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As I was setting out on the project in Troy, I found that there are a number of programs and incentives that make it a no‑brainer to decarbonizing the building’s heating systems. In our case, using air‑source heat pumps (two‑way ACs) would allow the unlock of tens of thousands of dollars of incentives. So, to get a sense of what this part of the project cost, I followed the traditional path of seeking out a professional to help me price it out. Since we are doing 12 apartments and a store, I knew this bill would be anything but small. The two installers that I spoke with specified a traditional mini‑split system with a compressor unit somewhere outside and one or more indoor units to distribute the heat/cold. After good and insightful conversation, the bids came in at $160K and $155K, both sounded very reasonable. What I did not know at the time was the alternative I had.

Installing compressors on rooftops and hanging off the side of a building requires both skilled installers and a good deal of electrical work to supply the units. But in the end, as an owner or tenant, I don’t care about any of that. All I want is reliable and inexpensive heating and cooling. So, when I came across a new class of product, the self‑installable window heat pumps, in a saddle form factor, I was immediately curious. These units do not require a professional installation. You hang the unit out the window, plug it in, and you are off to the races. Unlike window AC units, the window is still usable. Once I thought through this new form factor and its positive implications from an operating perspective, the next question was cost. In most situations ease of use and convenience drive a premium into a product’s price. But what about these?

I first saw these units at the New York Build Expo and was instantly impressed. At that time, I was not yet thinking we would need them for the Troy project, so I never asked about the cost. In one of those strange coincidences that are hard to explain, I saw a post on my LinkedIn feed from Gradient Comfort a couple of weeks ago from someone in my network. It was at that point that I realized that I knew the company CEO, small world. My curiosity was piqued about the price. So, I reached out to my local sales rep to get a price.

In my mind, I was anchored by the prices of the other bids. So, I was almost shocked when the price came in at $70K. Even better, with the decarbonization credits handled by the vendor, the price drops to $40K. At first, I was very doubtful, it seemed too good to be true. I could save over $100K and still install the newest heating and cooling technology? I dug into the product’s specifications, discussed how this product will be accepted by the local building code compliance, and looked into other field deployments of this tech. It didn’t take long. After a couple of hours, I knew this was both legit and disruptive.

I realized that when I first saw this technology it was presented as a solution to decarbonize large apartment buildings with old oil or gas boilers. In my mind I didn’t make the connection until months after I first saw this technology. The funny thing is, most of the breakthroughs that actually move your life or your business forward don’t come from grinding harder inside the same narrow lane. They come from bumping into something new, letting it bother you in a productive way, and then connecting it to something you already know.

The real engine of value creation is a mind that stays porous, curious, and willing to explore ideas that don’t have an obvious payoff yet. Creative thinking isn’t about being whimsical, it’s about building a bigger internal library so you can recognize patterns other people miss. The more inputs you expose yourself to, the more raw material you have for insight. And when you start stitching those inputs together, a detail from a building, a behavior from a landlord, a principle from a completely different domain, you unlock leverage that looks like intuition from the outside but is really just accumulated dots finally connecting.

At the end of the day, this is the same discipline great product managers use: ignore the noise, ignore the feature lists, ignore the shiny distractions, and anchor everything to the outcome the user actually cares about. In this case, it’s simple, reliable, and inexpensive heat and AC. That’s the “job to be done.” And once you frame it that way, the rest of the analysis snaps into place. You stop obsessing over form factors and marketing claims and start evaluating which solution consistently delivers the outcome with the least friction, the lowest lifetime cost, and the fewest surprises. Creative, curious, exploratory thinking isn’t abstract; it’s a practical tool for uncovering better paths to the same goal. When you stay focused on the outcome, you see value where others see novelty, and you avoid paying a premium for complexity that doesn’t move the needle.

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By now, I am sure you have heard the term “landlord special” more than a few times to describe how some owners treat their property. If not, “landlord special” is the home‑improvement equivalent of putting lipstick on a raccoon: a fast, cheap, suspiciously shiny “fix” that solves nothing but looks acceptable from six feet away if you squint and the lights are off. Like all things, landlords come on a spectrum: from those who deserve to go to jail to those making sure loving families have a place to raise a family. As someone who has seen this business from the inside for almost 30 years, I have come to the conclusion that there are four basic categories of landlord quality.

Over the years, I’ve learned that the real story of a building isn’t in the listing photos, it’s in the tiny decisions an owner makes when no one is watching. The trim that doesn’t quite meet the wall, the outlet that was “good enough,” the paint job that stops half an inch before the corner. These details reveal the mindset behind the property, and once you start noticing them, you can’t unsee them. They’re the breadcrumbs that tell you exactly what kind of owner you’re dealing with.

The Operator - this owner understands that they are investing in a property, a town, and its people. Continuously maintaining and upgrading properties to drive the highest quality customers and premium top-of-the-market rents. This does not mean luxury it means that even if you own a trailer park, you target the best trailer park residents in your area. This operator knows that quality tenants will dramatically reduce operating headaches and ensure more consistent cash flows. Most importantly when the time will come to sell the property it will bring a premium for it’s exceptional level of maintenance and top-of-market rents.

The Investor - this type of landlord fails to understand that they are providing a service to customers, they think they own some kind of bond that pays a dividend with no attention work or reinvestment. While they understand how to maintain the value of the asset, fix and maintain the property, they never really invest to dramatically improve their property. These landlords create flip opportunities for future buyers. They refuse to make upgrades that will drive value to the next owner since some cannot be captured by raising rents. In the end, failing to combat the aging of a property will slowly erode value and lead to sales at the bottom of the appraisal comps range.

The Honest Slumlord - this owner will only act when they are forced to by the authorities. They see tenants as walking ATMs that “owe” them money every month. If you walk into an apartment showing in a unit that had clearly not been cleaned, see messes behind the kitchen stove, and everything painted over with way too many layers of paint these are the primary clues. The best thing about this type of landlord is that their lack of shame makes it so much easier to identify them and see through their bullshit. That said, many of these lanlords provide low cost alternatives, so long as you are willing to struggle to get everty fix done.

The Lying Slumlord - this type of landlord is a little hard to detect. This type of landlord cleans and repairs place before renting them out, giving you the impression of a professional operator. In reality, they will cover over dangerous defect and hide everything. Some of these landlords have tens or hundreds of violations that had been left unaddressed for years. The difference is that they put on a good show when you are renting your place, but if you find the building is infested with roaches or mice, get ready for dealing with the smallest and dirties roommates that you can never evict.

There was an NYC landlord whose buildings went months without heat, hallways dark because the wiring was never repaired, front doors that wouldn’t lock, and ceilings that sagged from leaks no one bothered to trace. HPD issued violations; he shrugged. Judges issued repair orders; he ignored them. Eventually the city stepped in, made the emergency fixes themselves, and sent him the bill, which he also ignored. By the time the marshal came knocking, it wasn’t about the broken boilers or the mold‑choked bathrooms anymore. It was about contempt the simple truth that you can only defy the law for so long before the law comes looking for you. And so he spent his days in a Rikers jumpsuit, a reminder that in housing, neglect isn’t just bad business; it can become a jail‑worthy choice.

It does not matter if you are a potential owner or potential tenant, understanding who is on the other side of the deal from you is crtical to understand the consequences of their behavior, there is a lot to read into from what is shown and what is hidden. As a potential tenant, they key is to understand how the relatioship with your landlord is likely to take shape. Sometimes, accepting a less than ideal landlord, may be a good tradeoff if the rent is cheap enough. The hardest part is assessing how much bullshit you will have to deal with before you get yourself tied up in a transaction that is really really hard to get out of. As a potetial buyer, you need to have your head on a swivle when it comes to identifying places when negtive value can be hidden: painting over black mold, buried oil tanks, foundation damage, and many others.

Once you start reading a building the way an operator does, you realize you are not just inspecting materials and systems. You are studying the person who made the decisions behind them. Every shortcut, every overpainted detail, every oddly timed repair is a clue about how this counterparty behaves when pressure shows up. That is why I treat the early phase of any deal as a quiet diagnostic. You gather signals, map their habits, and only then bring in the lens of game theory to understand how their incentives shape the moves they are likely to make. Once you see the pattern, you can predict where the friction will come from and design a strategy that increases the probability of extracting real value before their operating style becomes your problem.

When it come to entering into any transaction where you are the customer, you can use general patterns and huristics to analyze the product more deeply. As a potential tenant you need to evaluate the physical space as well as the landlord’s service, you are paying for both. As a buyer, you need to know as much as possible about the property where much of what is most important to know is behind the walls. And once you learn to read those signals, you start to realize you are not just diagnosing a building, you are forecasting the behavior of the person who shaped it. Every landlord type leaves a signature pattern, and once you recognize it, you can impute the problems that are almost guaranteed to surface later. The Operator’s building tells you the surprises will be minimal and the numbers will hold. The Investor’s building tells you the bones are fine but the deferred upgrades will land in your lap. The Speculator’s building tells you the real work hasn’t even started. And the Slumlord’s building tells you to run the other way or price the deal like you are buying a distressed asset at auction. Pattern recognition becomes a form of underwriting. You are not guessing anymore. You are assigning probabilities, estimating the true cost of their habits, and baking that into your offer before the first negotiation even begins. That is how you protect your downside and capture the upside the previous owner never saw.

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Over the last year and a half, the forces driving adoption of AI have been irresistible. Product enhancements enabling active retrieval of online information, composition, and its presentation have dramatically increased the usefulness of these tools for property developers. A second area of enhancements has also made a profound difference in the usefulness of these tools, namely the ability to access local archives of information. This functionality means that the individual context of each deal and the uniqueness of its structure and location can all be considered when working to solve the hard problems. As a developer working on an individual property in an individual town, most of the critical project context will come from the work done by architects, engineers, and lawyers. In other words, your contracts and your designs.

In the last few weeks, I have come to realize that the improvements in these AI products are really beginning to add value to the work I do. There has been a great deal of chatter in real estate media and online communities about the use of AI to relieve the drudgery of repetitive tasks, specifically tenant communications and administrative tasks. Since I do not manage properties on behalf of others, these are not tasks I am trying to avoid. I want to know my tenants. I want to know what is going on with my building. So for me, adding a layer that dissociates me from my business seems unwise. I keep my properties at the highest level of maintenance and work hard to select reliable people to occupy my units. If things don’t break and neighbors act decent, you get very few calls, emails, or texts from tenants. For those times when tenants do reach out, a simple appointment with an appliance repair vendor, exterminator, or plumber will be enough to resolve the issue. You don’t need to triage problems if you invest to prevent a majority of them in the first place. That is why, for me, the value in AI tools is more closely linked to property development strategy and financing than tenant request handling and scheduling.

As someone that started their career in municipal government and later worked in market research and business strategy, I think I am exceptionally good at researching government and policy‑related stuff. And that is exactly where I found AI tools to create the most leverage for me. Between the state and federal historic restoration incentives, state and federal energy efficiency incentives, state and local industrial development initiatives, federal economic development incentives, and public/private initiatives, there are so many opportunities for benefits to the project that it is almost too hard to wrap your mind around if you have not been in commercial property development. While most of this is somewhat new to me, my real estate and municipal government experience gives me just enough knowledge to make me dangerous. Why? Because it used to be required that you were smart enough to ask the right questions AND find the right answers. With AI, you only need to be half as good, you only need to know how to ask the right questions. So, I asked a whole lot of questions about any type of program I could find, and used AI to find some more.

We knew our current project in Troy was in the historic district before we even owned it. What we did not know was if the building was qualified, the magnitude of incentives, and the cost of compliance. Our building, a brick Italianate from the 1830s with a 1900s makeover in the downtown Troy historic district, opened the door to the Federal Historic Rehabilitation Tax Credit. The program offers a 20% credit on qualified rehab costs for income‑producing buildings listed on (or eligible for) the National Register or located in a historic district. Since 80 4th Street is a contributing structure in Troy’s district and our renovation is substantial, we initially qualified. New York State stacks another credit on top, up to 30% for small projects. But certified historic restoration comes with a steep premium: SHPO‑approved materials, preservation architects, historically accurate windows, and NPS‑compliant methods can push a $1.5 million project toward $3 million. Without large capital gains to offset, the economics flipped. The credits were powerful, but the cost structure only made sense for investors playing a different tax game.

We also discovered that the building was in a Federal Opportunity Zone, which was renewed shortly after we acquired the property. OZ rules allow investors to roll capital gains into a project, defer taxes, and pay no capital gains tax on appreciation after a 10‑year hold. For someone investing their capital gains, that could mean six‑figure tax savings if the property appreciates. To qualify, we structured the project as a Qualified Opportunity Fund and confirmed our renovation easily met the “substantial improvement” test. OZ status didn’t give us free money, but it unlocked cheaper equity, an advantage we wouldn’t have spotted without the help of AI.

Energy incentive questions led us to find another layer of programs. The federal 179D deduction could save us several thousand dollars for energy‑efficient upgrades, while the 45L credit offers $2,500–$5,000 per apartment for high‑performance units, potentially $30,000–$60,000 across our 12 planned units. NYSERDA programs and utility rebates for heat pumps, insulation, and solar could add tens of thousands more. AI helped us identify the exact efficiency targets, certifications, and paperwork required, turning what used to be a maze of obscure programs into a clear checklist.

On the local side, the Troy Industrial Development Authority became a major win. After reviewing past deals and submitting an application, we are going to pursue a 10‑year PILOT agreement that will save on property taxes, provide a sales‑tax exemption on materials for the building project, and a $10,000 mortgage‑recording‑tax waiver. These savings directly improve project viability and allow us to reinvest in better finishes and systems. AI helped us parse through the program guidelines with ease to understand our qualification and potential benefit.

Leveraging AI made it possible for us to discover incentive programs we did not know existed, helped us avoid wasting time on programs we would not be eligible for, and helped us to quickly quantify and prioritize all the others. When you start working with these tools, the first shift is learning to treat AI like a junior analyst with infinite stamina. It won’t guess what you want, and it won’t magically intuit the structure of a problem. But if you give it clear constraints, defined outputs, and a well‑framed question, it will return leverage that compounds. The second shift is realizing that none of this works without a local archive. Your contracts, drawings, pro formas, emails, and municipal correspondence are the real intellectual capital of a deal, and the moment you centralize them, cleanly, consistently, and in a way that’s queryable, you unlock a level of clarity that simply didn’t exist before. If the AI knows enough about your project it can tell you if you will meet the qualification criteria. From there, the discipline becomes using AI as a second brain. Run your numbers manually, then run them again through the model. When the two disagree, don’t panic; investigate. The gap is where risk hides, and closing that gap is where judgment sharpens. AI is often right, but sometimes wrong. Don’t trust, just verify.

As you move deeper into a project, you’ll notice that AI is most valuable in the fog‑of‑war phase, the stretch where you’re still decoding the architect’s drawing, comparing contractor bids, or trying to understand the real constraints buried inside a code section. The faster you collapse uncertainty, the faster you can move, and these tools are built for exactly that kind of compression. As a decision maker, I can now gather far more data and throw my research tentacles much farther than Google’s basic search engine ever let me do. Simply put, I can only take advantage of programs and incentives if I know they exist. If you can scale up your ability to gather and synthesize information every decision you make should yield better outcomes.

In the end, the developers who thrive in this new era won’t be the ones who memorize the most rules or grind the longest hours. They’ll be the ones who learn to direct intelligence, human and AI, with precision. AI doesn’t replace judgment; it clears the noise that used to cloud it. When you pair your lived experience with a tool that can retrieve, summarize, and structure information at scale, you stop operating as a single mind and start operating as a system. That is the real leverage. And once you feel it, you won’t go back.

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Over the last three months, I’ve been working with multiple general contractors to find a partner who can bring this project to completion. The construction industry is full of people who assume every client is out to cheat them. That mindset makes it hard to build trust. So I created a process that would give each vendor enough time and space to reveal who they really are. The goal was simple. Separate serious operators from everyone else.

The first principle of this strategy is honesty. The bidding process is a competition designed to uncover the best vendor. After several disappointing experiences with contractors who overpromised and underdelivered, I decided to run a more rigorous selection process. This is a multi‑million‑dollar contract. I wasn’t going to sign with a company I had never worked with. So I acted as my own general contractor for the early phases and used small, contained projects as pilots.

Start with demolition or a small construction scope. Once you’ve completed enough of that pilot, you will know whether this vendor is someone you want to trust with a multi‑year project. It is more conservative and more work than the industry norm, but it dramatically reduces the risk of getting stuck with the wrong contractor. A short multi‑week pilot tells you more about a vendor than any glossy proposal ever will.

For our pilots, we worked with Company A to reframe and build the new roof. We targeted the carriage house demolition as the pilot for another GC. The second candidate, Company B, initially looked like a strong partner. They had been operating in town for over 30 years, had offices across the street from the job site, and owned and renovated their own building. Their bid for the demolition came in about 15 percent above another vendor. Because I believe in transparency, I told Company B where their bid landed and who beat them. I wanted to understand how they created value to justify the higher price.

When I called to review the scope, I mentioned that a competing bid had come in lower and wanted to understand the difference. I made it clear that price and value are not the same thing. I even gave an example. I am working with a boutique architecture firm that is far from the cheapest, but they deliver value that justifies the premium. Instead of engaging in that conversation, the contractor on the other end of the line became irritated and drifted into ad hominem, painting me as “too cheap” to hire good vendors. Not a great look when you are trying to win a multi‑million‑dollar contract.

Then the truth slipped out. When I named the competitor who underbid him, the owner of Company B snapped back with “That young guy? I can’t underbid him.” What he didn’t understand was that I wasn’t negotiating price. Not yet. I wanted him to show me what I would get by paying more. Instead, he got angry and blew the deal for himself. He didn’t even take the time to explain his service. It became obvious that there would be no value conversation and no bid on the larger project. Company B’s owner gave up before the fight even started.

A couple of weeks later, I got a call from the other co‑owner of Company B asking about the status of the demolition bid. At this point, I was confused and irritated. Was the left hand talking to the right hand at all? I explained that I had been hoping to get a larger bid from the company, but the owner had made it clear there was no interest in discussing the scope in any meaningful way.

A lack of transparency around pricing is a red flag. It is one thing to pay a premium for something you understand. It is another to pay a premium when you have no idea what you are buying. These were my three key takeaways that disqualified this contractor:

• The immediate reaction to the competitor’s name and the ad hominem attack revealed a track record of losing bids to that competitor.

• Refusing a conversation around value creation is a strong indicator that there is no real value difference.

• A lack of skin in the game. When a vendor constantly says they “don’t need the business,” they are signaling indifference. In a long project, that vendor will cut and run the moment they face real risk.

While all of this was happening, I was also speaking with another GC, Company C. For the first two weeks of the bid process, I sent weekly follow‑up emails to each vendor. Company C replied that they were working on it. After a conversation with the architect in week three, it became clear that Company C had not reviewed the latest drawings. I gave them the benefit of the doubt and chalked it up to human error. Otherwise, that signal alone would have been immediately disqualifying. I sent a three‑way email to Company C and the architect to close the loop and get the process moving.

Company C came recommended by a local plumber I used on a small job early in the project. We had gone back and forth a few times about coordinating drawings and understanding the scope. Unfortunately, when the bid finally came in, it didn’t cover what I had requested. Instead of giving me a GC‑level quote to bring the project to completion, the bid assumed I would contract all the individual trades myself. Worse, it didn’t include enough detail to confirm that it covered the architectural scope, and the architect reported zero follow‑up or questions during the bid process.

Lying or misdirection around scope and pricing is the reddest flag there is. As an operator, accurate information is the blood your business runs on. These were my two key takeaways that disqualified this contractor:

• Vendors always put on their best face when closing a new deal. If this is Company C at their best, then when things get difficult, they will make sure you bear the losses.

• Refusing to listen to the client. I asked for a specific bid on a specific scope. That is not what I got.

The lesson in all of this is simple. Pilot projects reveal the truth. They show you how a vendor communicates, how they handle pressure, how they respond to competition, and whether they can follow instructions. In construction, the wrong partner can cost you years. The right partner earns your trust one small project at a time.

If you want to implement a similar strategy on your own project, you do not need a massive budget or a decade of experience. You need a clear process and the discipline to stick to it. Here is a simple step by step approach you can use.

1. Define the end state and the stakes
   Before speaking to any contractor, write down what “done” means. Include timeline, budget range, and expected finish level. Be honest about the stakes. A primary home, long‑term hold, or flip each demand different levels of caution. This clarity anchors every vendor conversation.

2. Break the project into pilot‑friendly chunks
   Identify small, self‑contained scopes like demolition, framing, or pouring a slab. Choose work big enough to reveal how a vendor operates but small enough to walk away from if needed. The goal isn’t saving money. It’s buying information.

3. Build a short list of candidates
   Get referrals from people who’ve built something similar. Architects, engineers, and trusted trades are reliable sources. Ignore glossy websites. Aim for three to five candidates so you get contrast without drowning in noise.

4. Set expectations in writing
   When requesting bids, send a clear written scope for the pilot and note that you’re also evaluating partners for the full project. Specify what you want in the bid: line items, assumptions, exclusions, and a rough schedule. You’re testing their ability to follow instructions and communicate.

5. Watch how they handle the bid process
   The bid itself is your first pilot. Track how quickly they respond, whether they ask smart questions, and if they actually read the drawings. Disorganized or evasive bidders won’t magically improve once paid. Treat every misstep as data.

6. Run the pilot like a real project
   Once awarded, manage the pilot with the same discipline as the full job. Use written change orders, track schedule, and hold brief site meetings. You’re not just buying a roof or a demolition. You’re watching how they plan, adapt, and respect your time and money.

7. Evaluate behavior, not just results
   Don’t just ask whether they finished. Ask how they finished. Did they communicate changes, own mistakes, and coordinate with others. A contractor who delivers work while burning relationships is a long‑term liability.

8. Have the value conversation early
   If a vendor is more expensive, ask what you get for the premium. Better supervision, faster schedule, stronger subs, or a real warranty can justify cost. If they get defensive or hostile, that’s your answer. Good operators explain value without attacking anyone.

9. Look for red flags and walk away quickly
   Treat certain behaviors as automatic disqualifiers: lying about scope or pricing, refusing value discussions, blaming everyone else, or bragging they “don’t need the work.” If this is how they act while trying to win your business, imagine them mid‑project.

10. Promote the right vendor from pilot to partner
    If a vendor communicates well, delivers what they promise, and handles the pilot professionally, then invite them to bid the full project. At that point, you’re choosing based on lived experience, not a number on a page. That’s worth far more than a small price difference.

This approach is slower and more work than picking the lowest bid and hoping for the best. It forces you to think like an operator, not just a customer. But the cost of a bad partner on a multi year construction project is measured in years, not just dollars. A disciplined pilot strategy lets you pay a small price up front to avoid a very large one later.

In the end, you are not just building a building. You are building a team. Pilot projects are how you find out who deserves to be on it.

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So, I found myself again at the crossroads of a critical decision. I couldn’t execute my original strategy without a partner, so I needed a new strategy. Given that our development projects are built around the unique attributes of each individual physical property, to execute this strategy again I would need to put in another six months of searching. Like all of my real estate career, I was actually working full‑time in a corporate environment. Since I had just landed a new gig, I decided to pivot to a new strategy that did not require as much searching, the cap rate vs. cost of debt arbitrage.

The cap rate vs. cost of debt arbitrage is fairly simple: if you can borrow all the money to buy a property at 4% and find a property with a 7% cap rate, you get 3% of the value of the property as annual cash flow. The twist in this scenario is that you are not borrowing the money for the new property by taking a mortgage on the new property; you borrow it all from the equity of another property. That’s exactly what we did. We were ready to be an all‑cash buyer at the depths of the pandemic.

Finding a 7% cap rate property anywhere near New York City is not easy. Investing in expensive neighborhoods where developers are looking to build million‑dollar condos means there is lots of speculative premium in the price. Those who invest in working‑class neighborhoods are operating properties for cash flow, not speculating on the next up‑and‑coming neighborhood. In 2021, that meant looking outside of NYC but close by. This strategy began to come together as we looked through hundreds of real estate listings within about a 250‑mile radius, from nearby Hoboken and Yonkers to the far‑away Lehigh Valley and Syracuse.

Using platforms like Zillow allows you to make a giant circle on a map, filter for multi‑family (since that’s my strategy), and sort the results by price (low to high). I would call this the “thrifting” strategy: look everywhere you would consider buying and see what the cheap stuff is. Why? Because we are not looking specifically for cheap properties; we are looking for inexpensive neighborhoods, there’s a big difference. We’re looking for places we may have never heard of or considered. In my case, I found Nodine Hill in Yonkers, NY. By 2021, I had lived and invested in Brooklyn for over 20 years, and I had never once even considered looking in Yonkers. In my mind, Yonkers was just a word I saw written in white letters on the green background of highway signs.

Once I started to find listings that met our investment criteria, we had another challenge: find a property where the cap rate is not a money pit of a building. You can always find “cheap” buildings; if the building is too rundown, it’s cheap now and expensive later. Nodine Hill is one of Yonkers’ oldest hilltop neighborhoods. Its name comes from the Nodine family, the landowners in the 1800s. As Yonkers industrialized along the Saw Mill River and Hudson waterfronts, workers moved uphill into neighborhoods like Nodine Hill, creating a dense, walkable residential district, just like my beloved home of Brooklyn.

Living in Nodine Hill gives you quick access to local highways, Yonkers public transit, a quick commute into NYC via Metro‑North, and rents at about 50% of NYC. Even better, Nodine Hill is right next to Yonkers’ downtown district for entertainment, nightlife, and culture. Nodine Hill fit into our strategic thesis of investing in places with deep community infrastructure: parks, public transit, schools, hospitals, and culture. Unfortunately, most of the buildings are old and in poor condition, our second strategic thesis. Poorly maintained neighborhood housing stock brings down prices. Some investors only care about the rent roll, ignoring the long‑term costs of maintenance. So, the best‑maintained and most expensive buildings don’t realize a market premium for their efforts. In reality, it is these properties that will be the cheapest buildings to own in the long term. The challenge: finding them.

In a place like Nodine Hill, buildings with wildly different levels of disrepair, which could clearly be seen by a seasoned investor in the sale listing photos, were being offered at approximately the same price. Why? I don’t know. What I did know is that it was good for buyers, and at that moment, I was a buyer. I had stumbled across a listing with a very interesting history and promising interior photos. This property was listed for $899K in 2018 and had been on the market for nearly three years. The interior photos also looked like major work had been done.

The beauty of this listing was that the market had already done most of the hard part of negotiating the premium for me. Once I confirmed that this building was in outstanding condition relative to its neighbors, I knew this was a deal worth pursuing. The jump in the asking price seen between 2017 and 2018 was after the building was gut‑renovated. In reality, the building was physically much newer, but the new rents could not cover the premium in the asking price. That is precisely why this building sat on the market with three years of price reductions. This is a perfect target for an owner‑operator: great bones that you don’t have to pay for.

When you look at the price‑history chart, the opportunity jumps out immediately. This wasn’t a property rocketing upward with demand; it was a seller chasing the market down for almost three years. Listed at $899,000 in late 2018, then cut to $849,000, then dropped again to $765,000, and still unable to move. Multiple listings, multiple removals, and finally a sale at $750,000 in 2021. Sold a full $149,000 below the original ask, even as interest rates dropped by nearly 1.5%. That pattern tells you everything: buyers weren’t biting, the seller kept blinking first, and the market was quietly signaling that the price needed to come back to earth. Most people see a messy listing history and scroll past. I see a seller who’s already been softened up by the market and a deal that’s been sitting there waiting for someone who actually knows how to read these signals.

And this is exactly where an all‑cash offer becomes more than a tactic — it’s a lifeline. Remember what was happening during the worst part of the COVID epidemic. Sellers weren’t just tired; they were rattled. They had watched their listing sit through multiple price cuts, watched buyers disappear, watched the world shut down, and suddenly the idea of “holding out for the right offer” felt like a luxury from a different era. Every month the property sat was another month of uncertainty, another mortgage payment, another reminder that the market wasn’t listening to their original price. By the time I stepped in, this seller had been through three years of failed listings and a global crisis that made liquidity king. So, when I show up with a clean, all‑cash offer, I’m not negotiating against their asking price, I’m negotiating against their exhaustion. Cash‑in‑hand during COVID wasn’t just attractive; it was stabilizing. It was certainty in a moment when certainty was in short supply. And sellers in that headspace don’t haggle. They exhale. They take the deal. They want out, and cash is the fastest exit door in the building.

At the end of the day, this is why I don’t get hung up on the noise. The market had already done half the negotiating for me, the seller was worn down by years of failed listings and a pandemic that rewired everyone’s sense of risk, and the numbers made sense the moment you stripped away the emotion. We bought this building for $750,000 in 2021. Today Zillow values it at $925,000, which is a $175,000 gain on paper. The building has also produced about 3 percent free cash flow each year, which comes out to roughly $90,000 over four years. The depreciation schedule has created more than eighty‑seven thousand dollars in deductions, which translates into about twenty‑one thousand dollars in tax savings. When you add it all together, the total upside so far is roughly $286,000, and that is before any future rent growth or operational improvements.

But the truth is less glamorous than the headline number. Even with all our diligence, all our inspections, and all our modeling, we still had to replace a boiler for fifteen thousand dollars because in this business things break, surprises happen, and the spreadsheet never survives first contact with reality. That is the game. You buy right, you stay calm when something goes sideways, and you let time and competence do the heavy lifting.

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Now that we have covered the shocking cost of trading real estate, let us dig into the value. When using a bank for a mortgage, there are few closing costs that you can avoid. The big two are the real estate broker, which is 6 percent of the deal, and the mortgage broker, 1 percent of the loan amount. Nearly all the other fees, other than taxes, can be avoided by paying cash. As a side note, while you can avoid costs like title insurance by paying cash, it may be a very unwise idea. So, if you put down 20 percent and borrow 80 percent, firing both brokers will save you 6.8 percent of the cost of the property, a sizable amount. But is it a smart move?

Most first time borrowers assume a mortgage broker and a loan officer are the same thing, but they are not. A loan officer works for a single bank and can only offer that bank’s products, which is great if you already know you want to borrow from that institution or you qualify for special relationship pricing. A mortgage broker, on the other hand, acts as an independent matchmaker, shopping across multiple lenders to find the best fit for your financial profile, property type, and timeline. Brokers often have access to niche programs or lenders you would never find on your own.

As with all professionals, real estate and mortgage brokers must provide value to justify their fee. While some clients may simply be looking for someone to unload the paperwork onto, too much headache finding a mortgage, borrowers like me are looking for a savvy market operator who knows the players and the hidden pockets of value. Measuring the value of a mortgage broker is simple: we compare their fee to the mortgage rate they can get. If a mortgage broker can get you a rate that is 0.5 percent lower for a 30-year mortgage, you get 28 years of savings for the price of 2 years. Not a bad deal. Sometimes, a broker can find a bank that will lend after all your individual effort failed. In those cases, only you can do the value calculation for determining what a finder’s fee should look like.

Another interesting twist in this market is who pays the broker’s fee. Sometimes we mere mortals need help finding a good deal, and sometimes the bank has the same problem. Sometimes they need to lend more badly than you need to borrow. So, in some cases, the bank will cover the mortgage broker’s fee. Counterintuitively, there are cases where hiring a professional gets you the best deal and costs nothing more. As my mother likes to say, “If you do not ask, the answer is always no.” So, when talking to brokers about the loans they can source, always ask specifically who pays the broker fees for each loan. Transparency matters: for every loan option a broker presents, you want to know who is paying them, how much, and whether that changes the rate you are being quoted. Once you understand the incentives, you can evaluate the deal with clear eyes instead of blind trust.

A mortgage broker becomes especially valuable when your situation does not fit neatly into a bank’s underwriting box. Self-employed borrowers, investors with multiple properties, people with complex income streams, or anyone buying an unusual asset often run into rigid bank rules that shut the door before the conversation starts. Brokers know which lenders specialize in these edge cases and can surface options you would never find on your own. They are also useful when speed matters, since some of their lenders can move far faster than traditional banks. In short, the more non-standard your profile or property, the more likely a broker is the difference between finding a lender and not.

By this point I am sure you have already asked yourself if I, the author, use mortgage brokers. My answer: always. If you are just dealing with single family houses that are ready to rent and your credit is good, you probably will find little value. On the other hand, if you are buying commercial, multi family, or anything else more complicated, a broker will nearly always be worth their fees. Even better, my mortgage broker is experienced and market savvy. He does not just collect bids; he actively negotiates the rate on my behalf as well as deal terms with significant financial implications, like prepayment penalties. While you cannot negotiate with the big banks like Citi, Wells, or Morgan, many local banks know that good borrowers are competitive. If your broker is good, they will also know which banks need to place loans to make their quotas.

While brokers can unlock real value, it is worth being clear eyed about the tradeoffs. Some brokers work with a limited panel of lenders, which means the shopping they do may not be as broad as you assume. Others may have preferred lender relationships that subtly influence which options they present first. Banks can also beat brokers on certain products, especially jumbo loans or situations where you have strong deposits and qualify for relationship pricing. And because brokers sit between you and the lender, communication or underwriting timelines can vary more than if you were working directly with a bank. None of these are deal breakers, but they are worth knowing so you can ask sharper questions and avoid surprises. My mortgage broker is Sam. If you are looking for a great mortgage broker in the New York City area, reach out to him. I am sure he will find you some great financing options.

Now that you know how brokers get paid, what they actually do behind the scenes, and where their incentives line up or do not with yours, you are in a far stronger position than most first time borrowers. The action items are simple: ask every broker who pays them and how much, confirm the range of lenders they work with, compare APRs instead of headline rates, and make sure their experience matches your specific borrower profile. The more you understand the landscape, the easier it becomes to spot a great broker and avoid the ones who are not adding real value.

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The real turning point came when I realized my greatest power wasn’t climbing the ladder, it was walking away from it. That single act of rebellion sparked the transformation from employee to owner, from rule‑follower to system‑builder, from surviving the workday to shaping an entirely different world.

Let me begin by admitting that for many people, the journey through a corporate career is and was a highly fulfilling endeavor, but that is definitely not true for everyone. With that out of the way, let me tell you how my journey working in corporations went.

Growing up, working in an office, wearing a suit, and carrying a briefcase was something our culture taught us to aspire to. The stability of being part of a large organization and the promise of income growth were the core value propositions of working for a big American corporation. It seemed like a worthwhile trade: my time in exchange for affording the American dream. But here’s the rub, there are millions of people who walk this path. So many, in fact, that the only way corporations deal with the volume is to standardize and productize both the process and the product: us, the people.

Let’s face it, they’re not hiding anything. The name of the process is Human Resources, it’s right there in the title of the people working for the corporations. They disguise it under flourishes of language, benefits, and culture, but they don’t care about you. Resources are consumed, outcomes are achieved, and waste is disposed of. They ask us to volunteer for the community, they ask us to mentor each other, they ask us to take care of each other, but in the end, the only thing that matters is your impact on their bottom line. That is the unspoken truth. It’s not inherently a bad thing, it’s just the way things work, it just sucks that they’re not upfront about it. It shouldn’t be hidden and disguised under layers of pablum about caring for community and people. The reality is that the people with the greatest share of the company’s financial profits are completely disconnected from the impacts of their decisions on the people in the organization.

In 2008, after the housing market crash, I was called into the office of an HR manager at my Wall Street job and told that I was being “redeployed into the economy.” Redeployed into the economy? What the fuck does that even mean? I was getting laid off along with a few hundred other folks. This was my fourth layoff in ten years. Four separate times, management failed, and we, the front-line workers, paid the price.

I’ve had the opportunity in my life to work in quite a few different organizations and office environments. But it all boils down to this: are you betting on your own personal success, or that of a corporation? Every day you go to work, you feel like your success is aligned with the company’s, until one day, it’s not. For some, shrugging it off, looking for a new job, and doing it all again seems like a perfectly normal thing to do. I mean, you have bills to pay, right? You have to work. This is the cycle that prevents most corporate workers from breaking free to bet on themselves. They’ve accepted being a drone in the corporate machine as their lot in life. Even corporate executives disdain much of how things work, but they’re rewarded far too handsomely to stop perpetuating the system.

In the early 2020s, I spent months at a media tech company building an optimizer for buying linear TV. It was one of those rare projects where everything actually worked. The model hit every performance target. It cut waste. It improved forecasting. It even impressed the teams and clients who usually rolled their eyes at anything new. For a moment, it felt like I was building something that might finally matter.

Then the whole thing stalled because leadership couldn’t agree on a pricing strategy. Meetings dragged on. Opinions shifted with the weather. No one wanted to commit to a direction that might make them responsible for the outcome. So the project sat there, fully functional and completely unusable, until someone quietly decided it was easier to shelve it than make a decision. Watching months of work get tossed aside because no one wanted to take ownership was the moment I realized how fragile meaning is inside a big company. You can do everything right and still end up with nothing to show for it.

In a system so large that you are completely powerless to change, sometimes the best option is to get out. Leave. Start a restaurant, a service, or manufacture something. Heck, you could even start a one-person consultancy. For me, it was real estate. I could build it part‑time while working my full‑time gig and grow the business in the shadows of my corporate day job. For you, it will likely be different, then again, you may be reading these posts to get into real estate. Regardless, if you’ve been grinding away in corporate for years and feel unfulfilled, it may be time to bet on yourself.

You don’t need to overhaul your life to figure out what you’re built for. Start with a simple 7‑day sprint. Each day, pick one small action: list three tasks you genuinely enjoy; ask two friends what they think you’re unusually good at; watch one YouTube tutorial on a skill you’ve always been curious about; or shadow someone doing work you admire. By the end of the week, choose one idea and run a tiny test, offer a micro‑service, post a simple “I’m trying this, who needs help?” message, or build a rough version of something you could sell. These small, low‑risk reps give you real data about what energizes you and what falls flat. Purpose isn’t discovered in your head; it’s built through motion. Start moving, and the path gets clearer fast.

Here’s a simple way to remember how to find what you’re B.U.I.L.T. for:

B: Break Down Your Interests
List the tasks, topics, and problems that naturally pull your attention. Keep it messy and honest.

U: Understand Your Natural Advantages
Ask a few people what they think you’re unusually good at. Look for patterns in what comes easily to you.

I: Initiate Micro‑Experiments
Run tiny, low‑risk tests: offer a small service, build a rough version, teach one person something you know.

L: Listen to Your Energy
Track what leaves you feeling charged versus drained. Energy is data. Treat it like a compass.

T: Test for Traction
See what gets interest, engagement, questions, or even one person saying, “I’d pay for that.”

In the end, the real victory wasn’t escaping a conference room or a calendar packed with meetings. It was reclaiming the one resource the corporate machine never intended to give back: time. Time to think, to build, to learn, to make choices that served a future I actually wanted. My corporate jobs never allowed me any of this. Financial freedom was never just about money. It was about creating a life where my hours were no longer rented out to the highest bidder. It was about waking up and knowing the day belonged to me.

That shift is what turned a quiet act of defiance into a new way of living. If you feel that pull too, trust it. The path to ownership begins the moment you decide your time is worth more than a salary. And once you take that step, you start to see that freedom is not a dream for other people. It is a skill you can learn and a life you can build, one decision at a time.

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In our case we had one not‑so‑simple issue. On the north side of the building, we needed to cut all the roof rafters along the north wall to make room for the wall we had to build up to support the new raised roof. The plan was to put the new roof above the old one, enclose the building for winter, and demolish the old roof inside the new space. The challenge was taking the load off the wall so we could cut the beams while safely transferring that load to the rest of the structure. The image that follows shows the inside of the north wall. Light streamed in through the opening where we removed the sheathing in preparation. Below the windows is the new ledge board to carry the load of the new wall and roof.

The key to pulling off this re‑roofing was to transfer the load from the main roof beam. The old roof system was simple: long rafters attached into the brick wall at both ends with a central beam running the length of the building to support the rafters. In the image below, the central beam is highlighted with a red line. Under that beam and perpendicular to it is a new 2x6 wall designed to spread the load off the main beam. Lucky for us, this old building was built to last centuries.

Once the load had been spread, it was time to cut the beams and build the new extension of the north wall. Unlike the south wall, which needed to be made of brick to comply with building code for fireproof property‑line walls, the north wall extension was wood framed. Spanning the north and south walls were the engineered timber I‑beam roof joists. Getting these long beams on site and hauled up to the roof was no small task, but unlike natural timbers, these are manufactured to length and will never bend, warp, or curl.

At the front of the building, where the roof meets and covers the cornice, we focused our efforts next. After removing the roof and cleaning out the top of the cornice, it became clear that the brick wall behind the cornice would have to be built up to provide additional support. Moreover, the internal wood structure that held up the cornice’s roof also had to be rebuilt. The cornice is one of the most prominent features of this architectural style, which added even more complication as we now needed to build a gutter into our refurbished cornice.

With all of the structure in place, it was finally time to close up this old beauty. We had removed the original roof back in September of ’25. Since then, the main building had been covered in plastic tarps and the carriage house had been left to the elements. Because we were demolishing and rebuilding most of the carriage house, nature’s course would only make it easier to take down that structure. That said, we were quickly approaching winter and needed to make sure the weather did not cause additional damage.

Roofs are one of the last places any investor should look to save money. Roofs are expensive to fix and are prone to high labor costs—especially when the roof is over five stories up and the worksite is in a crowded downtown location. Things get expensive very quickly. That is why investing in high‑quality materials is more about preventing future maintenance costs than anything else. Sure, we could use cheap plywood, tar paper, and shingles, but doing things for the long term now will probably increase the cost by about 25% while likely increasing the lifespan of the roof by 300% to 400%. For long‑term investors, it’s a no‑brainer.

As a side note, it’s worth acknowledging that many quality‑first construction practices run directly against the incentives that drive most financial investors. When your business model depends on turning a property in twelve to thirty‑six months, the difference between a material that lasts twenty years and one that lasts fifty is irrelevant. The investor won’t be around to deal with the failure, so their rational move is to buy the cheapest option that will survive inspection and hold together long enough to close. It’s not ignorance; it’s the predictable outcome of a system that rewards short‑term gains and ignores long‑term liabilities. Pro‑forma models rarely account for reduced maintenance costs or extended service life, so those benefits never show up in the spreadsheet. What does show up is the immediate hit to the budget when you choose better sheathing, higher‑grade shingles, or corrosion‑resistant fasteners. And when the spreadsheet is the only thing steering the ship, the default becomes doing the bare minimum required to sell the asset and move on.

But that logic only serves people who never intend to live with the consequences of their decisions. Owner‑operators don’t have that luxury. If you plan to hold a property for years or decades, the “minimum viable product” mindset becomes a liability. Cheap materials fail early, create cascading problems, and force you into a cycle of constant patching that quietly drains time, money, and attention. The big institutional players can afford to think in quarters; you can’t. If you want a building that stays dry, stable, and low‑maintenance, don’t copy the habits of investors who are already planning their exit. Build for the person who will still be dealing with the roof ten winters from now, because that person is you.

In the following posts in this series, we will cover demolishing and removing the old roof joists, securing the north wall addition, and shingling the roof. But before we move on, it’s worth pausing on the real lesson buried in this phase of the project: small, intentional upgrades in materials can produce outsized returns in durability, safety, and long‑term cost control. Spending an extra 10–25% on better sheathing, straighter lumber, corrosion‑resistant fasteners, or higher‑grade shingles isn’t about luxury, it’s about engineering a roof that lasts decades longer and demands far fewer emergency interventions. The math is simple: a roof that needs patching every few years quietly drains time and money, while a roof built with materials that resist moisture, movement, and UV breakdown pays for itself many times over.

If you want to apply this thinking to your own projects, start by identifying the components most exposed to weather or structural stress and upgrade those first. Choose sheathing with proper exterior ratings, shingles with proven wind and impact resistance, and fasteners designed for that specific job. Inspect every board before it goes up, reject anything that’s warped or wet, and store materials properly so they don’t fail before installation even begins. On the management side, sequence the work so nothing gets rushed—good materials only perform well when they’re installed under the right conditions. These small decisions compound into a structure that stays tight, dry, and low‑maintenance for years, turning a modest upfront premium into a long‑term win.

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Let me put it this way: this project costs as much as a fully loaded Ford F‑150. While most people are confident that they can make the right decision with that kind of money simply by spending a couple of hours reading reviews and doing test drives, few would take on a construction project of the same size. In reality, both are $100K decisions. The difference is that the car decreases in price every day, while the house you improve will likely do the opposite. There is so much room for error in construction projects, but most people think it is the other way around. Losing money on a new car is a certainty. There is only some chance, which you can reduce through diligence, that project overruns will hit your wallet.

With that context in mind, let’s review how we got here and how we made sure that our research, careful planning, and attentive execution paid off.

Like most parts of a real estate deal, the new roof addition started as a line item on a financial model. When it all started, we knew we had a very old building with a very old roof. In our model we accounted for the removal of the old roof, the abatement of the asbestos, and the replacement of the roof. Adding up the costs of simply fixing what was there, the numbers started to run up quite quickly, nearly $70K of spending without any significant impact on the revenue line. That is a painful expense. So, in trying to create a revenue offset to this expense, we came up with the idea of raising the roof to substantially increase the habitable area of the building.

In real estate there is a concept called “highest and best use.” In other words, what is the best structure that maximizes benefit while remaining legally and financially feasible. In our plan, one part of that strategy looks like the drawing below. I highlighted the old roof on the plans in red and the new roof in green.

Once we had drawings from the architect and engineer, we were ready to start executing on the new roof. We began by applying to the Troy Code Enforcement Office for a permit. As part of this process, environmental testing is required to make sure that no harmful material is released into the community as a result of the project. In our case, we knew we had asbestos since we did the testing shortly after acquiring the building. So our second step was to remove all the hazardous material we found.

As we covered in Oh Shit, Asbestos! What now?, we found a contractor and got all of the asbestos removed. What was left were century‑old wooden planks covered in tar on the carriage house, and the same on the main building but covered in a white plastic. While removing the asbestos, we found out that some of the black tar used to seal the roof also had to be removed. Since this tar was smeared on the roof and along the brick parapets, a significant portion from both structures had to be removed.

While the parapets were still standing, much of what we repaired could probably have been pushed off for a few years. But since we were already there doing the work, we chose to spend a little today to avoid massive repair bills in the coming years. We had to find a mason. The parapet along the neighboring building had to be extended, and the parapet on the other side had to be rebuilt. There were also a couple of old chimneys that needed to be taken down above the roofline and backfilled with new brick to reinforce the wall. In the end, the tops of all the walls will have been rebuilt, a new roof structure will be stronger, and the historic cornice has been refurbished for another hundred years of service.

At this point it may seem like adding this space will cost far more than it could ever return. If you only look at the roof and this one floor, that assessment would be correct. But here is the rub: this building had a very old roof that needed demolishing and remediation, the parapets were already worn out and needed rebuilding, and many of the existing roof joists had fire damage. These are all things we would have had to fix even if we did not increase the livable space. So, counterintuitively, spending significantly more money turned a liability into an asset. The new space will produce much more revenue than the bank will charge us in loan payments. A perfect opportunity for our strategy to generate marginal free cash flow.

A project like this rarely fits into a single chapter. The roof alone has enough moving parts, surprises, and judgment calls to justify its own series, which is exactly why we are taking it step by step. Each phase builds on the last. By slowing down and looking closely at what is happening behind the scenes, you start to understand how these decisions shape the long‑term health of a property.

If you are following along with your own project in mind, this is the moment to practice thinking like an investor instead of a spectator. Ask yourself what the work is really solving. Look at the structure, the materials, the timeline, and the tradeoffs. When you train yourself to see the underlying logic, you stop reacting to problems and start anticipating them. That shift is what separates a confident owner from someone who feels at the mercy of the building.

As we move into the next part of the series, keep one simple habit in mind. Before you touch anything, write down the outcome you want and the constraints you are working within. It sounds small, but it forces clarity. Clarity makes the next decision easier, and a string of easier decisions is how you finish a project that once felt too big to start.

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Real estate is no different. The industry is full of neat little rules that promise clarity but erase the nuance that actually matters. They make beginners feel safe, but they also blind them to opportunity. Once you understand that the world is not orderly and never has been, you stop trying to force it into a shape that feels comfortable. You start learning how to operate inside the chaos instead of trying to escape it. And that is where the real advantage begins.

Many people would rather trade the effort of doing their own analysis for a simple rule, even if that means missing out on an entire swath of opportunity. It never ceases to amaze me how much some people will pay to avoid even the most minimal effort.

Do not get me wrong. Systems, processes, and simplicity matter. The problem with heuristics is that rules of thumb are easily misapplied. They are like the blinders put on carriage horses. They reduce noise and distractions that might spook you, but they also narrow your field of vision so much that you lose any sense of what you are missing.

Focus is important, but the bigger picture always provides more optionality. If the path you are fixated on gets blocked and your vision is restricted, you only have two choices. You can quit or you can brute force your way through. If you cannot see a better way around the problem, you cannot pivot to a simpler solution. And that is precisely why trying to reduce a business to simple rules that always apply is a fool’s errand.

You are smart enough to evaluate situations on their merits. So with our blinders off and our wits about us, we go about our business. For some people, this is simply too much chaos. Too many decisions. Too much thinking. But with enough experience, you stop fearing the chaos. You embrace it. The fear that paralyzes others becomes opportunity in the making.

If you are confident you can solve almost any problem, you will find that the opportunities wrapped in hard problems are exactly where the market assigns the least value. That is where the outsized returns live. If you are competing in a dense field, you have to be better than many other racers. If you are competing in a race with only one competitor, you just need to finish.

Old buildings are a perfect example. There are too many things hidden in the walls to ever fully understand the true scope of a project. It is about making educated decisions regarding the risks you are facing. And funny enough, while older buildings come with more complications, they are also usually built far better than most contemporary structures. They just do not make them like they used to.

To succeed, you find the niche where your unique talents create value in ways others cannot or will not. I am very good at very messy. The projects that wreck financial models and blow up timelines. That is where I thrive.

As you work to start or grow your business, take time to think about where your skills add the most value. Are you organized. Are you great at networking. Are you a strong leader. By understanding your strengths, you can choose deals that align with what you are best at and maximize your chance of success.

Maybe you are better off buying a property with tenants already in place, where your strategy focuses on operations. There is a wide range of ways to own and operate rental property. Historic properties tend to be model breaking and rule defying. If you are a rigid plan follower who needs a high degree of order, they may not be for you.

As you define your long term strategy, consider the full spectrum. Office buildings with tenants in place. Ground up single family development. Commercial retail. Urban historic multifamily. RV and mobile home parks. Short term rentals. Storage facilities. Small bay industrial. Each requires a different skill set. The needs, clients, and challenges of industrial tenants differ from retail tenants, and both differ even more from residential real estate, where you are in the business of providing families with homes.

Choosing the right real estate strategy is not about copying what is popular or chasing whatever asset class is trending on social media. It is about understanding how you think, operate, and make decisions when the stakes are high and the variables are messy. Every property type carries its own flavor of chaos. Some require operational grit. Others demand analytical depth. Some reward creativity more than precision. The investors who thrive are not the ones who try to master everything. They are the ones who match their innate strengths to the type of chaos they are best equipped to manage. When you align your skills with the right strategy, you stop fighting the work and start compounding your edge.

Here is a simple step by step guide to help you align your strengths with the right strategy.

1. Audit your natural strengths under pressure
2. Identify the type of work you actually enjoy
3. Match your skills to the property type’s risk profile

A few examples:

Multifamily: capex shocks and tenant churn, good for operators with strong systems
Retail: tenant concentration risk, good for negotiators and market analysts
Industrial: rollover cliffs, good for planners who think in timelines
Hospitality: demand volatility, good for dynamic and creative operators
Office: leasing friction and long downtime, good for relationship builders who play the long game
Mobile home parks: regulatory scrutiny and aging infrastructure, good for patient operators with strong people skills
Self storage: hyper local demand swings, good for systems driven operators who excel at pricing and automation

4. Test your fit with small, low commitment reps
5. Build a strategy that amplifies your edge, not your weaknesses

In the end, real estate does not reward the people who chase certainty. It rewards the people who learn to operate without it. The investors who last are not the ones with the prettiest spreadsheets or the most optimistic pro formas. They are the ones who understand that every deal is a negotiation with the unknown. Risk is not a footnote at the bottom of the model. It is the entire game. And the sooner you stop trying to eliminate it and start learning how to live with it, the faster you build the kind of resilience that compounds.

You do not need perfect information to make good decisions. You need a framework that keeps you alive when the improbable shows up at your door. Do that with consistency, and you will find that chaos is not the enemy. It is the environment. And if you can learn to navigate it with clarity and discipline, you will discover what seasoned investors already know. The real edge is not predicting the future. It is surviving long enough to benefit from it.

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I never had much interest in finance or banking when I was younger. I naively thought those businesses were all about money, when in reality I had it backwards. As I learned more about the role of banking and finance, I began to realize that the old adage “It is about return of capital, not just return on capital” is at the heart of everything. The most important part of investing is getting your money back. The second most important part is getting back more. Lending money at 20 percent interest might sound like a great investment, but it is a terrible one if the borrowers fail to pay you back. The key word in that sentence is “if.” Why is “if” so important? Because it is the only word that really matters. Whenever you hand someone money, whether a bank or a store clerk, there is always a chance that what you get back is far from what you expected. That is risk.

You may buy an item and discover you were cheated, or deposit cash at a bank that later goes bankrupt. No matter how small the chance, there is always a chance. Risk is never zero. Combine this idea with the notion that investors always want their money back as a bare minimum outcome, and it becomes clear that most investing is about managing risk, not managing money. For me, this realization was an epiphany. It reframed my entire understanding of investment strategy. Risk is the great equalizer. It is the lens through which we compare options for deploying capital. Your cousin’s new restaurant may promise 25 percent annual returns, but one in three restaurants fail within two years. That means there is a one third chance you will get nothing back and two thirds chance you will earn 25 percent. The opportunity matters, but the chance of losing everything matters more.

Things rarely turn out exactly as planned, which is why thinking in terms of risk is a critical perspective. Everything carries some level of risk, even depositing cash at the bank. There is a tiny chance the bank will fail and an even tinier chance the FDIC will not pay out deposit insurance. The probability is incredibly low, but risk is never zero.

In real estate, most investors use financial models that account for risk, but those models rarely show or explain it. A simple example is the vacancy reserve. Look closely at any residential property financial model and you will see a line item for vacancy, often set at 5 percent. It is a convenient placeholder, but not a true indicator of risk. The reality looks more like this: when an apartment becomes vacant, you can expect to lose at least one month of rent. You might be lucky and re lease immediately, or unlucky in a weak market and sit vacant for several months. The 5 percent rule of thumb is just an average. Reserving for it does not mean you are free from risk. Real risk is about preparing for the worst-case scenario, not the average bad day at the office.

Here are four ways to break down the outcome of a vacancy and a probability of each:

If you own a single rental house and your tenant loses their job, you will lose 8 percent of annual revenue each month until the unit is re-leased. The real risk is not the average 5 percent, it is the possibility of losing far more. That does not mean you need to be ready for the worst case on day one. It means you need to build resilience to low probability events. In tactical terms, the vacancy reserve is money you must save to build a proper operating capital reserve. The real risk is not having enough saved when the unexpected happens.

Thinking in terms of risk is a critical skill because it forces you to work through scenarios. If you think through possible outcomes, you can plan for what happens in both best case and worst-case situations. You need to know if there is a scenario that could ruin your business and the probability that it may happen. It does not matter how profitable a property could be if a catastrophic event leaves you unable to collect rent and facing foreclosure. Remember: “It is about return of capital, not just return on capital.” The scenarios you must avoid are the ones that put you out of business. If you fail to identify them, you will only realize you are in trouble once you are already neck deep in it.

When you face uncertainty, apply scenario-based thinking. Work through these steps:

1. Define the problem you need to resolve

2. Identify the key uncertainties you face

3. Decide how many scenario outcomes reflect reality

4. Define scenario outcomes and forecast their probabilities

5. Test your readiness to survive each scenario

If you have the misfortune of non-paying tenants who only leave by eviction, are you prepared to lose three to six months of rent plus thousands in legal fees? Can you absorb that loss, or would it be catastrophic? While unlikely if you screen tenants properly, it is not impossible. To be resilient, you need a plan to survive. Over time you can build reserves and resilience, but as you start and grow your business you must take calculated risks. If you never buy a lottery ticket you never lose, but you also never win.

In the end, successful investing is not about predicting a single outcome but about preparing for a range of possibilities. Just as a chess master studies the board and looks several moves ahead, weighing the probability of each response from an opponent, an investor must think through scenarios and their likelihoods. The strength of a chess player lies not in assuming the opponent will make the obvious move but in preparing for the unexpected one that could change the game. In the same way, the strength of an investor lies in anticipating both the best and the worst cases and building a strategy that can withstand them. Success comes not from certainty but from resilience, from the ability to survive the most dangerous moves while being ready to seize opportunity when the board opens in your favor.

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For most people, the discomfort of having to tell a stranger something that could be perceived as a negative comment is enough for them to tell persistent and pervasive white lies like “you look great in that!” This behavior can be generalized to a rule of thumb: if a stranger has no personal stake in expressing their opinion, they will tell you what you want to hear, not what they actually think. It turns out that asking people for an opinion that may cause them some perceived discomfort, no matter how small, is nearly always answered with the respondent’s best guess at what you want to hear. Maybe I’m not normal, maybe I’m on the autism spectrum, but separating the truth from convenient white lies became an exhausting exercise in trying to understand the people around me.

In a home where parents of European and Middle Eastern descent set the tone of communication, being direct, pointed, but always nice, made it very easy to understand what people meant. It was simple, they told you what they meant. Living in a culture rife with conflict aversion, the American northeast, and most of American culture in general, made finding success in business environments far more difficult than it needed to be. The compounding effect of everyday truth bending along with a seeming inability to take constructive criticism unless it is couched in a ton of caveats, in hopes that the audience is not offended, leads to an everyday fog of uncertainty around everyone’s intentions. I have found I often need to pause and take the time to think over personal interactions, recalling the words, body language, motives, and incentives of people I am doing business with. It is in this reflection time that I evaluate the motives of those I am doing business with.

There are too many people out there who believe any way to make money that is not explicitly illegal is in play. In other words, they believe that if you are too naive to know better, they can and should take financial advantage of the situation. It is precisely because there are too many shifty characters in the construction industry that nearly every interaction has to be handled with a great deal of care. If you think things are any better for the contractors, think again. There are just as many dishonest customers as there are vendors. That means every single contractor is going to have their guard up just as much as you. It’s sad, but because of a small number of bad actors that are very hard to weed out, the level of care and caution needed to vet vendors before handing over money is far greater than in most other business environments.

So, what does all of this mean when it comes to real estate investing and property development? It means that estimates will generally be much more than the real cost, it means the project timelines will almost always be too optimistic, it means that anything not explicitly specified in the contract or blueprints is not included in the price. You should assume that everyone you are paying money to is telling you what you want to hear. There are very few in this industry who do enough recurring business with any individual vendor for them to see you as little more than a passing opportunity to make a buck. I know this sounds like I am super-jaded, maybe to an extreme, but I have found that the sharply dressed smiling faces are far more likely to take advantage of you than the callous-covered hands of a grouchy plumber or electrician. The less they care about how the truth makes me feel, the more I want them as a vendor on my team.

Here are five strategies to use when starting your vetting process:

1. Start with a smaller job - Giving a vendor the opportunity to show you their true colors does not require more than a small project. Going through all the phases of a small project is like doing some dating before getting married.

2. Push for concrete details - Very detailed design specifications, line-item budgets, deliverable dates, and quality warranties are critical to ensuring the expected deliverables are defined.

3. Meeting small commitments - Throughout the introductory process, the contract negotiations, and the design review process, look for on-time deliverables. Showing up on time, bringing a full crew to the job, and being on-site every day until the job is done are critical to delivering a project on schedule. Vendors that can’t nail a small project will cause mayhem on a larger project.

4. Watch for change orders - There is always something unexpected. While most projects will require contract change orders to accommodate work that was not covered by the original project proposal, change orders are the place where unsavory vendors frequently find an exploit. They underbid the project, but once they are embedded and the project gets rolling, they begin to push for change orders that dramatically impact the budget.

5. Ask for line-item breakdowns and invoices - Honest operators will show you. Detailed budget breakdowns provide opportunities to effectively renegotiate and reallocate budget, particularly when a large collection of work is canceled due to scope changes.

At the end of the day, real estate is about people. And people, as we’ve experienced, rarely hand you the unvarnished truth. They hedge, they soften, they tell you what they think you want to hear. That’s not cynicism; it’s human nature. The trick is learning to read between the lines, to separate the polite nods from the genuine commitments, to recognize when someone’s “yes” is really a “no” wrapped in social padding, and to quickly adjust our expectations.

The investors who thrive aren’t the ones who demand perfection or expect everyone to play fair. They’re the ones who build systems to uncover honesty: testing small promises before trusting big ones, insisting on transparency in numbers, and watching actions more than words. Over time, you’ll find that the fog lifts. The contractors who deliver, the tenants who pay, and the partners who show up are the partners you build your business with.

Here’s the alchemy: once you stop chasing the illusion of easy answers and start embracing the messy reality of human behavior, you gain control. You stop being surprised by dishonesty and start rewarding integrity. You stop wasting energy on the noise and start compounding trust into wealth. That’s the real transformation, turning everyday interactions into gold, not because everyone is honest, but because you’ve learned how to uncover the ones who are.

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Finding other people to join your endeavor is a critical skill every business owner needs to master. When managing real estate, the process of finding other people starts small with vendors like plumbers and electricians. If your boiler is leaking, it’s easy to let go and let the professional take care of it, probably because you have no idea how to do it yourself. There are times when letting go is obvious and times when it is a lot harder. Once you take on an ongoing activity or responsibility in operating your business, you learn it and master it. As someone who knows how these things should be done, it becomes much more difficult to hand that responsibility to another person. Using our boiler example, you can only be critical of the plumber’s work if you understand the problem and know the appropriate solution. Otherwise, you trust the professional and their judgment.

As an experienced investor, the Troy project would probably present challenges that we have not faced in our other projects, but given our experience, we were probably going to end up with a bunch of challenges we have dealt with in the past. We have confidence, not hubris. After all, this is the largest construction project we have undertaken. That said, some of our past projects were more technically complex from an engineering standpoint. Besides scale, another challenge is the new market we are entering: Troy. We have no historical relationships with local vendors to build on, no relationship with the local building department, and little knowledge about the ins and outs of Troy building code. But otherwise, from scheduling to budgeting and administrative paperwork, we can do it all in-house. So, we didn’t need a full-service general contractor, a GC; we only needed help with on-site project oversight and a repository of existing vendor relationships that we could leverage. We had to let go and find someone who can do it better.

About a year ago, when we started this project, our architect introduced us to a local contractor specializing in high-end residential projects. During our first meeting, I shared my approach and philosophy with Rob and walked him through our strategy. As someone who takes enormous care to ensure that I only do business with good people and ensure my relationships are a win-win, it is nice to see the vendors you are screening working toward the same goal. Working with a vendor that shares this mentality feels like working with a teammate to collectively solve a problem. Working with vendors who solely focus on money feels like an adversarial contact sport, not a healthy day-to-day work environment.

When working on a project with professional vendors, most of the on-site supervision is about verifying that the contractor completed all the tasks, is working safely, and is progressing in a timely manner. Given the number of trades, the main challenge is coordinating information and resources. In a project renovating a 200-year-old building, the problems are a combination of too much information and not enough information at the same time. There are too many details, specialists, licenses, and products. At the same time, there is not enough information about the condition of the structure or all of the possible remediations that will be needed to bring the residential units to completion.

As we navigate the complexities of the Troy project, I’m reminded that the most successful entrepreneurs aren’t those who can do everything themselves; they’re the ones who know when to bring in the right people and how to build relationships that create mutual success. Rob and his team have become exactly what we needed: partners who share our values and bring local expertise that would take us years to develop on our own.

The canvas of your business is always growing, and at some point, you’ll face the same choice we did: continue painting alone and limit your growth, or find trusted partners who can help you create something bigger than you could achieve solo. The key isn’t just finding vendors, it’s finding the right people who approach business as a collaborative problem-solving exercise, not a zero-sum game.

What challenges are you holding onto that you should be letting go of? Take 10 minutes this week to identify one area of your life or business where bringing in the right partner could accelerate your growth. Sometimes the bravest business decision isn’t doing more, it’s trusting the right people to help you do better.

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On our Troy project, mayhem has reared its ugly head, challenging us to solve some difficult problems right now. This episode of mayhem began with the removal of the asbestos roof. While the removal went smoothly, the details of our post-project expectations were not well defined. While we focused on ensuring that all licenses and permits were in place, along with a competitive set of bids and a detailed scope of work, we neglected to focus on the after-project details—specifically the temporary roof. Having never needed a temporary roof, we had no experience defining or verifying these requirements. So, while the job went smoothly, the mayhem only became visible when the first rainstorm came.

For a week after the old roofing was bagged up and removed from the project, sunshine and warm temperatures lulled us into a sense of complacency. The passing days of upstate New York fall brought rain and the discovery that the temporary roof used by the abatement contractor was useless. A rainstorm rolled in, and the entire job site was soaked. Sure, there was a huge plastic sheet covering the roof, but the nails left over from the roof tear-out had shredded the plastic as it undulated in the wind during those recent summer days. During the storm, water came in everywhere, and the tenant still living on site had some of her belongings get soaked.

In hindsight, we should have spent more time focusing on the details of the scope of work defined in our agreement. While 6-mil plastic is thick for a garbage bag, for temporary roofing, polyester tarps are your best bet. For temporary roofs, tarps should be installed on 2x4s attached to the roof structure so they don’t rub against those nasty nails that shredded our first temporary roof. After experiencing indoor showers on the job, we called in professional roofers to put a proper temporary roof on.

The long-term resolution of our problem is a new roof, of course. The only complication is that we’ve chosen to raise the roof to convert the building’s fifth floor from a 100-year-old attic into amazing loft space for a couple of apartments. So while dealing with rain coming in, we also have to find masons to repair the parapet walls, framers to build the structure for the new roof, and roofers to put on the new roof. For all of that to happen, the architect needs to draw up the designs, the engineer needs to ensure all structural elements are safe, and all documentation needs to be submitted to the municipality to get a permit for this work.

One of our main challenges has been delays caused by our engineering firm. In this business, the buck stops with the person specifying the design. Nothing can move forward until the architect and engineer “stamp” the plans. Once the plans are stamped, the architect and engineer have put their professional licenses and insurance on the line. The stamp is a legal act where the professionals take responsibility for the design and hope they use the highest professional standards. In our case, there were many complicating factors, not least of which is that we’re dealing with a more than 200-year-old building that already had a floor added about 100 years ago.

As you can see in the drawings, we need to demolish some old chimneys, repair the parapets, add sill plates, frame up the structure, and build an entirely new roof.

The current source of our mayhem is an unprepared engineering firm. In short, sometimes critical team members drop the ball. The difference with this particular team member is that they are critical to orchestrating the project implementation plan. In construction, nothing can move forward until a licensed professional has certified that the new construction and its methods will result in a safe structure built in a safe manner. For simple construction, the architect will probably feel comfortable without an engineer, but when you’re tearing off the roof and blowing out the entire back wall, real calculations are needed to ensure safety. In the end, it all lands on the shoulders of the engineer. When the engineer fails to deliver in a timely manner, everyone waits.

Real estate investing delays aren’t just inconvenient, they’re nearly unavoidable in historic buildings. Engineering setbacks and professional tardiness can feel like running through a pool of molasses. How you respond to these challenges will define your long-term success more than the delays themselves. Here are five strategies to help navigate delays:

Expect friction, plan for slack. Build buffers into your timelines and budgets. A 6-month rehab might take 8 months. A permit promised in 2 weeks could stretch to 6. Padding your expectations isn’t pessimism; it’s strategic realism.

Vet for reliability, not just credentials. References and repeat engagements are gold. On this project, we felt it would be best to work with a team that had closely worked with our architecture studio in the past. Unfortunately, their history of timely delivery of quality work didn’t materialize this time.

Document everything. Keep written records of agreements, updates, and changes. It’s not just about protecting yourself—it’s about creating a culture of professionalism.

Stay calm, stay curious. Delays often reveal deeper inefficiencies. Use them as diagnostic tools. Ask if this is a one-off issue or a symptom of a broken workflow. Every hiccup is a chance to refine your systems.

Lead with empathy but enforce boundaries. People make mistakes. Life happens. But your investment deserves respect. Be firm, fair, clear about expectations, and don’t be afraid to pivot when standards aren’t met. Hire slowly and fire quickly.

Real estate isn’t just about bricks and cash flow; it’s about resilience. The most successful investors aren’t the ones who avoid problems, but those who build systems that absorb them. So when the engineer misses another deadline or the contractor goes silent, take a breath, adjust your plan, and keep building. Your future portfolio will thank you.

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