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Jan 5, 2017 · 16m · top-founders

EP 530: Shut Down $2m Business, Why with CEO Shawn Livermore

Sean Livermore · 7m spoken Nathan Latka · 6m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The Top, host Nathan Latka interviews ZipTask founder Shawn Livermore, who candidly explains why he chose to shut down his startup after raising $650,000 and generating nearly $2 million in revenue. Livermore shares vital lessons on market validation, failed acquisition talks, and his professional transition to Carvana and authorship.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 47.9% of the talking time here. How this is scored →

Nathan as informed peer 3.5 Guest teaching 2.8 Guest disagreement 1.3 Nathan pushing back 2.8
05100:0010:000:28–5:27 · Nathan as informed peer 4/10 Weekly Giveaway Winner Announcement and Entry Rules Nathan introduces the show and quickly digs into ZipTask's metrics, revenue, and funding history. Livermore is transparent and open about his company's failure and the toll it took on him.5:27–8:25 · Nathan as informed peer 3/10 Founding Journey, Product Pivots, and Market Validation Livermore provides an extended breakdown of his business journey, pivots from generic task outsourcing to niche office tasks, and market validation lessons. Latka mostly listens while briefly plugging his own referral links.8:26–10:44 · Nathan as informed peer 5/10 Explaining the Failed Acquisition and Wind-Down Decision Nathan cuts Livermore off to force him to answer why he did not sell or flip the business. When Sean explains the lack of unique IP or personnel for an acqui-hire, Nathan pushes back asserting that the customer list alone should have had sale value.10:45–14:48 · Nathan as informed peer 2/10 Mid-Roll Sponsor Segment: Jamf Now Device Management The segment includes mid-roll advertisements followed by the standard rapid-fire Famous Five round, where Livermore provides concise answers about his favorite tools and advice.0:28–5:27 · Guest teaching 2/10 Weekly Giveaway Winner Announcement and Entry Rules Nathan introduces the show and quickly digs into ZipTask's metrics, revenue, and funding history. Livermore is transparent and open about his company's failure and the toll it took on him.5:27–8:25 · Guest teaching 4/10 Founding Journey, Product Pivots, and Market Validation Livermore provides an extended breakdown of his business journey, pivots from generic task outsourcing to niche office tasks, and market validation lessons. Latka mostly listens while briefly plugging his own referral links.8:26–10:44 · Guest teaching 4/10 Explaining the Failed Acquisition and Wind-Down Decision Nathan cuts Livermore off to force him to answer why he did not sell or flip the business. When Sean explains the lack of unique IP or personnel for an acqui-hire, Nathan pushes back asserting that the customer list alone should have had sale value.10:45–14:48 · Guest teaching 1/10 Mid-Roll Sponsor Segment: Jamf Now Device Management The segment includes mid-roll advertisements followed by the standard rapid-fire Famous Five round, where Livermore provides concise answers about his favorite tools and advice.0:28–5:27 · Guest disagreement 1/10 Weekly Giveaway Winner Announcement and Entry Rules Nathan introduces the show and quickly digs into ZipTask's metrics, revenue, and funding history. Livermore is transparent and open about his company's failure and the toll it took on him.5:27–8:25 · Guest disagreement 1/10 Founding Journey, Product Pivots, and Market Validation Livermore provides an extended breakdown of his business journey, pivots from generic task outsourcing to niche office tasks, and market validation lessons. Latka mostly listens while briefly plugging his own referral links.8:26–10:44 · Guest disagreement 2/10 Explaining the Failed Acquisition and Wind-Down Decision Nathan cuts Livermore off to force him to answer why he did not sell or flip the business. When Sean explains the lack of unique IP or personnel for an acqui-hire, Nathan pushes back asserting that the customer list alone should have had sale value.10:45–14:48 · Guest disagreement 1/10 Mid-Roll Sponsor Segment: Jamf Now Device Management The segment includes mid-roll advertisements followed by the standard rapid-fire Famous Five round, where Livermore provides concise answers about his favorite tools and advice.0:28–5:27 · Nathan pushing back 2/10 Weekly Giveaway Winner Announcement and Entry Rules Nathan introduces the show and quickly digs into ZipTask's metrics, revenue, and funding history. Livermore is transparent and open about his company's failure and the toll it took on him.5:27–8:25 · Nathan pushing back 1/10 Founding Journey, Product Pivots, and Market Validation Livermore provides an extended breakdown of his business journey, pivots from generic task outsourcing to niche office tasks, and market validation lessons. Latka mostly listens while briefly plugging his own referral links.8:26–10:44 · Nathan pushing back 6/10 Explaining the Failed Acquisition and Wind-Down Decision Nathan cuts Livermore off to force him to answer why he did not sell or flip the business. When Sean explains the lack of unique IP or personnel for an acqui-hire, Nathan pushes back asserting that the customer list alone should have had sale value.10:45–14:48 · Nathan pushing back 2/10 Mid-Roll Sponsor Segment: Jamf Now Device Management The segment includes mid-roll advertisements followed by the standard rapid-fire Famous Five round, where Livermore provides concise answers about his favorite tools and advice.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 81.8% · guest 18.2%0:00 · Nathan 81.8% · guest 18.2%3:00 · Nathan 16.5% · guest 83.5%3:00 · Nathan 16.5% · guest 83.5%6:00 · Nathan 11.7% · guest 88.3%6:00 · Nathan 11.7% · guest 88.3%9:00 · Nathan 52.8% · guest 47.2%9:00 · Nathan 52.8% · guest 47.2%12:00 · Nathan 54.9% · guest 45.1%12:00 · Nathan 54.9% · guest 45.1%15:00 · Nathan 98.7% · guest 1.3%15:00 · Nathan 98.7% · guest 1.3%
Sharpest disagreement ▶ 8:30 Sean firmly details failed acquisition reality

Sean firmly counters the simplistic notion of selling the company by listing the ten-plus acquisition meetings he held with major players like Upwork that fell through due to insufficient IP and team size.

 Hardest push from Nathan ▶ 8:25 Nathan interrupts and demands to know why the company was not flipped

Nathan cuts off Sean's lengthy narrative to refocus the interview on why he did not monetize or flip the company's assets and customer list.

 Biggest teaching moment ▶ 8:32 Sean explains M&A criteria regarding IP and team size

Sean educates Nathan on why high peak revenue alone does not guarantee an acquisition when there is neither proprietary IP nor an engineering team for an acqui-hire.

 Nathan holds their own ▶ 9:10 Nathan argues customer list value

Nathan brings his own business acumen to bear, insisting that a business generating over one hundred thousand dollars a month possesses an inherently valuable customer database.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Weekly Giveaway Winner Announcement and Entry Rules 4212 Nathan introduces the show and quickly digs into ZipTask's metrics, revenue, and funding history. Livermore is transparent and open about his company's failure and the toll it took on him.
Founding Journey, Product Pivots, and Market Validation 3411 Livermore provides an extended breakdown of his business journey, pivots from generic task outsourcing to niche office tasks, and market validation lessons. Latka mostly listens while briefly plugging his own referral links.
Explaining the Failed Acquisition and Wind-Down Decision 5426 Nathan cuts Livermore off to force him to answer why he did not sell or flip the business. When Sean explains the lack of unique IP or personnel for an acqui-hire, Nathan pushes back asserting that the customer list alone should have had sale value.
Mid-Roll Sponsor Segment: Jamf Now Device Management 2112 The segment includes mid-roll advertisements followed by the standard rapid-fire Famous Five round, where Livermore provides concise answers about his favorite tools and advice.

Statements from this episode (5)

Disclosure
Livermore: ZipTask raised about $650,000 across four seed rounds
“So we raised four seed rounds. First total, I think came up to about 650,000.”
Sean Livermore Jan 5, 2017 ▶ 3:30
Disclosure
Livermore: ZipTask was dissolved in September 2016
“Dissolved the corporation this year, in fact, just the last couple months here... September, 2016.”
Sean Livermore Jan 5, 2017 ▶ 4:18
Disclosure
Livermore: ZipTask peaked at about $107,000 in monthly revenue
“Best month was about a 107,000 dollars of revenue.”
Sean Livermore Jan 5, 2017 ▶ 5:04
Disclosure
Livermore: ZipTask raised $200K from Pasadena Angels investor who became co-founder
“And we raised, I raised a 200,000 from an angel investor at the Pasadena angels. Who later, his name was Stan, and he later jumped in as an actual co-founder to kind of help us get the thing off the ground”
Sean Livermore Jan 5, 2017 ▶ 7:31
Assertion Partly supported
Guy Suter's Notion.ai raised $10 million while still pre-revenue
“His company Notion.ai is pre-revenue, but they raised ten million dollars.”
Nathan Latka Jan 5, 2017 ▶ 15:19
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