Public Service, Property and Hustle: How I Built My Own Version of the American Dream

I was born in the Bronx in 1981 into a family in which public service was not an abstract concept. It was simply what people around me did.

My mother worked for New York State at the Arthur Kill Correctional Facility on Staten Island. When that prison closed, she transferred to Fishkill Correctional Facility. Her parents—my maternal grandparents—both worked at the City University of New York’s City College. On my father’s side, my grandmother worked for the New York City Board of Education.

Government work, in one form or another, runs deeply through my family.

Perhaps it is not surprising, then, that I eventually made a career in New York City government myself. What I could not have predicted was the route I would take to get there—or that a career in public service would become just one part of a much larger effort to build the life I wanted.

My family moved around somewhat when I was young. After the Bronx, we spent several years in New City, in Rockland County, followed by a period in Forest Hills, Queens, before eventually settling in Roslyn Heights on Long Island.

My father was an endodontist, and by the time I was growing up in Roslyn Heights he had created a very good life for our family.

I understood from a young age that when I eventually had a family of my own, I wanted to be able to give them a life at least equal to the one my father had given me.

That became one of my benchmarks for success.

The interesting part is that I got there by taking almost the opposite path.

My father became a highly trained dental specialist. I became a civil servant, accumulated graduate degrees, invested in real estate and spent years juggling a government career with what can only be described as a different type of hustle.

Different road. Similar destination.

And that has taught me quite a bit about how many different ways there are to “make it.”

An Education That Didn’t Follow a Straight Line

I graduated from The Wheatley School in Old Westbury in 1999.

Wheatley had an enormous influence on me. It was an academically ambitious environment in which college was essentially assumed to be the next step.

I went to the University at Albany and studied history, with a minor in political science.

But even that description does not quite capture what I actually studied.

I jokingly refer to legislative affairs as my unofficial major.

I accumulated more than 36 credits through legislative internships and related work, allowing me to complete college in three years. Those experiences exposed me to government not merely as something discussed in textbooks, but as an institution populated by real people making real decisions.

I worked around the legislative process in Albany and had opportunities that, looking back, were remarkable for someone so young. I had the opportunity to intern for former President Bill Clinton and, through my political and legislative experiences, met figures including Gov. George Pataki, then-Assemblyman and now State Comptroller Thomas DiNapoli, then-Council Member and now Attorney General Letitia James, and former Mayor Michael Bloomberg.

Politics and government stopped being distant things that happened on television.

They became workplaces.

After graduating from Albany, I enrolled at Albany Law School.

I lasted one semester.

At the time, I simply wasn’t happy there. Walking away from law school could easily have looked like failure, particularly after setting out on a professional track that seemed clear and prestigious.

I returned home to Roslyn Heights instead.

It turned out to be one of many moments in my life when abandoning the conventional route created room for another one.

I subsequently earned a Master of Public Administration from Baruch College, followed by an MBA with a concentration in Computer Information Systems.

One of the interesting things about studying in New York is that the classroom can sometimes become a cross-section of the city itself. During my MBA studies, Carl Heastie—who would later become speaker of the New York State Assembly—was in one of my classes.

I later earned a Master of Public Health in Health Policy and Management from Columbia University. Chelsea Clinton was among my classmates during my time there.

Years later, while balancing career and family, I went back yet again and completed a Doctor of Public Health at SUNY Downstate in 2025.

If there is a pattern in my education, it is that I have rarely been able to leave well enough alone.

Government interested me.

So did management.

Management led me toward business.

Technology became increasingly important.

Health policy interested me.

Eventually, those subjects that might once have seemed disconnected became surprisingly complementary.

Today I work at the intersection of government, technology, finance, procurement and administration.

Sometimes Other People See Something in You First

Interestingly, before I ever thought of myself as an entrepreneur, someone else saw it.

Years ago, I was dating someone who herself owned a technology website built around a knowledge-sharing model that, in some respects, anticipated the kind of online question-and-answer community later made famous by platforms such as Stack Overflow.

She viewed me as entrepreneurial before I viewed myself that way.

At the time, I am not sure I agreed.

I had a government job. I was accumulating degrees. I wasn’t building a startup or walking around calling myself a founder.

But in retrospect, I understand what she was seeing.

Entrepreneurship does not always begin with incorporating a company or pitching investors.

Sometimes it is simply a way of looking at the world.

You see an opportunity.

You calculate the downside.

You try something other people might not try.

You look for ways to make limited resources work harder.

And you accept that sometimes you are going to be wrong.

That part of my personality was there long before I had a word for it.

The Finance Class in Which I Earned a C

One of the stranger lessons from my education is that some of the classes that influenced me most were not necessarily the ones in which I earned my best grades.

I took finance and earned a C.

Yet I absorbed enough from that class—and particularly from my professor—to begin thinking differently about markets, risk, leverage and volatility.

I have come to believe that sometimes the subjects in which we struggle most are precisely the subjects in which we have the most room to grow.

A high grade can confirm what you already understand.

A poor grade can tell you where the frontier is.

For me, finance became one of those frontiers.

At one point, I made what I now recognize was an extraordinarily aggressive financial decision. After tuition was paid, I had student-loan proceeds intended to cover living expenses. Rather than simply spending all of those funds on consumption, I began trading instruments tied to the VIX—the market’s volatility index—using what I had learned about financial markets.

It was risky.

I would not present it as a blueprint for anyone else.

But it worked for me.

And it became one of the pivotal financial episodes of my early adulthood.

Earlier that same year, I had already managed to purchase a legitimate one-bedroom apartment in a doorman building in Murray Hill in Manhattan.

Then I did something that, even looking back, seems improbable.

I purchased my first investment property for approximately $130,000.

In cash.

For someone building his career in government rather than medicine, law or Wall Street, that was an important moment.

It was evidence that there might be more than one path to the financial life I was trying to construct.

And yet the irony is hard to miss.

The finance class that helped give me some of the intellectual tools to do it was a class in which I had received a C.

That experience permanently changed the way I think about grades.

Education matters enormously.

Grades matter somewhat.

But what ultimately matters is what you retain, what you apply and what you do with what you learned.

The Accidental Lesson That Led Me Into Real Estate

My interest in real estate had actually begun even earlier, and in a much less dramatic way:

I needed somewhere to live for the summer.

While I was in Albany working for the Legislature, a friend whom I had attended both high school and college with introduced me to his landlord.

Without that introduction, I might not have had a place to stay that summer.

More importantly, I might never have gotten an inside look at what being a landlord actually entailed.

Until then, real-estate ownership was mostly an abstraction to me.

Suddenly, I could see the mechanics.

Someone owned this property.

Someone had bought it, financed it, maintained it and rented it.

The rent I paid was part of an operating business.

That realization stayed with me.

Sometimes the experiences that change the trajectory of your life don’t announce themselves when they happen.

My friend never went on to pursue what most people would consider conventional financial success. Instead, he followed his father’s path working with horses—something he genuinely loves.

And as I’ve gotten older, I have come to appreciate that he may have succeeded in an equally important way.

He built a life around something he loves.

Money is one measurement of success.

It is not the only one.

I remain grateful to him because a seemingly ordinary introduction helped change the direction of my financial life.

Another friend—also someone I knew from both high school and college—would play an even more direct role.

We bought my first two investment properties together.

Then we kept going.

Properties three through ten followed.

Real estate eventually became a substantial part of my financial life.

But I would caution anyone against confusing owning rental properties with passive income.

There was very little passive about it.

There were mortgages, contractors, tenants, vacancies, insurance policies, property taxes, assessments, repairs and renovations.

There were good tenants and bad ones.

There were deals that worked beautifully and others that looked considerably better on a spreadsheet than they felt while living through them.

Over the years, my holdings expanded across New York and Florida.

Real estate taught me things that no MBA course ever could.

It taught me to understand cash flow.

It taught me to negotiate.

It taught me the danger of leverage.

It taught me how expensive deferred maintenance can become.

It taught me that every asset comes with obligations.

It also taught me that wealth is often built much less dramatically than people imagine:

One mortgage payment.

One renovation.

One rent check.

One decision at a time.

Meanwhile, I Became a Career Civil Servant

While all of this was happening, I was building another career simultaneously.

I entered New York City government in May 2004 at 23 years old.

Today, more than 22 years later, I serve as Director of IT Procurement and Budget for the New York City Department of Correction’s Information Technology Division.

My job is difficult to explain at a cocktail party.

Essentially, I work at the intersection between what technology professionals say an agency needs and the complicated financial, procurement and regulatory machinery through which New York City government must actually acquire it.

That can involve telecommunications, software, network infrastructure, cybersecurity, professional services, maintenance, hardware and large capital projects.

A technology group can identify the perfect technical solution, but government cannot simply pull out a credit card and buy it.

Someone has to determine the appropriate procurement vehicle.

Someone has to establish funding.

Someone has to evaluate whether the price is fair and reasonable.

Someone has to translate technical requirements into scopes, contracts, purchase orders and capital requests.

Someone has to answer the questions of oversight agencies.

Someone has to think about audits before an auditor ever arrives.

That is the world in which I have built my career.

In a typical year, my operation deals with hundreds of procurement actions and approximately 20 contracts. I have been responsible for an IT operating portfolio exceeding $20 million and work associated with a long-term capital program measured in the hundreds of millions.

Those figures are significant not because they sound impressive, but because it is public money.

I have always felt an obligation to approach taxpayer dollars with the same skepticism I would apply to my own.

Why does this cost this much?

Is there another vendor?

What did we pay last time?

What is the discount?

Can we negotiate?

Do we actually need it?

What happens if we don’t buy it?

That mindset has saved the City money, but it has also shaped the way I think outside of government.

Procurement, investing and real estate all reward many of the same habits:

Question assumptions.

Understand the numbers.

Negotiate.

Document your decisions.

What Public Service Gave Me

It would also be misleading to tell my story without acknowledging how much my public-service career itself made possible.

Government employment gave me stability.

It gave me health coverage.

It gave me a pension structure.

It gave me predictable income while I was accepting risks elsewhere.

And, critically, it gave me access to the Public Service Loan Forgiveness program.

Over the course of all those degrees, I accumulated an enormous student-loan balance.

Eventually, approximately $262,000 of my remaining student-loan debt was forgiven through Public Service Loan Forgiveness after I satisfied the program’s requirements.

There is an interesting symmetry in that.

Education helped me become a more capable public servant.

Public service, in turn, ultimately helped resolve the debt I had accumulated pursuing that education.

That is one reason I resist simplistic descriptions of government employment as either an easy path or an economically inferior one.

Compensation is more complicated than salary.

A public-sector career is a package.

Salary matters.

So does a pension.

So does health insurance.

So does job stability.

So do loan-forgiveness programs when applicable.

So does the ability to plan over decades.

Those benefits created a foundation from which I could take risks in other areas of my life.

A Different Kind of Hustle

There were years in which, from the outside, my life probably looked unnecessarily complicated.

I was working in City government.

Going to school.

Trading and investing.

Managing properties.

Looking for investments.

Handling renovations.

Raising a family.

Saving for retirement.

Thinking about the next opportunity.

But there was a purpose behind it.

I remembered the standard of living my father had created for me.

I wanted to be able to provide that same security—or better—for my own family someday.

My father’s path was through dentistry.

Mine was through public service, education, investing and entrepreneurship.

His earning power came principally from his profession.

Mine developed through several streams working together.

I never became an endodontist.

I didn’t need to.

I found my own route.

And thankfully, I reached the goal I had set for myself.

Returning to Roslyn Heights

There is a particular satisfaction in eventually bringing your own family back to the place where you grew up.

I am now married with two young children, Dylan and Brooke, and we live in the same school district from which I graduated.

I once sat in those classrooms.

Now my children are growing up there.

That experience has changed the way I think about success.

When I was younger, success was easy to measure.

Get the degree.

Get the promotion.

Increase the salary.

Buy another property.

Grow the retirement account.

Those things still matter.

But being a husband and father changes the scoreboard.

Now success is also having enough flexibility to be present for your children.

It is creating stability.

It is giving your family experiences.

It is being able to help a parent as she gets older.

It is knowing that an unexpected expense is inconvenient rather than catastrophic.

And eventually, I hope, it will mean having the financial independence to choose work because I find it meaningful rather than because I require the paycheck.

Four Generations of Public Service

When I think about my career now, I sometimes see it as part of a much longer family story.

My maternal grandparents worked at City College.

My paternal grandmother worked for the Board of Education.

My mother worked in New York State corrections, first at Arthur Kill and later at Fishkill.

And I have spent more than two decades working for the City of New York.

Different agencies.

Different generations.

Different jobs.

But the same broad tradition.

Public employment has helped generations of families like mine build stable middle- and upper-middle-class lives.

That is something worth remembering in an era when government workers are sometimes reduced to caricatures.

A public-sector career can provide much more than a paycheck.

It can provide health insurance.

A pension.

Professional development.

Educational opportunities.

Stability.

And, if you use those advantages wisely, a foundation from which to build other things.

That last point has been particularly important in my life.

The stability of my government career gave me the confidence to accept risk elsewhere.

I could buy property.

I could invest.

I could continue my education.

I could think long term.

In that sense, my City career and my entrepreneurial activities were never opposing forces.

One made the other easier.

There Is More Than One Way to Make It

At 45, I have also become much less certain that financial achievement is the only meaningful definition of success.

I think again about the friend who introduced me to his landlord all those years ago.

By the conventional financial scoreboard, our lives went in very different directions.

But he followed his father into working with horses because that is what he loves.

There is something admirable about that.

Another friend became my partner in the first investments that fundamentally changed my financial trajectory.

Someone I once dated saw an entrepreneurial instinct in me before I recognized it myself.

A finance professor taught me ideas I ended up applying far beyond the grade I received in his class.

My father created one model for success.

My mother and grandparents showed me another through public service.

My friends unexpectedly helped create others.

The older I get, the more I believe the mistake is assuming there is only one road.

For one person, “making it” may mean becoming a doctor.

For another, becoming financially independent.

For another, owning a business.

For someone else, it may simply mean spending your working life around horses because that is where you are happiest.

The objective is not to duplicate someone else’s life.

It is to build one that works for you.

What Comes Next

I am now at an interesting midpoint.

I have been in City service for more than 22 years. Under my pension plan, I can retire at 57. If I stay until then, I will have accumulated roughly 36 years of public service.

Twelve years once would have sounded like an eternity.

At 45, it doesn’t.

I have begun thinking about what the second act might look like.

Higher education interests me.

After spending decades practicing public administration, procurement, budgeting, management and technology—and after earning a doctorate—I can envision eventually combining teaching with academic administration.

There is something appealing about completing that circle.

I spent much of my twenties sitting in classrooms at night after working all day.

Maybe I will spend part of my sixties standing in front of one.

And I would want to teach students not merely what textbooks say about government, but what actually happens when theory collides with budgets, vendors, regulations, deadlines, politics and operational necessity.

That is where public administration actually lives.

I would also want students to understand something my own experience taught me:

The grade is not necessarily the lesson.

The class in which you struggle may ultimately teach you more than the class in which you earn an A.

The career you abandon may create room for a better one.

The person who makes a casual introduction may alter your financial future.

And the stable government job that looks unexciting to someone at 23 may turn out to be one of the foundations upon which an extraordinary number of other opportunities can be built.

The Lesson I Would Give a Young Public Servant

If I could say one thing to someone beginning a government career today, it would be this:

Do not confuse stability with complacency.

Use stability.

Learn everything you can.

Continue your education.

Take the employer match.

Understand your pension.

Fund your retirement accounts.

Understand every benefit your public-service career makes available to you.

Build skills that have value outside your current job.

Buy assets if and when you can responsibly afford them.

Take calculated risks—but understand that a risk that works out is still a risk.

Develop more than one source of opportunity.

And pay attention to the people you meet along the way.

The person who alters your life may not be a CEO, politician or professor.

He may simply be your friend’s landlord.

My own life is proof of that.

A kid born in the Bronx moved through New City, Forest Hills and Roslyn Heights.

He finished college in three years largely by immersing himself in legislative internships.

He met presidents, governors, legislators and future leaders of New York.

He went to law school and quit after a semester.

He entered City government at 23.

He kept going to school.

He earned a C in finance and nevertheless used lessons from that class in ways that helped change his financial trajectory.

He bought a Manhattan apartment.

He managed to purchase his first investment property for $130,000 in cash.

He bought rental properties with friends.

He ultimately accumulated four graduate degrees, including a doctorate.

He accumulated substantial student debt along the way and later had approximately $262,000 forgiven through the Public Service Loan Forgiveness program.

He built a career managing public money and technology procurement.

He became a husband and father.

And, by a route almost completely different from his father’s, he eventually created the kind of life he had hoped one day to provide for his own family.

I am proud of that.

But at 45, I am also increasingly aware that accumulating things—degrees, properties, titles, savings—isn’t the ultimate objective.

The purpose of building options is eventually to use them.

For most of my adult life, I have concentrated on building.

The next chapter is going to be about deciding what all of that building was for.