When it comes to investing, it helps to know when to take a risk.
Self-made millionaires Michael "Rooster" McConaughey and Wayne "Butch" Gilliam, veterans of the oil and gas pipeline industry, said they have respect for entrepreneurs who take a chance, but they have to be smart about it.
"To me, the less responsibility you got, the less people you got to take care of, is the best time to go all in," McConaughey said.
He suggested that entrepreneurs with families or other financial responsibilities should be more calculated about risk-taking.
"If we feel in our heart that we've got a good product and a good person, that's when it's time to take a risk," Gilliam said.
Watch "West Texas Investors Club" on CNBC Tuesday at 10 p.m. ET.