Category Archives: Work

Applying portfolio reforms to postsecondary problems

I just got back from a trip to New Orleans, which continues to be a well of friendship and inspiration.

I. Where should you spend the next philanthropic dollar? 

In a few conversations, the following questions came up:

  1. Are the kids we serve going to succeed in life after high school? What will their lives be like when they are 30? Will they be living meaningful and happy lives?
  2. Is the marginal dollar of philanthropy best spent on making the K-12 system better (after 10 years of improvements) or trying to overhaul the post-secondary landscape?
  3. If you wanted to radically improve post-secondary, what would you do?

II. Post-Secondy portfolio 

The K-12 portfolio mindset entails viewing an educational system in terms of operators (running schools) and seats (how many students are served).

This mindset could also be applied to post-secondary.

By 2020 or so, New Orleans will be graduating around 3,000 students a year.

Let’s say that about 1,500 of them will be prepared to succeed in a four year college; 1,000 of them will be prepared to succeed in a 1 to 2 year credentialing program; and 500 of them will need deep support to enter the workforce and exit crisis situations.

Of the four year college students, you might need 500 to 1,000 “KIPP to College” type supports to ensure students make it through.

For the credentialing programs, you’d need 1,000 seats that can reliably produce students with employable credentials.

For the crisis students, you’d need employment and social service operators that could transition students into jobs.

III. Post-Secondary investment intermediaries 

Instead of assuming this will naturally happen in New Orleans (or any other city), you could capitalize a new or existing non-profit intermediary to launch, recruit, and support post-secondary providers.

At the outset, the intermediary would create a business plan where it laid out how money it would need to get X% coverage on the aforementioned 3,000 seats.

High-Quality existing local providers (like the coding bootcamp Operation Spark) could cover some of the seats, and national providers like Match Beyond could be recruited in.

Overtime, you’d expand what was working, close what wasn’t, and support new entrepreneurs to keep innovation going.

IV. Getting funding streams right

Most states subsidize mediocre public universities; the federal government tops this off with Pell grants.

To make the 3,000 seat post-secondary strategy viable, you’d need to blend a mixture of public support and tuition to make providers sustainable.

Louisiana’s course choice provides a revenue stream for programs that started working with kids while they’re in high school.

Creating a new university that housed many of these programs could allow for the accessing of Pell grants.

Wage contigent loan programs could also be an option for programs that were consistently placing graduates in high-performing jobs.

V. Who are the entrepreneurs that will seek out the 10x play?

The early New Orleans K12 entrepreneurs felt that they could deliver something to students that was significantly better than the existing system.

They were right.

A post-secondary transformation won’t happen on its own.

It will take a set of entrepreneurs to put forth a plan, galvanize funding, and spend a decade building the new system.

Is this the right play? If so, who will step up?

These major cities could afford a $10K per family basic income w/o raising taxes

There’s been a lot of talk recently about the pros and cons of a universal basic income.

There’s also been a lot of talk about how expensive this would be.

But, from my quick analysis, I actually think quite a few major cities could institute a child based basic income utilizing only existing tax revenues.

I. Numerous big cities spend over $20,000 per student

Getting accurate city per-pupil spending amounts can be a near impossible task, but nearly all sources I reviewed showed that Washington D.C., Newark, and New York City spend at least ~$18K a student. I think Boston spends around this as well.

And higher end estimates get closer to $25-30K per student.

For the sake of modeling out how to end child poverty, let’s assume ~$20K per student.

II. Giving $5K per student per year basic income back to families

Let’s say that starting next school year, each of these cities decided to reduce public education spending from $20K to $15K per student, and instead of giving this money back to taxpayers, provided a universal basic income of $5K per child back to families.

Assuming your average family has about two kids in the public school system, that’s $10K per family.

That won’t make any family rich, but it would probably get most families out of deep poverty.

III. A $5K per student spending reduction would likely not lead to major education losses

Dropping to $15K per student would still put these cities ahead of the national average of ~$10K per student. Even adjusting for cost of living differences, none of the cities would be that far off typical educational spending.

To get a taste for what cities are able to achieve with various students and spending, see below:


The above is by no means an accurate picture of school system effectiveness, as it’s based on absolute scores rather than growth; however, it provides decent evidence that schools systems that spend $10K-15K to student can still achieve relatively ok outcomes.

50% of the top ten adjusted scoring cities in the country are located in Texas and Florida, both of which spend very modestly.

Ultimately, the students in Washington D.C., Newark, and New York City are different than students in other cities, so we can’t make any claims with 100% confidence, but the experience of other cities suggests that spending $15K per student is enough to provide an education on par with other major cities across the country.

IV. What do you think parents would want?

Somebody should poll this question, but I expect families that have two children would rather have $10K in cash per year / $15K in education spending rather than $0K in cash / $20K in education spending.

For many of these families, $10K per year would be absolutely game changing.

It would be very interesting for an aspiring politician to run on this as a single issue platform. Or to take the issue to a popular referendum.

V. Trade off that no one explicitly made

Here’s the thing: every marginal $1K increase in education spending can be justified at the time. There’s always a compelling financial ask to be made when families in poverty are struggling to get a great education.

But, eventually, these marginal increases can lead to spending allocations that just might be out of line with what families want and what might be in the public interest.

My guess is that providing a $5K per student basic income to families – and reducing educational spending by the same amount – would increase the welfare of families in some cities.


The Climb

Every career is different.

But, anecdotally, the below trajectory is a common path I see amongst people who have accomplished a lot for others.

Of course, there are other paths, but for what’s it worth, here are some thoughts on this path.

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High Achiever Phase

At the beginning of your education and career, you are for the most part only accountable for your own performance, as well as perhaps the performance of a few others.

If you can execute, you can get a lot done. This is not to say that there won’t be ups and downs as you progress, but, professionally speaking, the ups and downs will be bound within a reasonable range and the overall trajectory will be up.

Failure, Massive Learning, Recovery

Then, at some point you will really fail.

Sometimes this failure will be known to the world; sometimes it will be known to your management team; sometimes it will be known by your board; sometimes it will only be known to you.

Given that there’s only so much you can fuck up when you’re early in your career and individually executing, your first spectacular failure will generally happen when you’re managing a large initiative, team, or organization.

Some people recover from this and some don’t.

Generally speaking, perseverance, self-awareness, ambition, constant learning, and a deep drive for improvement help someone rebound from major failure (which might be one event or a dark year or two).

I also imagine certain elements of privilege (social capital, race, money, etc.) help, which is unfair.

Sometimes people have to change roles or organizations to fully rebound.

Sometimes they don’t.

The Climb

Ideally, the lessons of your failure are engrained so deeply that you never fail this hard again.

I don’t think it is great for an individual, in the career sense, to fail fast and to fail often.

You should improve enough that you train yourself to mitigate major downsides while giving yourself shots at high upsides.

Some of your upsides will hit for reasonable successes, while some will hit for astounding successes.

But spectacular failures should generally be avoided.

With a good understanding of your own strengths and weaknesses, you should be able to build the right teams and enter into the right situations to give yourself a decent chance of doing great things for others.

Once you’ve entered The Climb, you can get in a virtuous cycle of challenge, growth, and success.

In Sum

Unfortunately, Massive Failure is often the entry ticket to The Climb.

Buckle up.

The Speed of One’s Mind

I just read this study in HBR on the correlation between working long hours (+48 hours) and excessive drinking (+21 drinks for men, +14 for woman). All told, they found that working long hours increased the odds that one is a heavy drinker by 11%.

This doesn’t seem like that much, all things considered, but it got me thinking about the issue.

I know many people who work +48 hours a week. I know many people who drink +21 drinks a week. I also am close with a couple of alcoholics. While I am not an alcoholic, I sometimes worry about alcohol’s habit forming effects.

On a personal level, both working and drinking manipulate the speed of my mind. When I am “on” all day – meetings, emails, calls, writing, tweeting, etc. – my mind works at very high speeds as it is absorbs and analyzes information. Caffeine also accelerates my mental speed.

There are only a few ways I know of to slow my mind down.

In order of will power needed, I can: meditate, work out, or have a drink or two.

That’s about it.

Given that working speed my minds up, and that drinking slows my mind down, I’m open to the idea that working a lot increases my tendency to drink.

However, when I’m not working I also can get bored and or anxious, which surely can lead to drinking as well.

For me, I think the biggest variable just ends up being will power.

Medication and working out require more of it, but they are surely a healthier method of putting on the mental brakes.

One last thought: I’m also open to the idea that constantly speeding up and slowing down’s one mind isn’t optimal either.

Much to consider.