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Jan 17, 2018 · 17m · top-founders

907 SaaS: How Proov Was Able to Raise $21m Pre Revenue

Toby Olshanetsky · 8m 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

Nathan Latka interviews Proov CEO Toby Olshanetsky on how the pilot-as-a-service platform raised $21.1 million pre-revenue, validated enterprise demand through free trial ecosystems, and transitioned into a high-growth SaaS business with $95,000 average contract values.

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 45% of the talking time here. How this is scored →

Nathan as informed peer 5.8 Guest teaching 2.0 Guest disagreement 2.2 Nathan pushing back 4.4
05100:0010:000:49–4:41 · Nathan as informed peer 6/10 Overview of Proov and Enterprise Pricing Model Nathan frames and summarizes Proov's value proposition and business model cleanly, clarifying ACV and testing grounds. The dynamic is respectful and collaborative.4:42–7:01 · Nathan as informed peer 4/10 Team Scaling and Coastal Israel Headquarters Nathan asks standard foundational questions about team size, location, and venture funding history, which Toby answers openly.7:01–9:55 · Nathan as informed peer 7/10 Platform Traction, Metrics, and Transition to Monetization Nathan sharply pushes back when Toby obfuscates the difference between free users and paying customers, demanding specific paying customer counts and calculating ARR on the spot.9:58–14:10 · Nathan as informed peer 7/10 Sponsor Break: ProsperWorks CRM Platform Solutions Includes a sponsor ad read and an intense exchange where Nathan rejects Toby's vague platitude ('give them the best service ever') and repeatedly clarifies that early users were non-paying.14:10–16:23 · Nathan as informed peer 5/10 Securing Venture Capital Backing via Free User Validation Nathan presses once more on whether due diligence involved paying vs free users before moving into the Famous Five rapid-fire questions and outro summary.0:49–4:41 · Guest teaching 3/10 Overview of Proov and Enterprise Pricing Model Nathan frames and summarizes Proov's value proposition and business model cleanly, clarifying ACV and testing grounds. The dynamic is respectful and collaborative.4:42–7:01 · Guest teaching 1/10 Team Scaling and Coastal Israel Headquarters Nathan asks standard foundational questions about team size, location, and venture funding history, which Toby answers openly.7:01–9:55 · Guest teaching 2/10 Platform Traction, Metrics, and Transition to Monetization Nathan sharply pushes back when Toby obfuscates the difference between free users and paying customers, demanding specific paying customer counts and calculating ARR on the spot.9:58–14:10 · Guest teaching 3/10 Sponsor Break: ProsperWorks CRM Platform Solutions Includes a sponsor ad read and an intense exchange where Nathan rejects Toby's vague platitude ('give them the best service ever') and repeatedly clarifies that early users were non-paying.14:10–16:23 · Guest teaching 1/10 Securing Venture Capital Backing via Free User Validation Nathan presses once more on whether due diligence involved paying vs free users before moving into the Famous Five rapid-fire questions and outro summary.0:49–4:41 · Guest disagreement 1/10 Overview of Proov and Enterprise Pricing Model Nathan frames and summarizes Proov's value proposition and business model cleanly, clarifying ACV and testing grounds. The dynamic is respectful and collaborative.4:42–7:01 · Guest disagreement 0/10 Team Scaling and Coastal Israel Headquarters Nathan asks standard foundational questions about team size, location, and venture funding history, which Toby answers openly.7:01–9:55 · Guest disagreement 4/10 Platform Traction, Metrics, and Transition to Monetization Nathan sharply pushes back when Toby obfuscates the difference between free users and paying customers, demanding specific paying customer counts and calculating ARR on the spot.9:58–14:10 · Guest disagreement 4/10 Sponsor Break: ProsperWorks CRM Platform Solutions Includes a sponsor ad read and an intense exchange where Nathan rejects Toby's vague platitude ('give them the best service ever') and repeatedly clarifies that early users were non-paying.14:10–16:23 · Guest disagreement 2/10 Securing Venture Capital Backing via Free User Validation Nathan presses once more on whether due diligence involved paying vs free users before moving into the Famous Five rapid-fire questions and outro summary.0:49–4:41 · Nathan pushing back 2/10 Overview of Proov and Enterprise Pricing Model Nathan frames and summarizes Proov's value proposition and business model cleanly, clarifying ACV and testing grounds. The dynamic is respectful and collaborative.4:42–7:01 · Nathan pushing back 1/10 Team Scaling and Coastal Israel Headquarters Nathan asks standard foundational questions about team size, location, and venture funding history, which Toby answers openly.7:01–9:55 · Nathan pushing back 7/10 Platform Traction, Metrics, and Transition to Monetization Nathan sharply pushes back when Toby obfuscates the difference between free users and paying customers, demanding specific paying customer counts and calculating ARR on the spot.9:58–14:10 · Nathan pushing back 7/10 Sponsor Break: ProsperWorks CRM Platform Solutions Includes a sponsor ad read and an intense exchange where Nathan rejects Toby's vague platitude ('give them the best service ever') and repeatedly clarifies that early users were non-paying.14:10–16:23 · Nathan pushing back 5/10 Securing Venture Capital Backing via Free User Validation Nathan presses once more on whether due diligence involved paying vs free users before moving into the Famous Five rapid-fire questions and outro summary.

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

0:00 · Nathan 47.3% · guest 52.7%0:00 · Nathan 47.3% · guest 52.7%3:00 · Nathan 21.5% · guest 78.5%3:00 · Nathan 21.5% · guest 78.5%6:00 · Nathan 35.5% · guest 64.5%6:00 · Nathan 35.5% · guest 64.5%9:00 · Nathan 73% · guest 27%9:00 · Nathan 73% · guest 27%12:00 · Nathan 33.1% · guest 66.9%12:00 · Nathan 33.1% · guest 66.9%15:00 · Nathan 65.8% · guest 34.2%15:00 · Nathan 65.8% · guest 34.2%
Sharpest disagreement ▶ 8:33 Toby deflects specific customer count and ARR math

Toby repeatedly counters Nathan's precise calculations with 'You said that, not me' rather than confirming hard ARR figures.

 Hardest push from Nathan ▶ 12:34 Nathan rejects generic 'best service' answer

Nathan cuts through Toby's vague response demanding concrete engineering metrics for user stickiness instead of fluff.

 Biggest teaching moment ▶ 2:18 Toby explains enterprise global testing legwork

Toby educates Nathan on the global enterprise pain point discovered after interviewing 170 companies across multiple continents.

 Nathan holds their own ▶ 8:11 Nathan corners Toby on paying versus free enterprise users

Nathan refuses to let Toby count 125 free platform enterprises as paying customers, pinning down the real paid figure to 'tens'.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Overview of Proov and Enterprise Pricing Model 6312 Nathan frames and summarizes Proov's value proposition and business model cleanly, clarifying ACV and testing grounds. The dynamic is respectful and collaborative.
Team Scaling and Coastal Israel Headquarters 4101 Nathan asks standard foundational questions about team size, location, and venture funding history, which Toby answers openly.
Platform Traction, Metrics, and Transition to Monetization 7247 Nathan sharply pushes back when Toby obfuscates the difference between free users and paying customers, demanding specific paying customer counts and calculating ARR on the spot.
Sponsor Break: ProsperWorks CRM Platform Solutions 7347 Includes a sponsor ad read and an intense exchange where Nathan rejects Toby's vague platitude ('give them the best service ever') and repeatedly clarifies that early users were non-paying.
Securing Venture Capital Backing via Free User Validation 5125 Nathan presses once more on whether due diligence involved paying vs free users before moving into the Famous Five rapid-fire questions and outro summary.

Statements from this episode (12)

Assertion Not checkable as stated
Olshanetsky: Proov Charges Enterprises Tens to Hundreds of Thousands Annually
“The enterprises are paying us between 10,010 of thousands of US dollars up to hundreds of thousands of US dollars.”
Toby Olshanetsky Jan 17, 2018 ▶ 1:44
Assertion Not checkable as stated
Olshanetsky: Proov Average Annual Contract Value Is $95,000
“95.”
Toby Olshanetsky Jan 17, 2018 ▶ 2:10
Disclosure
Olshanetsky: Proov has scaled to over 40 employees
“We are 40 something.”
Toby Olshanetsky Jan 17, 2018 ▶ 4:48
Assertion Supported
Olshanetsky: Proov Has Raised $21.1 Million in Total Venture Funding
“21.1.”
Toby Olshanetsky Jan 17, 2018 ▶ 6:08
Assertion Not checkable as stated
Olshanetsky: Proov hosts 125 enterprises and rejected two-thirds of 3,500 startup applicants
“We have a 125 enterprises on the platform, and again, it's a growing on a daily basis. We have a thousand and something, thousand and chain startups out of 3500 startups that requested to apply to prove. So you can see that almost two third of the vendors that…”
Toby Olshanetsky Jan 17, 2018 ▶ 7:06
Disclosure
Proov Launched Paid Monetization for the First Time in January 2018
“We just actually, you know, congratulations to us. We just opened the monetization this month.”
Toby Olshanetsky Jan 17, 2018 ▶ 7:49
Assertion Not checkable as stated
Olshanetsky: Proov has between 10 and 100 paying enterprise customers
“Tens of enterprises. Tens of enterprises. It's more than a 10.”
Toby Olshanetsky Jan 17, 2018 ▶ 8:27
Assertion Not checkable as stated
Olshanetsky: 15% of Proov's team is sales and marketing
“Well, the majority of the company still is R&D. I would say about 15% of the team is sales and marketing.”
Toby Olshanetsky Jan 17, 2018 ▶ 11:36
Disclosure
Olshanetsky: Proov is hiring 15 salespeople
“And we are hiring like crazy. I'm hiring right now, 15 salespeople.”
Toby Olshanetsky Jan 17, 2018 ▶ 11:45
Assertion Not checkable as stated
Olshanetsky: Proov conducted 170 customer interviews before coding
“When we build the company. We did this 170 interviews. To understand the pain. And that was before we started coding. And then we did our MVP. Then we launched a semi alpha pre beta again with 10 customers to understand if we understood correctly the pain. The…”
Toby Olshanetsky Jan 17, 2018 ▶ 13:27
Disclosure
Proov Raised $21M Pre-Revenue by Having Investors Interview Free Users
“And our investors, when they did the due diligence, they want to speak with customers and we gave them a very big customer list and they spoke with them and they understood how, you know, all the pains that we are solving them and how much money we are saving …”
Toby Olshanetsky Jan 17, 2018 ▶ 14:35
Assertion Supported
Olshanetsky: Proov is my seventh startup
“If, well, this is my seven startups.”
Toby Olshanetsky Jan 17, 2018 ▶ 15:52
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