Did I Buy at the Wrong Time?

Did I Buy at the Wrong Time?

In 2024 I started buying again.

Rates had moved. The frenzy had cooled. Sellers were softer. I told myself the market had already taken enough of a dive to justify stepping back in. It felt disciplined at the time, not emotional. I wasn’t chasing 2021. I was buying below peak comps.

I was also early.

Some of the BRRRR’s I completed are fine. They cash flow modestly, we left some money into the deals. Nothing sexy, but they’re stable. A few flips, though, well...those hurt. Not catastrophic. Not career-ending. But real money. The kind of losses that make you stare at a spreadsheet a little longer than usual and question whether you’re learning or just repeating cycles. Let’s just say I am fortunate that I have excess resources to take the losses on these...cause at one time these would have knocked me out.

On a couple properties we pulled them off the market and kept them as rentals instead of realizing the loss. That decision may age well. Or it may just delay pain. Time will tell.

So the honest question I’ve been wrestling with is this:

Was I wrong then... and am I wrong now?

Because here’s what I know about many of you reading this.

You got kicked in the teeth over the last few years. Margins compressed. Days on market stretched. Buyers disappeared mid-escrow. Private lenders tightened. Hard money got expensive. And some of you cannot afford another misstep.

Going backwards again is the fear. The fear isn’t missing a deal...or missing a market cycle.

Going backwards.

I get it...I don’t want to do that again.

Where I Was Wrong

I thought the correction had mostly happened. What I underestimated was duration.

Price drops don’t happen in one dramatic move. They grind. Sellers resist. Buyers wait. Cap rates adjust slowly. Comps lag. Builders keep delivering inventory they started 18 months ago.

Markets rarely crash cleanly. They deflate unevenly.

In 2024 I wasn’t reckless. But I was assuming stabilization would come faster than it did.

That assumption cost me on flips.

The Bigger Question: Timing vs Structure

The mistake wasn’t buying. The mistake was assuming timing would carry more weight than structure. If you are trying to call the bottom perfectly, you will either:

Only one of those builds position.

The real question isn’t “Is this the bottom?” It’s “Can I survive being early?”

That shift changed how I’m underwriting today.

What I’m Doing Differently Now

I’m not waiting for a headline that says, “Official Bottom Confirmed.”

That never comes in real time.

Instead, I’m focusing on controllables.

1. Multiple Exit Strategies — Non-Negotiable

If the deal only works as a flip, I pass (most of the time...)

I need:

If I can’t pivot, I don’t enter. It is WAY better to NOT HAVE TO buy a deal. Never get caught into ‘having’ to buy something. That is the death of many investors, I saw it more than once before the 2021 market, and I’ve seen it many times since.

2024 taught me that velocity without flexibility is just disguised risk.

2. Buy Box Tightening

I’m not chasing fringe neighborhoods, busy streets, weird properties.

Not stretching on ARV.

Not banking on appreciation.

I’m underwriting to today’s rents and today’s buyer pool. If appreciation happens later, great. If not, I must be able to live with the position.

3. Lower Leverage, Even If Returns Look Smaller

This one hurts the ego. Lower leverage reduces upside on paper. But it dramatically reduces the chance of forced sales.

The goal right now isn’t maximizing the ROI. It’s eliminating the possibility of being cornered. Protect the DOWNSIDE before focusing on the UPSIDE.

4. Longer Time Horizon Assumption

I’m assuming I may need to hold 3-5 years on anything I buy. If that timeline makes me uncomfortable, that’s a signal.

Flippers hate this mindset because it slows income. Recovering house flippers understand it builds resilience.

5. Underwriting for Boring

If the deal feels exciting, I slow down. If it feels almost too conservative, I look closer.

Adrenaline has cost me more than spreadsheets ever have.

So... Am I Wrong Now?

Maybe...

Markets can grind longer than anyone expects. Rates could stay elevated. Inventory could build. Liquidity could tighten further.

But here’s what’s different: I’m not betting on timing. I’m building a position that can absorb being early.

That’s the difference between speculation and operating.

If you structure correctly, being early becomes tolerable. If you structure incorrectly, being early becomes fatal.

The fear many of you are feeling isn’t about investing. It’s about not surviving another mistake.

That’s rational. The solution though, isn’t waiting forever.

It’s designing deals that don’t require perfection.

Income vs Wealth

When I was deep in flipping, I needed constant wins to feel momentum.

Velocity creates dopamine. Closings create validation. But velocity also creates fragility when margins compress.

Wealth building feels slower. Less dramatic. Sometimes even boring. But it doesn’t require perfect timing. It requires durability.

If you’re scared of going backwards, it may be because you were running too fast before.

There’s nothing wrong with that. I did it for years.

Just don’t confuse speed with safety.

If you’re on the sidelines but want to move

Model for worst case everything. Worst case ARV, worst case budget, worst case...If it still works for you, proceed.

Model worst-case refinance rates. Do NOT bet on lower rates...that’s what got a lot of investors in this problem to begin with. They are a gift if they happen, not guaranteed.

Stress test rents 10% lower than market (especially in certain markets...like Austin Tx)

Ask: “If I’m wrong for two years, can I survive?”

Certainty doesn’t come from calling bottoms. It comes from removing fragility.

Trenches Update

That assumption no longer scares me.

Looking for Funding?

If you’re looking at deals right now and need capital structured conservatively, we’re actively lending on disciplined single-family investments up 1-4 units (have a bigger deal? Ask, we sometimes like those too).

If the numbers work, we move fast.

Good luck!

Tarl Yarber

PS: I would love to meet you in person. REI Summit is coming up quick, prices go up Feb 27th. Come out to Austin and meet other investors like myself, in the trenches, working daily on figuring out this real estate market. Use Tarl10 for a discount. Go to www.reisummit2026.com.

Need funding?

We’re actively lending on disciplined single-family deals. If the numbers make sense and the structure protects the downside, we move fast.