Punching Above Your Weight as a Founder: Why I invested in Bizly

I'm a founder.

Sure, I'm an investor, too, but I started Brooklyn Bridge Ventures, the firm I invest out of.  That means that in addition to thinking about what kinds of investments I'm going to make, I need to think about where I'm going to work, payroll, business cards, all that stuff.  

As we've seen, the "business stack" of a variety of services entrepreneurs run on everyday has changed dramatically over the last few years.  Google Apps enabled e-mail on demand without a server, Uber enables transportation on demand, and WeWork offers space on demand.

The reason why WeWork became so successful was because they realized that space wasn't just about space.  It was about support--how could they make your work life easier?  That meant over-investing in technology to improve convenience and connect their members.  

In this way, space is something more than just a room with chairs and a table.

Founders know that space needs to be something more when they interact with clients and customers, when they onboard people, and when they focus on culture through offsites and events.  It's not just about people in a room, but a particular environment they want to create.  Just last week, I had a meeting with my Limited Partners at the Highline Hotel--a beautiful building that used to be part of a seminary built in the early 1800's.  The room was eclectic and cool, and afterwards I adjourned to its beautiful outdoor courtyard to meet up with a potential new investor that I had invested to come to the meeting.  

It was exactly the kind of vibe I wanted.  High quality, but interesting and comfortable.  

And yes, I closed that investor.  I also closed on a seriously great sandwich at the hotel bar.  The food their is excellent.  

I got the space through Bizly, a company that I invested in that just launched to the public today.  Bizly takes advantage of the vast supply of conference space in some of the best and coolest designed hotels in the world, as well as the top notch staffs that run them.

With a Bizly room, you get all the benefits of doing your meetings in a hotel--food and beverage service, someone to help you with A/V, and the ability to hit up a lobby bar or restaurant before or after--without all the hassle.  No faxing, phone calls or contracts required.

Businesspeople know how important all these amenities can be, because it's more than just a room that closes a deal or that inspires a team to come up with a new insight at an offsite.  

I'm excited to work with Ron Shah on this company and it's a testament to the kind of long term relationships that have building the deal flow pipeline at Brooklyn Bridge Ventures.  I was introduced to Ron almost three years ago by one of my investors as someone I should invite to my annual Shake Shack party.  He was an investor at his own firm at the time--a fund that had a lot of international LPs.  He had a lot of insight into the business travel market from the perspective of a small fund trying to impress a lot of big names--and after a year plus of talking with him through various iterations of the business, I decided to back what became Bizly.  

It just makes sense--take advantage of the best existing supply without the overhead of needing to own or rent that supply yourself.  

I'm excited to see it come to fruition and I'll offer up a discount code.  Use "BBV" and get $25 towards a very cool meeting space at Bizly.


I love Donald Trump voters.

I do.  

And you should, too, no matter who you're voting for.

Because that's the only choice... Cory Booker is right.  

Love your neighbor.  That's step one.

Calling them stupid, racist, or anything else isn't going to change their minds.  It's only going to reenforce the very reasons why they're voting for Trump in the first place.

They've been left out by nearly every politician they've ever come across.  They've fought for our country and they're now out of work.  They've worked hard to instill a set of values in their families and they see a world where those values are changing rapidly.  

They fear for their safety--and for anyone who hasn't turned off the news in disgust, wouldn't you, too?

Sometimes I think that's the real enemy, by the way...   Not Trump, not Hillary, but the fucking television. 

Do I really need to know about every single time someone gets killed in a terrible way in the world?  I hate the news for making me think of the world as a terrible place--and making money off of it.

You want to hate someone?  Hate CNN for profiting off our fear.  

Some of Trump's supporters align their values with what Trump talks about, but a great many simply do not feel comfortable voting for Hillary Clinton--or they don't like Bill Clinton.  

They're disgusted by Bill's extramarital affairs and his behavior in the White House.  I can respect that--but I would respect it more if they held Donald Trump to the same standard.  

I love the fact that they feel a strong sense of moral obligation and that this election for them is about trust.

They don't like hearing about lying, about e-mails, about cover-ups.  I wonder what they think when they hear that Trump won't show us what's on his tax return?  I have to imagine that makes them upset--because that's the kind of covering up they don't like about Hillary.

For once, they just want someone elected to come clean and be honest.  I respect that.

And it is because I do care about *all* of the people in this country that it made me sick to listen to Donald Trump speak at the RNC last week--because I knew that his supporters were being lied to.

You may have worked in a *real* job--building something--not something ridiculous like I do where I invest rich people's money to try and find the next Facebook.  I get that probably shouldn't be a job and you might not respect me for it.  Sometimes, I don't believe it myself that I get paid to do that.

You toiled hard on a line making the very things I use everyday and then, one day, your plant closed.  Or, maybe you worked in one of those places that collapsed when the town's major employer picked up shop and moved away.

Foreign countries and executives looking after their bottom line "stole" your economic security and that of your friends, family, and neighbors.

So when Trump says he's going to bring those jobs back, that sounds great.  I get it.

Only... it's never going to happen.  That's just not the way the world works.  

The stock market pressures companies to look after only their bottom line, our current capitalist, public market system makes it impossible for corporate CEOs to look after anything different.  

They get fired when the stock goes down.

If you don't like capitalism--well, that's a different story.  We could go with socialism, but I'm pretty sure you don't want that either.  

And in fact, since the 1970's, that kind of bottom line thinking is pretty much why you've been getting screwed as a middle class.  Someone came up with the notion that the point of a company wasn't to employ people or care about the community--it was to make its owner's money.

It's not China's fault or trade agreements.  Those are just the *effects* of this kind of thinking.  They're not the cause.  You were getting screwed long before anyone signed any kind of trade agreement.  Your wages haven't been going up for a long, long time.  You were simply being screwed slowly.  

Your plant closing just made it more obvious.

You know what else screwed you?  Technology.

We make machines that allow companies to do more with less.  It happened in the 1800's with the industrial revolution.  It happened when we built farm machines.  

Here's a scary thing: It sure as hell is going to happen to the trucking industry.  

If you drive a truck for a living, you are going to get replaced by a machine sometime in the next twenty years--because that's just how fucking crazy good technology has become.  They can make robots who beat humans in chess, and now they make 'em better drivers, because they don't need sleep and they're always looking in every direction at all times.  

Deny it all you want or hate me for it, but it's going to happen.

That's not the fault of the Democrats or Republicans or China or anyone else.

The only solution is for you to get help--for someone to reach out and say "Hey, we care about you and your lost job, so we're going train you to make those robots or run some other kind of thing--to be a drone pilot or help rebuild our crumbling infrastructure or some such thing."

Who knows what the jobs of the future will be like.

Whatever it is, you and millions of other people are going to need someone to care about you.

The Republican party isn't the party of that kind of care.  They'll treat you like you're lazy or don't want to work--that you should be able to just "find a job" if you're able.  That's been the party platform for years--everyone for himself.

I have to imagine you're voting for Trump because you're pissed off the way this country has worked or not worked for you--and that you feel like you're getting the short end of the stick.

So do you really want to elect a man that made firing someone--telling them they can no longer work--into *entertainment*?

If you've ever been let go at a job--if you ever thought your boss took the least bit of pleasure in letting you go, in telling you that you could no longer support your family--wouldn't you think of them as the sickest most vile human being on the planet?  

You'd hate them.

Yet, that's exactly what Donald Trump has made a career of doing--exploiting the bankruptcy system, pulling millions of dollars out of all his companies while they fold time and time again.

It's the saddest thing in the world to hear these stories of small business people just like you who were told to accept pennies on the dollar for their hard work for Donald Trump's companies or to try to sue him in court.  

He plays bankruptcy like it's a game.  He thinks laying people off is a game to be played and he's very good at it.

I don't wish being fired on anyone.  It's nothing to joke about and nothing to make into entertainment.

What I want you to experience, and what everyone should experience, is hope.  I have to imagine that's what you want for your kids, too.

Hope motivates.  It inspires.

Can you honestly say that the Republican National Convention made you and your family hopeful?  Did you think of the world as a place you wanted to live in?

There is a reality in the world that probably isn't as good as the Democrats painted it to be, but I know it isn't as bad as the Republicans are making it out to be either.  If future generations are even going to bother to try to make the world a better place--they have to be hopeful about it.  

They have to want to go into it and reach out to it.

No one is going to solve the problems in the Middle East without learning a little Arabic--and if the idea of your kids learning Arabic in schools freaks you out, I totally get it.  

But, I'm sorry, the bomb thing isn't working.  

The Middle East has been blown up so many times we've lost count.  We need someone to figure out smart solutions, not just assume that blowing people up fixes everything.

That's what religious extremists want to do to us!!

Ever stop to think that maybe had anyone loved or cared about any of these kids willing to blow themselves up and just talked them off the ledge we could change their minds?

Isn't that the definition of stupidity?  Doing the same thing over and over again and expecting a different result?

The world isn't made better with locks and walls.

You know who locks keep out?  Honest people.

Bad people will do what they'll do.  They can't be eliminated or destroyed.  Evil will always exist.  We've never ever made it go away--but we've created a lot more of it by following those who told us they could.  

That's been our biggest downfall, actually--following people who told us they were going to beat the bad guy and that we should suspend our civil liberties to do so.

Don't believe a guy that he'll protect your Constitutional right to own a gun when he's willing to violate someone else's right to free speech by suing the heck out of them if he doesn't like them.  

When you start fucking with the Constitution, everything is game.  Everything.  

July 4th is my favorite holiday.  I love fireworks and summer and I like seeing all the flags.  I love this country.  I like seeing us run over other people in the Olympics, and I can watch Rocky IV over and over again, because I grew up in a time where it was cool to beat the Russian guy.

I grew up liking when the military wins.  I was in junior high when I remember being pissed off that Bush wouldn't let Stormin' Norman go all the way to Baghdad to take out Saddam. 

I was also a kid, and the world isn't a game anymore.  

What sucks the most about the world is that it's a lot more complex than winning or losing.  

Anyone who says otherwise is treating you like a child--and that pisses me off.  

Anyone who says it's all about law and order and blowing people up who want to kill us doesn't understand that you can't blow a bunch of people up without making someone hate you.   So you think you can blow every last ISIS member up--but then some other nutball riles up a group to gain power by telling them look at all the devastation the US caused.  And they'll believe it, because their lives will suck.  Extremists are desperate and hopeless.  

Not all of them will turn to violence, but that's the nature of violence today.  You don't need armies.  You just need to push one or two people over the edge.  You can't stop that.  It sucks, but you'll never snuff out every single last extremist with a conventional army.

It only takes one person to show up in Times Square with a bomb strapped to themselves to give CNN something to make money off again.

But you know who *is* going to stop those people?  

That kid who bothered to learn Arabic--or who grew up speaking it after his family immigrated here, who loves this country because we let his family escape the shit hole situation he came from in a Syrian civil war.  

Anyone who thinks it's easy to find solutions to terrorism or the economy is treating you like you're stupid.  They think nothing of you and they're willing to tell you anything to get the power that comes with your vote.

I care enough about you to say that, even if you don't agree.



The Myth of the Top Investor

Someone asked me recently if they should raise a fund, because they had access to investments that were being made by "top, brand name investors".  

Whether there even is such a thing relies heavily on your perspective.

It is absolutely true that many of the firms you've heard of being called the "top" funds consistently perform in the top quartile, even decile, of all funds, over time--Sequoia, Accel, etc.

If you drill into that data, what you wind up seeing is that they get a disproportionate access to many of the "once in a lifetime" type exits--the Facebooks, Whatsapps, Googles, etc.

They do not, necessarily, have a better than average winning percentage.

So what does that mean?

It means that if you ever have an opportunity to be a Limited Partner in Sequoia, and to do so over multiple funds--with a very long term (20+ years) time horizon--you should probably do it.  A few home runs over time will likely net you huge returns in the end.  

What doesn't it mean?

What it doesn't mean is that by co-investing with them, you're guaranteed any success.  For one, the sample size is far too small for you to have that much more of a chance of being in those one or two deals.  Unless you're doing lots and lots of deals, your own chances of being in one that hits is far too low for it to make a difference whether Sequoia is in one of them.  In fact, there's a good chance that if you're an average Joe and they're in your deal, they might not be showing the same kind of conviction in this opportunity they would if they were trying to take the whole thing.

It also doesn't mean that, if you're an entrepreneur, they're the right partner for you.  Much like those damn Yankees, these winning franchises have had a number of employees come and go over the years, many of whom weren't so good at their jobs.  On the Yankees, for every Derek Jeter, you had a few Bubby Crosbys.  So you might get a top partner on your deal at one of these firms--someone who is responsible for the kinds of multi-generational wealth creation kinds of deals, or you might get someone who is relatively new, or simply has yet to prove out their Midas touch when it comes to investing.  

Perhaps the investor you're turning down is the next pre-Twitter Fred Wilson.  Was Fred a "great" investor before Twitter, or did the experiences and network that he picked up in that deal put him into an elite class?  Probably a little bit of both--but he certainly didn't have the same kind of brand beforehand, and I'm sure lost a deal or two to "top" firms because of that.  

In fact, most investors would agree that as a founder, *you* are the one that creates the value.  You may decide you want Benchmark in your round for signalling purposes, because you know they're seen as successful, but you would undoubtedly be just as successful no matter who you took money from.

Does Harvard make smart kids or do smart kids want to go to Harvard?  Would they have done just fine anywhere else?

On top of all this, these "top" firms aren't the only ones who get into these top deals.  Given the size of these funds, they often don't participate with more than a token amount, if at all, in the seed rounds of top returners.  They simply can't manage deals that small on a regular basis because of the time and effort for the amount of money at stake.  So, from a fund perspective, there are certainly other funds that do just as well in a given cycle.  

Lastly, it takes a long time and many many funds to tell whether or not the funds that we think of as top are actually top performers--and even then it's not clear that they're built to last several generations of partners.  

There are some funds that, in the last seven years, have raised four or five funds.  We're *just* seeing whether or not their first fund is a good performer now and now they're managing a fund that is perhaps five to ten times larger than that original size.  For all we know, the three or four funds after that are complete clunkers.  Deals look great until they aren't anymore--Theranos, Fab--these are the kinds of opportunities that enable you to raise another fund or maybe even two because of the on paper returns.  They may or may not win out in the end.

To say that a firm is a top performer when they started out with $50mm and are now managing $500mm or more seems ludicrous to me.  It's a completely different game at that size, and the work being done is likely now spread out across many more people than just the original partners who made that first fund successful.  On top of that, they probably did nothing in that first fund other than invest.  Now, they're spending a lot of time managing staff, going to board meetings--and much less of their time is spent sourcing and investing.  

There's also a difference between "top" and "brand name" investors.  There are lots of investors who have built brands in the last few years--names of people that we may associate an exit or two with, but whose full track record we really haven't seen.  A lot of times, their record is two early to tell and other times, it may not be all it's cracked up to be.  Also, it could have been just dumb luck that isn't likely to be replicated again.  Is every Uber angel investor likely to be the finder of the next big deal?

So before you start aiming to work with or follow "top" investors, think long and hard about what you're getting yourself into and what you're likely to experience.  There's a lot of star power in the venture capital world right now around both individuals and firms--and everyone is trying to convince themselves that getting closer to the light will cause some to shine on them, too.  

The Thing About the Best Pitches

The best pitches have a hook.  The very first sentence gets me leaning forward, not back.

They have an unrelenting storyline--and they don't let a boring team slide get in the way if your team isn't the most exciting part of what you're doing.  

They mostly talk about where you're going, because the what you've done up until now in a seed pitch usually isn't that much.

The best pitches acknowledge the reason why we're here--for you to ask me for money and for me to make a bundle of it investing in you.  If we don't talk about how that's going to happen, what's the point?  Ask for an amount, tell me what you're going to do with it, and tell me how that leads to a big exit.

They don't come from templates.  Every startup is different.

They don't have the word advisor in them--because that's just a code word for "Someone who didn't invest, but probably could have."

The best pitches follow the word problem with... you know... an actual problem, versus something that maybe could be better but otherwise has been working ok for quite a while now at a huge scale.  

The best pitches are ambitious--they ask for enough and aim to do something big.

They're told, not read--it's your story and if you can't remember it, no one else will.

Confessions of a Privileged White Male and Former Conservative

I was born in Brooklyn in 1979, which means that the number one issue growing up in the 1980's and early 1990's was crime.  In 1990, there were 2,245 murders in the city, nearly 10x the annual rate we have now.

By the way, I'm white and back then, similar to now, you can't talk about crime without taking about race.

I grew up in Bensonhurst.  You might remember that as the area of Brooklyn where Yusef Hawkins was killed in 1989.  Hawkins, who was black, and a group of his black friends came to the neighborhood to buy a car posted in an ad.  They walked right into a group of Italian kids (I'm 1/2 Italian) who were waiting to ambush a group of black or latino guys who supposedly had dated a neighborhood girl.  Hawkins and his friends were attacked by a group of over a dozen young white men with baseball bats, and one who had a gun.  

He was shot to death at the age of 16.

Around the neighborhood, people whispered about what black kids were doing in "our" neighborhood and how they weren't supposed to be there.  

Actually, no, they didn't whisper.  

They said it out loud--all the time--just like people are talking now about how struggling on the ground with a cop (or not struggling at all or "heightened circumstances") is a justification for getting shot by one.  

I was socialized to think of crime as the kind of thing where whites were the victim and people of color were the perpetrators.

What I didn't know at the time was how much the media reinforced that.  Crimes with white victims get disproportionately covered, especially when they are committed by blacks.  

I didn't know either that most people get killed by their own race.  As a white person, I'm about ten times more likely to get killed by another white person as I am likely to be killed by anyone of color.  

That's not what I thought as a kid.  I never would have believed that stat.  

So when we elected a "tough on crime" Republican Mayor, Rudy Giuliani, that cemented my Republican leanings.  I mean, why would you be anything other than tough on crime?  Was soft on crime even a position that reasonable people would take?

I didn't remember at all that, actually, Giuliani's black predecessor, David Dinkins, presided over the beginning of NYC's historic drop in crime.  I also didn't remember that he, not Giuliani, hired Police Commissioner Ray Kelly.  What he also did, unlike Giuliani, was advocate civilian review boards and neighborhood policing where cops worked together with their communities as partners.  

I was for the death penalty--because there were some really bad people out there and they didn't seem to deserve to be alive.

I never read the statistics about how the death penalty was more expensive, and not a deterrent to crime at all.  

I felt on the Republican side of a lot of other issues, too... 

Welfare?  A handout.  People should work for a living.  After all, my parents did.  Both of them.

I didn't see how far ahead of the game I was having two parents at home, neither of whom had spent any time incarcerated.  

Abortion?  How could you be for killing babies?

I didn't bother looking into the policies that tied into abortion, like women's health, contraception availability, sex education, etc.  I'll never ever be "pro" abortion, but when you start looking at unwanted pregnancy as the key statistic to address and not abortion itself, you realize that the only way you solve that is with policies that include a women's right to make decisions around her own body.

And, of course, it was cool having a strong military.  Kicking Saddam's ass out of Kuwait made us feel good and patriotic.  Smart bombs were cool and I was all for paying for more of them.  

I didn't know enough about the Middle East to understand how badly we could fuck things up there in the future and what we would unleash when we opened Pandora's Box.  They don't exactly teach you much about the Middle East when you grow up on European centered history.

Drugs?  Against them--even today.  I don't use them myself, never did, and can't see any good reasons to recommend that anyone else start.  So, if you're against something, you make it a crime, right?

I didn't understand the plague that widespread incarceration for drug offenses would bring disproportionately upon communities of color.  Over 45% of our prison population is in there for drug offenses.  Even though white Americans are more likely than black Americans to have used most kinds of illegal drugs, including cocaine, marijuana and LSD, blacks are arrested for drug possession three times more often.  I never thought about what happens to people both in prison and after prison--and what happens to families and kids and the cumulative effect it has on communities when black men disappear and return unable to find work because of their record.

I also didn't know what I had.  We didn't think of ourselves as rich.  We felt pretty average.  My dad was on the fire department, and semi-retired into running a little accounting practice out of our house.  My mom was a teacher's aide in the school system.  I went to private Catholic schools, but mostly on scholarship.   There were things we couldn't afford for sure.  We didn't eat out much, nor did we go on expensive vacations.  Our big trip was driving down to Disney World by car when I was 10.  I made NYU, but couldn't afford to go.  

We didn't feel "privileged" at all.  We felt middle class, even though we above the middle of NYC's per capita household income.  

In fact, up until as recently as a year ago, the word privilege, especially in the phrase "white privilege" made me bristle.  I was incredibly bothered by the idea that somehow I was a "have" and that I didn't get to where I was purely on my own work ethic.  

No one likes to thank the wind at their back--particularly not middle class white people.

I was way more "self made" than the Ivy Leaguers who went into finance.  I was proud of the fact that I was the Fordham grad in a crowd of Harvard, MIT and Princeton at my investment internship.  Being the local guy climbing up from the mailroom (which was literally my first job), was part of my identity.  My family's name isn't on any buildings and they didn't have the money to fund my investments, so I felt like I didn't have help to break into my industry.

I quickly forgot that I had ever interviewed at McDonald's for a summer job.  I also forgot that I was embarrassed to do so.  My brothers were embarrassed on my behalf when they found out that I had applied.  Flipping burgers wasn't something anyone in our family was going to do--so they both actually found me the same kind of "respectable" mailroom job at their respective brokerage firms on Wall Street.  

We never specifically said that I shouldn't flip burgers because I was white--but that's what it was.  We were just somehow "past that stage" economically and socially, so I was able to use my family connections to get a more respectable job.  Nevermind that I had friends who worked at summer beach clubs.  It seemed fine to be handing someone in a mostly white environment their burger, while the Golden Arches seemed "beneath me".  

Getting that mailroom job through connections wasn't the same, in our eyes, as the way wealthy white people used the "Old Boy's Club".  That was something else altogether.  This was just what you did for your family to "help out."  I felt lucky to have that connection, but not privileged.  

My high school was a scholarship school.  Regis is one of the best high schools in the country and it specifically tries to diversify its student base.  Compared to neighboring schools like Marymount and Sacred Heart, where tuitions were almost $20,000 a year at the time, I didn't feel privileged at all.

What I didn't see was the compounding interest of privilege.  I succeeded, I thought, because I did well in school--but I never thought about the advantages I had.  I had two educated, working parents.  My mom found a flexible job where she could be home when I was home--and my dad's business was largely out of the house as well.  Even though I grew up in a time of high crime in New York City, I lived in a low crime area.  I "avoided" drugs, but I was never really exposed to them.

These are all things that statistically were more likely to be the case because I was white. 

But it extends even further back than that.  My dad had healthcare and a small pension because he had a civil service job--but had he been black, he would have been a lot less likely to get on the fire department.  Look at the numbers.  Even if he did, he probably wouldn't have felt welcome enough to put twenty years on.

We owned our house--and that was the basis of our financial security.  I never gave much thought to the likelihood of getting a mortgage or being able to buy a decent house in a low crime neighborhood if you were black in NYC in the 1960's.

Sure, my grandparents were poor in the Depression--but because they were white, no one could refuse to rent to them.  They didn't make much money, but they worked.  Black unemployment during the Depression was twice the rate of whites--so while it felt like a lot of people they knew in their neighborhood lost their jobs, they never knew how bad it was in neighborhoods of color.

Their parents came here as immigrants who had nothing around 1915, but at least they weren't a generation or two removed from slavery.  That's, you know, a pretty decent advantage that no one talked about because they had no way of feeling it.  I imagine it was easy to feel like the lowest person on the totem pole at the time when you ignore the blacks below you.

Whether we realized it or not, everything was easier for us, for generations--and privilege compounds like a high yield bond.  

That didn't mean we didn't all work hard--but we didn't know what it would mean to have to work that much harder if we were people of color.  Not being aware of that formed the basis of our beliefs about the world. 

What started to change for me was my interest in numbers.  I'm an extremely logical person, and I always press for facts, statistics and the "truth" behind things.  

The truth, as it seems, is a little more complicated.  

When you start asking "why" and "how" instead of "what" you get a much less black and white view of solutions to society's problems.  You start seeing the failure of prisons, of capital punishment, of the anti-abortion movement, of the drug war, and of US foreign policy.  

These aren't opinions.  They're provable facts.  The failures are measurable.  

You start looking at the cash flows in poor neighborhoods, where you probably don't own your property, and your landlord doesn't live locally.  When you pay rent and when you shop at big box retailers and fast food joints, you literally suck profit out of your own pocket and redistribute it to the owners of equity--i.e. not poor people.  

Locally owned means "the money stays here" and where I grew up, we never ate at a fast food chain and we nearly always shopped at places owned by our neighbors.  

It keeps going...  How about unemployment rates among the formerly incarcerated?

That's one that hit home, because I knew someone who got arrested for a white collar crime.  

This person is white.  

They had a good lawyer.

They never did any jail time, but they then had a mark on their record that made employment more difficult.  

Thankfully, this person had family support.  They were able to start a business in another line of work, aided by the fact that someone in their family owned a building where they could get started for cheap.  

I realized how different this would be if they were black.

If they were black, they would have been less likely to get a white collar job in the first place--so their "theft" of money would have been more likely to come out of a cash register than a retirement account.  Let's not even go there for a moment--that if you steal money, your sentence really depends on where you stole it--but let's think about the aftermath.

It would have been a lot less likely that this person could have had the connections to find and hire a top lawyer.  They would have been more likely to actually do prison time and that much less likely to have someone in their family own some property to help them get off the ground in another business.

I remember this person's family being worried about where he might have to serve community service--hoping that it wasn't a bad neighborhood.

"You know what's a bad neighborhood?" I said.

"Prison.  At least he doesn't have to work there."

Prison was a bad place.  I knew that much.  I knew people didn't come out of it better than they went in--and I imagined that to survive in prison, you probably had to do things and become a person who wouldn't exactly reenter society so easily.  That's when you start to realize that prison is a cycle--one that starts with the factors that lead to crime, like poverty, lack of employment opportunity, lack of positive role models--because big chunks of your community are missing.  

Then you think about your chances of being sent there.  It is statistical fact that you're more likely to be stopped by a cop if you are black and if you're actually caught doing anything, your sentence is likely to be tougher.

It snowballs from there.  It's now very obvious to me how "fighting crime" results in criminalisation, oppression, and discrimination.  We have to find better ways to bring people back from the edge of society, even when they turn to crime.  This includes sex workers as well--one of the most marginalized populations that gets caught up in continual cycles of abuse.

Funny enough, now that drugs have become more and more of a problem in white communities, you're starting to see the white people in power become more sympathetic to the disease of addiction versus the crime of it.  

You know what else I didn't realize?  The power of speaking out and of pushing people to think.

That's where I originally failed on gay marriage.  

Unlike a lot of Conservatives--I never had a problem with gay marriage.  That, too, is a product of being in NYC.  Ten or so years ago, however, I thought this was the kind of thing states should decide--that you shouldn't force right on people who were wrong.  I thought that you were better off letting states topple like dominos--because *of course* freedom to marry whoever you wanted to marry was inevitable, right?

It had never occurred to me that nothing is inevitable, and that the other side feels like they're on the right side of history just as much as you do--and that if their way of life feels threatened, they'll work even harder than you will to turn the tide.  

It didn't occur to me that if you don't lead by strong and loud example and national law, you empower those who seek to discriminate and even worse, act violently towards the LGBT community.  

You make unequal treatment ok if you don't do everything you can to stop it everywhere.

That was the wrong position to take, but I got it right when the country finally did.  

In 2008, we had a choice in this country to follow someone who understood that problems are complex and require nuanced solutions--that strong isn't always the answer, especially when paired with wrong.  The campaign and presidency of Barack Obama was a turning point for me politically, because I had come to realize a lot about where I had come from.  

in 2008, I was in a failing business that I had started.  Yet, I could feel just how far I was from really having any problems.

It didn't matter what my bank account or credit card statement said--there were no worries that I could pull out of it.  I knew I would have no problem getting hired for my next job.  I had family support, community support, and my failure could be worn like a badge of courage.  The $550,000 of investor money that I "lost" would see not nearly the kind of lifetime punishment that someone who stole $550 would experience.

That's when you get the sneaking suspicion that you've got something in the bank that not everyone does.  

Over six years, culminating in the news that a little black kid got shot carrying a toy gun that looked way less harmful than the toy guns you ran around with as a kid, I learned for sure that I am privileged.

I am privileged by being white. 

I am privileged by being male.

I am privileged by being straight.  

So, what do I do about it?  

Seems the most obvious thing to do after realization is education.  When someone tells you that you have a disease, you read up on it.  You don't just talk out of your ass about it.  

You start listening.  

I'm happy to get suggestions on books and essays and such via Twitter.  (I don't like comments because they're an unmanageable medium for me.)

Second, I imagine, I'll try to make others in my circle aware of it.  If I can do that in some small way through my personal brand and footprint, I hope I can help affect some change.

Third, is that I will continue to participate in activities that promote diversity and inclusion.  

At the Brooklyn Bridge Park Boathouse, we have built a diverse community of volunteers and paddlers who are regaining ownership of their environment and improving their health through activity.  This includes advocating on behalf of the Park's own diverse constituency with respect to neighboring, mostly white and wealthy, communities.

It means raising money for tech inclusion programs like ScriptEd, which teaches a diverse base of students how to code. 

To me, it also means being accessible in my job as a startup investor--and doing away with systematic exclusion tactics like the "warm intro" where you can only break into the tech community if you already know people in it.  It doesn't mean that I'm doing anything other than trying to make money for my investors--a responsibility I take very seriously.  I'm not an impact investor, but I know who I invest in makes an impact.

It means being conscious about how I screen opportunities.  It means speaking and taking pitches in front of more diverse communities.  It means judging pitches in the context of the person--and knowing that the very same company is going to get presented very differently to me when a white male is pitching versus a black female.  Language will be different and so will the signals that we typically associate with confidence.  

I don't have perfect answers to what to do about any of these situations, but I'm up for listening and I'm definitely more aware about what my status means than I ever have been.