How to Pick the Right Contractor for Your Next Project

TLDR

Contractors are not one category. Ross sorts them into four types and three tiers, then uses eight experience-based signals to estimate where a vendor may fit before hiring. The signals are patterns, not proof; documents, scope, references, and actual performance still matter.

Table of Contents

• The Four Types of Contractor
• The Five You Actually Need
• The Three Tiers on the Spectrum
• Eight Pre-Hire Signals
• The Non-Starters
• Recruiting, Not Interrogating
• Where to Find These Guys
• FAQ

The Four Types of Contractor

Most nightmare contractor stories start with treating contractor as one big category. There are four types, and each type fits a different job.

I think of it like packing lunches. A general contractor hands you the packed lunch. A specific job contractor sells you the sandwich. An all-arounder makes the whole lunch but not at competition quality. A laborer has to be walked through every step from which side the peanut butter goes on.

Pro Tip

You do not pick one of these forever. Most flips use a blend. An all-arounder handles the bulk of the work. Specific job contractors handle the licensed trades. That is the manage-it-yourself method in practice.

The Five You Actually Need

You do not need fifteen contractors in your phone. You need five to run a flip.

1. An all-arounder. This is the meat and potatoes. They handle demo, cleanout, floors, paint, cabinets, baseboards, exterior repairs, landscaping, siding, decks, hardware, doors. One contractor with a crew running most of your scope.
2. An HVAC contractor. Licensed, can pull permits.
3. An electrician. Licensed, can pull permits.
4. A plumber. Licensed, can pull permits.
5. A roofer. Some all-arounders will do roofing, but a dedicated roofer does it cheaper and better. Save the all-arounder’s bandwidth for the rest of the scope.

A few nice-to-haves come next as you grow. A framer or structural guy for work an all-arounder should not touch. A drywall crew if you are doing a gut with more than ten or fifteen new sheets. A tree guy. A concrete guy for driveways and sidewalks. A mason for block walls and retaining walls.

Five to start. Nice-to-haves come with experience.

The Three Tiers on the Spectrum

Within each type, contractors live on a three-tier spectrum. Low, middle, high. The same trade can be low tier or high tier depending on how the business is run.

The source includes a free companion table. Use the current Contractor Spectrum while you read the signals below.

Quality here is not craftsmanship. It is scope discipline. Did they deliver what was agreed inside whatever tolerance the job required? I painted my own home office with the cheapest guy I could find, one flat white color, no caulking, spray everything. They did exactly what I asked. That is quality to me. Expectation set, expectation met.

For real estate investing, I live in the middle tier. Sometimes I push up a little, sometimes I push down a little, depending on the project. Low tier has burned me hard enough that I stay away for anything that matters. High tier makes sense only for complex jobs I cannot break down, and over time those jobs get rarer as my own knowledge grows.

Ross’s reason for favoring the middle is bigger than price. These are often small-business owners supporting families and crews. He values being able to give good jobs to people who care about the work, treat them well in return, and build relationships that can last a decade.

Dumb Mistake

Ross received $15,000-to-$20,000 bids to paint a three-story brick building, then another person offered to do it for $600. Ross passed on that paint job but hired him for smaller floors-and-paint jobs. A few jobs later, flooring and tools disappeared from a job site and Ross never saw him again. His lesson was that chasing the cheapest option can create costs far beyond the bid.

Eight Pre-Hire Signals

Ross calls these nine indicators in the video but actually names eight. This page preserves the eight he identifies. He also repeatedly warns that there are outliers and says there is nothing inherently wrong with people at any tier. These are patterns from his experience, not a license to judge competence from appearance alone.

1. Their vehicle

Low tier drives a beater car with a fridge strapped to the roof or wood hanging out the windows. Middle tier drives a work van or work truck, not new, maybe with a magnetic sign or a basic decal. High tier is branded, wrapped, jacked-up tires, brand new.

2. Crew structure

Low tier is a solo guy with buddies who also do not know what they are doing. Middle tier is the owner on the job site every day with a small crew, or a sharp operator running a couple of crews they personally manage. High tier is uniformed crews where the owner is nowhere near the job.

3. Google-ability

Low tier does not exist online. Middle tier has a website you can find by searching the company name. High tier shows up on the front page, knows SEO, runs the map pack, has a long review list.

4. Main marketing method

Low tier has no marketing, maybe a burner phone. Middle tier runs mostly on repeat business and referrals, with simple business cards. High tier runs ads, billboards, CRM, the full machine.

5. Tools and gear

Low tier has whatever is on the back of the truck, sometimes borrowed or sometimes stolen. Middle tier owns their own tools, reasonable organization, van might be messy because they are working. High tier is commercial grade, systematic setup, everything new.

6. Clothing and appearance

Low tier is baggy sweatshirts, ripped non-branded clothes. Middle tier is Carhartts, Dickies, actual workwear with paint or drywall stains because they work with their hands. High tier is branded clean shirts, clean hands, often because the person at your door is a salesperson.

7. Sales tone and positioning

Low tier is desperate. “I will beat any price, I can start today.” Middle tier is curious and measured. Wants to build a relationship. Local, cares about the work. High tier is confident and selective. Unless they sense you will overpay, in which case they get very friendly.

8. Email address

Low tier has no email or a big-dog-at-aol dot com. Middle tier is company-name at gmail, sometimes a real G Suite domain. High tier has branded email signatures, full corporate polish.

The “I can do anything” line belongs to the sales-tone signal above; the source does not provide a ninth item. Ross uses the signals to form an initial hypothesis, not a mechanical score.

The Non-Starters

Signals put a contractor on the spectrum. Non-starters take them off it entirely.

• General liability insurance. Required.
• Workers comp or a workers comp exemption. Required. Otherwise you are carrying the liability.
• License if the trade requires one. Specific to your municipality.
• Permit pulling ability. If the job needs a permit, they need to be able to pull it.
• Required identity, tax, and work documentation. Verify the documents the relationship and local law actually require; do not make assumptions from appearance, accent, or national origin.
• W9 or a business entity. Sole proprietor is fine if legit. The paperwork has to be clean.

If any of these are missing on a trade where they matter, you cannot hire them. No matter how good they looked on the spectrum.

Licensing, insurance, worker-classification, and permit requirements differ by jurisdiction and contract structure. Confirm the current requirements with the relevant licensing office, insurer, and professional adviser.

Recruiting, Not Interrogating

This is the part most new investors get wrong. You are not a customer calling for a quote. You are a recruiter building a depth chart.

A depth chart is like a football roster. You have a starting electrician, a second-string electrician, a third. Over time, every slot gets filled. When the starter is too busy, you go to the bench. That depth is what takes the fear out of running projects. When something goes sideways, you already have a backup.

The way you approach a contractor matters. You are not desperate and you are not demanding. You are also not treating them like a public service that owes you their time. This is relationship capital. The two-way respect is the whole game.

My intro usually sounds like this. “Hey, I am an investor. I do flips and rentals. What I value is building relationships with guys I can work with over a long period. I know investors have a reputation for wanting things cheap. That is not what I want. I want reasonable prices, work we agree on up front, and when the job is done, I pay quickly. That is what I pride myself on. Hope we can build something.”

Then you get their contact info, add them to your CRM, and follow up when a real job comes up. That CRM can be a notebook, a spreadsheet, or a full Airtable base. What matters is that you keep it.

Key Concept

You do not verify the non-starters up front in a cold intro. You verify them right before you hire, in a low-key “I am sure you have all this stuff, right? Insurance, workers comp, ID, W9?” That lands differently than a checklist.

Where to Find These Guys

The five main places I find contractors.

• Home Depot and Lowe’s. Roughly 90% of the all-arounders I have hired started with a conversation at a big-box store in the morning when working guys are picking up materials.
• Trade supply houses. Drywall supply, electrical supply, plumbing supply, HVAC supply. Specific job contractors tend to shop at their trade’s supply house, not at Home Depot.
• Public encounters. A work truck at a gas station can create a natural conversation opener. The source also says not to interrupt crews at lunch.
• Referrals, with a filter. Referrals from other investors are tricky because any investor with a great all-arounder is not eager to share the number. Referrals from homeowners for licensed trades are often better. Plumbers, electricians, and roofers share easier because no single client fills their calendar.
• Driving for dollars for contractors. The source describes approaching crews seen while driving, while warning against interrupting a job site or trying to take another investor’s contractor. Treat the homeowner-renovation example as one sourcing story, not blanket permission to solicit any crew.

Five places, regular reps, growing depth chart. That is how you build the roster. Ross’s closing point is that the ability to find, manage, and keep good contractors is the real strength in this business. Without it, owners can get stuck in the contractor black hole; with it, each project adds skill and relationships.

FAQ

I am just starting out. Do I really need five contractors in my phone before my first flip?

No. Ross says the depth chart grows over time and may not exist on the first project. The five roles describe the compact roster he eventually wants available, not a pre-closing quota.

What do I do when my starter contractor cannot take the job?

You go to the second string on your depth chart. That is the whole point of building the chart before you need it. The stress in this game comes from not having a backup. With a backup, nothing is a crisis.

Should I ever hire low tier to save money?

Ross says he generally works in the middle and sometimes moves up or down depending on the outcome he needs. His $600-bid story explains why a low price does not establish low total cost.

What if a contractor refuses to show proof of insurance or workers comp?

Ross treats required insurance, workers-comp coverage or an applicable exemption, licensing, permit ability, and tax paperwork as non-starters. Which documents are required depends on the jurisdiction and working relationship.

Why does Ross usually manage trades instead of hiring a general contractor?

In this framework, a general contractor delivers the whole package and charges for taking on that coordination. Ross built his investing operation by learning to manage the smaller roster himself. That is his operating model, not a claim that every owner should act as a GC or may do so without the required license.