Jul 1, 2026 · 39 min · 12 segments
People spend three to five years saving $100,000 then lose it in three to five months chasing the wrong oil and gas deal. Courtney has personally invested in over 100 wells and manages a portfolio of…
Paul H. GrahamHostCourtneyGuest
There's a big concern that I've had specifically within oil and gas, where it's almost like I've seen people spend three to five years saving up $100,000 and then losing it in three to five months.

Certainly, we've seen that in 2021 with, call it that timeframe, with multifamily.

But sometimes that can also oil and gas investments, they think of losing all their money or making it super silly big.

Like why do you think there is that such difference in perspective within oil and gas?
That's a great question.
And I think that the first thing I always get asked is what is the likelihood of drilling a dry hole? That's everybody's biggest concern.
And I think investments today, people will invest in deals and they'll drill and drill and then they're not able to recover anything out of the ground.
I think that's the biggest problem and the biggest caveat around investing in oil and gas is Yes, you can get some great tax benefits, but you actually want to get a return on your money as well.

That's going to be like another piece, right? So tax benefit wise, IDCs, right? Intangible drilling costs.

I talked to a CPA, I think it was last year, but they just had no idea what that was.

It was like, you can't, you know, just anyways, it's like it's in the tax code.

Now that could be an edge case, right? So certainly you want your CPA to understand oil and gas.

Granted, how much do they actually, who knows? And that's probably a different episode, right? Today, as we think about oil and gas investing, like what kind of conversations cash flow side or are they even concerned about cash flow versus more of this appreciation and cash flow and potential tax strategy side? What do people really care about with investing in oil and gas?

There's a big concern that I've had specifically within oil and gas, where it's almost like I've seen people spend three to five years saving up $100,000 and then losing it in three to five months.

Certainly, we've seen that in 2021 with, call it that timeframe, with multifamily.

But sometimes that can also oil and gas investments, they think of losing all their money or making it super silly big.

Like why do you think there is that such difference in perspective within oil and gas?
That's a great question.
And I think that the first thing I always get asked is what is the likelihood of drilling a dry hole? That's everybody's biggest concern.
And I think investments today, people will invest in deals and they'll drill and drill and then they're not able to recover anything out of the ground.
I think that's the biggest problem and the biggest caveat around investing in oil and gas is Yes, you can get some great tax benefits, but you actually want to get a return on your money as well.

That's going to be like another piece, right? So tax benefit wise, IDCs, right? Intangible drilling costs.

I talked to a CPA, I think it was last year, but they just had no idea what that was.

It was like, you can't, you know, just anyways, it's like it's in the tax code.

Now that could be an edge case, right? So certainly you want your CPA to understand oil and gas.

Granted, how much do they actually, who knows? And that's probably a different episode, right? Today, as we think about oil and gas investing, like what kind of conversations cash flow side or are they even concerned about cash flow versus more of this appreciation and cash flow and potential tax strategy side? What do people really care about with investing in oil and gas?
The rest of this transcript — segmented and speaker-labeled, so you land on the exact moment something was said
Search every transcript — by keyword, by phrase, or by meaning, across every show Radar indexes
Trends — what is surging across podcasts, measured against its own baseline
Alerts — when a name you follow appears in a newly indexed episode
No account is needed to search Radar.