The story of failing AI startup in 2023

16 Nov 2023

Almost a year ago, a month after ChatGPT was released, I and my friend began working on AskGuru: an AI toolkit designed for customer support software providers. Essentially, it’s a collection of easy-to-integrate tools that enable these providers to incorporate AI features such as Q&A over documents and chats, summarization, and semantic search into various aspects of their product, whether it’s a customer-facing chatbot or a copilot tool for agents.

Recently, my co-founder left to join another company, so I thought it would be a great time to look back and reflect on what we did and what we learned building AI startup in 2023.

Converging to the idea

Applying ChatGPT to customer support was a pretty obvious idea. It promised to benefit both customers using self-service FAQs and agents by speeding up responses and reducing the need for first-line support. So, we started digging in.

We developed a prototype and reached out to industry experts for feedback. This eventually led us to LiveChat incubator where LiveChat agents tested our agent assistant tool (this tool later became an app on the LiveChat marketplace). From these tests, it became clear that leveraging internal documents and previous chats improves the chatbot’s ability to respond accurately without involving an agent. It worked great for answering straightforward questions like “What’s the maximum file size for upload?” but at the same time it struggled with action-oriented queries such as “I want to cancel my subscription.”. Overall, we looked at this experiment as a positive sign and started thinking about our unique edge.

Looking at AI customer support competitors like Yuma, OpenSight, Parabolic, we noticed that everyone was targeting end clients — teams responsible for customer support, individual merchants, or outsourcing companies. However, we felt that this approach had a downside: most clients were already using customer support software like Zendesk, Intercom, and a long tail of smaller ones which meant we should create numerous integrations similar to our LiveChat collaboration. But large software providers would inevitably introduce native AI features, which would always outperform non-native marketplace apps. Indeed, we saw signs that LiveChat was developing its own AI solutions [1], making us realize that our marketplace app might eventually become redundant over time.

This realization led us to a hypothesis that was driving the development of AskGuru for these months: SMBs in the Customer support and Knowledge Management software development fields, who have the resources but lack the engineering capacity, would prefer to buy ready-to-use AI tools rather than develop them in-house. We believed it was crucial for these smaller CS/KMS providers to integrate ChatGPT-powered features immediately for automatic Q&A, dialogue summarization, semantic retrieval, and more. This urgency comes from observing major players like Intercom, Zendesk, and Zoho rapidly incorporating AI into their offerings [2], with smaller companies likely to follow suit.

Approaching the market

We began with a top-down approach, reaching out to CEOs considering integrating AI into their existing products, CPOs to quickly test their AI product hypotheses with us, and CTOs, suggesting they use our services instead of developing AI features internally. Our primary outreach tool was LinkedIn, and we did everything manually.

At one point, we experimented by embedding a Q&A demo on prospective clients’ websites, but it didn’t really impact our conversion rates. Numbers broke down like this:

total companies at stage % of total reached % conversion from previous stage
reached 484 100.00% N/A
replied 89 18.39% 18.39%
had a call 24 4.96% 26.97%
had a pilot 10 2.07% 41.67%
customer 2 0.41% 20.00%

On average, we reached 1.95 people within each organization.

We also got involved in the Pioneer acceleration program [3] and spent a great month in San Francisco as well as landed a YC Interview for S23 batch but it didn’t worked out [4].

Why it didn’t work out as expected

We didn’t gain as much traction as we hoped for several reasons:

  1. We weren’t solving a burning business problem

    I often come across bold statements on LinkedIn like “In the future, businesses will be divided into two categories: those who have embraced AI, and those who have fallen behind”. This might give the impression that every SaaS company is rushing to integrate AI into their products. However, from what we’ve seen, this isn’t the case. The majority of SMBs in customer support and knowledge management software are still focused on their pre-AI boom roadmaps. Some have non-urgent plans to experiment with AI, perhaps integrating basic features like summarization or adjusting the tone of voice, but there’s no sense of urgency or rush.

  2. ROI of embedding AI features is unclear

    It’s tough to quantify the benefits of adding AI features like dialogue summaries for agents or enhanced Q&A support. And when you consider the need to replicate and update client data to a third-party service, it becomes even more uncertain if this direction is worth pursuing.

  3. Software providers prefer comprehensive, end-to-end solutions over toolkits

    What we figured out via top-down selling is that SaaS companies in our space prefer having a complete solution – like a chat popup or a WhatsApp bot – rather than a set of building blocks. A better strategy is to develop a full-fledged product with clear value for the end-user (like a chat popup) and use providers as white-labeled distribution partners, rather than trying to convince them to build on our stack.

One more thing we noticed is that by reaching out and offering our toolkit, considering the issues mentioned above, we ended up looking almost identical to those companies that regularly spam my email and LinkedIn with software development outsourcing offers. And I didn’t like that.

Building in the AI space

A situation when the product is not gaining much traction is not unique in any sense. It’s often a good time to pause, reflect on learnings, and maybe pivot. But here’s the thing: I’m not keen on continuing to develop a product where OpenAI API lies at the core.

Half a year ago I was convinced that building additional features around a powerful foundation AI model is a viable strategy. However, OpenAI’s recent updates [5] [6] including the Assistants API with RAG, history thread management and code interpreter show that they’re aiming to be more than just a provider of foundation models. They’re willing to be an all-in-one AI development platform. This shift makes it risky to have their API as the backbone of a product because there’s always the chance that OpenAI might add features that make my product obsolete.

A common strategy for creating a unique selling point is collecting client data to fine-tune custom models, creating a so-called “data flywheel”. For me, it is hard to agree with that because no company wants their data used as training material for a model that will eventually serve their competitors. This means that I will end up fine-tuning models for each client with their data, which isn’t scalable and involves a lot of manual work. That means that everything I need is a single Q&A RAG model, finetuned to utilize context and follow a specific output format. Such a model could be finetuned on a synthetic dataset from GPT4 outputs without the need for a flywheel.

An even bigger question is whether local models are necessary at all when OpenAI’s models are so efficient. In our interviews, we’ve often heard companies express concerns about using OpenAI’s API, fearing it might compromise their clients’ data. These companies generally fall into three categories:

  1. Those who simply don’t need or want AI.

  2. Those who don’t trust OpenAI API but trust established providers like Azure OpenAI Service.

  3. Companies in sectors like banking, insurance, or consulting. Many haven’t moved to cloud computing and rely on their own data centers. For them, the return on investment for AI features like Q&A and summarization isn’t clear, given the need for significant CPU, RAM, or GPU resources.

Given that, I don’t think any local models are needed in a customer support space.

Generally, AI has become too commoditized to be the central feature of a product. It’s now just another tool, like a database or cloud service. It is especially sad for me as a Machine Learning engineer!

Rant about chatbots

It could be worth continuing to try to find a unique edge and developing a product that stands out from those quickly built on the OpenAI stack. However, I realized that I don’t have a strong passion for customer support as a whole. In my entire life, I’ve never had a case where a bot actually solved my problem. Either I managed to find the information or take the action myself (like changing a delivery address), or my request was so specific that it wasn’t covered by scripts or documentation and needed a real person’s help.

While working on AskGuru, I’ve come to believe that the existence of chatbots for information and actions is more about poor UX/UI and the absence of a solid search engine like Algolia. The real value in a chat popup, in my view, is the live agent. They can do things and access info not readily available to users, like escalating technical bugs or handling complaints and disputes.

What I would do differently next time

The main thing I’d change at the start is to have more interviews with actual users of the product we planned (like support agents and chatbot users), rather than just customers (in our case, those who provide customer support or knowledge management software). Gaining insights from real users helps in understanding ROI for the planned solution and shaping the offering to match real product value, not just vague customer expectations. It could even prevent us from working on a stillborn product earlier. And, I should’ve read The Mom Test before diving into heavy interviewing.

Another aspect I’d focus on is the market size. When we narrowed down to selling to SMBs, we didn’t properly research the market. For a while, this didn’t bother us, but as we reached every potential customer out there it turned out that the market wasn’t as large as we hoped [7].

We spent a lot of time on unproductive back-and-forth communication and free pilots. In hindsight, implementing paid pilots might have helped us understand real demand faster and filter out those who didn’t need our product.

Sometimes, we got distracted and started exploring adjacent areas, like providing software for BPO outsourcing companies or even developing an education platform. However, I didn’t find this helpful. It pulled the focus away from our main business, preventing us from either developing it further or realizing that it wasn’t worth pursuing at all.

Closing thoughts

For me, the effort I put into something is directly linked to the sense of belonging to the project I am working on. When running a startup this feeling is extreme, and I really enjoyed working at full capacity most of the time.

Another great thing I discovered about being a founder is that there is nobody to blame. I hate when people, including myself, use external attribution to justify failures. This was a common frustration in my corporate job, where policies, directions, choices, and people were often beyond my influence. But in a startup, there’s literally no one else to blame. It’s me who chose the industry, the clients, partners, and investors. At the end of the day, I’m solely responsible for the product’s success or failure.

For now, I’ll continue supporting our existing users and explore what I can work on next.

Tech details

The main value proposition of AskGuru is Q&A over PDFs, crawled websites, markdown, and plain text files. We’ve enhanced this with several features:

AskGuru is primarily designed for use via a web API. This allows our clients to natively integrate our features into their products, such as a Knowledge Base provider improving their search results with our answers. Additionally, we made a chat popup for embedding a chat-over-docs widget on websites and a Livechat marketplace app to assist agents in preparing responses.

The stack we have:

These components interact as shown here:

We self-host everything on standard VMs across AWS, Vultr, and GCP, using docker-compose. We don’t use services like Managed Databases or Cloud Run offered by cloud providers because it makes us feel bounded to specific provider. It paid off when our GCP credits [8] ran out and we were able to move everything to AWS within an hour, thanks to the credits we had from NVIDIA Inception program. While self-hosting raises questions about database backups and microservice scalability, our relatively low request volume (averaging 100/day) has meant these are not immediate concerns.

Flow of handling a user request

The central feature of AskGuru is the GET /answer endpoint, which provides responses to user inquiries based on certain parameters. The flowchart below illustrates the process of handling these requests:

Vector databases

We used Milvus for storing vector embeddings. We enjoyed working with their Python SDK and exploring their docs. Once we encountered an issue where Milvus consuming excessive CPU while idle [9] but the Milvus team responded swiftly and efficiently, helping me resolve the issue ASAP. Other challenges, such as eventual consistency and switching message brokers, were resolved by reviewing the docs and config files.

Despite my positive experience with Milvus, I’m inclined not to use any vector database for my next project. The sole feature I require from a vector database is indexing for quick retrieval, and I don’t see the need to manage an entire separate database just for this one functionality. Instead, I’m considering some extensions to existing, established databases like those available for PostgreSQL [10] [11].

From my perspective, the vector databases field currently seems more focused on marketing tactics (like which database OpenAI uses in their sample notebooks [12]), connectors to outer world (such as SDKs [13]), and tutorials for a quick start, rather than an actual competition of quality and speed. Given the additional overhead of integrating a new database for just a single vector indexing feature, and considering the presence of traditional databases like PostgreSQL, which I plan to use anyway, the value proposition just isn’t there for me.

Open sourcing the work

We’ve decided to share the code we wrote, hoping it might be useful to someone someday:


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