Playbook

How to Start Digital Products With AI, Step by Step

Built only from the steps described in 11 sourced Digital Products cases. Each step is attributed to the case it comes from; we do not add steps of our own.

Updated October 20, 202611 cases with steps
Step 1

How they started

  1. Start with proven expertise

    Years of writing wedding speeches for clients.

    From Jen Glantz (Bridesmaid for Hire), step 1. About $6,300/mo passive income (all sources), Self-Reported

  2. Research the buyer

    Streamers and YouTube creators need channel art.

    From Eftakhairul Islam, step 1. About $3,000/mo, Self-Reported

  3. Research audience problems

    Validate demand before building.

    From Rebecca Beach, step 1. Up to $20,000/mo, Self-Reported

  4. Learn the tool hands-on

    He spent hours a day using ChatGPT and reading what others published about it.

    From Lance Junck, step 1. $34,913 profit, Independently Documented

  5. Learn the platform

    She took an online Etsy course and started with seasonal printables.

    From Claudine Lam, step 1. Over CA$34,000 (about $25,000) in sales since 2022, Independently Documented

  6. Post daily

    Daily LinkedIn posts, a Substack newsletter and a YouTube channel.

    From AI Never Sleeps (Jonathan Chan), step 1. $19.2K in one month, Self-Reported

  7. Find an early niche

    Tumbler designs had little competition at the start.

    From Bailey Designed Co. (Bailey), step 1. $340,000 revenue, Self-Reported

  8. Study what already sells

    He bought and read competitors' books to see what they included.

    From Joe Popelas, step 1. Over $1M in one year, Self-Reported

  9. Sell digital templates

    She lists business templates on Etsy, with nothing to print or ship.

    From Desiree Sandison, step 1. About $34,400 in 11 months, Self-Reported

  10. Fund it with exits

    He sold eight tools and used the money.

    From Ben Issen (Side School), step 1. Six figures in revenue within a few months, Self-Reported

  11. Build a newsletter audience

    A daily AI newsletter with 100K+ subscribers.

    From Ben Tossell (Ben's Bites), step 1. 7-figure business, Self-Reported

Steps 2 to 3

What they did next

  1. Train a tool on your own work

    More than 200 of her speeches.

    From Jen Glantz (Bridesmaid for Hire), step 2. About $6,300/mo passive income (all sources), Self-Reported

  2. Price below the service

    $35 for the tool versus $397 for the service.

    From Jen Glantz (Bridesmaid for Hire), step 3. About $6,300/mo passive income (all sources), Self-Reported

  3. Generate with Midjourney

    The Basic plan was enough to start.

    From Eftakhairul Islam, step 2. About $3,000/mo, Self-Reported

  4. List on Etsy

    Marketplace traffic instead of building an audience first.

    From Eftakhairul Islam, step 3. About $3,000/mo, Self-Reported

  5. Sketch and prompt

    Upload a sketch so the AI understands the layout.

    From Rebecca Beach, step 2. Up to $20,000/mo, Self-Reported

  6. Generate and design

    AI for code and visuals, Canva for final design.

    From Rebecca Beach, step 3. Up to $20,000/mo, Self-Reported

  7. Film a beginner course

    A course of more than seven hours with 50 lectures, filmed in three weeks.

    From Lance Junck, step 2. $34,913 profit, Independently Documented

  8. Publish on Udemy

    Priced at $20 at the time of the article, launched in late December 2022.

    From Lance Junck, step 3. $34,913 profit, Independently Documented

  9. Switch to evergreen products

    Budgeting guides and savings challenges sold far more consistently.

    From Claudine Lam, step 2. Over CA$34,000 (about $25,000) in sales since 2022, Independently Documented

  10. Draft listings with ChatGPT

    She uses ChatGPT for a base description and edits it to match the product.

    From Claudine Lam, step 3. Over CA$34,000 (about $25,000) in sales since 2022, Independently Documented

  11. Sell a cohort course

    The 8-week Zero to Builder course sells at $2,999 a seat; the first cohort sold out.

    From AI Never Sleeps (Jonathan Chan), step 2. $19.2K in one month, Self-Reported

  12. Add a community

    A paid Skool community and selective agency work.

    From AI Never Sleeps (Jonathan Chan), step 3. $19.2K in one month, Self-Reported

  13. Add volume

    About 600 listings by June 2022; designs take about 5 minutes each.

    From Bailey Designed Co. (Bailey), step 2. $340,000 revenue, Self-Reported

  14. Launch a membership

    $43 a month for all designs, about 300 new each month.

    From Bailey Designed Co. (Bailey), step 3. $340,000 revenue, Self-Reported

  15. Outline and generate with AI

    ChatGPT makes the outline, then each chapter topic is generated in turn.

    From Joe Popelas, step 2. Over $1M in one year, Self-Reported

  16. Advertise on Pinterest

    He runs consideration campaigns, then conversion campaigns.

    From Joe Popelas, step 3. Over $1M in one year, Self-Reported

  17. Draft with ChatGPT

    She asks for industry-specific content for each template.

    From Desiree Sandison, step 2. About $34,400 in 11 months, Self-Reported

  18. Edit to sound human

    She rewrites the drafts rather than copying them.

    From Desiree Sandison, step 3. About $34,400 in 11 months, Self-Reported

  19. Build lean

    He launched with a small setup.

    From Ben Issen (Side School), step 2. Six figures in revenue within a few months, Self-Reported

  20. Sell directly

    Growth was sales-driven.

    From Ben Issen (Side School), step 3. Six figures in revenue within a few months, Self-Reported

  21. Pivot to education

    An AI education portal.

    From Ben Tossell (Ben's Bites), step 2. 7-figure business, Self-Reported

  22. Sell lifetime access

    A one-time lifetime plan instead of monthly billing.

    From Ben Tossell (Ben's Bites), step 3. 7-figure business, Self-Reported

Step 4 and later

How they grew

  1. Raise prices

    Courses moved from $27 and $47 up to $97 to $997.

    From Rebecca Beach, step 4. Up to $20,000/mo, Self-Reported

  2. Rank and promote

    He used his SEO and marketing experience to rank in Udemy search and promoted the course on LinkedIn.

    From Lance Junck, step 4. $34,913 profit, Independently Documented

  3. Extend to companies

    He also took paid speaking and training work teaching companies to use ChatGPT.

    From Lance Junck, step 5. $34,913 profit, Independently Documented

  4. Iterate on what sells

    She keeps adjusting fonts, colors and content on products that sell even a little.

    From Claudine Lam, step 4. Over CA$34,000 (about $25,000) in sales since 2022, Independently Documented

FAQ

Digital Products: common questions

How much do people make with Digital Products and AI?

Across the 6 of our 11 sourced cases that report a monthly figure, amounts range from $3,000 to $28,333 a month, with a median of $19,200. These are what each source reports, not typical results.

How much does it cost to start?

Low; mainly software subscriptions in our cases. 1 of 11 cases disclose a startup cost.

How long until the first dollar?

Not consistently disclosed in our cases. This comes from what our cases report.

Which AI tools do these cases use most?

ChatGPT (6 cases), Etsy (5 cases), Midjourney (3 cases), Canva (3 cases), Ideogram (1 case). Only tools named in the sources are counted.

How reliable are these income figures?

2 of 11 cases are independently documented, meaning a news outlet says it reviewed records. 9 are self-reported. Every case links its source.

What are the main risks?

Marketplaces are crowded with similar AI-made products. Copyright status of AI-generated art can be unclear. Low prices mean high volume is needed.

How many of these cases say when they made their first dollar?

5 of 11 cases state a time to first revenue. For example: Rebecca Beach: "Not applicable; the business has existed since 2018"; Lance Junck: "Within the first week (90 students enrolled, per the source)"; Claudine Lam: "January 2022, when she made CA$3.45 net profit; about four months to her first 100 sales". The rest do not say, so treat any single timeline as one example, not a norm.

What went wrong or held these cases back?

11 of 11 cases list limitations or risks drawn from their sources. Examples: Jen Glantz (Bridesmaid for Hire): Exact income from the AI tool is not given; Eftakhairul Islam: Shop not named, so figures cannot be checked; Rebecca Beach: Builds on 25 years of design and development experience. Each case page lists them in full.

Do I have to report this income to the IRS if I never get a 1099-K?

Yes. The IRS says that whether or not you receive a Form 1099-K, you must report all income from selling goods or services on your tax return. Payment apps and online marketplaces must send a 1099-K when payments for goods or services total over $20,000 in more than 200 transactions, but they may send one for lower amounts. Source: IRS, "Understanding your Form 1099-K" (irs.gov/businesses/understanding-your-form-1099-k), checked 2026-10-20. General information, not tax advice.

Do I owe self-employment tax on side hustle income in the US?

According to the IRS, you must pay self-employment tax and file Schedule SE if your net earnings from self-employment were $400 or more. The rate is 15.3% (12.4% Social Security and 2.9% Medicare), and you may need to pay estimated taxes quarterly. Source: IRS, "Self-employment tax (Social Security and Medicare taxes)" (irs.gov/businesses/small-businesses-self-employed/self-employment-tax-social-security-and-medicare-taxes), checked 2026-10-20. General information, not tax advice.

Data guides

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