What I Wish I Knew Before My First House Flip

TLDR
For deals one through three, Ross would focus on one great front-end buy and finish it before adding more risk. He would then build a rental base, improve deal flow, shrink the rehab, and repeat one narrow property type until the work became a system.

Table of Contents

Deals 1 Through 3: One Great Deal

Ross left a corporate job because he wanted real estate to become his profession. He planned quickly, bought the next flip he could find, and learned many lessons the hard way.

If he started again, the main goal would be a great deal on the front end. He says that one thing solves many later problems.

Set Up the Basics Without Getting Stuck

Ross would set up an LLC and checking account, but he would not let the setup become analysis paralysis. He jokes that he has formed companies from a bank parking lot. The point is speed and perspective, not a universal legal or tax instruction.

Go Direct to the Seller

Ross would:

  1. buy a list for the market;
  2. start with a proven list filter;
  3. send simple direct mail;
  4. use a separate local phone number; and
  5. create a basic website or landing page that shows he is local.

The source gives a rough funnel for 1,000 mail pieces: about 10 calls, three appointments, one contract, and a 60% to 70% chance that the contract closes. Those are Ross’s example numbers, not a guarantee.

Scope, Fund, and Finish One Job

Once the house is under contract, Ross would make a detailed scope of work, take photos and video, and use the budget to seek a hard money commitment. Contractors may give soft bids before closing, then firm them up once access is available.

For the first three deals, he would keep personal spending tight and avoid looking for the next house until the current one was sold or refinanced. He would allow 12 to 18 months to finish the first three without forcing speed.

The Loss That Changed the Goal

Ross made money on his first flip and thought it proved his skill. In hindsight, the rising market had helped him.

He then took on larger projects until one deal wiped out everything he had made from the earlier flips. The rentals he had bought during his corporate years had kept rising in value and gave him a base.

That changed the goal. Flips create cash and experience. Long-term rentals build the portfolio.

Deals 4 Through 8: Build the Rental Base

Ross would focus on his first BRRRR: buy, renovate, rent, and refinance. Instead of selling the finished house to a retail buyer, the refinance pays off the short-term loan and lets him keep the rental.

He would add two vendors:

He would also add deal channels, such as cold calling or digital marketing, and keep building the contractor pool.

The main insight is that better buying can shrink the renovation. Before Ross knew how to find a great deal, he had to create value through a large rehab. Better front-end deals let him take on simpler work.

A high-skill side move is a wholetail: buy an off-market property, then list it on the MLS or Zillow without doing the full rehab. Ross separately describes seller-financed and subject to deals as powerful options that may reduce cash needed at closing. Those structures still carry real obligations and risks.

Deals 8 Through 15: Repeat One Lane

Ross says some of the strategies that moved him forward came from a guy across the street. Once those ideas entered the system, he could stop treating every house like a new invention.

His lane became B- or C-class houses under 1,500 square feet with about $0 to $60,000 of renovation work. Bigger jobs needed more problem solving and more bandwidth.

The goal is for each job to look like the last. Same class, size, area, scope pattern, and vendors. Ross compares it with Monopoly: finish one color group before chasing every color on the board.

After Deal 15: The All-Weather Approach

After the first 15 deals and a stable system, Ross would choose a clear target for property type, partners, and money. Only then would he look up and add another lane.

He says the next operating model comes down to four things:

  1. get better deals;
  2. build smarter scopes;
  3. manage projects hard; and
  4. keep improving the vendor bench.

That is the all weather approach. Read I Only Do These Four Things After 15 Years of Flipping for the full framework.

FAQ

What matters most on the first deal?

A great front-end buy. Then build the most detailed scope you can, secure the funding, and finish the one project before adding risk.

Should I start deal two before deal one is done?

Ross says no for the first few deals. He would wait until the current deal was sold or refinanced.

Should I skip flipping and go straight to rentals?

The source uses flipping to build cash and skill, then BRRRR to start the rental base. The right order still depends on the deal and funding available.

Why repeat the same kind of house?

Repeated houses reduce new decisions. The scope, contractor needs, budget, and likely problems become easier to predict.