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Jan 4, 2020 · 17m · top-founders

1624 Why This Founder is Totally Happy Running 2 Businesses At Once

Jake Kring · 9m 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

Serial entrepreneur Jake Kring explains how he simultaneously operates Parrot QA, a lean SaaS functional testing tool, alongside Skylight, a multi-million-dollar e-commerce digital frame business. He outlines his customer acquisition metrics, the psychology of balancing multiple projects, and the advantages of bootstrapping over traditional venture capital.

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 39% of the talking time here. How this is scored →

Nathan as informed peer 5.8 Guest teaching 3.5 Guest disagreement 1.8 Nathan pushing back 3.0
05100:0010:000:53–3:33 · Nathan as informed peer 5/10 Parrot QA Product Mechanics and Pricing Model Nathan tests the product beforehand on getlatka.com and asks specific technical questions regarding SSL certificates and firewalls. Jake clarifies the difference between SSL and basic auth firewalls in a straightforward manner.3:33–6:29 · Nathan as informed peer 7/10 Scripted.com Acquisition and Jake's Transition from Xenon Nathan demonstrates deep inside knowledge of Scripted, Xenon Ventures, and Jonathan, even quoting recent revenue numbers and churn rates from Scripted's new CEO. Jake provides transparent context around his burnout and departure.6:30–11:21 · Nathan as informed peer 6/10 Comparing Skylight E-Commerce with Parrot QA Nathan presses Jake on why he is dividing his time and whether giant tech competitors like Amazon and Facebook will crush Skylight. Jake defends the e-commerce business by highlighting its niche focus on older non-tech-savvy demographics.11:22–15:47 · Nathan as informed peer 5/10 Customer Acquisition Economics and Team Structure Nathan analyzes the Facebook CAC and 10-12 month payback period for Parrot QA. Jake educates on VC-founder misalignment and corrects Nathan regarding Scripted's actual investors.0:53–3:33 · Guest teaching 3/10 Parrot QA Product Mechanics and Pricing Model Nathan tests the product beforehand on getlatka.com and asks specific technical questions regarding SSL certificates and firewalls. Jake clarifies the difference between SSL and basic auth firewalls in a straightforward manner.3:33–6:29 · Guest teaching 2/10 Scripted.com Acquisition and Jake's Transition from Xenon Nathan demonstrates deep inside knowledge of Scripted, Xenon Ventures, and Jonathan, even quoting recent revenue numbers and churn rates from Scripted's new CEO. Jake provides transparent context around his burnout and departure.6:30–11:21 · Guest teaching 4/10 Comparing Skylight E-Commerce with Parrot QA Nathan presses Jake on why he is dividing his time and whether giant tech competitors like Amazon and Facebook will crush Skylight. Jake defends the e-commerce business by highlighting its niche focus on older non-tech-savvy demographics.11:22–15:47 · Guest teaching 5/10 Customer Acquisition Economics and Team Structure Nathan analyzes the Facebook CAC and 10-12 month payback period for Parrot QA. Jake educates on VC-founder misalignment and corrects Nathan regarding Scripted's actual investors.0:53–3:33 · Guest disagreement 1/10 Parrot QA Product Mechanics and Pricing Model Nathan tests the product beforehand on getlatka.com and asks specific technical questions regarding SSL certificates and firewalls. Jake clarifies the difference between SSL and basic auth firewalls in a straightforward manner.3:33–6:29 · Guest disagreement 1/10 Scripted.com Acquisition and Jake's Transition from Xenon Nathan demonstrates deep inside knowledge of Scripted, Xenon Ventures, and Jonathan, even quoting recent revenue numbers and churn rates from Scripted's new CEO. Jake provides transparent context around his burnout and departure.6:30–11:21 · Guest disagreement 3/10 Comparing Skylight E-Commerce with Parrot QA Nathan presses Jake on why he is dividing his time and whether giant tech competitors like Amazon and Facebook will crush Skylight. Jake defends the e-commerce business by highlighting its niche focus on older non-tech-savvy demographics.11:22–15:47 · Guest disagreement 2/10 Customer Acquisition Economics and Team Structure Nathan analyzes the Facebook CAC and 10-12 month payback period for Parrot QA. Jake educates on VC-founder misalignment and corrects Nathan regarding Scripted's actual investors.0:53–3:33 · Nathan pushing back 2/10 Parrot QA Product Mechanics and Pricing Model Nathan tests the product beforehand on getlatka.com and asks specific technical questions regarding SSL certificates and firewalls. Jake clarifies the difference between SSL and basic auth firewalls in a straightforward manner.3:33–6:29 · Nathan pushing back 2/10 Scripted.com Acquisition and Jake's Transition from Xenon Nathan demonstrates deep inside knowledge of Scripted, Xenon Ventures, and Jonathan, even quoting recent revenue numbers and churn rates from Scripted's new CEO. Jake provides transparent context around his burnout and departure.6:30–11:21 · Nathan pushing back 5/10 Comparing Skylight E-Commerce with Parrot QA Nathan presses Jake on why he is dividing his time and whether giant tech competitors like Amazon and Facebook will crush Skylight. Jake defends the e-commerce business by highlighting its niche focus on older non-tech-savvy demographics.11:22–15:47 · Nathan pushing back 3/10 Customer Acquisition Economics and Team Structure Nathan analyzes the Facebook CAC and 10-12 month payback period for Parrot QA. Jake educates on VC-founder misalignment and corrects Nathan regarding Scripted's actual investors.

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

0:00 · Nathan 58.5% · guest 41.5%0:00 · Nathan 58.5% · guest 41.5%3:00 · Nathan 22.4% · guest 77.6%3:00 · Nathan 22.4% · guest 77.6%6:00 · Nathan 44.4% · guest 55.6%6:00 · Nathan 44.4% · guest 55.6%9:00 · Nathan 41.9% · guest 58.1%9:00 · Nathan 41.9% · guest 58.1%12:00 · Nathan 22.9% · guest 77.1%12:00 · Nathan 22.9% · guest 77.1%15:00 · Nathan 45.1% · guest 54.9%15:00 · Nathan 45.1% · guest 54.9%
Sharpest disagreement ▶ 8:44 Rejecting the big tech threat premise

Jake rejects Nathan's suggestion that Amazon and Facebook smart displays will crush Skylight by explaining his specific target audience.

 Hardest push from Nathan ▶ 8:00 Pressing on lack of focus

Nathan directly challenges Jake on why he lacks the confidence to go all in on a fast-growing QA SaaS market.

 Biggest teaching moment ▶ 14:10 Correcting VC assumptions and investor list

Jake corrects Nathan's guess about Bessemer/Andreessen funding by listing the actual investors and explaining how venture capital economics fail smaller profitable businesses.

 Nathan holds their own ▶ 6:04 Quoting Scripted post-acquisition metrics

Nathan demonstrates intimate industry expertise by citing Scripted's exact recent customer numbers, monthly revenue ($250k), and sub-2% churn.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Parrot QA Product Mechanics and Pricing Model 5312 Nathan tests the product beforehand on getlatka.com and asks specific technical questions regarding SSL certificates and firewalls. Jake clarifies the difference between SSL and basic auth firewalls in a straightforward manner.
Scripted.com Acquisition and Jake's Transition from Xenon 7212 Nathan demonstrates deep inside knowledge of Scripted, Xenon Ventures, and Jonathan, even quoting recent revenue numbers and churn rates from Scripted's new CEO. Jake provides transparent context around his burnout and departure.
Comparing Skylight E-Commerce with Parrot QA 6435 Nathan presses Jake on why he is dividing his time and whether giant tech competitors like Amazon and Facebook will crush Skylight. Jake defends the e-commerce business by highlighting its niche focus on older non-tech-savvy demographics.
Customer Acquisition Economics and Team Structure 5523 Nathan analyzes the Facebook CAC and 10-12 month payback period for Parrot QA. Jake educates on VC-founder misalignment and corrects Nathan regarding Scripted's actual investors.

Statements from this episode (8)

Disclosure
Parrot QA averages $100 monthly ARPU across two pricing tiers
“A hundred bucks is our average revenue per user. We have a 49 dollar tier and a one 99 tier, and we sort of split between those. And then we've got a sort of high touch model, but most are in the 49 to one 99.”
Jake Kring Jan 4, 2020 ▶ 1:43
Assertion Not checkable as stated
Scripted grew 2.5x and turned profitable in 2017
“I, we had a really good year in 2017. We grew it two and a half X. It got profitable under Xenon for really its first time in, in, in scripted history.”
Jake Kring Jan 4, 2020 ▶ 5:33
Assertion Not checkable as stated
Parrot QA currently has only five total customers
“Only five.”
Jake Kring Jan 4, 2020 ▶ 7:52
Insight
Strong e-commerce businesses achieve EBITDA margins between 30% and 40%
“Good e-commerce margins are in the 30 to 40 range.”
Jake Kring Jan 4, 2020 ▶ 10:08
Assertion Not checkable as stated
Parrot QA spends roughly $1,000 per customer acquired via Facebook ads
“Facebook largely is the acquisition channel. It cost me about a thousand dollars to acquire a customer on Facebook.”
Jake Kring Jan 4, 2020 ▶ 12:07
Insight
Founders and VCs rarely align on $5M to $10M exit outcomes
“It's actually fairly rare that entrepreneurs and VCs are totally aligned in that entrepreneurs can have great outcomes with five to ten million dollar businesses, and VCs can't, and that's not their model, and the second they get a whiff that something is movi…”
Jake Kring Jan 4, 2020 ▶ 14:26
Insight
Venture capital discards great businesses that do not fit unicorn molds
“There's a lot of great businesses that get, that are sort of the exhaust of the VC ecosystem that get left in the dust because they don't fit the unicorn mold. And that's too bad because a lot of that value gets lost.”
Jake Kring Jan 4, 2020 ▶ 15:00
Assertion Not checkable as stated
Skylight grew 3x in 2019 and projects double-digit millions in revenue
“We saw three X growth this year. If we do that again, I mean, this will be more than double digit million business and, you know, run by a few people.”
Jake Kring Jan 4, 2020 ▶ 15:32
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