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Dec 6, 2019 · 19m · top-founders

1595 Chegg Founder's New SaaS Company Breaks $7m ARR To Help CNBC Communicate

Osman Rashid · 9m spoken
0:00 / 0:00

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In this interview, serial entrepreneur Osman Rashid explains how his SaaS platform, Convo, scaled to over $7 million in ARR by delivering in-context document collaboration for enterprise frontline workers while maintaining disciplined capital efficiency and sub-five percent churn.

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 47.2% of the talking time here. How this is scored →

Nathan as informed peer 5.5 Guest teaching 2.0 Guest disagreement 2.2 Nathan pushing back 5.0
05100:0010:001:10–5:07 · Nathan as informed peer 5/10 Defining Convo and Differentiating from Slack Nathan directly challenges Osman's elevator pitch, asserting it sounds virtually identical to Slack. Osman clarifies the core distinction around document collaboration versus pure messaging before Nathan drills into pricing and target ACVs.5:08–8:48 · Nathan as informed peer 5/10 Founding Timeline and Distributed Team in Pakistan Osman explains their distributed team setup in Pakistan and enterprise customer base like CNBC and H&M. Nathan pushes for concrete scale figures when Osman tries to keep user counts private.8:48–10:55 · Nathan as informed peer 5/10 Capital Strategy and Controlled Burn Rate Nathan playfully gives Osman a hard time for raising institutional money instead of bootstrapping. Osman explains his capital-efficient philosophy and personal investment to avoid Silicon Valley boom-and-bust traps.10:56–14:37 · Nathan as informed peer 8/10 Churn Metrics, Cohort Expansion, and Explosive Growth Nathan repeatedly refuses Osman's conflation of top-line revenue growth with net retention and churn. Nathan forcefully breaks down cohort mathematics to force an exact net expansion figure.14:39–17:56 · Nathan as informed peer 8/10 Customer Acquisition Cost and Payback Economics When Osman declines to disclose top-line revenue, Nathan traps him by multiplying his previously admitted figures of $7 per seat by 100k+ seats. Osman deflects with humor while Nathan insists the math holds.17:56–18:46 · Nathan as informed peer 2/10 Famous Five Rapid-Fire Questions Nathan runs through standard Famous Five rapid-fire questions covering favorite business books, CEOs, sleep, and advice to his younger self.1:10–5:07 · Guest teaching 3/10 Defining Convo and Differentiating from Slack Nathan directly challenges Osman's elevator pitch, asserting it sounds virtually identical to Slack. Osman clarifies the core distinction around document collaboration versus pure messaging before Nathan drills into pricing and target ACVs.5:08–8:48 · Guest teaching 3/10 Founding Timeline and Distributed Team in Pakistan Osman explains their distributed team setup in Pakistan and enterprise customer base like CNBC and H&M. Nathan pushes for concrete scale figures when Osman tries to keep user counts private.8:48–10:55 · Guest teaching 3/10 Capital Strategy and Controlled Burn Rate Nathan playfully gives Osman a hard time for raising institutional money instead of bootstrapping. Osman explains his capital-efficient philosophy and personal investment to avoid Silicon Valley boom-and-bust traps.10:56–14:37 · Guest teaching 1/10 Churn Metrics, Cohort Expansion, and Explosive Growth Nathan repeatedly refuses Osman's conflation of top-line revenue growth with net retention and churn. Nathan forcefully breaks down cohort mathematics to force an exact net expansion figure.14:39–17:56 · Guest teaching 2/10 Customer Acquisition Cost and Payback Economics When Osman declines to disclose top-line revenue, Nathan traps him by multiplying his previously admitted figures of $7 per seat by 100k+ seats. Osman deflects with humor while Nathan insists the math holds.17:56–18:46 · Guest teaching 0/10 Famous Five Rapid-Fire Questions Nathan runs through standard Famous Five rapid-fire questions covering favorite business books, CEOs, sleep, and advice to his younger self.1:10–5:07 · Guest disagreement 2/10 Defining Convo and Differentiating from Slack Nathan directly challenges Osman's elevator pitch, asserting it sounds virtually identical to Slack. Osman clarifies the core distinction around document collaboration versus pure messaging before Nathan drills into pricing and target ACVs.5:08–8:48 · Guest disagreement 2/10 Founding Timeline and Distributed Team in Pakistan Osman explains their distributed team setup in Pakistan and enterprise customer base like CNBC and H&M. Nathan pushes for concrete scale figures when Osman tries to keep user counts private.8:48–10:55 · Guest disagreement 2/10 Capital Strategy and Controlled Burn Rate Nathan playfully gives Osman a hard time for raising institutional money instead of bootstrapping. Osman explains his capital-efficient philosophy and personal investment to avoid Silicon Valley boom-and-bust traps.10:56–14:37 · Guest disagreement 3/10 Churn Metrics, Cohort Expansion, and Explosive Growth Nathan repeatedly refuses Osman's conflation of top-line revenue growth with net retention and churn. Nathan forcefully breaks down cohort mathematics to force an exact net expansion figure.14:39–17:56 · Guest disagreement 4/10 Customer Acquisition Cost and Payback Economics When Osman declines to disclose top-line revenue, Nathan traps him by multiplying his previously admitted figures of $7 per seat by 100k+ seats. Osman deflects with humor while Nathan insists the math holds.17:56–18:46 · Guest disagreement 0/10 Famous Five Rapid-Fire Questions Nathan runs through standard Famous Five rapid-fire questions covering favorite business books, CEOs, sleep, and advice to his younger self.1:10–5:07 · Nathan pushing back 6/10 Defining Convo and Differentiating from Slack Nathan directly challenges Osman's elevator pitch, asserting it sounds virtually identical to Slack. Osman clarifies the core distinction around document collaboration versus pure messaging before Nathan drills into pricing and target ACVs.5:08–8:48 · Nathan pushing back 4/10 Founding Timeline and Distributed Team in Pakistan Osman explains their distributed team setup in Pakistan and enterprise customer base like CNBC and H&M. Nathan pushes for concrete scale figures when Osman tries to keep user counts private.8:48–10:55 · Nathan pushing back 3/10 Capital Strategy and Controlled Burn Rate Nathan playfully gives Osman a hard time for raising institutional money instead of bootstrapping. Osman explains his capital-efficient philosophy and personal investment to avoid Silicon Valley boom-and-bust traps.10:56–14:37 · Nathan pushing back 8/10 Churn Metrics, Cohort Expansion, and Explosive Growth Nathan repeatedly refuses Osman's conflation of top-line revenue growth with net retention and churn. Nathan forcefully breaks down cohort mathematics to force an exact net expansion figure.14:39–17:56 · Nathan pushing back 8/10 Customer Acquisition Cost and Payback Economics When Osman declines to disclose top-line revenue, Nathan traps him by multiplying his previously admitted figures of $7 per seat by 100k+ seats. Osman deflects with humor while Nathan insists the math holds.17:56–18:46 · Nathan pushing back 1/10 Famous Five Rapid-Fire Questions Nathan runs through standard Famous Five rapid-fire questions covering favorite business books, CEOs, sleep, and advice to his younger self.

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

0:00 · Nathan 50.2% · guest 49.8%0:00 · Nathan 50.2% · guest 49.8%3:00 · Nathan 38.2% · guest 61.8%3:00 · Nathan 38.2% · guest 61.8%6:00 · Nathan 37.2% · guest 62.8%6:00 · Nathan 37.2% · guest 62.8%9:00 · Nathan 31.3% · guest 68.7%9:00 · Nathan 31.3% · guest 68.7%12:00 · Nathan 55.7% · guest 44.3%12:00 · Nathan 55.7% · guest 44.3%15:00 · Nathan 55.2% · guest 44.8%15:00 · Nathan 55.2% · guest 44.8%18:00 · Nathan 79.7% · guest 20.3%18:00 · Nathan 79.7% · guest 20.3%
Sharpest disagreement ▶ 16:36 Osman stonewalls revenue questions

Osman outright declines to answer Nathan's revenue questions and deflects Nathan's derived math by quipping that it's a free country.

 Hardest push from Nathan ▶ 13:18 Nathan rejects conflation of top-line growth and churn

Nathan bluntly interrupts Osman to point out that overall revenue growth does not answer the question about cohort retention and expansion.

 Biggest teaching moment ▶ 1:56 Osman distinguishes Convo's document workflows from Slack

Osman educates Nathan on why Convo is not just a Slack clone, citing McKinsey data showing 97% of use cases involve group document collaboration rather than chat.

 Nathan holds their own ▶ 16:49 Nathan traps Osman with arithmetic deductions

Nathan demonstrates sharp financial command by taking Osman's disclosed price per seat and total seat count to mathematically prove the company's monthly run-rate.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Defining Convo and Differentiating from Slack 5326 Nathan directly challenges Osman's elevator pitch, asserting it sounds virtually identical to Slack. Osman clarifies the core distinction around document collaboration versus pure messaging before Nathan drills into pricing and target ACVs.
Founding Timeline and Distributed Team in Pakistan 5324 Osman explains their distributed team setup in Pakistan and enterprise customer base like CNBC and H&M. Nathan pushes for concrete scale figures when Osman tries to keep user counts private.
Capital Strategy and Controlled Burn Rate 5323 Nathan playfully gives Osman a hard time for raising institutional money instead of bootstrapping. Osman explains his capital-efficient philosophy and personal investment to avoid Silicon Valley boom-and-bust traps.
Churn Metrics, Cohort Expansion, and Explosive Growth 8138 Nathan repeatedly refuses Osman's conflation of top-line revenue growth with net retention and churn. Nathan forcefully breaks down cohort mathematics to force an exact net expansion figure.
Customer Acquisition Cost and Payback Economics 8248 When Osman declines to disclose top-line revenue, Nathan traps him by multiplying his previously admitted figures of $7 per seat by 100k+ seats. Osman deflects with humor while Nathan insists the math holds.
Famous Five Rapid-Fire Questions 2001 Nathan runs through standard Famous Five rapid-fire questions covering favorite business books, CEOs, sleep, and advice to his younger self.

Statements from this episode (16)

Assertion Not checkable as stated
97% of Convo Usage Is Document Collaboration, Not Messaging
“Our use case really is three percent of us as users for messaging, so we frankly plan to integrate with products like Slack. 97% of our use case is people working on a document or a conversation in large groups”
Osman Rashid Dec 6, 2019 ▶ 2:17
Assertion Not checkable as stated
Convo Averages Roughly $7 Per User Per Month
“So our I would say we average around seven dollars per user per month is what a customer pays us.”
Osman Rashid Dec 6, 2019 ▶ 3:06
Assertion Not checkable as stated
Convo's Largest Customer H&M Deploys Platform to 15,000 Employees
“So our largest customer is H&M, which has 15,000 employees on the platform.”
Osman Rashid Dec 6, 2019 ▶ 3:18
Assertion Not checkable as stated
80% of Large Retailer Workforces Like H&M Lack Corporate Email
“Because in a large entity, such as H&M, 80% of your workforce doesn't have email.”
Osman Rashid Dec 6, 2019 ▶ 4:01
Assertion Not checkable as stated
Convo Employs Roughly 65 People Globally
“We are roughly 65 people across the globe.”
Osman Rashid Dec 6, 2019 ▶ 5:19
Assertion Not checkable as stated
Convo Has Roughly 250 Total Customers
“So we have roughly 250 customers.”
Osman Rashid Dec 6, 2019 ▶ 6:11
Assertion Not checkable as stated
CNBC Runs All Breaking News Operations Through Convo's Collaboration Tool
“One of our customers is CNBC and all breaking news that happens on CNBC goes through Convo because that's the breaking news group uses Convo as the collaboration tool as well”
Osman Rashid Dec 6, 2019 ▶ 6:15
Assertion Not checkable as stated
Convo Currently Has Over 100,000 Paid User Seats
“What I can tell you, it's, you know, it's in the six figures.”
Osman Rashid Dec 6, 2019 ▶ 7:21
Assertion Supported
Convo Has Raised Roughly $9 Million in Total Capital
“So we're roughly at nine million dollars.”
Osman Rashid Dec 6, 2019 ▶ 9:13
Assertion Not checkable as stated
Convo Operates With Zero Full-Time Marketing Staff
“And frankly, we don't really even have, you know anyone in full-time marketing, we have so much, we have customers coming in.”
Osman Rashid Dec 6, 2019 ▶ 9:35
Assertion Not checkable as stated
Convo Is Currently Approaching Profitability
“That's accurate, but we are near profitability.”
Osman Rashid Dec 6, 2019 ▶ 10:27
Assertion Not checkable as stated
Over 90% of Convo Customers With 20+ Users Never Churn
“So what we find is 90 plus of our customers, 90% plus of our customers who have gone to more than 20 users, they don't churn.”
Osman Rashid Dec 6, 2019 ▶ 11:19
Assertion Not checkable as stated
Convo's Annual Gross Revenue Churn Is Below 5%
“It's below five percent actually.”
Osman Rashid Dec 6, 2019 ▶ 12:21
Assertion Not checkable as stated
Convo Averages 250% Cohort Expansion Per Customer Over 12 Months
“Yeah, look, I mean, the cohorts in which you come in from a customer, say a customer that started in 2017, right? We, if we take a look at that as a cohort, we see almost 250% growth on average within, within a customer.”
Osman Rashid Dec 6, 2019 ▶ 13:41
Insight
A 24-Month CAC Payback Is Acceptable With Five-Year Enterprise Retention
“So you're willing to, you know, pay twice as much as what the value would be in the first year. Cause if a customer is staying for five years, you're doing pretty well.”
Osman Rashid Dec 6, 2019 ▶ 15:09
Prediction Not checkable as stated
Convo Expects 5x Growth in Q1 2019 Over Full-Year 2018
“We're at the stage where we can predict five X growth just in the first quarter over all of 2018.”
Osman Rashid Dec 6, 2019 ▶ 15:47
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