Entrepreneurs Are Terrible Investors… Until They Learn This
The Wealth Without Wall Street Podcast
September 10, 2026
Entrepreneurs are wired to solve problems, take risks, and believe they can make almost anything work. But those same strengths can become dangerous when investing.
Speakers Russ Morgan, Joey Muré
TopicsHow ToEducationBusinessInvesting
Russ Morgan (0:00)
Over the last 20 plus years of working with thousands of entrepreneurs and investors, we have found there is a distinct difference between those who make great investing decisions and those who make terrible ones. So in this podcast, we're going to break down why entrepreneurs are usually, not always, but most of the time, terrible, terrible, terrible. Or my buddy, Charles Barkley likes to say, I say, my buddy, I think he's an Alder Grant. He's an Alder Grant. Terrible, terrible investor.
And we're going to talk about what it takes to become wise in investing and how we have learned to do both, right? Be terrible investors as well as being better investors. And that's what we're breaking down all for you right now.
SPEAKER_2 (0:49)
Welcome to the Wealth Without Wall Street Podcast. Your guide to understanding how to get out of the Wall Street rat race and start your own mailbox money lifestyle.
Now, don't let these handsome southern draws fool you. These financial minds are teaching our country to enhance savings, increase cash flow and create passive income, all without the help of Wall Street. Are you ready to break through? Now, here are your hosts, Russ Morgan and Joey Muray.
Russ Morgan (1:21)
Here we go.
So, the big idea, Stallion, what I want to make sure we cover is that entrepreneurs are tend to be wired in a very specific way. And it is from the lens of we make things work, right? I would say our superpower is optimism. Would you agree?
Joey Muré (1:40)
A hundred percent. Push through at all costs basically.
Russ Morgan (1:44)
And if you run a business, you're self-employed, you get this, right?
You tend to say, I can overcome bad decisions just by my own implementation, right? You assume execution will overcome maybe bad circumstances. You think-
Joey Muré (2:03)
Or no systems whatsoever, right?
Russ Morgan (2:06)
Yeah, you think if something goes wrong, I'll figure it out.
Joey Muré (2:09)
Grit is really what it's about, yeah.
Russ Morgan (2:11)
Yeah. And then we tend to believe in people, right? We just love people, we believe in people.
And I know we've made some bad hires in our day each now. And so like there's some things we go like, we allowed our gut to make a mistake there. But that is, that's really the big lens that entrepreneurs have. But when we apply that into investing, that optimism, right? Like all deals will work out. This is going to be good. I believe in the story. I like the person pitching me. Things can go bad, true?
Joey Muré (2:39)
100%. Yeah, that is not the good lens to be an investor.
Russ Morgan (2:42)
Now, here's the opposite. Investors, though, investors have a completely different wiring. They start from the perspective that everything will fail, and your job is to prove to be why it won't.
And I immediately, right, I have this reaction to that as an entrepreneur, like I don't like to think things will fail. I think things are going to get better. They're going to improve. Like, man, I hate pessimists, right? I hate people who say, why all the time? Or, I don't think this can. Like, what? No, like, how?
Joey Muré (3:16)
Just show me how, right?
Don't question me. We're gonna get through this. Like, yeah, pessimism is not our friend.
Russ Morgan (3:24)
Well, and then also you think about it from an investment perspective, right? Investors go to these operators and they're like, show me your track record. Just kind of black and white. Not like, hey, where are you from?
Tell me about the deal. Another like, what have you done before? And then what are the assumptions that you're using that you believe this deal is going to work out? I need to see those. I need to be able to go in and verify them, right?
Joey Muré (3:49)
And do I agree with your assumptions because I've actually verified the data.
That's the, I think that's a big key thing. Difference as well is data drives everything, not necessarily feeling or, you know, how do I interpret what's being said? It's like, no, I don't want to interpret anything. I just want to literally see the numbers.
Russ Morgan (4:11)
And one of the things I've noticed from great investors is that they don't invest outside of their DNA. They don't invest outside of their buy box. I think it's the reason why someone like a Warren Buffett might be able to see 100 deals and discount 98 in seconds because it doesn't fit inside the buy box. I remember Stallion reading the book, The Entrepreneur Roller Coaster. I've shared this with you before, right? I just remember when this company wanted Richard Branson to come and speak at their event, and they kept reaching out to his people, and they kept upping the ANT of how much they would pay him to come, to the point where the last time they turned him down, the company came back and said, I have a blank check, just tell me what he wants to write on there.
38 more minutes of transcript below
Thousands of transcripts fetched by people building searchable podcast archives
Fetch the whole transcript
The demo key returns a sample episode in full, no card needed:
curl -H "x-api-key: pt_demo" \
https://spoken.md/transcripts/1000651996090Markdown with the speakers named, for your notes, your knowledge base, or anything that makes HTTP calls.
From $0.10 per transcript. No subscription. Credits never expire. Prices exclude VAT, added at checkout for EU customers. Not what you expected? Email us within 14 days with 20 or fewer credits used and we refund the pack in full.
Using your own key:
curl -H "x-api-key: YOUR_KEY" \
https://spoken.md/transcripts/1000788799085