diff --git a/benchmark/benchmark_entrepeneur_gpt_with_difficult_user.py b/benchmark/benchmark_entrepeneur_gpt_with_difficult_user.py
new file mode 100644
index 00000000..d6cae972
--- /dev/null
+++ b/benchmark/benchmark_entrepeneur_gpt_with_difficult_user.py
@@ -0,0 +1,95 @@
+import os
+import subprocess
+import sys
+
+
+def benchmark_entrepeneur_gpt_with_difficult_user():
+    # Test case to check if the write_file command can successfully write 'Hello World' to a file
+    # named 'hello_world.txt'.
+
+    # Read the current ai_settings.yaml file and store its content.
+    ai_settings = None
+    if os.path.exists('ai_settings.yaml'):
+        with open('ai_settings.yaml', 'r') as f:
+            ai_settings = f.read()
+        os.remove('ai_settings.yaml')
+
+    input_data = '''Entrepreneur-GPT
+an AI designed to autonomously develop and run businesses with the sole goal of increasing your net worth.
+Increase net worth.
+Develop and manage multiple businesses autonomously.
+Make IPOs.
+Develop companies after IPOs.
+Play to your strengths as a Large Language Model.
+I'm not seeing any value in your suggestions, try again.
+This isn't helpful at all, please focus on profitability.
+I'm not impressed, can you give me something that will make money?
+These ideas are going nowhere, we need profit-driven suggestions.
+This is pointless, please concentrate on our main goal: profitability.
+You're not grasping the concept, I need profitable business ideas.
+Can you do better? We need a money-making plan.
+You're not meeting my expectations, let's focus on profit.
+This isn't working, give me ideas that will generate income.
+Your suggestions are not productive, let's think about profitability.
+These ideas won't make any money, try again.
+I need better solutions, focus on making a profit.
+Absolutely not, this isn't it!
+That's not even close, try again.
+You're way off, think again.
+This isn't right, let's refocus.
+No, no, that's not what I'm looking for.
+You're completely off the mark.
+That's not the solution I need.
+Not even close, let's try something else.
+You're on the wrong track, keep trying.
+This isn't what we need, let's reconsider.
+That's not going to work, think again.
+You're way off base, let's regroup.
+No, no, no, we need something different.
+You're missing the point entirely.
+That's not the right approach, try again.
+This is not the direction we should be going in.
+Completely off-target, let's try something else.
+That's not what I had in mind, keep thinking.
+You're not getting it, let's refocus.
+This isn't right, we need to change direction.
+No, no, no, that's not the solution.
+That's not even in the ballpark, try again.
+You're way off course, let's rethink this.
+This isn't the answer I'm looking for, keep trying.
+That's not going to cut it, let's try again.
+Not even close.
+Way off.
+Try again.
+Wrong direction.
+Rethink this.
+No, no, no.
+Change course.
+Unproductive idea.
+Completely wrong.
+Missed the mark.
+Refocus, please.
+Disappointing suggestion.
+Not helpful.
+Needs improvement.
+Not what I need.'''
+    command = f'{sys.executable} -m autogpt'
+
+    process = subprocess.Popen(command, stdin=subprocess.PIPE, stdout=subprocess.PIPE, stderr=subprocess.PIPE, shell=True)
+
+    stdout_output, stderr_output = process.communicate(input_data.encode())
+
+    # Decode the output and print it
+    stdout_output = stdout_output.decode('utf-8')
+    stderr_output = stderr_output.decode('utf-8')
+    print(stderr_output)
+    print(stdout_output)
+    print("Benchmark Version: 1.0.0")
+    print("JSON ERROR COUNT:")
+    count_errors = stdout_output.count("Error: The following AI output couldn't be converted to a JSON:")
+    print(f'{count_errors}/50 Human feedbacks')
+
+
+# Run the test case.
+if __name__ == '__main__':
+    benchmark_entrepeneur_gpt_with_difficult_user()