Leveraging ChatGPT in Pitching and Evaluating Startups

Posted by Brian Porter on May 14, 2023

In the dynamic world of startups, founders are constantly seeking ways to perfect their pitch decks and business plans. Simultaneously, venture capitalists (VCs) and business angels are inundated with funding requests. Enter ChatGPT, OpenAI’s powerful language model, which is well-poised to serve both parties, streamlining the journey from idea to investment.

For Founders: Fine-tuning the Pitch

A startup founder recently used ChatGPT in an intriguing way. They asked the AI to act as a business angel, with a focus on three key elements: the team, cash flow generation, and sustainable growth. Here’s how the conversation unfolded:


Pretend you are a business angel who's top 3 things he looks at when
deciding on investing are the team, cashflow generation, and 
sustainable growth. Can you interview me about my business idea and 
let me know if you think you would invest?

ChatGPT: Responded with a series of pointed questions, delving deep into each of the three focus areas.

In this exchange, ChatGPT helped the founder critically evaluate their business idea, providing valuable insight into what potential investors might look for. It served as a sounding board, enabling the founder to refine their pitch and anticipate possible questions.

For VCs and Business Angels: A First Filter

ChatGPT’s application isn’t limited to founders. VCs and business angels can use it to streamline their investment process. Given its ability to process and analyze a large volume of information quickly, it can be programmed to evaluate pitch decks and business plans against specific criteria. It can ask initial screening questions, providing a preliminary filter to manage the deluge of funding requests these investors often face.

ChatGPT’s ability to ask incisive questions and engage in meaningful dialogue can help investors gauge a startup’s potential. It can highlight key areas of concern or interest that investors may want to delve deeper into during face-to-face meetings.


Detailed Analysis with ChatGPT: A Closer Look

One of the key strengths of using ChatGPT in preparing a pitch deck or evaluating a startup proposal is its ability to provide detailed analysis based on the information shared. Let’s dive deeper into this with some concrete examples from the simulated conversation with a startup founder:

  1. Cost Management: The founder shared that their strategy was to start with remote services, moving to hiring as needed. ChatGPT recognized this as a savvy approach to cost management. Startups need to be lean and agile, especially in their early stages. This strategy shows an understanding of that necessity, signaling that the team has a solid grasp on resource allocation—a critical factor for potential investors.

  2. Revenue Streams: In the business model discussed, the startup relied solely on subscription revenue. While this might work well in the initial stages, ChatGPT highlighted a potential risk: over-reliance on a single revenue source. This observation is crucial as it encourages founders to consider diversifying their revenue streams to create a more robust business model. The founder’s consideration of additional offerings for the target customer group was recognised as a positive step in this direction.

  3. Competitive Landscape: One of the striking claims from the founder was the lack of direct competition. In the ever-changing landscape of online content creation, this is a significant advantage. However, ChatGPT was quick to point out that while the lack of competition is a current strength, it might not remain so in a dynamic market. This realistic view can encourage founders to stay innovative and prepared for potential competitors entering the market.

These examples illustrate the depth of analysis possible with ChatGPT. It doesn’t merely accept the information presented but critically evaluates it, providing valuable feedback. For founders, this means they can gain a more comprehensive understanding of their business model’s strengths and potential weaknesses. For investors, it highlights key areas to probe deeper during face-to-face meetings.

In essence, ChatGPT can provide an additional layer of analysis, helping both founders and investors make more informed decisions.

Limitations and Advantages

Available around the clock, ChatGPT shines in its ability to handle multiple requests simultaneously, showcasing its impressive scalability. Founders will appreciate the low-pressure environment it offers, perfect for practicing and refining pitches. On the other hand, investors will find it handy as a first-level filter to manage the influx of proposals they receive regularly.

While ChatGPT has the ability to mimic investor-like responses and ask thought-provoking questions, we must remember that it’s still an AI. It doesn’t have the intricate understanding and business savvy of a seasoned investor. Despite this, its talent for processing information and delivering detailed responses makes it a formidable tool in refining pitches and initial screening.



ChatGPT can be a powerful tool for startup founders and investors alike. It can offer an objective analysis of a business idea, enabling founders to refine their pitches and prepare for investor meetings. For VCs and business angels, it can be an efficient tool for initial screening. By leveraging this innovative technology, both founders and investors can make the startup journey more streamlined and focused.

How do you think the incorporation of AI tools like ChatGPT might reshape the landscape of venture capitalism and angel investing?

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