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Aug 29, 2021 · 16m · top-founders

Webboss Raised $500k on $1m Vlauation in 2015. Where are they now?

Kev Wilson · 7m spoken Nathan Latka · 6m spoken Eric Yuan · 4s 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 with Nathan Latka, Webboss founder Kev Wilson discusses the challenges of scaling his all-in-one CMS platform, managing a revenue model split between recurring SaaS and custom agency services, and navigating future fundraising and distribution strategies.

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 47.1% of the talking time here. How this is scored →

Nathan as informed peer 5.5 Guest teaching 1.8 Guest disagreement 2.8 Nathan pushing back 5.0
05100:0010:003:08–5:58 · Nathan as informed peer 6/10 Referral Partnerships and Services vs. SaaS Revenue Latka drills down into the company's financial model, actively untangling Kev's confused reporting of monthly versus annualized numbers and separating pure SaaS revenue from custom services.5:59–8:21 · Nathan as informed peer 5/10 Fundraising Ambitions, Team Size, and Low Churn Latka questions Kev's valuation targets of 5 to 6 million on flat revenues, while probing the team composition, low churn dynamics, and design switching architecture.8:24–14:47 · Nathan as informed peer 8/10 Sponsor Break: Remote.com HR and Payroll Platform Following the sponsor break, Latka strongly pushes back against Kev's reliance on AppSumo lifetime deals, warning that deal seekers overwhelm support channels and destroy SaaS unit economics. Kev actively pushes back, arguing developers will purchase subsequent sites at standard rates.14:48–16:44 · Nathan as informed peer 3/10 Famous Five Rapid Fire and Episode Conclusion In the Famous Five segment, Kev deflects several questions including tools and his age, before candidly acknowledging missteps in his initial investment structuring.3:08–5:58 · Guest teaching 2/10 Referral Partnerships and Services vs. SaaS Revenue Latka drills down into the company's financial model, actively untangling Kev's confused reporting of monthly versus annualized numbers and separating pure SaaS revenue from custom services.5:59–8:21 · Guest teaching 2/10 Fundraising Ambitions, Team Size, and Low Churn Latka questions Kev's valuation targets of 5 to 6 million on flat revenues, while probing the team composition, low churn dynamics, and design switching architecture.8:24–14:47 · Guest teaching 2/10 Sponsor Break: Remote.com HR and Payroll Platform Following the sponsor break, Latka strongly pushes back against Kev's reliance on AppSumo lifetime deals, warning that deal seekers overwhelm support channels and destroy SaaS unit economics. Kev actively pushes back, arguing developers will purchase subsequent sites at standard rates.14:48–16:44 · Guest teaching 1/10 Famous Five Rapid Fire and Episode Conclusion In the Famous Five segment, Kev deflects several questions including tools and his age, before candidly acknowledging missteps in his initial investment structuring.3:08–5:58 · Guest disagreement 1/10 Referral Partnerships and Services vs. SaaS Revenue Latka drills down into the company's financial model, actively untangling Kev's confused reporting of monthly versus annualized numbers and separating pure SaaS revenue from custom services.5:59–8:21 · Guest disagreement 2/10 Fundraising Ambitions, Team Size, and Low Churn Latka questions Kev's valuation targets of 5 to 6 million on flat revenues, while probing the team composition, low churn dynamics, and design switching architecture.8:24–14:47 · Guest disagreement 5/10 Sponsor Break: Remote.com HR and Payroll Platform Following the sponsor break, Latka strongly pushes back against Kev's reliance on AppSumo lifetime deals, warning that deal seekers overwhelm support channels and destroy SaaS unit economics. Kev actively pushes back, arguing developers will purchase subsequent sites at standard rates.14:48–16:44 · Guest disagreement 3/10 Famous Five Rapid Fire and Episode Conclusion In the Famous Five segment, Kev deflects several questions including tools and his age, before candidly acknowledging missteps in his initial investment structuring.3:08–5:58 · Nathan pushing back 5/10 Referral Partnerships and Services vs. SaaS Revenue Latka drills down into the company's financial model, actively untangling Kev's confused reporting of monthly versus annualized numbers and separating pure SaaS revenue from custom services.5:59–8:21 · Nathan pushing back 4/10 Fundraising Ambitions, Team Size, and Low Churn Latka questions Kev's valuation targets of 5 to 6 million on flat revenues, while probing the team composition, low churn dynamics, and design switching architecture.8:24–14:47 · Nathan pushing back 8/10 Sponsor Break: Remote.com HR and Payroll Platform Following the sponsor break, Latka strongly pushes back against Kev's reliance on AppSumo lifetime deals, warning that deal seekers overwhelm support channels and destroy SaaS unit economics. Kev actively pushes back, arguing developers will purchase subsequent sites at standard rates.14:48–16:44 · Nathan pushing back 3/10 Famous Five Rapid Fire and Episode Conclusion In the Famous Five segment, Kev deflects several questions including tools and his age, before candidly acknowledging missteps in his initial investment structuring.

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

0:00 · Nathan 67% · guest 33%0:00 · Nathan 67% · guest 33%3:00 · Nathan 30.8% · guest 69.2%3:00 · Nathan 30.8% · guest 69.2%6:00 · Nathan 46% · guest 54%6:00 · Nathan 46% · guest 54%9:00 · Nathan 54.8% · guest 45.2%9:00 · Nathan 54.8% · guest 45.2%12:00 · Nathan 36.7% · guest 63.3%12:00 · Nathan 36.7% · guest 63.3%15:00 · Nathan 46.3% · guest 53.7%15:00 · Nathan 46.3% · guest 53.7%
Sharpest disagreement ▶ 12:37 Kev defends AppSumo conversion potential

Kev firmly rejects Latka's categorization of AppSumo buyers, insisting that developers who buy the tool will inevitably pay full price for subsequent client builds.

 Hardest push from Nathan ▶ 11:36 Latka warns against the AppSumo cash drug

Latka forcefully rejects the premise that lifetime deals provide durable growth, detailing how bargain hunters consume costly support bandwidth without converting to MRR.

 Biggest teaching moment ▶ 7:13 Kev explains modular design switching

Kev educates Latka on why WebBoss achieves near-zero churn, explaining their unique modular architecture that allows instant seasonal site redeployments without rebuilding content.

 Nathan holds their own ▶ 12:23 Latka compares AppSumo buyers to JCPenney discount shoppers

Latka leverages industry case studies to explain SaaS consumer psychology, highlighting why bargain hunters rarely convert to ongoing monthly subscriptions.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Referral Partnerships and Services vs. SaaS Revenue 6215 Latka drills down into the company's financial model, actively untangling Kev's confused reporting of monthly versus annualized numbers and separating pure SaaS revenue from custom services.
Fundraising Ambitions, Team Size, and Low Churn 5224 Latka questions Kev's valuation targets of 5 to 6 million on flat revenues, while probing the team composition, low churn dynamics, and design switching architecture.
Sponsor Break: Remote.com HR and Payroll Platform 8258 Following the sponsor break, Latka strongly pushes back against Kev's reliance on AppSumo lifetime deals, warning that deal seekers overwhelm support channels and destroy SaaS unit economics. Kev actively pushes back, arguing developers will purchase subsequent sites at standard rates.
Famous Five Rapid Fire and Episode Conclusion 3133 In the Famous Five segment, Kev deflects several questions including tools and his age, before candidly acknowledging missteps in his initial investment structuring.

Statements from this episode (10)

Disclosure
Wilson: Webboss raised approximately $500,000
“About half a million dollars.”
Kev Wilson Aug 29, 2021 ▶ 2:39
Disclosure
Wilson: Webboss raised funding at a £1 million valuation
“Yeah, we did those just on a million pounds basis.”
Kev Wilson Aug 29, 2021 ▶ 2:56
Assertion Not checkable as stated
Wilson says Webboss monthly revenue grew from $5,000 to $20,000
“We're doing now, trying to think back then, it's, we're doing around about 20,000 a month now. And back then it's probably about five or six I would say.”
Kev Wilson Aug 29, 2021 ▶ 4:09
Disclosure
Wilson: Webboss built an exclusive white-label platform for Ryman
“We've got a new, another company we've just started working with, Ryman. They're the biggest stationers in the UK, got 220 stores. And we've just done a white label version of the product for them. So that's an exclusive.”
Kev Wilson Aug 29, 2021 ▶ 4:56
Disclosure
Wilson: Webboss targets a $5M to $6M valuation for its next fundraise
“I'm looking at five to six.”
Kev Wilson Aug 29, 2021 ▶ 6:18
Assertion Not checkable as stated
Wilson: Customer churn at Webboss is virtually nil
“It's virtually nil.”
Kev Wilson Aug 29, 2021 ▶ 7:14
Disclosure
Wilson: Co-founders own just over half of Webboss equity
“Me and Luke are going just over half of the company.”
Kev Wilson Aug 29, 2021 ▶ 8:15
Assertion Supported
Latka: Many SaaS Companies Running AppSumo Deals Go Out of Business
“There's many SaaS companies, by the way, that have done AppSumo deals That have gone out of business.”
Nathan Latka Aug 29, 2021 ▶ 13:20
Opinion
Wilson claims Webboss is more sophisticated natively than WordPress
“I mean, our, I mean, our system does much more than WordPress. I mean, if you get WordPress is a page editor, isn't it? A lot of plugins and other people have made web bosses, a very sophisticated page editor with all the plugins you need already built into it…”
Kev Wilson Aug 29, 2021 ▶ 14:04
Assertion Not checkable as stated
Latka: WebBoss is flat at $20k monthly revenue with 200+ customers
“They were doing 20,000 dollars a month about a year ago. Still doing about 20,000 dollars a month because of COVID. They've been flat, but they've got over 200 customers. They're about breaking today with a team of four.”
Nathan Latka Aug 29, 2021 ▶ 16:33
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