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Jul 31, 2019 · 23m · top-founders

1467 Olark Founded 2007, $14.4M+ in ARR, So Why Did New Live Chat Players Get All The Love?

Ben Congleton · 13m spoken Nathan Latka · 7m 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 interview, host Nathan Latka speaks with Olark co-founder and CEO Ben Congleton about bootstrapping a live chat SaaS business to over $14 million in annual recurring revenue. Congleton explains how Olark navigates platform competition, implements disciplined SMB pricing, and manages a sustainable, remote-first workforce.

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 36.9% of the talking time here. How this is scored →

Nathan as informed peer 4.4 Guest teaching 2.8 Guest disagreement 2.4 Nathan pushing back 3.2
05100:0010:0020:000:00–2:10 · Nathan as informed peer 0/10 Book Promotion: How to Be a Capitalist Without Any Capital Nathan delivers a solo promotional monologue for his book and introduces the background of Olark.2:10–5:45 · Nathan as informed peer 4/10 Introducing Ben Congleton and Olark's Core Value Proposition Ben describes Olark's inception as a side project during his PhD and discusses raising a negligible $85k.5:45–8:56 · Nathan as informed peer 6/10 Customer Count Milestones and Financial Privacy Debate Nathan calculates estimated monthly revenue of $1.2M and repeatedly pushes for updated metrics, but Ben stonewalls with 'no comment'.8:57–13:37 · Nathan as informed peer 4/10 Structuring the Executive Search for a Head of Marketing Ben outlines his company's remote executive hiring framework, including paying candidates to complete practical homework assignments.13:37–19:37 · Nathan as informed peer 8/10 Platform Risks: When Integration Partners Become Competitors Nathan benchmarks churn metrics using data from over 3,000 SaaS founder interviews, while Ben defends predictable pricing over VC-driven usage tiers.0:00–2:10 · Guest teaching 0/10 Book Promotion: How to Be a Capitalist Without Any Capital Nathan delivers a solo promotional monologue for his book and introduces the background of Olark.2:10–5:45 · Guest teaching 2/10 Introducing Ben Congleton and Olark's Core Value Proposition Ben describes Olark's inception as a side project during his PhD and discusses raising a negligible $85k.5:45–8:56 · Guest teaching 2/10 Customer Count Milestones and Financial Privacy Debate Nathan calculates estimated monthly revenue of $1.2M and repeatedly pushes for updated metrics, but Ben stonewalls with 'no comment'.8:57–13:37 · Guest teaching 4/10 Structuring the Executive Search for a Head of Marketing Ben outlines his company's remote executive hiring framework, including paying candidates to complete practical homework assignments.13:37–19:37 · Guest teaching 6/10 Platform Risks: When Integration Partners Become Competitors Nathan benchmarks churn metrics using data from over 3,000 SaaS founder interviews, while Ben defends predictable pricing over VC-driven usage tiers.0:00–2:10 · Guest disagreement 0/10 Book Promotion: How to Be a Capitalist Without Any Capital Nathan delivers a solo promotional monologue for his book and introduces the background of Olark.2:10–5:45 · Guest disagreement 1/10 Introducing Ben Congleton and Olark's Core Value Proposition Ben describes Olark's inception as a side project during his PhD and discusses raising a negligible $85k.5:45–8:56 · Guest disagreement 6/10 Customer Count Milestones and Financial Privacy Debate Nathan calculates estimated monthly revenue of $1.2M and repeatedly pushes for updated metrics, but Ben stonewalls with 'no comment'.8:57–13:37 · Guest disagreement 1/10 Structuring the Executive Search for a Head of Marketing Ben outlines his company's remote executive hiring framework, including paying candidates to complete practical homework assignments.13:37–19:37 · Guest disagreement 4/10 Platform Risks: When Integration Partners Become Competitors Nathan benchmarks churn metrics using data from over 3,000 SaaS founder interviews, while Ben defends predictable pricing over VC-driven usage tiers.0:00–2:10 · Nathan pushing back 0/10 Book Promotion: How to Be a Capitalist Without Any Capital Nathan delivers a solo promotional monologue for his book and introduces the background of Olark.2:10–5:45 · Nathan pushing back 1/10 Introducing Ben Congleton and Olark's Core Value Proposition Ben describes Olark's inception as a side project during his PhD and discusses raising a negligible $85k.5:45–8:56 · Nathan pushing back 7/10 Customer Count Milestones and Financial Privacy Debate Nathan calculates estimated monthly revenue of $1.2M and repeatedly pushes for updated metrics, but Ben stonewalls with 'no comment'.8:57–13:37 · Nathan pushing back 2/10 Structuring the Executive Search for a Head of Marketing Ben outlines his company's remote executive hiring framework, including paying candidates to complete practical homework assignments.13:37–19:37 · Nathan pushing back 6/10 Platform Risks: When Integration Partners Become Competitors Nathan benchmarks churn metrics using data from over 3,000 SaaS founder interviews, while Ben defends predictable pricing over VC-driven usage tiers.

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

0:00 · Nathan 86.5% · guest 13.5%0:00 · Nathan 86.5% · guest 13.5%3:00 · Nathan 25.3% · guest 74.7%3:00 · Nathan 25.3% · guest 74.7%6:00 · Nathan 40.3% · guest 59.7%6:00 · Nathan 40.3% · guest 59.7%9:00 · Nathan 12.7% · guest 87.3%9:00 · Nathan 12.7% · guest 87.3%12:00 · Nathan 25.9% · guest 74.1%12:00 · Nathan 25.9% · guest 74.1%15:00 · Nathan 23.4% · guest 76.6%15:00 · Nathan 23.4% · guest 76.6%18:00 · Nathan 38.3% · guest 61.7%18:00 · Nathan 38.3% · guest 61.7%21:00 · Nathan 43.1% · guest 56.9%21:00 · Nathan 43.1% · guest 56.9%
Sharpest disagreement ▶ 6:26 Ben stonewalls revenue and customer questions

Ben firmly cuts off Nathan's revenue estimation attempts with a direct 'no comment' and refuses to validate current customer numbers.

 Hardest push from Nathan ▶ 6:26 Nathan challenges Ben's refusal to discuss revenue

Nathan refuses to back off after Ben's deflection, emphasizing that he is only multiplying the numbers Ben already provided.

 Biggest teaching moment ▶ 14:00 Ben reveals platform risk with integration partners

Ben explains how Olark's top growth engine was dismantled when former marketing partners like HubSpot built their own competing chat tools.

 Nathan holds their own ▶ 16:54 Nathan asserts industry benchmarks from 3,000 SaaS interviews

Nathan demonstrates authority by citing data across thousands of SaaS company interviews to define standard logo churn and net revenue retention thresholds.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Book Promotion: How to Be a Capitalist Without Any Capital 0000 Nathan delivers a solo promotional monologue for his book and introduces the background of Olark.
Introducing Ben Congleton and Olark's Core Value Proposition 4211 Ben describes Olark's inception as a side project during his PhD and discusses raising a negligible $85k.
Customer Count Milestones and Financial Privacy Debate 6267 Nathan calculates estimated monthly revenue of $1.2M and repeatedly pushes for updated metrics, but Ben stonewalls with 'no comment'.
Structuring the Executive Search for a Head of Marketing 4412 Ben outlines his company's remote executive hiring framework, including paying candidates to complete practical homework assignments.
Platform Risks: When Integration Partners Become Competitors 8646 Nathan benchmarks churn metrics using data from over 3,000 SaaS founder interviews, while Ben defends predictable pricing over VC-driven usage tiers.

Statements from this episode (13)

Assertion Not checkable as stated
Olark B2B Clients Generate Over $5M Annually From Chat Leads
“If you're a B to B business, we have customers that have generated, you know, upwards of five million dollars a year from leads coming off of chat.”
Ben Congleton Jul 31, 2019 ▶ 3:03
Disclosure
Olark's Average Customer Pays Under $100 Per Month
“On average, a customer of ours pays us like, you know, in the range of, we'll say under a hundred bucks.”
Ben Congleton Jul 31, 2019 ▶ 3:20
Disclosure
Olark Raised Only $85,000 in Total Outside Capital
“Well, we raised 85 K total, so you can figure out whether that's bootstrapped or not, but I think for any modern company, that's nothing.”
Ben Congleton Jul 31, 2019 ▶ 4:06
Assertion Supported
Olark Passed 12,000 Customers at Its Last Public Milestone
“The public number I use is like over 12 K.”
Ben Congleton Jul 31, 2019 ▶ 5:52
Assertion Contradicted
Olark Created the First Floating Website Chat Box Widget
“And then over time because we are the first people who put this little floating chat box on the internet that created some virality. So like, you know, someone adds this to the site they see it's Olark and then they want it for their own site. Nowadays, that s…”
Ben Congleton Jul 31, 2019 ▶ 7:43
Insight
Powered-By Chat Widgets Drive More Viral Growth in B2B SaaS
“Like for example, if you're an e-commerce company, like we end up getting less customers that way. If we were, if you're a B to B SaaS company, you'd see more. I imagine that both drift and intercom have seen like similar growth sort of based on where they're …”
Ben Congleton Jul 31, 2019 ▶ 8:29
Disclosure
Olark Pays Executive Candidates to Complete Interview Homework Assignments
“We actually did something pretty interesting where we paid people to do homework. So we gave them a bunch of stats that were kind of made up numbers, but pretty close to our real numbers and said like, hey give us like what opportunities you see, what assumpti…”
Ben Congleton Jul 31, 2019 ▶ 11:33
Disclosure
Olark's Partner Marketing Channel Broke When Partners Built Native Chat
“Well, I think like historically, Olark had a very strong partner marketing channel. And what ended up happening is those partners started building chat. And so what we realized was that while that worked really well in the early days, it no longer works strate…”
Ben Congleton Jul 31, 2019 ▶ 14:00
Assertion Not checkable as stated
Almost Every Platform Offering Chat Today Was Once an Olark Partner
“Like basically anyone who has chat now was an Olark partner in the past.”
Ben Congleton Jul 31, 2019 ▶ 14:44
Opinion
Ben Congleton: Zendesk Hasn't Evolved Its Chat Product in Four Years
“Our chat is far superior to these bolt on chat products, like say HubSpot or, you know, Zendesk hasn't evolved their chat in like four years since they bought Zopim.”
Ben Congleton Jul 31, 2019 ▶ 14:53
Insight
Seat-Based Pricing Alone Cannot Drive SMB SaaS Expansion Revenue
“I don't think you can do it on pure seats. I think that was I think that's basically just a challenge of the SMB target. I think you need to have add-ons.”
Ben Congleton Jul 31, 2019 ▶ 17:29
Insight
Usage-Based Pricing Creates Unpredictable Software Costs for SMB Customers
“I think if you look at sort of some of the competitors pricing where people are charging like for usage based pricing, I mean, it's pretty interesting, but as a SMB, it makes your pricing like super unpredictable.”
Ben Congleton Jul 31, 2019 ▶ 17:42
Opinion
VC-Backed SaaS Competitors Must Hike Prices to Justify Valuations
“And I think also like, I'm not trying to maximize overall enterprise value. I think those guys have maximized overall enterprise value. They need that because they need to drive cost up significantly to justify their valuation, which I don't need to do.”
Ben Congleton Jul 31, 2019 ▶ 19:13
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