20VC: DFJ's Josh Stein on Why VCs Must Adapt To Their Founders, The Major Transition Points For Aaron Levie @ Box & Why SaaS Startups Are Growing At A Rate Never Seen Before

20VC: DFJ's Josh Stein on Why VCs Must Adapt To Their Founders, The Major Transition Points For Aaron Levie @ Box & Why SaaS Startups Are Growing At A Rate Never Seen Before

Josh Stein is Partner @ DFJ where his current board responsibilities include Box (NYSE: BOX), Chartbeat, LaunchDarkly, LendKey, SugarCRM, and previous guests with me on SaaStr in Periscope and Talkdesk. He is also actively involved with the firm's investments in AngelList, Doximity and Twilio (NYSE: TWLO) just to name a few. Prior to joining DFJ, Josh was a VP at Telephia, where he managed a group providing strategic analysis and information to the nation's largest wireless carrier. Previously, Josh was a co-founder for ViaFone (NYSE: SY), a DFJ portfolio company and a leading provider of wireless enterprise applications. Josh met the DFJ team when the firm co-led ViaFone's Series A investment.

In Today's Episode You Will Learn:

1.) How Josh made his way from the world of operations to Partner @ DFJ?

2.) How does Josh analyze the VC/ Founder fit? How does Josh look to build trust and transparency in that relationship? What is an example of how Josh has changed his style to fit the character of an entrepreneur?

3.) Question from Greg Sands: What did Josh see in the early days of Box with a young Aaron Levie, what was it that made him so excited?

4.) Question from Mamoon Hamid @ Social Capital: Looking at Box today, what will it take for Box to 10x their value? What needs to happen in the market? What needs to happen to the product roadmap?

5.) Question from Jason Lemkin @ SaaStr: How is it that we are seeing companies like TalkDesk and Twilio grow at a rate never seen before in today's SaaS environment?

Items Mentioned In Today's Show:

Josh's Fave Blog: TermSheet

Josh's Fave Book: Insanely Simple: The Obsession That Drives Apple's Success

Josh's Most Recent Investment: LaunchDarkly

As always you can follow Harry, The Twenty Minute VC and Josh on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

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Episoder(1425)

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20VC OGs: SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price | Airwallex Raises $330M and The Battle with Keith Rabois | Netflix Acquires Warner Brothers | IPO Market Predictions for 2026: Anthropic, Stripe, Databricks and SpaceX

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20VC: Inside Bending Spoons Acquisition Machine: Evernote, Eventbrite, Vimeo | How Evernote Evaluates Acquisitions and New Product Ideas | How Evernote Mastered Product Launches, User Retention and Monetisation with Federico Simionato

20VC: Inside Bending Spoons Acquisition Machine: Evernote, Eventbrite, Vimeo | How Evernote Evaluates Acquisitions and New Product Ideas | How Evernote Mastered Product Launches, User Retention and Monetisation with Federico Simionato

Bending Spoons is the acquisition machine of the tech world. They have acquired the likes of Evernote, Vimeo, Eventbrite, Streamyard and more. However, they never open their gates to the secrets behin...

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20VC: Thrive & OpenAI Partnership | Eventbrite Acquired for $500M | Databricks Raising $5BN at $134BN Valuation: Cheap or Not? | Why SaaS is Like Japan and The TAM Trap in Software

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AGENDA: 04:20 Thrive and OpenAI Partnership  07:14 Databricks Raising $5BN at $134BN Valuation: Cheap or Not? 17:39 Eventbrite Acquired by Bending Spoons for $500M 21:39 Pagerduty's $1BN Market Cap, J...

4 Des 20251h 12min

20VC: Scale, Surge, Turing, Mercor: Who Wins & Who Loses in Data Labelling | Is Revenue in Data Labelling Real or GMV? | Why 99% of Knowledge Work Will Go and What Happens Then? | Why SaaS is Dead in a World of AI with Jonathan Siddharth @ Turing

20VC: Scale, Surge, Turing, Mercor: Who Wins & Who Loses in Data Labelling | Is Revenue in Data Labelling Real or GMV? | Why 99% of Knowledge Work Will Go and What Happens Then? | Why SaaS is Dead in a World of AI with Jonathan Siddharth @ Turing

Jonathan Siddharth is Founder and CEO of Turing, one of the fastest-growing AI companies advancing frontier models. Jonathan has led the company to an astonishing $300M ARR with just $225M raised and ...

1 Des 20251h 8min

20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

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John McMahon is widely regarded as one of the greatest enterprise-software sales leaders of all time. He's the only person to have served as Chief Revenue Officer at five public software companies: PT...

28 Nov 20251h 8min

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20VC: Anthropic Raises $30BN from Microsoft and NVIDIA | NVIDIA Core Business Threatened by TPU | Sam Altman's "War Mode" Analysed | Sierra Hits $100M ARR: Justifies $10BN Price? | Lovable Hits $200M ARR & Rumoured $6BN Round

AGENDA: 04:06 Anthropic's $30BN Investment from Microsoft and NVIDIA 07:01 Google vs. OpenAI: Sam Altman's "War Mode" Memo 15:27 NVIDIA's Customer Concentration: Bull or Bear 22:12 Is "War Mode" BS: D...

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20VC: Base44's Maor Shlomo on How Vibe Coding Will Kill SaaS and Salesforce | Why it is BS that Vibe Coding Platforms Do Not Have Defensibility and Bad Margins | Why He Worries About Google, Not Replit and Lovable | Why Long Anthropic, Not OpenAI?

Maor Shlomo is the Founder and CEO of Base44, the AI building platform that Maor built from idea to $80M acquisition by Wix, in just 8 months. Today the company serves millions of users and will hit $...

24 Nov 20251h 11min

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