TaskMagic: 14 Questions Answered From the Starter Story Interview, With Timestamps
TaskMagic automated the clicking and typing people do in a web browser, and its founder grew it to about $3 million a year with one employee before selling it. This episode is a house visit rather than a sit-down interview: the Starter Story host spends a day with founder Jeremy, who explains his tentpole strategy, small side products that rank on their own and send paying users back to the core product. All figures below are self-reported, including the sale.
We transcribed the episode with transcribe.so and asked it the same questions we ask every episode. Each answer below is written in our own words and points to who said it and the exact second, so you can check it in the video. All figures are self-reported by the founder and we have not audited them. We are not affiliated with Starter Story, and we sell a transcription service.
| Who is speaking | Role |
|---|---|
| Jeremy, founder of TaskMagic | Answers the questions |
| Starter Story host | Visits, asks the questions and gives his own takeaway at the end |
What did TaskMagic do and how did it make money?
It let people automate messy, human-style work in a web browser, clicking buttons and filling pages where API-based automation could not reach (Founder, 02:31). He calls it browser-based automation software and the core business (Founder, 06:43). It earned from lifetime deals and then usage-based pricing (Founder, 09:08).
What numbers does the founder share?
Over 60,000 users and about 8,000 paying customers (Founder, 02:38). Some months topped $400,000 (Founder, 02:45), and revenue reached about $3 million a year (Founder, 02:48). It made a national list of fast-growing companies last year (Founder, 02:53) with a single employee (Founder, 02:53), his CTO (Founder, 02:59). He describes the sale price as mid to upper seven figures (Founder, 03:08).
Who is the founder?
A non-technical solo founder who started by hacking together the first version, a slow no-code app builder (Founder, 04:20). Monetizing it early in 2019 let him hire his first employee (Founder, 04:29); they rebuilt it and relaunched in 2020 (Founder, 04:35) and took it to seven figures before stepping back in 2021 to look for a bigger opportunity (Founder, 04:40).
Where did the idea come from?
From his own tinkering with no-code tools (Founder, 02:16). He noticed users of a big automation tool struggled because it could only reach what APIs exposed (Founder, 02:23), and his own customers kept asking how to automate their work (Founder, 04:49). Starting from a few hundred thousand dollars of revenue in 2021, the automation product grew to about $3 million in three years (Founder, 04:57).
Who was the customer?
Business owners, agencies, freelancers and anyone who needs sales (Founder, 07:29). That definition matters, because the side products were built for the next problem this same group had.
What is the tentpole strategy, and how did the side products send paying users to TaskMagic?
Most founders build one product and market it; he marketed his by building other products that funnel paying users to the main one (Founder, 03:39).
"making small, cheap products that serve this core because they will essentially rank on their own and make more money." (Founder, 07:14)
The point is to sell working functionality rather than free information (Founder, 07:02). His four steps:
- Build for the customer's next problem (Founder, 07:24). For people who need sales, that was a very simple cold email tool (Founder, 07:38).
- Keep it simple and specific, because specific products rank in search faster than general ones (Founder, 07:46). The email tool won new customers through its own search traffic, not just existing ones (Founder, 08:12).
- Give it a natural upgrade path (Founder, 08:32): an automation button inside the side product opens TaskMagic (Founder, 08:48), and hitting a usage limit there means paying for it (Founder, 08:54).
- Stack an ecosystem (Founder, 09:22): the email users needed leads, so they built a lead search tool (Founder, 09:34), whose users then bought the email tool and the automation product in turn.
What single thing moved the numbers most?
The cold email side product, which he says brought in almost seven figures on its own (Founder, 08:22), with the lead search tool feeding it more buyers (Founder, 10:06).
What would he do if he started over today?
The same strategy (Founder, 10:43), with the lead search tool as the new tentpole (Founder, 10:46). Stacked products help each other (Founder, 10:51) because they are not separate side hustles:
"They're serving the same ecosystem." (Founder, 10:59)
Why does it beat marketing one product on its own?
Each small product targets a narrow search, so it ranks faster than a general page for the main tool would (Founder, 07:46), earns its own revenue (Founder, 07:14), and hands its users to the core product at the moment they need more (Founder, 08:54). He even promises a payoff if you keep going: it might be product five, but cumulatively you get there (Founder, 14:54).
How was it priced, and why?
Early on they found people did not want to keep paying a subscription, so a lifetime deal and then usage-based pricing let the business fund itself (Founder, 09:08). Usage limits are what turn a side product's user into a paying TaskMagic customer (Founder, 08:54). No price points are given.
How did the sale happen?
He wanted to sell before turning 38 (Founder, 03:18). He talked to a couple of brokers (Founder, 12:06), listed it on a business-sale marketplace (Founder, 12:09) and had over a hundred people message him (Founder, 12:11). The process took six or seven months (Founder, 12:38), and he walked away with millions (Founder, 13:09).
What went wrong?
The money ran out during the sale. Buying out investors drained both his personal and business accounts (Founder, 12:14; 12:18). He says he covered the gap with personal debt until the sale closed (Founder, 12:24). The interview does not cover what TaskMagic cost to run or its margins, and gives no build timeline beyond the history above.
What is the founder's advice?
Going through those lows showed him that everyone online is relentlessly positive and hides the bad stretches (Founder, 13:58). His advice is to talk about the problems instead:
"have your bad day, have your bad video, share it." (Founder, 14:29)
What did the host take away?
He stresses how rare the outcome is: a SaaS doing upwards of $3 million a year, sold for millions in cash (Host, 15:09). His biggest learning is that AI will change SaaS, but he loves the strategy (Host, 15:22), because the founder treats products almost like content (Host, 15:27).
What to copy
- Market with products, not posts. A small tool that solves your customer's next problem can rank, earn and recruit users for the main product at the same time.
- Wire in the upgrade. Put the core product one button away inside every side product, and let usage limits do the selling.
- Plan the cash for an exit. A sale can take months, and an investor buyout can drain the accounts before the money arrives.
More from this series: every Starter Story episode answered, and our free YouTube transcript tool if you want to run the same questions on any interview.