Your AI Written Business Plans and Funding Proposals are Failing — Here’s How to Fix It

A lot of people are quietly using AI to write business plans, grant proposals, and funding pitches… and it shows.

In this video, I walk through why AI-written documents often sound generic, hollow, and “robotic” — and how to fix it using a simple, strategic process. AI isn’t the problem. Misusing it is.

You’ll learn:
The red flags that instantly reveal an AI-written plan or proposal
Why most people get generic, low-credibility output from ChatGPT
A 5-step process to turn AI into a strategic collaborator instead of a copy machine
How to feed AI real data, context, and strategy so your plans actually stand up to funder/investor scrutiny
The 10 critical questions you must answer before you ever type your first prompt
How to use AI for nonprofits, startups, and growth-stage companies without losing your unique voice

I’ve personally used this process and these prompt sequences to help raise hundreds of thousands of dollars (approaching $1M) in funding and support.

Get the Bulletproof Plan Builder Prompt Sequence
These are the exact prompt flows I use to help build:

Nonprofit grant and funding proposals

Startup business plans and investor decks

Growth-stage strategic plans and new revenue vertical cases

DM/comment “PROMPTS” and I’ll send it to you.

Chapters
0:00 – Why people are embarrassed to admit they use AI
0:48 – AI is just another technology (if you use it right)
1:53 – How I can spot AI-written plans in 10 seconds
2:54 – The 5 big red flags of bad AI writing
3:23 – Red flag: Generic language & “business Mad Libs”
3:56 – Red flag: No unique voice or founder perspective
4:07 – Red flag: Internal inconsistencies & broken logic
4:33 – Red flag: No data, no citations, no proof
5:13 – Red flag: Too perfect, too sterile… and emojis
5:57 – Why this happens: Misunderstanding what AI actually does
6:22 – The “contractor vs. blueprint” AI metaphor
7:18 – Fixing bad AI output: the 5-step method
7:28 – Step 1: Setting clear context in your prompts
8:16 – Step 2: Breaking the plan into stages (not one big prompt)
10:14 – Step 3: Feeding AI real data instead of letting it guess
11:14 – Step 4: Revising & asking AI to analyze its own weaknesses
11:58 – Step 5: Verifying and validating with your own judgment
12:22 – The missing key: pre-prompt clarity
13:09 – Do a “data dump” before you ever open ChatGPT
13:30 – The 10 universal questions to answer before you prompt
14:21 – Extra inputs for nonprofits, startups, and growth-stage companies
15:21 – Ask AI what info it needs to do its best work
16:22 – When AI stops guessing and becomes your accelerator
16:49 – Final takeaways: clarity, prompt strategy, refinement
17:18 – The Bulletproof Plan Builder Prompt Sequence (how to get it)
18:02 – Final encouragement on using AI as a powerful tool

Caldwell works with nonprofits, startups, and growth-stage companies to turn clarity, capital, and execution into real results — including strategic planning, funding strategies, and growth initiatives.

If you want help using AI to build fundable plans instead of generic ones, stay tuned — more videos are coming.

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