When one of the big names on the market is calling for a collapse, what’s the average investor to do? Create a peace of mind hedge.   

(00:22) Jason Moser and Dylan Lewis discuss:

- Nassim Taleb’s recent calls for a market drop and why he’s focused on the U.S. dollar, domestic debt, and S&P 500 concentration. 

- What investors can learn from someone focused on tail-risk hedging.

- The peace of mind hedges investors can put in place for their own portfolios 

(19:35) Asit Sharma and Mary Long discuss Sonos’s ongoing recovery after rushing to release an app before it was ready for prime time. 

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Companies discussed: AAPL, MSFT, NVDA, SONO

Host: Dylan Lewis

Guests: Jason Moser, Mary Long, Asit Sharma

Producer: Mary Long

Engineers: RIck Engdahl

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Clouds are gathering over the Sunshine State’s housing market. Especially along the state’s Gulf Coast, housing inventory is up and buyer interest is slowing. WSJ’s Deborah Acosta talks through the cooling-off of one of America’s biggest housing booms and what it says about what it means to live in Florida now.

Further Listening:

- Is Asheville No Longer a 'Climate Haven? 

- Years After Surfside Collapse, Florida Condos Are In Crisis 

Further Reading:

- The Great Florida Migration Is Coming Undone 

- Why the Tampa Area Is So Vulnerable to a Hurricane 

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Todays show:

Cacheflow’s Sarika Garg joins Alex Wilhelm to discuss the challenges of B2B software sales (4:26), finding product-market fit (14:08), HubSpot's acquisition of Cacheflow (17:32), and more!

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Timestamps:

(0:00) Cacheflow’s Sarika Garg joins Alex

(2:25) Sarika Garg's startup journey and founding of Cacheflow

(4:26) Challenges in B2B software sales, managing billing complexities, and SaaS explosion

(10:09) Initial funding, product development, and growth

(10:34) AssemblyAI - Get 100 free hours to start building at https://www.assemblyai.com/twist

(14:08) Finding product-market fit and scaling strategies

(17:32) HubSpot's acquisition of Cacheflow

(21:20) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(22:24) Preparing for Series A and positioning as an AI company

(24:57) Deal with HubSpot and integration plans

(29:41) Runway - Sign up at ⁠https://runway.com/twist⁠ to get your first 3 months free

(30:58) Diverse cap table, early exit, and founder lessons

(33:45) Importance of a part-time CFO and organizational efficiency

(37:26) Integration with HubSpot's Commerce Hub

(39:02) Shifts in SaaS buying behavior and future plans at HubSpot

(47:01) Remote work’s impact

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Check out Cacheflow: https://www.getcacheflow.com

Check out Alex’s articles on Cacheflow:

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Follow Sarika:

X: https://x.com/sarikagarg

LinkedIn: https://www.linkedin.com/in/sarikagarg

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X: https://x.com/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm

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Thank you to our partners:

(10:34) AssemblyAI - Get 100 free hours to start building at https://www.assemblyai.com/twist

(21:20) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(29:41) Runway - Sign up at ⁠https://runway.com/twist to get your first 3 months free

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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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Check out Jason’s suite of newsletters: https://substack.com/@calacanis

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Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

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In our final episode, we get a break in the case of the missing minister: According to our sources, Chinese officials were told that Qin disappeared due to an explosive allegation. We dig into that story and its consequences for Fu and for Qin – Xi Jinping’s trusted aide. 

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In the second episode of our investigation, we examine the life and career of Fu Xiaotian: the prominent Chinese TV host who had an affair with Qin Gang. Like Qin, Fu was sharp and ambitious, but her high-flying career would come to an abrupt halt. And like Qin, she would also mysteriously disappear. 

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Last year, China’s foreign minister, Qin Gang, suddenly disappeared. Qin was a rising star in Chinese politics and a protegé of China’s strongman leader, Xi Jinping. In the first episode of our three-part investigation, we chart Qin’s rise and begin to untangle the mystery of his disappearance.

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Drew Houston has now been CEO of Dropbox for over 17 years. In my latest conversation, he opens up about the pivotal leadership lessons he's learned, the mistakes that shaped the company, and the true challenges of going head-to-head with big tech. We also dive into the highs and lows of fundraising, how valuations can make or break a company trajectory, and discuss the opportunities AI presents for the future of work.

[0:00] Intro

[0:44] AI Opportunities for Dropbox

[5:57] Dropbox's AI Principles

[7:52] Introducing Dropbox Dash

[9:18] AI Enhancements in Search

[12:33] Personal Productivity with AI

[17:10] Memo-First Culture at Dropbox

[22:15] Reflections on Leadership and Growth

[31:21] Early Challenges and Viral Growth

[48:22] Facing Fierce Competition

[51:51] Strategic Shift to Collaboration

[53:20] Navigating Internal Challenges

[55:18] Reevaluating Productivity

[1:03:07] The Birth of Dash

[1:16:32] You Don't Want to Feel Like a Victim

[1:30:29] Closing Thoughts and Lessons Learned

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Justin Hrabovsky

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1

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About the Show

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.

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Todays show:

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Timestamps:

(00:00) Kruze COO, Scott Orn, joins Jason

(0:21) The best financial advice VCs give startups, managing cash flow, and the risks of over-fundraising

(5:19) Growth strategies for early-stage startups and accounting methods

(8:28) Legal aspects of financial representation and maintaining credibility with VCs

(15:00) Building an effective financial plan for your startup

(17:47) Historical perspectives on funding and the importance of regulatory considerations

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Check out Kruze: https://kruzeconsulting.com

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Check out the TWIST500: https://www.twist500.com

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Follow Scott:

LinkedIn: https://www.linkedin.com/in/scottorn

X: https://twitter.com/scottorn

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Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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Check out Jason’s suite of newsletters: https://substack.com/@calacanis

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Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

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Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

NotebookLM from Google Labs has become the breakout viral AI product of the year. The feature that catapulted it to viral fame is Audio Overview, which generates eerily realistic two-host podcast audio from any input you upload—written doc, audio or video file, or even a PDF. But to describe NotebookLM as a “podcast generator” is to vastly undersell it. The real magic of the product is in offering multi-modal dimensions to explore your own content in new ways—with context that’s surprisingly additive. 200-page training manuals become synthesized into digestible chapters, turned into a 10-minute podcast—or both—and shared with the sales team, just to cite one example. Raiza Martin and Jason Speilman join us to discuss how the magic happens, and what’s next for source-grounded AI.

Hosted by: Sonya Huang and Pat Grady, Sequoia Capital

Professional risk takers—poker players and hedge fund managers, crypto true-believers and blue-chip art collectors—can teach us a lot about navigating the uncertainty of the 21st century, says statistician and analyst Nate Silver. He embedded himself within the worlds of Doyle Brunson, Peter Thiel, Sam Bankman-Fried, Sam Altman and many others and now comes to Commonwealth Club World Affairs to share insight into a range of issues that affect everyone, from the frontiers of finance to the future of AI.

In his bestselling book The Signal and the Noise, Silver showed how forecasting would define the age of Big Data. Now, in his riveting new book On the Edge, Silver investigates "The River"—those whose mastery of risk allows them to shape and dominate so much of modern life. The River has increasing amounts of wealth and power in our society, and understanding their mindset—including the flaws in their thinking—is key to understanding what drives technology and the global economy today.

There are certain commonalities in this otherwise diverse group: high tolerance for risk; appreciation of uncertainty; affinity for numbers; skill at de-coupling; self-reliance and a distrust of the conventional wisdom. For these people, complexity is baked in, and the work is how to navigate it, without going beyond the pale.

Join us in-person or online as Silver takes you behind the scenes from casinos to venture capital firms to the FTX inner sanctum to meetings of the effective altruism movement

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