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Sep 25, 2020 · 44m · mad

Fireside Chat: David Cancel (Founder & CEO, Drift) with Matt Turck (Partner, FirstMark)

David Cancel · 32m spoken Matt Turck · 6m spoken
0:00 / 0:00
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In this Data Driven NYC fireside chat, host Matt Turck interviews Drift Founder and CEO David Cancel about his journey as a serial entrepreneur, the evolution of conversational AI, and how Drift is transforming B2B sales and marketing. Cancel shares strategic insights on category creation, enterprise automation, customer-centric company culture, and the acceleration of digital transformation.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Matt holds 15.5% of the talking time here. How this is scored →

Matt as informed peer 3.5 Guest teaching 3.5 Guest disagreement 1.9 Matt pushing back 0.8
05100:0015:0030:000:33–7:08 · Matt as informed peer 4/10 David Cancel's Founder Journey and Career Background Matt demonstrates strong preparation by citing exact funding figures, company stats, and specific previous ventures like Performable. David gently reframes his college exit as fading away rather than dropping out, but the interaction remains warm and collaborative.7:08–14:32 · Matt as informed peer 4/10 Drift's Conversational Live Chat and Enterprise Routing Matt asks informed questions about enterprise routing, Account-Based Marketing targeting, and Drift's multi-product architecture. David educates the host on how traditional batch CRMs fail real-time routing needs, requiring Drift to build an ad-server style routing engine.14:32–19:45 · Matt as informed peer 4/10 Conversational AI, Machine Learning Chatbots, and AI Designers Matt probes into the mechanics of AI designers and network data effects across customers. David challenges prevailing enterprise software tropes, arguing that customers care about outcomes and experiences rather than underlying AI specs.19:45–25:02 · Matt as informed peer 4/10 Future of Software Automation and Rethinking Traditional CRMs Matt asks if Drift aims to become the central system of record or complement existing stacks. David aggressively criticizes current B2B software stacks and traditional CRMs, calling manual data entry ledger systems insane and non-viable long term.25:02–28:30 · Matt as informed peer 4/10 Conversational Email and Automatic Contact Data Capture Matt demonstrates awareness of Drift's email signature contact parsing features. David explains how standard marketing emails brokenly operate as one-way blasts and how Drift converts them into two-way conversational routing.28:30–32:25 · Matt as informed peer 3/10 Red Ocean Strategy, Category Creation, and Global Branding Matt asks about positioning and category creation in a noisy market. David pushes back on classic Blue Ocean strategy dogma, asserting that markets without competitors usually aren't real markets and explaining why entering red oceans with a paradigm shift is superior.32:25–36:27 · Matt as informed peer 3/10 Monetization Evolution, High-Velocity Inside Sales, and Pandemic Impact Matt prompts David on go-to-market transitions from freemium to enterprise. David details high-velocity inside sales and describes how the pandemic permanently accelerated enterprise digital transformation by ten years.36:27–44:46 · Matt as informed peer 2/10 Audience Q&A on Product Roadmap, Culture, COVID-19, and B2C Matt and moderator Jack facilitate audience Q&A covering culture, implementation speeds, and B2C use cases. David offers insights into Drift's core philosophy that every internal product idea is fundamentally wrong until validated by customer feedback.0:33–7:08 · Guest teaching 2/10 David Cancel's Founder Journey and Career Background Matt demonstrates strong preparation by citing exact funding figures, company stats, and specific previous ventures like Performable. David gently reframes his college exit as fading away rather than dropping out, but the interaction remains warm and collaborative.7:08–14:32 · Guest teaching 3/10 Drift's Conversational Live Chat and Enterprise Routing Matt asks informed questions about enterprise routing, Account-Based Marketing targeting, and Drift's multi-product architecture. David educates the host on how traditional batch CRMs fail real-time routing needs, requiring Drift to build an ad-server style routing engine.14:32–19:45 · Guest teaching 4/10 Conversational AI, Machine Learning Chatbots, and AI Designers Matt probes into the mechanics of AI designers and network data effects across customers. David challenges prevailing enterprise software tropes, arguing that customers care about outcomes and experiences rather than underlying AI specs.19:45–25:02 · Guest teaching 5/10 Future of Software Automation and Rethinking Traditional CRMs Matt asks if Drift aims to become the central system of record or complement existing stacks. David aggressively criticizes current B2B software stacks and traditional CRMs, calling manual data entry ledger systems insane and non-viable long term.25:02–28:30 · Guest teaching 3/10 Conversational Email and Automatic Contact Data Capture Matt demonstrates awareness of Drift's email signature contact parsing features. David explains how standard marketing emails brokenly operate as one-way blasts and how Drift converts them into two-way conversational routing.28:30–32:25 · Guest teaching 5/10 Red Ocean Strategy, Category Creation, and Global Branding Matt asks about positioning and category creation in a noisy market. David pushes back on classic Blue Ocean strategy dogma, asserting that markets without competitors usually aren't real markets and explaining why entering red oceans with a paradigm shift is superior.32:25–36:27 · Guest teaching 3/10 Monetization Evolution, High-Velocity Inside Sales, and Pandemic Impact Matt prompts David on go-to-market transitions from freemium to enterprise. David details high-velocity inside sales and describes how the pandemic permanently accelerated enterprise digital transformation by ten years.36:27–44:46 · Guest teaching 3/10 Audience Q&A on Product Roadmap, Culture, COVID-19, and B2C Matt and moderator Jack facilitate audience Q&A covering culture, implementation speeds, and B2C use cases. David offers insights into Drift's core philosophy that every internal product idea is fundamentally wrong until validated by customer feedback.0:33–7:08 · Guest disagreement 1/10 David Cancel's Founder Journey and Career Background Matt demonstrates strong preparation by citing exact funding figures, company stats, and specific previous ventures like Performable. David gently reframes his college exit as fading away rather than dropping out, but the interaction remains warm and collaborative.7:08–14:32 · Guest disagreement 1/10 Drift's Conversational Live Chat and Enterprise Routing Matt asks informed questions about enterprise routing, Account-Based Marketing targeting, and Drift's multi-product architecture. David educates the host on how traditional batch CRMs fail real-time routing needs, requiring Drift to build an ad-server style routing engine.14:32–19:45 · Guest disagreement 3/10 Conversational AI, Machine Learning Chatbots, and AI Designers Matt probes into the mechanics of AI designers and network data effects across customers. David challenges prevailing enterprise software tropes, arguing that customers care about outcomes and experiences rather than underlying AI specs.19:45–25:02 · Guest disagreement 4/10 Future of Software Automation and Rethinking Traditional CRMs Matt asks if Drift aims to become the central system of record or complement existing stacks. David aggressively criticizes current B2B software stacks and traditional CRMs, calling manual data entry ledger systems insane and non-viable long term.25:02–28:30 · Guest disagreement 1/10 Conversational Email and Automatic Contact Data Capture Matt demonstrates awareness of Drift's email signature contact parsing features. David explains how standard marketing emails brokenly operate as one-way blasts and how Drift converts them into two-way conversational routing.28:30–32:25 · Guest disagreement 3/10 Red Ocean Strategy, Category Creation, and Global Branding Matt asks about positioning and category creation in a noisy market. David pushes back on classic Blue Ocean strategy dogma, asserting that markets without competitors usually aren't real markets and explaining why entering red oceans with a paradigm shift is superior.32:25–36:27 · Guest disagreement 1/10 Monetization Evolution, High-Velocity Inside Sales, and Pandemic Impact Matt prompts David on go-to-market transitions from freemium to enterprise. David details high-velocity inside sales and describes how the pandemic permanently accelerated enterprise digital transformation by ten years.36:27–44:46 · Guest disagreement 1/10 Audience Q&A on Product Roadmap, Culture, COVID-19, and B2C Matt and moderator Jack facilitate audience Q&A covering culture, implementation speeds, and B2C use cases. David offers insights into Drift's core philosophy that every internal product idea is fundamentally wrong until validated by customer feedback.0:33–7:08 · Matt pushing back 1/10 David Cancel's Founder Journey and Career Background Matt demonstrates strong preparation by citing exact funding figures, company stats, and specific previous ventures like Performable. David gently reframes his college exit as fading away rather than dropping out, but the interaction remains warm and collaborative.7:08–14:32 · Matt pushing back 1/10 Drift's Conversational Live Chat and Enterprise Routing Matt asks informed questions about enterprise routing, Account-Based Marketing targeting, and Drift's multi-product architecture. David educates the host on how traditional batch CRMs fail real-time routing needs, requiring Drift to build an ad-server style routing engine.14:32–19:45 · Matt pushing back 1/10 Conversational AI, Machine Learning Chatbots, and AI Designers Matt probes into the mechanics of AI designers and network data effects across customers. David challenges prevailing enterprise software tropes, arguing that customers care about outcomes and experiences rather than underlying AI specs.19:45–25:02 · Matt pushing back 1/10 Future of Software Automation and Rethinking Traditional CRMs Matt asks if Drift aims to become the central system of record or complement existing stacks. David aggressively criticizes current B2B software stacks and traditional CRMs, calling manual data entry ledger systems insane and non-viable long term.25:02–28:30 · Matt pushing back 0/10 Conversational Email and Automatic Contact Data Capture Matt demonstrates awareness of Drift's email signature contact parsing features. David explains how standard marketing emails brokenly operate as one-way blasts and how Drift converts them into two-way conversational routing.28:30–32:25 · Matt pushing back 1/10 Red Ocean Strategy, Category Creation, and Global Branding Matt asks about positioning and category creation in a noisy market. David pushes back on classic Blue Ocean strategy dogma, asserting that markets without competitors usually aren't real markets and explaining why entering red oceans with a paradigm shift is superior.32:25–36:27 · Matt pushing back 1/10 Monetization Evolution, High-Velocity Inside Sales, and Pandemic Impact Matt prompts David on go-to-market transitions from freemium to enterprise. David details high-velocity inside sales and describes how the pandemic permanently accelerated enterprise digital transformation by ten years.36:27–44:46 · Matt pushing back 0/10 Audience Q&A on Product Roadmap, Culture, COVID-19, and B2C Matt and moderator Jack facilitate audience Q&A covering culture, implementation speeds, and B2C use cases. David offers insights into Drift's core philosophy that every internal product idea is fundamentally wrong until validated by customer feedback.

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

0:00 · Matt 66.3% · guest 33.7%0:00 · Matt 66.3% · guest 33.7%3:00 · Matt 9.8% · guest 90.2%3:00 · Matt 9.8% · guest 90.2%6:00 · Matt 32.2% · guest 67.8%6:00 · Matt 32.2% · guest 67.8%9:00 · Matt 13.6% · guest 86.4%9:00 · Matt 13.6% · guest 86.4%12:00 · Matt 12.6% · guest 87.4%12:00 · Matt 12.6% · guest 87.4%15:00 · Matt 16.8% · guest 83.2%15:00 · Matt 16.8% · guest 83.2%18:00 · Matt 15.1% · guest 84.9%18:00 · Matt 15.1% · guest 84.9%21:00 · Matt 17.2% · guest 82.8%21:00 · Matt 17.2% · guest 82.8%24:00 · Matt 4% · guest 96%24:00 · Matt 4% · guest 96%27:00 · Matt 24.8% · guest 75.2%27:00 · Matt 24.8% · guest 75.2%30:00 · Matt 4.7% · guest 95.3%30:00 · Matt 4.7% · guest 95.3%33:00 · Matt 0.3% · guest 99.7%33:00 · Matt 0.3% · guest 99.7%36:00 · Matt 9.3% · guest 90.7%36:00 · Matt 9.3% · guest 90.7%39:00 · Matt 0% · guest 100%39:00 · Matt 0% · guest 100%42:00 · Matt 17% · guest 83%42:00 · Matt 17% · guest 83%
Sharpest disagreement ▶ 21:09 Rejection of 50-100 stitched software tools stack

David explicitly rejects standard enterprise software stack practices, stating directly that if someone believes stitching together 50 to 100 tools with Zapier is the future, they are mistaken.

 Hardest push from Matt ▶ 22:35 Probing system of record ambition

Matt presses David directly on whether Drift intends to replace existing enterprise systems to become the underlying system of record or if it is merely partnering.

 Biggest teaching moment ▶ 24:04 Reframing CRM as an insane ledger system

David re-educates on CRM architecture, demonstrating why manual human data entry into a centralized ledger is fundamentally flawed because reps have zero incentive to log data correctly.

 Matt holds his own ▶ 4:50 Detailed knowledge of Performable's early profile innovations

Matt interrupts to accurately identify David's former company Performable and highlights its pioneering work in omnichannel user-based marketing profiles.
the scores for every segment, with the reasoning behind each
ChapterTopicMatt as informed peerGuest teachingGuest disagreementMatt pushing backWhy
David Cancel's Founder Journey and Career Background 4211 Matt demonstrates strong preparation by citing exact funding figures, company stats, and specific previous ventures like Performable. David gently reframes his college exit as fading away rather than dropping out, but the interaction remains warm and collaborative.
Drift's Conversational Live Chat and Enterprise Routing 4311 Matt asks informed questions about enterprise routing, Account-Based Marketing targeting, and Drift's multi-product architecture. David educates the host on how traditional batch CRMs fail real-time routing needs, requiring Drift to build an ad-server style routing engine.
Conversational AI, Machine Learning Chatbots, and AI Designers 4431 Matt probes into the mechanics of AI designers and network data effects across customers. David challenges prevailing enterprise software tropes, arguing that customers care about outcomes and experiences rather than underlying AI specs.
Future of Software Automation and Rethinking Traditional CRMs 4541 Matt asks if Drift aims to become the central system of record or complement existing stacks. David aggressively criticizes current B2B software stacks and traditional CRMs, calling manual data entry ledger systems insane and non-viable long term.
Conversational Email and Automatic Contact Data Capture 4310 Matt demonstrates awareness of Drift's email signature contact parsing features. David explains how standard marketing emails brokenly operate as one-way blasts and how Drift converts them into two-way conversational routing.
Red Ocean Strategy, Category Creation, and Global Branding 3531 Matt asks about positioning and category creation in a noisy market. David pushes back on classic Blue Ocean strategy dogma, asserting that markets without competitors usually aren't real markets and explaining why entering red oceans with a paradigm shift is superior.
Monetization Evolution, High-Velocity Inside Sales, and Pandemic Impact 3311 Matt prompts David on go-to-market transitions from freemium to enterprise. David details high-velocity inside sales and describes how the pandemic permanently accelerated enterprise digital transformation by ten years.
Audience Q&A on Product Roadmap, Culture, COVID-19, and B2C 2310 Matt and moderator Jack facilitate audience Q&A covering culture, implementation speeds, and B2C use cases. David offers insights into Drift's core philosophy that every internal product idea is fundamentally wrong until validated by customer feedback.

Statements from this episode (11)

Assertion Not checkable as stated
Cancel: B2B sales control has shifted entirely from sellers to buyers
“We were moving from a world where the company controlled the buying process, largely in the B to B space to a world where the buyer had all, all the control.”
David Cancel Sep 25, 2020 ▶ 6:39
Disclosure
Cancel: Drift is secretly building a new CRM based on conversational data
“Basically what we've been trying to do from the beginning, which is invisible to everyone is that we are trying to build a new type of CRM. And we believe that we're doing that on a different type of data model, which is largely driven by conversation conversa…”
David Cancel Sep 25, 2020 ▶ 8:12
Assertion Not checkable as stated
Cancel: Legacy CRM architectures like Salesforce were not built for real-time interactions
“And most systems, again, when we think about all those systems, whether you could put together all the sales forces you want and all the add ons and the 50 to a hundred tools that people put on top of those existing systems today, none of them were built for a…”
David Cancel Sep 25, 2020 ▶ 13:39
Assertion Supported
Cancel: Drift was likely the first to deploy website sales qualification bots
“We feel like we were probably the first ones that really did that from a website standpoint, which is like the sales qualification bot, right?”
David Cancel Sep 25, 2020 ▶ 14:48
Prediction Not checkable as stated
Cancel: Enterprise software will move away from dozens of loosely coupled tools
“I think the reality that we're in, especially in the, in our context where we are in sales and marketing software right in the world of Salesforce and all those kinds of tools is like the re the idea that you need 50 to a hundred tools, which is not an exagger…”
David Cancel Sep 25, 2020 ▶ 21:17
Opinion
Cancel: Traditional CRMs reliant on manual human data entry are insane
“Again, like this idea that we have today of a CRM or centralized place for, to keep all this information is a pretty insane system, right? This idea that humans enter things into one big ledger and they have to enter it in a certain format and all those humans…”
David Cancel Sep 25, 2020 ▶ 24:04
Insight
Cancel: A market without competition usually is not a real market
“Most of the time a market that has no competition is not a market.”
David Cancel Sep 25, 2020 ▶ 29:25
Disclosure
Cancel: Drift targeted the commoditized CRM market via a paradigm shift
“Look, I want to go into the most commoditized market possible, right? Really we're going, trying to go in the CRM market. And so I want to go in that red ocean, but what I want to understand going in is understand that it's a red ocean, understand that we need…”
David Cancel Sep 25, 2020 ▶ 29:36
Insight
Cancel: COVID-19 accelerated digital transformation in Drift's market by 10 years
“We believe that we've seen a 10 year acceleration in digital transformation in our market easily.”
David Cancel Sep 25, 2020 ▶ 36:03
Prediction Not checkable as stated
Cancel: B2B shift to online sales channels will permanently persist post-COVID
“I think that behavior change won't go back. And so some of it will go back, but from an efficiency standpoint, it's too efficient and the incentives are set up for companies to continue to go that way.”
David Cancel Sep 25, 2020 ▶ 41:43
Assertion Not checkable as stated
Cancel: Peloton sells 40% to 50% of bikes through website messaging
“They sell, you know, somewhere like between 40 and 50% of their bikes over website messages.”
David Cancel Sep 25, 2020 ▶ 43:10
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