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Oct 21, 2019 · 22m · top-founders

1549 Why Did He Leave a $60m Revenue "Unicorn"?

Lonnie Szneiberg · 11m spoken
0:00 / 0:00

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Entrepreneur Lonnie Szneiberg discusses why he transitioned from leading the $60M digital giant Investing.com to founding Oi Chao, a fast-growing Brazilian SaaS startup tackling millions of annual labor compliance lawsuits through automated time tracking.

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 40.6% of the talking time here. How this is scored →

Nathan as informed peer 4.9 Guest teaching 2.0 Guest disagreement 2.7 Nathan pushing back 6.0
05100:0010:0020:001:34–5:04 · Nathan as informed peer 5/10 Addressing Brazil's Labor Lawsuits with Oi Chao Nathan repeatedly interrupts Lonnie to pin down unit economics and per-seat pricing, lecturing him on the basic mathematical definition of an average when the guest gives evasive ranges.5:04–7:15 · Nathan as informed peer 7/10 Launch Timeline and Growth Target to One Million ARR Nathan forcefully challenges Lonnie's projection of hitting $1M ARR by explaining the law of large numbers and illustrating how early percentage growth inevitably decays.7:17–9:56 · Nathan as informed peer 6/10 Clarifying Trial Mechanics and Current Monthly Revenue A tense exchange occurs as Lonnie refuses to confirm a simple revenue estimate derived from his own numbers, prompting Nathan to confront him on why he is making the conversation difficult.9:56–14:10 · Nathan as informed peer 6/10 Fundraising Strategy and Capital Allocation When Lonnie admits he is hesitant to share numbers, Nathan pushes back by explaining the educational mission of SaaS interviews over fluffy PR, though Lonnie provides a clear activation metric of seven active employees.14:11–16:11 · Nathan as informed peer 5/10 Customer Acquisition Strategy, Payback, and Team Distribution Nathan stops Lonnie from dodging CAC questions with testing disclaimers and forces him to state his target payback period as a business decision.16:11–20:14 · Nathan as informed peer 4/10 Explaining the Transition from Investing.com to Oi Chao Nathan intensely interrogates Lonnie's narrative about leaving a $60M company to start a new SaaS app, alleging potential founder conflict, while Lonnie calmly explains the reality of transitioning to a board advisory role after eight years.20:14–21:53 · Nathan as informed peer 1/10 The Famous Five Rapid-Fire Questions Standard concluding Famous Five rapid-fire section with quick, collaborative responses regarding habits, sleep, and CEO role models.1:34–5:04 · Guest teaching 2/10 Addressing Brazil's Labor Lawsuits with Oi Chao Nathan repeatedly interrupts Lonnie to pin down unit economics and per-seat pricing, lecturing him on the basic mathematical definition of an average when the guest gives evasive ranges.5:04–7:15 · Guest teaching 2/10 Launch Timeline and Growth Target to One Million ARR Nathan forcefully challenges Lonnie's projection of hitting $1M ARR by explaining the law of large numbers and illustrating how early percentage growth inevitably decays.7:17–9:56 · Guest teaching 1/10 Clarifying Trial Mechanics and Current Monthly Revenue A tense exchange occurs as Lonnie refuses to confirm a simple revenue estimate derived from his own numbers, prompting Nathan to confront him on why he is making the conversation difficult.9:56–14:10 · Guest teaching 3/10 Fundraising Strategy and Capital Allocation When Lonnie admits he is hesitant to share numbers, Nathan pushes back by explaining the educational mission of SaaS interviews over fluffy PR, though Lonnie provides a clear activation metric of seven active employees.14:11–16:11 · Guest teaching 1/10 Customer Acquisition Strategy, Payback, and Team Distribution Nathan stops Lonnie from dodging CAC questions with testing disclaimers and forces him to state his target payback period as a business decision.16:11–20:14 · Guest teaching 4/10 Explaining the Transition from Investing.com to Oi Chao Nathan intensely interrogates Lonnie's narrative about leaving a $60M company to start a new SaaS app, alleging potential founder conflict, while Lonnie calmly explains the reality of transitioning to a board advisory role after eight years.20:14–21:53 · Guest teaching 1/10 The Famous Five Rapid-Fire Questions Standard concluding Famous Five rapid-fire section with quick, collaborative responses regarding habits, sleep, and CEO role models.1:34–5:04 · Guest disagreement 2/10 Addressing Brazil's Labor Lawsuits with Oi Chao Nathan repeatedly interrupts Lonnie to pin down unit economics and per-seat pricing, lecturing him on the basic mathematical definition of an average when the guest gives evasive ranges.5:04–7:15 · Guest disagreement 3/10 Launch Timeline and Growth Target to One Million ARR Nathan forcefully challenges Lonnie's projection of hitting $1M ARR by explaining the law of large numbers and illustrating how early percentage growth inevitably decays.7:17–9:56 · Guest disagreement 5/10 Clarifying Trial Mechanics and Current Monthly Revenue A tense exchange occurs as Lonnie refuses to confirm a simple revenue estimate derived from his own numbers, prompting Nathan to confront him on why he is making the conversation difficult.9:56–14:10 · Guest disagreement 3/10 Fundraising Strategy and Capital Allocation When Lonnie admits he is hesitant to share numbers, Nathan pushes back by explaining the educational mission of SaaS interviews over fluffy PR, though Lonnie provides a clear activation metric of seven active employees.14:11–16:11 · Guest disagreement 2/10 Customer Acquisition Strategy, Payback, and Team Distribution Nathan stops Lonnie from dodging CAC questions with testing disclaimers and forces him to state his target payback period as a business decision.16:11–20:14 · Guest disagreement 4/10 Explaining the Transition from Investing.com to Oi Chao Nathan intensely interrogates Lonnie's narrative about leaving a $60M company to start a new SaaS app, alleging potential founder conflict, while Lonnie calmly explains the reality of transitioning to a board advisory role after eight years.20:14–21:53 · Guest disagreement 0/10 The Famous Five Rapid-Fire Questions Standard concluding Famous Five rapid-fire section with quick, collaborative responses regarding habits, sleep, and CEO role models.1:34–5:04 · Nathan pushing back 6/10 Addressing Brazil's Labor Lawsuits with Oi Chao Nathan repeatedly interrupts Lonnie to pin down unit economics and per-seat pricing, lecturing him on the basic mathematical definition of an average when the guest gives evasive ranges.5:04–7:15 · Nathan pushing back 7/10 Launch Timeline and Growth Target to One Million ARR Nathan forcefully challenges Lonnie's projection of hitting $1M ARR by explaining the law of large numbers and illustrating how early percentage growth inevitably decays.7:17–9:56 · Nathan pushing back 8/10 Clarifying Trial Mechanics and Current Monthly Revenue A tense exchange occurs as Lonnie refuses to confirm a simple revenue estimate derived from his own numbers, prompting Nathan to confront him on why he is making the conversation difficult.9:56–14:10 · Nathan pushing back 6/10 Fundraising Strategy and Capital Allocation When Lonnie admits he is hesitant to share numbers, Nathan pushes back by explaining the educational mission of SaaS interviews over fluffy PR, though Lonnie provides a clear activation metric of seven active employees.14:11–16:11 · Nathan pushing back 6/10 Customer Acquisition Strategy, Payback, and Team Distribution Nathan stops Lonnie from dodging CAC questions with testing disclaimers and forces him to state his target payback period as a business decision.16:11–20:14 · Nathan pushing back 8/10 Explaining the Transition from Investing.com to Oi Chao Nathan intensely interrogates Lonnie's narrative about leaving a $60M company to start a new SaaS app, alleging potential founder conflict, while Lonnie calmly explains the reality of transitioning to a board advisory role after eight years.20:14–21:53 · Nathan pushing back 1/10 The Famous Five Rapid-Fire Questions Standard concluding Famous Five rapid-fire section with quick, collaborative responses regarding habits, sleep, and CEO role models.

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

0:00 · Nathan 49.3% · guest 50.7%0:00 · Nathan 49.3% · guest 50.7%3:00 · Nathan 29.4% · guest 70.6%3:00 · Nathan 29.4% · guest 70.6%6:00 · Nathan 45.8% · guest 54.2%6:00 · Nathan 45.8% · guest 54.2%9:00 · Nathan 42.5% · guest 57.5%9:00 · Nathan 42.5% · guest 57.5%12:00 · Nathan 39.1% · guest 60.9%12:00 · Nathan 39.1% · guest 60.9%15:00 · Nathan 44.6% · guest 55.4%15:00 · Nathan 44.6% · guest 55.4%18:00 · Nathan 24.9% · guest 75.1%18:00 · Nathan 24.9% · guest 75.1%21:00 · Nathan 56.6% · guest 43.4%21:00 · Nathan 56.6% · guest 43.4%
Sharpest disagreement ▶ 9:15 Lonnie stonewalls on current monthly revenue metrics

Lonnie explicitly refuses to validate Nathan's revenue calculation, digging in his heels and stating he is not going to reveal specific current figures.

 Hardest push from Nathan ▶ 19:26 Nathan presses on potential founder fallout at Investing.com

Nathan refuses to accept Lonnie's smooth transition story, aggressively asserting that nobody leaves a unicorn rocket ship without an internal fight.

 Biggest teaching moment ▶ 18:28 Lonnie explains his transition from operational founder to advisor

Lonnie clarifies the operational lifecycle of an eight-year-old profitable business, educating Nathan on how mature executive teams allow founding partners to advise rather than run daily operations.

 Nathan holds their own ▶ 5:57 Nathan dismantles growth rate extrapolation using law of large numbers

Nathan steps in with mathematical SaaS logic, showing that exponential month-over-month growth from a low base cannot be realistically maintained into large revenue milestones.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Addressing Brazil's Labor Lawsuits with Oi Chao 5226 Nathan repeatedly interrupts Lonnie to pin down unit economics and per-seat pricing, lecturing him on the basic mathematical definition of an average when the guest gives evasive ranges.
Launch Timeline and Growth Target to One Million ARR 7237 Nathan forcefully challenges Lonnie's projection of hitting $1M ARR by explaining the law of large numbers and illustrating how early percentage growth inevitably decays.
Clarifying Trial Mechanics and Current Monthly Revenue 6158 A tense exchange occurs as Lonnie refuses to confirm a simple revenue estimate derived from his own numbers, prompting Nathan to confront him on why he is making the conversation difficult.
Fundraising Strategy and Capital Allocation 6336 When Lonnie admits he is hesitant to share numbers, Nathan pushes back by explaining the educational mission of SaaS interviews over fluffy PR, though Lonnie provides a clear activation metric of seven active employees.
Customer Acquisition Strategy, Payback, and Team Distribution 5126 Nathan stops Lonnie from dodging CAC questions with testing disclaimers and forces him to state his target payback period as a business decision.
Explaining the Transition from Investing.com to Oi Chao 4448 Nathan intensely interrogates Lonnie's narrative about leaving a $60M company to start a new SaaS app, alleging potential founder conflict, while Lonnie calmly explains the reality of transitioning to a board advisory role after eight years.
The Famous Five Rapid-Fire Questions 1101 Standard concluding Famous Five rapid-fire section with quick, collaborative responses regarding habits, sleep, and CEO role models.

Statements from this episode (13)

Assertion Supported
Szneiberg: Investing.com surpassed Bloomberg in web traffic with 100M monthly sessions
“We just surpassed Bloomberg in traffic recently with a hundred million sessions a month on the site alone.”
Lonnie Szneiberg Oct 21, 2019 ▶ 1:24
Assertion Supported
Szneiberg: Brazil sees three million labor lawsuits annually
“There is a big issue in Brazil which is related as I, as you said, there are three million lawsuits a year”
Lonnie Szneiberg Oct 21, 2019 ▶ 1:47
Assertion Not checkable as stated
Oi Tchau serves 5,000-plus employee enterprises and runs government pilots
“We have various companies with over 5000 people and some of the actually the government is also looking into it. Testing some tools. We're running some pilots.”
Lonnie Szneiberg Oct 21, 2019 ▶ 3:19
Assertion Not checkable as stated
Average Oi Tchau customer pays over $100 per month
“On average, it's about a hundred and a hundred and some dollars. And sometimes again, like if you look at the majority of the companies, we're looking at small businesses, but then you have major companies with thousand employees and up, which would change the…”
Lonnie Szneiberg Oct 21, 2019 ▶ 4:24
Prediction Not checkable as stated
Oi Tchau targets $1 million ARR by August 2019
“I can't say that we're expecting the current growth rate to reach a million dollar a year revenue by August next year. If the current rate continues.”
Lonnie Szneiberg Oct 21, 2019 ▶ 5:46
Opinion
Brazilian labor laws drive demand for Oi Tchau compliance tools
“There is a legislation issue in Brazil, which works in our favor. So actually the government is pushing the businesses towards this, these tools and there aren't many out there. And not, not familiar with another tool that offer the same complexity as ours.”
Lonnie Szneiberg Oct 21, 2019 ▶ 6:12
Prediction Not checkable as stated
Oi Tchau will reach profitability before raising additional capital
“We're hoping to, well, we're gonna, not hoping we're gonna reach profitability before, before any additional investment.”
Lonnie Szneiberg Oct 21, 2019 ▶ 10:08
Disclosure
Oi Tchau has raised $1.6 million to date
“We have I didn't say we were, we raised until now 1.6.”
Lonnie Szneiberg Oct 21, 2019 ▶ 10:49
Assertion Not checkable as stated
Szneiberg: Oi Tchau churn only occurs from business closures or mass layoffs
“The only companies leaving us were actually the ones that went out of business for some reason and decided to fire most of their staff.”
Lonnie Szneiberg Oct 21, 2019 ▶ 11:33
Assertion Not checkable as stated
Szneiberg: About eight companies have churned from Oi Tchau to date
“We had about until now eight companies.”
Lonnie Szneiberg Oct 21, 2019 ▶ 11:57
Insight
Szneiberg: Onboarding over seven employees drives Oi Tchau demo conversions
“Once they install the application and invite invite over seven employees the demo usually continues for a while. Like there's no The people don't stop the demo, and it helps us to get to the conversion point.”
Lonnie Szneiberg Oct 21, 2019 ▶ 13:45
Disclosure
Szneiberg targets a two- to three-month CAC payback period
“Probably the customer acquisition, probably the first two, three months.”
Lonnie Szneiberg Oct 21, 2019 ▶ 15:22
Assertion Not checkable as stated
Investing.com reached profitability within seven months of launch
“And being very original back in 2007, we were able to grow the company and reach profitability after seven months.”
Lonnie Szneiberg Oct 21, 2019 ▶ 18:04
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