🎧 How to Run a Profitable One-person Internet Business Using AI

Ben Tossell shows us the future of building businesses online

Every illustration/Zapier.

TL;DR: Today we’re releasing a new episode of our podcast How Do You Use ChatGPT? I go in depth with Ben Tossell, the founder of Ben’s Bites, a daily AI newsletter with over 100,000 subscribers, and an investor in early-stage AI startups. We dive into leveraging AI to identify opportunities online, run businesses efficiently, and evaluate their performance. Watch on X or YouTube, or listen on Spotify or Apple Podcasts.


You can build and run a one-person internet business that earns half a million dollars in annual revenue—with AI. My guest for this episode, Ben Tossell, showed me how. 

Ben Tossell runs Ben’s Bites, an incredible daily AI newsletter with over 100,000 subscribers that I read every day, and invests in promising early-stage AI startups. He’s also an experienced founder whose no-code platform Makerpad was acquired by Zapier. 

Ben is really good at identifying profitable internet businesses that can be run with a small team and not a lot of capital. I sat down with Ben to understand how he has integrated AI into his workflow to find business opportunities online, run these ventures efficiently, and evaluate their performance. As we talk, Ben takes me through the remarkable toolkit of AI tools he has assembled for each of these functions.

This episode is a must-watch for anyone who is curious about using AI to bootstrap a profitable internet business. Here’s a taste:

  • Opt for the optimum AI tool. As AI evolves, Ben believes that using different AI tools to determine which one is most appropriate for a given use case is a valuable exercise. “Which tool is best for this thing versus I’m just going to default to ChatGPT for everything” is a question about which he often reminds himself.
  • ChatGPT as a business strategist. When Ben finds a business model interesting, his AI tool of choice is ChatGPT. He analyzes the model by asking ChatGPT questions like, “What's a similar kind of business to this? Where else would this kind of thing be useful? How would you think about building that kind of company?”

Ben is fascinated by companies that package and sell data in useful ways, convinced that a solo entrepreneur could viably scale such a business to $500,000 a year. A leader in this industry is market intelligence company Yardstiq, which offers access to interviews conducted by analysts with Fortune 500 companies that use software tools, with the aim of helping prospective purchasers gain a deeper understanding of the software before making a big investment.

In this interview, Ben walks us through how he dove deep into Yardstiq’s business to better understand the industry. Ben’s starting point was a screenshot shared by the Yardstiq CEO on Twitter that captured a transcribed snippet of an interview conducted by its analysts. 

  • Build your MVP with ChatGPT. After uploading the screenshot to ChatGPT, Ben tried to reverse-engineer the questions Yardstiq analysts ask software clients during interviews. This is useful if Ben wants to build a similar kind of data company because “we have a[n] MVP, this is our very basic form for how we would go and ask people questions.”
  • Push ChatGPT by giving it more context. Ben uploaded more data, including snippets of other Yardstiq transcripts, to ChatGPT, prompting it to refine the questions it had previously generated. After doing this a few times and getting similar responses, he concluded, “That is most likely what the question is, given all of this data.”
  • Generate compelling landing page copy. Armed with a basic set of questions, Ben shifted his focus to other aspects of the business. He liked the copy on Yardstiq’s landing page “because it was just so on the nose,” and wondered how it could be even sharper, so he brainstormed with ChatGPT, asking it to “improve the landing page copy.”

Ben was curious about a similar business idea centered around data—a platform for crowd-sourced, anonymous reviews of AI tools—and used ChatGPT to explore the opportunity. 

  • Flesh out your business plan with ChatGPT. After explaining his business idea to ChatGPT, Ben asked about the best way to kickstart the business and solicit reviews. ChatGPT generated a detailed guide including sections on “research and planning, identify your niche, research competitors, [and] website development.” 
  • Level with ChatGPT based on your expertise. As an experienced founder, Ben thought ChatGPT’s advice was too “generalized,” and prompted it to focus on the “content collection part” of the business.
  • Use ChatGPT to extract information from rabbit holes. One of ChatGPT’s strategies to curate content—incentivizing early reviewers by offering them rewards—reminds Ben of anonymous job review site Glassdoor, leading him to wonder, “How did that start? How did they start getting people to write reviews on a site like that?” Intrigued, Ben started a new chat and asked ChatGPT about Glassdoor’s founding story and revenue model.

In the next segment of the interview, I ask Ben how AI helps him run his business more efficiently. Ben launched the premium version of his newsletter Ben’s Bites Pro a few months ago, and says that having “AI sparring partners” integrated in his workflow has made the “actual process of creating a post so much more fluid.” 

  • Synthesize transcripts with AI. After interviewing a founder for his newsletter, Ben got the transcript from note-taking app Supernormal and uploaded it to one of Google’s Gemini models, prompting the model to help him write a blog post. Gemini segments the information and highlights important quotes. “[I]t's this strange writing partner that helps me do a lot of the work,” Ben says. 
  • Create an arsenal of AI tools. Ben also used frontend interface TypingMind, which allows users to interact with different LLMs like Claude, GPT-4, and Gemini on a single platform, to analyze the same transcript. Ben’s next step was using Lex, the word processor Every incubated, to organize the responses and write his own article. “What works somewhere, take it, remix it, and make it your own,” he adds.
  • Refine drafts with Lex. After writing the first draft, Ben fine-tuned in Lex by using the AI-powered features to check the piece for “brevity and readability.” This was Ben’s “favorite part,” he says, because “it really helps me at the end…I could have said this so much shorter.”

In the final part of the episode, Ben shows me how he used AI to evaluate business data.

  • Analyze survey data with ChatGPT. Ben conducted a survey of his newsletter readers, asking them why they stayed subscribed to Ben’s Bites, and used ChatGPT to distill insights from the data. He uploaded the survey data as a CSV file, prompting ChatGPT to summarize people’s opinions and run a sentiment analysis.
  • Outsource time-consuming tasks to AI. When Ben needed to find specific discrepancies between two spreadsheets, he used data-analysis tool Julius AI to run a comparison. Even though he was unsure of how long this would take, he explains that “it’s more like a smaller task than if I was trying to do this manually.”

Running a business involves juggling an endless number of tasks, and Ben thinks that AI empowers solo entrepreneurs and small companies because “you spend less time doing the things that you don't want to be spending any time on and it helps you with the things that you want to spend time on, [to] do them more efficiently as well.” 

You can check out the episode on X, Spotify, Apple Podcasts, or YouTube. Links and timestamps are below:

Timestamps:
  1. Introduction: 01:02
  2. How to use ChatGPT as a business strategist 14:40
  3. Ben builds an MVP with ChatGPT 23:45
  4. Use ChatGPT to kickstart your business 41:31
  5. Ben uses AI to extract valuable information from internet rabbit holes 44:54
  6. How to turn interview transcripts into compelling articles 54:51
  7. Ben refines his blog post with Lex 59:34
  8. Use ChatGPT to analyze business data 1:06:52
  9. Offload time-consuming tasks to AI 1:09:11
  10. How AI is enabling people to run profitable businesses with not a lot of resources 1:11:09

What do you use ChatGPT for? Have you found any interesting or surprising use cases? We want to hear from you—and we might even interview you. Reply here to talk to me!

Miss an episode? Catch up on my recent conversations with investor Jesse Beyroutey, a16z Podcast host Steph Smith, economist Tyler Cowen, writer and entrepreneur David Perell, Notion engineer Linus Lee, and others, and learn how they use ChatGPT.

If you’re enjoying my work, here are a few things I recommend:

The transcript of this episode is for paying subscribers.


Thanks to Rhea Purohit for editorial support.

Dan Shipper is the cofounder and CEO of Every, where he writes the Chain of Thought column and hosts the podcast How Do You Use ChatGPT? You can follow him on X at @danshipper and on LinkedIn, and Every on X at @every and on LinkedIn.

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