How an Expert House Flipper Would Start Over

TLDR
Thirteen years in, this is what I’d do if I had to start over: for deals 1-3, find one great deal, don’t overcomplicate the corporate structure, and save cash. For deals 3-8, minimize renovations, buy a rental, and get a property manager. For deals 8-15, go inch-wide and mile-deep on one profile; then scale with partners.

Table of Contents

Thinking in Phases

At the time of this recording it’s exactly 13 years since I closed on my first flip. I thought, what would I do if I started over today? That’s what this whole thing is about.

I’m going to break the answer into phases: deal one through three, deal three through eight, deal eight through 15, and beyond.

The reason I think in phases is that most people get freaked out about flipping because you see a hundred different strategies from a hundred different gurus. You have to set up an LLC in Wyoming for some tax reason. You have to know all these things about entity structure and liability. You have to pick between wholesaling, flipping, BRRRs, or subject-to.

I don’t think real estate investing is actually that complex. People talk about the complexity because hiring them or paying for their service is how they make money. In business, you need something to sell and someone to sell it to. In flipping, you need a house that can make you money and a way to get it to the finish line. The rest is fluff. Maybe necessary fluff, but not necessary to get started.

Most people don’t start. And not starting has a real cost that nobody talks about.

How I Actually Started

I actually had two starts. The first was rental houses while I had a high-paying corporate job. I bought rent-ready stuff with bank loans. The delay between each rental was just saving up the 20% down payment, which is the real bottleneck for most people getting into this.

Here’s the math that got me hooked. A $300,000 house bought today, owned for 30 years, at a conservative 3% appreciation, is worth $728,000. The 30-year mortgage is paid down to zero. That’s where most people’s wealth comes from. And the tenant pays the mortgage, not you, if you’re underwriting the deal correctly.

My thought was: if that formula works on one house, why wouldn’t I own a hundred of them? That’s the game.

But those first rentals took me years. I wanted to break away from the corporate job and use flipping to supercharge the cash.

Two things pushed me. I saw the company’s profit-and-loss statement each month and thought, “I’m making that happen. I want that bottom line to be mine.” Then, while working in Omaha, I was eating at Subway when a Lincoln Town Car arrived with an old man and a crew. I do not know if it was Warren Buffett, but in my head it was. That was the final push toward building something of my own.

I did it way too early.

I bought a flip from a wholesaler with a humongous project. I was going to take the roof off and build a second story. No experience with anything like that. After I bought the property, the foundation was crumbling. So I rebuilt the whole foundation from the inside of the house because I was terrified of permits. I was digging 10-foot sections, three feet deep, because I was in Colorado and the frost line is three feet. Wheelbarrows of dirt through the house, out to a dumpster. Pour a footing, build cinder block on top, repeat.

550 days straight on that property. I pocketed around $200,000 on the sale. Sounds great. But I drew personal savings to pay interest. I sold my truck to keep going. I lived in a tent in the backyard at the job site, then in a pop-up camper on the ground.

And the biggest lie of all is that I thought the $200,000 was from being a good flipper. It wasn’t. It wasn’t from forced equity from the construction. It wasn’t from a good deal on the front end, because I didn’t get a good deal. It was pure market appreciation. I rode a wave. If I had sat on the couch and done nothing for 550 days, I’d have made the same money.

Common Mistake
Don’t confuse market appreciation with skill. The market made me $200,000. I thought I’d earned it, so naturally I took on an even bigger project next. That was a catastrophic mistake that took me years to reverse.

If I could do it again, I would have stayed in the corporate job longer, bought more rentals on the side, and built a better position before I went all in. But I was young, single, no kids, so I could do stupid stuff like live in a tent. Here’s what I’d actually do now.

Deals 1-3: Find One Deal

The goal on these three deals is one thing: find a great deal on the front end. Not complicated corporate structure, not a perfect CRM, not systems. Just one deal that actually makes money.

Set up the company and bank account. That was my first administrative step in the source. An LLC and separate account can help establish the business, but they are not a guarantee of liability protection. Formation, contracts, insurance, licensing, guarantees, and how you actually operate all matter, so set it up with qualified local advice.

Focus 95% of your effort on deal finding. You only need one deal right now. Pull a list from PropStream, Property Radar, or BatchList. Pick absentee owners in the hottest neighborhoods that you want to buy in. The up-and-coming areas with other flips going on. I’d want houses 700 to 1,600 square feet, owned more than two years, 30+ years old, right in the heart of town.

Send mail. Yellow Letter is one I’ve used. My planning assumption in the source was about a 1% postcard response, improving with practice, and roughly 1,000 to 2,000 pieces to try to produce a deal. That is not a response guarantee. Work the phones. Keep people in a spreadsheet, not a CRM. Bonus: set up a landing page so you look local, because being local is an advantage against the out-of-state wholesalers who are sending the same kind of mail.

Get a deal under contract. Then take the actual deal to hard money lenders. My plan was to allow 30 to 45 days before closing so I had time to arrange funding. A strong contract and deal make that conversation real, but financing still depends on the lender, borrower, property, and terms.

What counts as a deal. Purchase price plus renovation at around 70% of the ARV. Broad, but real. Run the actual math, but 70% will get you there.

Meet contractors before close. You probably can’t get them into the house yet. Show them your scope of work, videos, and detailed notes. Take the pressure off by saying, “I know you can’t give me an exact price because you haven’t seen the property. I just want a ballpark so we can start building a relationship. Once I close, I’ll get you in there.” That way if the deal falls out, you haven’t wasted their time building relationship capital.

Tight leash on personal finances. Build in a lot of financial contingency. There will be surprises. Even with experience there are surprises, and the first one can take you out of the game. I’d expect deal one to include a $40,000 to $70,000 renovation. Something small enough to manage, big enough to force me to learn.

List the property. Use a real real estate agent, or list it for sale by owner through a real estate brokerage so you get on the MLS without looking like a desperate seller. Never a true FSBO listing. That just signals “this house is worth less.”

Don’t start marketing for deal two until deal one is closed. No overlap. Preserve bandwidth.

Pro Tip
Deals 1-3 take 12 to 18 months. That’s okay. You’re not in a hurry here. You’re gaining skills, experience, and cash. The first million dollars is the hardest one to make because it’s about the skills, not the money.

Deals 3-8: Minimize the Renovation

When I actually did this, I went the opposite direction. Bigger projects, then bigger, then bigger, until I finally had a project that broke me. I had to fire every subcontractor I was working with and finish the biggest project of my life alone. Lots of lessons in there.

What I’d actually do: go smaller, not bigger.

Hunt wholetail deals and cosmetic flips. Where there’s barely any construction. You got such a good deal on the front end that the value was added at purchase, not by the rehab. These are hard deals to find but at this point I’m getting better and better at finding them. Minimizing construction reduces risk at the exact moment I should be reducing risk.

Buy the first rental. In the recording I named Certain Lending and Kiavi as non-bank lenders I had used for 30-year rental loans based on appraised value. Programs and terms change, so treat those as examples from the recording rather than current endorsements. The goal was to BRRRR without draining the cash reserve.

Get a property manager. Don’t spend the time managing the rental. Focus is fine-tuning deal finding, not learning property management from scratch.

Upgrade the deal-finding channels. Add a channel. I briefly floated cold calling condemnation lists, then immediately took it back because heavy-rehab prospects fight this phase’s goal of smaller renovations. The example I kept was a city water-off list, where lawfully available, because loss of service can signal distress.

Build a real CRM. Probably Airtable or something similar. Not a paid service, because the monthly fee cuts into cash reserves. Cash is still the focus.

Keep hard money loans. Don’t start paying cash. Keep the cash reserves. Cash in this game is the power to make the right decisions. It’s not about buying houses with cash, it’s about never making a decision from a position of scarcity.

Small overlap between projects. Once a project is through inspection resolution, start marketing for the next one. Not before.

Pro tip: look for subject-to and seller financing. I treated these as bonus opportunities. A subject to purchase leaves the existing loan in the seller’s name while title changes, and seller financing makes the seller the lender. I also said subject-to is not simple. Existing loan terms, due-on-sale risk, disclosures, documents, servicing, insurance, and local law need qualified review before either structure is used.

Deals 3-8 take another 16-24 months. Not speeding up. Gaining skills, cash, and now a rental.

Deals 8-15: Inch Wide, Mile Deep

After my big-project disaster I adopted a different strategy, closer to what I use now but not quite. I was trying a lot of different things and wasn’t near as laser-focused as I should have been.

If I had to do it again, I’d be even more focused.

Nothing but the exact property profile I want. Inch wide, mile deep. Every project has the same process, the same look, the same finish. You can’t tell them apart on a spreadsheet. Can’t tell them apart in photos.

Build every system around that profile. The scope of work template, the pay schedule, the hardware package, the paint colors, the flooring, the cabinets. Same every time. Speed and repeatability come from sameness.

Up the rental count. By the end of 15 deals, I’d want at least three, ideally five, rentals.

This is the phase where the work is the base. All the different things you want to try, that’s fun, and you get to have fun after you build the base. Build the base first.

Deals 8-15 is the period where discipline beats curiosity.

Beyond Deal 15: Supercharge With Partners

This is where my actual story picks up. I felt ready to take on partners, especially money partners who weren’t interested in being as active in the field as I was. They bring cash, I bring execution.

I built a construction company, a wholesale company, a property management company. All I did was real estate. Partners, lots of them, mostly cash, most not local. Other partners were more active. We raised private equity and private equity funds. Lots of growth.

End of that huge growth period, I downsized a lot of it.

If I had to do it differently now, I’d still build through partnerships, but I’d be picky. Specific about what partnerships look like, separation of duties, expectations both ways. When you’re growing fast the first time, more is better and you don’t think about that. Second time around I would.

Key Concept
You build real wealth in real estate by accumulating rental properties and compounding them. Flipping is the cash engine that feeds the rental portfolio. Partners are the multiplier once you have the system. Don’t skip ahead to partners before you have the system.

FAQ

I’m brand new and don’t have the corporate job or savings. Can I still do this?

The path in this source assumes staying employed, saving the required cash, and first buying rent-ready property. My first property was an owner-occupied home that later became a rental; the next purchase required 20 percent down. The recording does not teach an FHA, VA, duplex, or fourplex shortcut.

How do I know if a deal is actually a deal?

Purchase plus renovation at around 70% of the ARV is the ballpark. Run the arv math in detail before you commit. If you can’t explain why the number works out of habit, you don’t have a deal yet, you have a hope.

Should I quit my corporate job to flip?

Not yet. I quit too early and paid for it with a 550-day project. Stay in the job, stack rentals on the side, and build skills. When you leave, leave with a cushion and a plan, not a wholesale deal that requires framing a second story when you have never done it.

How long between deals 1, 2, and 3?

I’d expect 12 to 18 months total. That phase builds the cash, experience, and skills needed for the shift into deals 3-8.

When do I start taking on partners?

In this start-over map, partnerships come after the 8-15 phase has built a repeatable property profile and base. The number is a sequence from this thought experiment, not a universal qualification rule. I would still be selective about duties and expectations on both sides.