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Mar 28, 2021 · 16m · top-founders

He Quit His Fulltime Gig for $5k/mo Side Project, What He's Doing Now

John Stern · 9m spoken Nathan Latka · 5m spoken Frank Bien · 4s spoken Eric Yuan · 4s spoken Vivek Bhaskaran · 2s spoken
0:00 / 0:00

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Nathan Latka interviews Ringpin co-founder John Stern about pivoting an omnichannel communication codebase into an enterprise physical-to-digital engagement platform. Stern discusses the realities of bootstrapping, API-led distribution partnerships, pricing models, and preparation for a multi-million-dollar venture capital round.

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 33.9% of the talking time here. How this is scored →

Nathan as informed peer 4.5 Guest teaching 2.8 Guest disagreement 1.7 Nathan pushing back 3.5
05100:0010:001:35–3:36 · Nathan as informed peer 4/10 Introducing John Stern and Ringpin Physical-to-Digital Platform Nathan introduces John and asks for concrete customer examples to explain Ringpin's physical-to-digital value proposition. John explains their use cases across retail and pizza shops, detailing how his early IT consulting background informed the SaaS product.3:37–6:51 · Nathan as informed peer 5/10 Ringpin Software Pricing and Enterprise Expansion Strategy Nathan drills into pricing tiers, contract sizes, and expansion revenue potential. John clarifies their starting price point of $2k per month and explains how watching QR code adoption in international markets prompted their pivot during the pandemic.6:51–9:32 · Nathan as informed peer 5/10 Scaling Distribution Through Postal.io and API Partnerships Nathan probes how Ringpin structures channel partnerships with Postal.io, questioning whether customers see Ringpin's branding or a white-label interface. Nathan pushes back when John's stated $2,000 per month rate conflicts with partner revenue-share economics.9:33–12:00 · Nathan as informed peer 5/10 Pivoting from Contact Center Software to Enterprise Experiences Nathan attempts to extrapolate Ringpin's top-line revenue by multiplying 45 customers by $2,000 to get $80k per month. John immediately rejects the premise, clarifying that legacy contact-center customers pay far less and current monthly revenue is under $5,000.12:01–14:41 · Nathan as informed peer 5/10 Interactive Video Partnerships and Developer-Led Growth Strategy Nathan identifies competitors like Drift and Intercom when analyzing Ringpin's video widgets and directly asks how the founders survive on under $5k MRR. John candidly explains the personal financial strain of bootstrapping and plans for a future $3M to $5M seed round.14:41–16:34 · Nathan as informed peer 3/10 The Famous Five Questions and Final Thoughts Nathan runs through his standard Famous Five rapid-fire questions covering favorite tools, CEO role models, sleep habits, and advice to John's younger self, before summarizing the company metrics in the outro.1:35–3:36 · Guest teaching 3/10 Introducing John Stern and Ringpin Physical-to-Digital Platform Nathan introduces John and asks for concrete customer examples to explain Ringpin's physical-to-digital value proposition. John explains their use cases across retail and pizza shops, detailing how his early IT consulting background informed the SaaS product.3:37–6:51 · Guest teaching 3/10 Ringpin Software Pricing and Enterprise Expansion Strategy Nathan drills into pricing tiers, contract sizes, and expansion revenue potential. John clarifies their starting price point of $2k per month and explains how watching QR code adoption in international markets prompted their pivot during the pandemic.6:51–9:32 · Guest teaching 3/10 Scaling Distribution Through Postal.io and API Partnerships Nathan probes how Ringpin structures channel partnerships with Postal.io, questioning whether customers see Ringpin's branding or a white-label interface. Nathan pushes back when John's stated $2,000 per month rate conflicts with partner revenue-share economics.9:33–12:00 · Guest teaching 5/10 Pivoting from Contact Center Software to Enterprise Experiences Nathan attempts to extrapolate Ringpin's top-line revenue by multiplying 45 customers by $2,000 to get $80k per month. John immediately rejects the premise, clarifying that legacy contact-center customers pay far less and current monthly revenue is under $5,000.12:01–14:41 · Guest teaching 2/10 Interactive Video Partnerships and Developer-Led Growth Strategy Nathan identifies competitors like Drift and Intercom when analyzing Ringpin's video widgets and directly asks how the founders survive on under $5k MRR. John candidly explains the personal financial strain of bootstrapping and plans for a future $3M to $5M seed round.14:41–16:34 · Guest teaching 1/10 The Famous Five Questions and Final Thoughts Nathan runs through his standard Famous Five rapid-fire questions covering favorite tools, CEO role models, sleep habits, and advice to John's younger self, before summarizing the company metrics in the outro.1:35–3:36 · Guest disagreement 1/10 Introducing John Stern and Ringpin Physical-to-Digital Platform Nathan introduces John and asks for concrete customer examples to explain Ringpin's physical-to-digital value proposition. John explains their use cases across retail and pizza shops, detailing how his early IT consulting background informed the SaaS product.3:37–6:51 · Guest disagreement 2/10 Ringpin Software Pricing and Enterprise Expansion Strategy Nathan drills into pricing tiers, contract sizes, and expansion revenue potential. John clarifies their starting price point of $2k per month and explains how watching QR code adoption in international markets prompted their pivot during the pandemic.6:51–9:32 · Guest disagreement 2/10 Scaling Distribution Through Postal.io and API Partnerships Nathan probes how Ringpin structures channel partnerships with Postal.io, questioning whether customers see Ringpin's branding or a white-label interface. Nathan pushes back when John's stated $2,000 per month rate conflicts with partner revenue-share economics.9:33–12:00 · Guest disagreement 3/10 Pivoting from Contact Center Software to Enterprise Experiences Nathan attempts to extrapolate Ringpin's top-line revenue by multiplying 45 customers by $2,000 to get $80k per month. John immediately rejects the premise, clarifying that legacy contact-center customers pay far less and current monthly revenue is under $5,000.12:01–14:41 · Guest disagreement 1/10 Interactive Video Partnerships and Developer-Led Growth Strategy Nathan identifies competitors like Drift and Intercom when analyzing Ringpin's video widgets and directly asks how the founders survive on under $5k MRR. John candidly explains the personal financial strain of bootstrapping and plans for a future $3M to $5M seed round.14:41–16:34 · Guest disagreement 1/10 The Famous Five Questions and Final Thoughts Nathan runs through his standard Famous Five rapid-fire questions covering favorite tools, CEO role models, sleep habits, and advice to John's younger self, before summarizing the company metrics in the outro.1:35–3:36 · Nathan pushing back 2/10 Introducing John Stern and Ringpin Physical-to-Digital Platform Nathan introduces John and asks for concrete customer examples to explain Ringpin's physical-to-digital value proposition. John explains their use cases across retail and pizza shops, detailing how his early IT consulting background informed the SaaS product.3:37–6:51 · Nathan pushing back 3/10 Ringpin Software Pricing and Enterprise Expansion Strategy Nathan drills into pricing tiers, contract sizes, and expansion revenue potential. John clarifies their starting price point of $2k per month and explains how watching QR code adoption in international markets prompted their pivot during the pandemic.6:51–9:32 · Nathan pushing back 5/10 Scaling Distribution Through Postal.io and API Partnerships Nathan probes how Ringpin structures channel partnerships with Postal.io, questioning whether customers see Ringpin's branding or a white-label interface. Nathan pushes back when John's stated $2,000 per month rate conflicts with partner revenue-share economics.9:33–12:00 · Nathan pushing back 6/10 Pivoting from Contact Center Software to Enterprise Experiences Nathan attempts to extrapolate Ringpin's top-line revenue by multiplying 45 customers by $2,000 to get $80k per month. John immediately rejects the premise, clarifying that legacy contact-center customers pay far less and current monthly revenue is under $5,000.12:01–14:41 · Nathan pushing back 4/10 Interactive Video Partnerships and Developer-Led Growth Strategy Nathan identifies competitors like Drift and Intercom when analyzing Ringpin's video widgets and directly asks how the founders survive on under $5k MRR. John candidly explains the personal financial strain of bootstrapping and plans for a future $3M to $5M seed round.14:41–16:34 · Nathan pushing back 1/10 The Famous Five Questions and Final Thoughts Nathan runs through his standard Famous Five rapid-fire questions covering favorite tools, CEO role models, sleep habits, and advice to John's younger self, before summarizing the company metrics in the outro.

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

0:00 · Nathan 57.5% · guest 42.5%0:00 · Nathan 57.5% · guest 42.5%3:00 · Nathan 19.4% · guest 80.6%3:00 · Nathan 19.4% · guest 80.6%6:00 · Nathan 29.2% · guest 70.8%6:00 · Nathan 29.2% · guest 70.8%9:00 · Nathan 23.7% · guest 76.3%9:00 · Nathan 23.7% · guest 76.3%12:00 · Nathan 33.4% · guest 66.6%12:00 · Nathan 33.4% · guest 66.6%15:00 · Nathan 47.7% · guest 52.3%15:00 · Nathan 47.7% · guest 52.3%
Sharpest disagreement ▶ 11:24 Directly rejecting Nathan's revenue extrapolation

John firmly shuts down Nathan's attempt to multiply total customer count by the new $2k monthly price tier, clarifying their actual MRR is under $5k.

 Hardest push from Nathan ▶ 8:40 Nathan presses on inconsistent partner pricing claims

Nathan refuses to accept that direct customers and strategic API channel partners pay the exact same $2,000 baseline price, prompting John to admit partner economics are still being tested.

 Biggest teaching moment ▶ 11:24 Educating on legacy contract mix versus new pricing

John corrects Nathan's assumption about customer revenue by explaining that legacy contact center clients represent historical baggage rather than current $2k contract values.

 Nathan holds their own ▶ 12:00 Nathan spots third-party video integration technology

Nathan demonstrates industry domain knowledge by correctly identifying the underlying widget architecture and comparing it to market leaders like Drift and Intercom.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing John Stern and Ringpin Physical-to-Digital Platform 4312 Nathan introduces John and asks for concrete customer examples to explain Ringpin's physical-to-digital value proposition. John explains their use cases across retail and pizza shops, detailing how his early IT consulting background informed the SaaS product.
Ringpin Software Pricing and Enterprise Expansion Strategy 5323 Nathan drills into pricing tiers, contract sizes, and expansion revenue potential. John clarifies their starting price point of $2k per month and explains how watching QR code adoption in international markets prompted their pivot during the pandemic.
Scaling Distribution Through Postal.io and API Partnerships 5325 Nathan probes how Ringpin structures channel partnerships with Postal.io, questioning whether customers see Ringpin's branding or a white-label interface. Nathan pushes back when John's stated $2,000 per month rate conflicts with partner revenue-share economics.
Pivoting from Contact Center Software to Enterprise Experiences 5536 Nathan attempts to extrapolate Ringpin's top-line revenue by multiplying 45 customers by $2,000 to get $80k per month. John immediately rejects the premise, clarifying that legacy contact-center customers pay far less and current monthly revenue is under $5,000.
Interactive Video Partnerships and Developer-Led Growth Strategy 5214 Nathan identifies competitors like Drift and Intercom when analyzing Ringpin's video widgets and directly asks how the founders survive on under $5k MRR. John candidly explains the personal financial strain of bootstrapping and plans for a future $3M to $5M seed round.
The Famous Five Questions and Final Thoughts 3111 Nathan runs through his standard Famous Five rapid-fire questions covering favorite tools, CEO role models, sleep habits, and advice to John's younger self, before summarizing the company metrics in the outro.

Statements from this episode (8)

Assertion Not checkable as stated
Stern: Ringpin supports 40 Toronto pizza shops on packaging campaigns
“We support 40 pizza shops in Toronto and they use us on their mailers, on their boxes in order to get customers to re-engage, leave reviews, buy more pizzas, all that type of stuff.”
John Stern Mar 28, 2021 ▶ 2:38
Disclosure
Stern: Ringpin typically has a $2,000 monthly pricing minimum
“Typically we have a minimum of like 2000 a month, but it really depends because there's so many different ways that you can use our software.”
John Stern Mar 28, 2021 ▶ 4:15
Disclosure
Stern: Ringpin avoids the restaurant sector due to heavy competition
“We actually kind of have stayed out of the restaurant area a little bit just because there's so many people competing for that right now.”
John Stern Mar 28, 2021 ▶ 6:22
Disclosure
Stern: Ringpin Targets Enterprise Customers Over SMB and Mid-Market
“Now we're going after enterprise instead of, you know, small business and bin market.”
John Stern Mar 28, 2021 ▶ 10:50
Disclosure
Stern: Ringpin Has About 45 Total Customers and Seven on New Product
“If we include the old ones, you know, we have probably about 45, but on the new stuff we have about seven probably.”
John Stern Mar 28, 2021 ▶ 11:04
Disclosure
Stern: Ringpin Has Bootstrapped Without Outside Funding
“Yeah, we've bootstrapped.”
John Stern Mar 28, 2021 ▶ 11:15
Disclosure
Stern: Ringpin Generates Under $5,000 Per Month in Revenue
“We're below 5000 a month in revenue right now.”
John Stern Mar 28, 2021 ▶ 11:28
Disclosure
Stern: Ringpin aims to raise $3M to $5M in upcoming round
“Probably three to five million.”
John Stern Mar 28, 2021 ▶ 14:19
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