Podcast Summary: The Insane Productivity of Andrew Ross Sorkin

Podcast: ACQ2 by Acquired
Hosts: Ben Gilbert, David Rosenthal
Guest: Andrew Ross Sorkin
Date: December 8, 2025

Episode Overview

This episode features a deep-dive interview with journalist, author, and DealBook founder Andrew Ross Sorkin. Rather than solely focusing on his new book "1929," Ben and David center the conversation on "how the heck" Sorkin manages his prolific output—spanning The New York Times DealBook newsletter, DealBook Summit, daily CNBC Squawk Box, bestselling books, and co-creating the TV show "Billions." Sorkin offers a rare, detailed account of his evolution in media, his routines and strategies, and the lessons learned about sourcing, interviewing, and building modern journalistic brands.

Key Topics and Discussion Points

1. Sorkin’s Daily Routine & Productivity Hacks

Typical Day Structure:
- 4:30am: Wakes, checks emails/Slack under covers, writes top of DealBook.
- 6-9am: Live on CNBC's Squawk Box.
- Post-9am: Works on DealBook, the newsletter, Summit, books, and other projects.
- “If you read DealBook at the top, it says: 'Good morning, Andrew here.' I’m writing that in the morning, every morning.” — Andrew Ross Sorkin [06:02]
Wardrobe Note: "Usually I’m in a suit all day... but I thought for you guys I’d wear a sweater." — Sorkin [02:19]

2. Origins and Transformation of DealBook

Teenage Beginnings:
- Sold ads and ran a sports magazine in high school.
- At 18, hustled his way into The New York Times by cold-calling and persistence.
Early Email Newsletter Pioneer:
- Launched DealBook in 2001 inside NYT—years before Substack, Stratechery, or mass email newsletters, inspired by getting scoops directly to businesspeople’s inboxes.
- Overcame internal skepticism about linking to competitors and fuss about the business model.
- “I told them we were going to make money on day one. And we did. Our first advertiser was Brooks Brothers.” — Sorkin [18:29]
Notable Growth:
- Original internal TAM was thought to be 30,000 subscribers; DealBook now has over 1 million. [18:13]

3. Journalistic Philosophy & Sourcing Lessons

On Source Motivation:
- “Every source has some motivation for why they’re talking to you... As long as I can confirm the information... I try not to worry too much about their ultimate incentives.” — Sorkin [21:11]
On Building Stories:
- Confirm tips from multiple sources, often starting at junior levels.
- Leverages the "jilted" (e.g., losing side of a deal) as sources.
- “Oftentimes a great story starts with, I call the jilted somebody... someone’s lost the auction, now they’re jilted... and that’s how a lot of stories start.” — Sorkin [24:06]
On Interview Tactics:
- Never shares questions in advance, but discusses themes to help guests prepare.
- Leverages the small talk and "wings" interactions to settle guests.
- "Most important time of an interview is that two minutes before it starts—trying to get them to settle." — Sorkin [39:06]
- Uses depersonalization when asking tough questions: “There’s this quote… When you hear that, you would say what?” [55:08]

4. DealBook Summit: Bringing Newsroom to the Stage

Conceived in 2011: To bring the newsletter’s characters to life and probe the “why” behind influential figures’ decisions.
Marathon Prep: Each interview (he does all of them back-to-back in one day) takes 15-30 hours to prepare. [37:11]
- Uses notes, contacts reporters, tracks priority questions.
- “I need to almost know it at a visceral level.” [47:39]
Summit Interviews: Blend politics, tech, and finance. 2025’s lineup includes leaders like Janet Yellen, David Ellison, Mary Barra, Dario Amodei, Alex Karp, Brian Armstrong, Larry Fink, Mr. Beast, Gavin Newsom, Halle Berry. [43:14–46:28]

5. On Taking Risks & Sorkin's Expanding Empire

Biggest Professional Leaps:
- Writing "Too Big to Fail" and "1929"
- Co-creating "Billions" (wrote the script on spec)
- Going on TV as an anchor
- "I think writing that book was a leap... I wasn't sure I could write a book." [61:45]
Balance Between Mediums: All projects (journalism, books, TV) feed on his core drive to understand people and motivations in business.

6. Business Model Insights

DealBook Revenue: 100% advertising/sponsorship supported, no paid subscriptions. Summit is also sponsorship-driven with public application for tickets. [58:33–59:54]

7. Personal Ethos & Advice

On Saying No: Sorkin says no to most incoming project ideas to focus and maintain high quality.
Take Every Project Personally:
- "I think you have to take everything personally... The most successful people I know take everything personally because they care deeply." [72:30]
Critiques from Journalism World: Sometimes called "too close to sources"—Sorkin defends this as necessary for nuanced, accurate storytelling. [73:06]

Notable Quotes and Moments

On Early Mornings:
“My day usually begins around 4:30 in the morning. I lie in bed with my phone under the covers looking at email, texts…” — Sorkin [05:36]
On Confirmation:
"You want to get 80 to 90% of the way there before asking the company for comment. If you get to 90%, it often behooves the company to tell you what’s happening." — Sorkin [26:01]
On Summit Prep:
“Each interview takes between 15 and 30 hours of prep… I keep notes all year, talk to people who know the guest, try to absorb facts and their disposition.” — Sorkin [37:11]
On Interview Dynamics:
"It's like a tennis rally—you want the ball to go back forth. Even if I hit into the corner, I want them to hit it back." — Sorkin [53:01]
On Doing the Work:
"The work is so evident when they listen to you... because the embedded questions and storytelling can't be done by AI." — Sorkin [50:28]
On DealBook’s Business Model:
"It’s really just, it was about reach. We've found we can make the economics of the business work pretty well under this scenario." — Sorkin [59:54]
On Risk & Media:
“Writing the book was a leap... I wasn't sure I could write a book… Co-creating Billions was a total leap, we had no idea if anyone would buy it.” — Sorkin [61:45]

Memorable Segments (Timestamps)

[02:16] Sorkin’s wardrobe playfulness (“suit versus sweater”)
[06:02] Daily DealBook writing habit
[09:01 - 13:20] Sorkin’s unconventional path into journalism from high school
[14:22 - 18:29] Birth of DealBook and internal skepticism at NYT
[19:51 - 20:50] The newsletter reply-as-source feedback loop
[21:11 - 24:06] How Sorkin thinks about sources and motivations
[32:27 - 33:33] DealBook Summit’s origin — “bring the newsletter to life”
[37:11] Summit prep time (15-30 hours per interview)
[46:03 - 46:40] This year’s Summit lineup and how Sorkin preps marathon interview days
[47:39] Interview flight path analogy (“JFK to LAX, weather may change”)
[55:08] The “depersonalized” tough-question technique
[59:48] The advertising-driven business model for DealBook and the Summit
[61:45] Sorkin on real "leaps" in his career
[72:30] Emphasizing taking everything personally as a path to excellence

Takeaways for Listeners

Sorkin’s energy comes from deep curiosity and relentless preparation; his workflow integrates his diverse projects but always centers on storytelling and people.
Breakthroughs (like DealBook’s success) come from solving a real pain—here, getting business news where bankers/lawyers would actually read it, well before industry trends caught up.
The most effective interviews—at the Summit or on TV—balance deep research with careful listening and providing a safe space for the subject to open up.
Critical business, policy, and technology leaders value DealBook as a must-read because of its accurate, nuanced reporting—and the instant feedback loop of email enables a richer, more dynamic approach to journalism.

Summary Table of Key Segments

| Timestamp | Segment | Highlight | |-----------|-------------------------------------------------|---------------------------------------------------------------------------------------------------------------------| | 04:30 | Sorkin’s morning routine | Wakes, writes newsletter, preps for live TV | | 14:22 | Launching DealBook newsletter | Preceded email news trend by a decade | | 19:51 | Reader replies as sources | Turns direct audience feedback into scoops | | 32:27 | DealBook Summit concept | “Pages of DealBook made real”—top leaders, candid interviews | | 37:11 | Interview prep methods | 15-30 hours per guest, year-long notes, talks to beat reporters | | 43:14 | 2025 Summit lineup announced | Major figures across business, politics, AI, tech | | 47:39 | Interview “flight path” philosophy | Plan structure, be ready to improvise | | 55:08 | Depersonalized tough questioning | “There’s this quote… What would you say to that?” | | 59:48 | DealBook revenue model | Advertising/sponsorship only; targeted for maximum reach over paid subscriptions | | 61:45 | Sorkin’s personal professional leaps | Books, Billions, on-spec creative work, and going on TV for the first time | | 72:30 | Ethos: Taking things personally | Argues true excellence comes from personal investment and feeling |

Concluding Thoughts

ACQ2’s interview with Andrew Ross Sorkin offers not only business and media history but also lessons in productivity, curiosity, and the art of reporting. Sorkin's transparency about process, his continued humility about risk, and openness about his fortune (“rookie errors,” “still could fail”) provide encouragement for builders and storytellers at any stage.

If you’re craving more, the full episode features further anecdotes—Billions, behind-the-scenes at Squawkbox, and more on DealBook’s place in the modern business conversation.

Best Quotes Recap:

"I think you have to take everything personally... it's the only way." — Andrew Ross Sorkin [72:30]

“My day usually begins around 4:30 in the morning. I lie in bed with my phone under the covers looking at email, texts…” — Sorkin [05:36]

"Each interview usually takes me between 15–30 hours of prep, typically." — Sorkin [37:11]

“I don’t know if it’s an empire... I think of it more as: I’m a journalist, writing and talking about what’s happening in this fascinating universe where business meets policy.” — Sorkin [68:43]

Listen for a masterclass in curiosity, hustle, and interviewing – and enjoy the banter between some of the smartest in modern business media.

Podcast Summary: The Insane Productivity of Andrew Ross Sorkin

Podcast: ACQ2 by Acquired
Hosts: Ben Gilbert, David Rosenthal
Guest: Andrew Ross Sorkin
Date: December 8, 2025

Episode Overview

Key Topics and Discussion Points

1. Sorkin’s Daily Routine & Productivity Hacks

Typical Day Structure:
- 4:30am: Wakes, checks emails/Slack under covers, writes top of DealBook.
- 6-9am: Live on CNBC's Squawk Box.
- Post-9am: Works on DealBook, the newsletter, Summit, books, and other projects.
- “If you read DealBook at the top, it says: 'Good morning, Andrew here.' I’m writing that in the morning, every morning.” — Andrew Ross Sorkin [06:02]
Wardrobe Note: "Usually I’m in a suit all day... but I thought for you guys I’d wear a sweater." — Sorkin [02:19]

2. Origins and Transformation of DealBook

Teenage Beginnings:
- Sold ads and ran a sports magazine in high school.
- At 18, hustled his way into The New York Times by cold-calling and persistence.
Early Email Newsletter Pioneer:
- Launched DealBook in 2001 inside NYT—years before Substack, Stratechery, or mass email newsletters, inspired by getting scoops directly to businesspeople’s inboxes.
- Overcame internal skepticism about linking to competitors and fuss about the business model.
- “I told them we were going to make money on day one. And we did. Our first advertiser was Brooks Brothers.” — Sorkin [18:29]
Notable Growth:
- Original internal TAM was thought to be 30,000 subscribers; DealBook now has over 1 million. [18:13]

3. Journalistic Philosophy & Sourcing Lessons

On Source Motivation:
- “Every source has some motivation for why they’re talking to you... As long as I can confirm the information... I try not to worry too much about their ultimate incentives.” — Sorkin [21:11]
On Building Stories:
- Confirm tips from multiple sources, often starting at junior levels.
- Leverages the "jilted" (e.g., losing side of a deal) as sources.
- “Oftentimes a great story starts with, I call the jilted somebody... someone’s lost the auction, now they’re jilted... and that’s how a lot of stories start.” — Sorkin [24:06]
On Interview Tactics:
- Never shares questions in advance, but discusses themes to help guests prepare.
- Leverages the small talk and "wings" interactions to settle guests.
- "Most important time of an interview is that two minutes before it starts—trying to get them to settle." — Sorkin [39:06]
- Uses depersonalization when asking tough questions: “There’s this quote… When you hear that, you would say what?” [55:08]

4. DealBook Summit: Bringing Newsroom to the Stage

Conceived in 2011: To bring the newsletter’s characters to life and probe the “why” behind influential figures’ decisions.
Marathon Prep: Each interview (he does all of them back-to-back in one day) takes 15-30 hours to prepare. [37:11]
- Uses notes, contacts reporters, tracks priority questions.
- “I need to almost know it at a visceral level.” [47:39]
Summit Interviews: Blend politics, tech, and finance. 2025’s lineup includes leaders like Janet Yellen, David Ellison, Mary Barra, Dario Amodei, Alex Karp, Brian Armstrong, Larry Fink, Mr. Beast, Gavin Newsom, Halle Berry. [43:14–46:28]

5. On Taking Risks & Sorkin's Expanding Empire

Biggest Professional Leaps:
- Writing "Too Big to Fail" and "1929"
- Co-creating "Billions" (wrote the script on spec)
- Going on TV as an anchor
- "I think writing that book was a leap... I wasn't sure I could write a book." [61:45]
Balance Between Mediums: All projects (journalism, books, TV) feed on his core drive to understand people and motivations in business.

6. Business Model Insights

DealBook Revenue: 100% advertising/sponsorship supported, no paid subscriptions. Summit is also sponsorship-driven with public application for tickets. [58:33–59:54]

7. Personal Ethos & Advice

On Saying No: Sorkin says no to most incoming project ideas to focus and maintain high quality.
Take Every Project Personally:
- "I think you have to take everything personally... The most successful people I know take everything personally because they care deeply." [72:30]
Critiques from Journalism World: Sometimes called "too close to sources"—Sorkin defends this as necessary for nuanced, accurate storytelling. [73:06]

Notable Quotes and Moments

On Early Mornings:
“My day usually begins around 4:30 in the morning. I lie in bed with my phone under the covers looking at email, texts…” — Sorkin [05:36]
On Confirmation:
"You want to get 80 to 90% of the way there before asking the company for comment. If you get to 90%, it often behooves the company to tell you what’s happening." — Sorkin [26:01]
On Summit Prep:
“Each interview takes between 15 and 30 hours of prep… I keep notes all year, talk to people who know the guest, try to absorb facts and their disposition.” — Sorkin [37:11]
On Interview Dynamics:
"It's like a tennis rally—you want the ball to go back forth. Even if I hit into the corner, I want them to hit it back." — Sorkin [53:01]
On Doing the Work:
"The work is so evident when they listen to you... because the embedded questions and storytelling can't be done by AI." — Sorkin [50:28]
On DealBook’s Business Model:
"It’s really just, it was about reach. We've found we can make the economics of the business work pretty well under this scenario." — Sorkin [59:54]
On Risk & Media:
“Writing the book was a leap... I wasn't sure I could write a book… Co-creating Billions was a total leap, we had no idea if anyone would buy it.” — Sorkin [61:45]

Memorable Segments (Timestamps)

[02:16] Sorkin’s wardrobe playfulness (“suit versus sweater”)
[06:02] Daily DealBook writing habit
[09:01 - 13:20] Sorkin’s unconventional path into journalism from high school
[14:22 - 18:29] Birth of DealBook and internal skepticism at NYT
[19:51 - 20:50] The newsletter reply-as-source feedback loop
[21:11 - 24:06] How Sorkin thinks about sources and motivations
[32:27 - 33:33] DealBook Summit’s origin — “bring the newsletter to life”
[37:11] Summit prep time (15-30 hours per interview)
[46:03 - 46:40] This year’s Summit lineup and how Sorkin preps marathon interview days
[47:39] Interview flight path analogy (“JFK to LAX, weather may change”)
[55:08] The “depersonalized” tough-question technique
[59:48] The advertising-driven business model for DealBook and the Summit
[61:45] Sorkin on real "leaps" in his career
[72:30] Emphasizing taking everything personally as a path to excellence

Takeaways for Listeners

Sorkin’s energy comes from deep curiosity and relentless preparation; his workflow integrates his diverse projects but always centers on storytelling and people.
Breakthroughs (like DealBook’s success) come from solving a real pain—here, getting business news where bankers/lawyers would actually read it, well before industry trends caught up.
The most effective interviews—at the Summit or on TV—balance deep research with careful listening and providing a safe space for the subject to open up.
Critical business, policy, and technology leaders value DealBook as a must-read because of its accurate, nuanced reporting—and the instant feedback loop of email enables a richer, more dynamic approach to journalism.

Summary Table of Key Segments

Concluding Thoughts

If you’re craving more, the full episode features further anecdotes—Billions, behind-the-scenes at Squawkbox, and more on DealBook’s place in the modern business conversation.

Best Quotes Recap:

"I think you have to take everything personally... it's the only way." — Andrew Ross Sorkin [72:30]

“My day usually begins around 4:30 in the morning. I lie in bed with my phone under the covers looking at email, texts…” — Sorkin [05:36]

"Each interview usually takes me between 15–30 hours of prep, typically." — Sorkin [37:11]

“I don’t know if it’s an empire... I think of it more as: I’m a journalist, writing and talking about what’s happening in this fascinating universe where business meets policy.” — Sorkin [68:43]

Listen for a masterclass in curiosity, hustle, and interviewing – and enjoy the banter between some of the smartest in modern business media.

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The Insane Productivity of Andrew Ross Sorkin

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Summary

Podcast Summary: The Insane Productivity of Andrew Ross Sorkin

Episode Overview

Key Topics and Discussion Points

1. Sorkin’s Daily Routine & Productivity Hacks

2. Origins and Transformation of DealBook

3. Journalistic Philosophy & Sourcing Lessons

4. DealBook Summit: Bringing Newsroom to the Stage

5. On Taking Risks & Sorkin's Expanding Empire

6. Business Model Insights

7. Personal Ethos & Advice

Notable Quotes and Moments

Memorable Segments (Timestamps)

Takeaways for Listeners

Summary Table of Key Segments

Concluding Thoughts

Summary

Podcast Summary: The Insane Productivity of Andrew Ross Sorkin

Episode Overview

Key Topics and Discussion Points

1. Sorkin’s Daily Routine & Productivity Hacks

2. Origins and Transformation of DealBook

3. Journalistic Philosophy & Sourcing Lessons

4. DealBook Summit: Bringing Newsroom to the Stage

5. On Taking Risks & Sorkin's Expanding Empire

6. Business Model Insights

7. Personal Ethos & Advice

Notable Quotes and Moments

Memorable Segments (Timestamps)

Takeaways for Listeners

Summary Table of Key Segments

Concluding Thoughts