned, the future of Montgomery, unless the state is willing to put capital into Montgomery to maintain local spots and build local restaurants, the city will begin to look like Moe’s. For everyone’s sake, I hope not. They can look to other cities, such as Detroit, which has managed to keep the local flare and support the people who have been there for generations.

Tomorrow, we begin the Legacy trilogy.

Chat GPT and AI

I am a big fan of the ability to work from home a few days a week. Everyone should have flexibility in their lives. It makes for a happier work culture. Most people do the right thing and get their work done no matter where they hang their hat on a particular day. Then some don’t.

Through my experiences, I know and have heard stories of employees working two jobs simultaneously. God knows why someone would want to do that, but eventually, everyone figures it out. The first question I ask is where integrity has gone.

Perhaps it is easier to pull this off with Chat GPT and AI. We are all asking ourselves how these technologies will change our world. Obviously, they help some people do two jobs at once. However, once that cat is out of the bag, their reputation will never be the same, as if they care.

Fred and I were talking about how this changes education. Our Government has cut back on education funding for decades, and it became very apparent during COVID that we need significant reforms. Everyone learns differently, from creatives to math brains. Some kids are behind the curve; others are way ahead. Technology can change that, allowing teachers to oversee their students in a different light—no longer cookie-cutter curriculums, but access to all curriculums.

When I grew up, I attended Lake Normandy Elementary School in MD. For whatever reason, Montgomery County used this facility as a new way to teach. The building had a library in the middle and quadrants for different grades. For instance, fifth and sixth graders were paired together in multiple areas to learn. A teacher never stood in front of the class but helped us each individually to learn at our own pace, and you had to be a self-starter. Unfortunately, my teacher was a serious stoner who hung out more than interacted with the kids.

I was curious but also a rebel, so instead of becoming the smartest kid in the class, I became the jacks, tetherball, and spit champion while never learning the basics, such as verbs and nouns. When I got to 7th grade, where there were seven classes a day in classic form, I found myself in an English class with the true slackers. I quickly caught up and was put in the top English class, although every day, I faked it until I made it.

Looking back at Lake Normandy, they might have been 50 years ahead of their time. The structure would be perfect for AI. They closed the school years ago, but there are many lessons to learn there. One lesson that should be taught is never to attempt to get away with two jobs at once while keeping your employers in the dark. It is not a good look, and it will eventually bite you in the ass.