ZipTask
Sean Livermore was a technology consultant in Southern California, commuting an hour each way to a day job in Irvine. The idea for ZipTask came to him in summer 2010 while he was driving. He saw that outsourcing technology work was broken. American businesses trying to save money on software development were matched with freelancers who had language barriers and economic pressures, and projects often failed. As Sean put it, the problem was "painful" and people "pull their hair out trying to get someone to develop software for them on the cheap."
Sean launched early, before he had validated the business model or gathered enough data about real outsourcing scenarios. He later brought in designer Jeff Sherwood, but said he needed co-founders with sales and growth skills that he did not have at the time. ZipTask pivoted in 2012 after raising $200,000 from an angel investor at the Pasadena Angels, who later joined as a co-founder. The pivot narrowed the offering from general tasks, such as moving a couch or writing code, to a focused niche around Word, Excel, and PowerPoint work for sales teams. The company was funded through four seed rounds totaling about $650,000, and it grew to about 30 people. Sean was building the company on nights and weekends while keeping his consulting job.
The source does not describe how ZipTask acquired its first paying customers or which channels drove growth. It says the company reached roughly $2 million in total revenue over about six years, and its best month brought in about $107,000.
Sean says ZipTask solved the problem it set out to solve, but the company still failed. Revenue was real, and the business model was proven to some degree. Sean met with about 10 potential acquirers, including Upwork (formerly Odesk and Elance), several consulting firms, and Japanese firms. None wanted to buy. The intellectual property was not differentiated enough for an asset acquisition, and the team was too small for an acqui-hire. By the end, monthly revenue had fallen to roughly $5,000 to $10,000 before the company was dissolved in September 2016. Sean's main lesson was to calculate risk carefully and avoid investing too many hours in something that is not working.
Sean dissolved ZipTask in 2016 and now works at Carvana, leading a team and advising its executives. He is also working on a book called *Obscurity* about people who produced significant work from unknown, deep-in-the-weeds positions.
- •ZipTask's revenue was real, but the lack of defensible IP and a team large enough for an acqui-hire meant no buyer would pay for the business, so its value stayed locked in operations.
- •Raising four seed rounds over six years shows that capital was the constraint on growth, and a company that cannot fund itself or find an exit can run out of runway even with paying customers.
- •Launching before validating the business model cost time and money, which suggests that early customer and scenario research matters more than speed to launch in marketplace businesses.
- •Sean's decision to dissolve the company rather than keep it running at a shrinking revenue base suggests that knowing when to stop is itself a deliberate skill worth developing.
- 1.Validate the real scenarios and pain points of both sides of a marketplace before building, since Sean launched prematurely and had to pivot.
- 2.Build a defensible asset, such as proprietary process, IP, or a differentiated niche, early so that the company has acquisition value if the business does not scale.
- 3.Recruit co-founders with sales and growth skills before you need them, since Sean noted he lacked those partners early on.
- 4.Set a clear time and capital limit in advance and decide what signals would justify continuing or shutting down.
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